SCHEDULE 14A INFORMATION
           PROXY STATEMENT PURSUANT TO SECTION 14(A) OF THE SECURITIES
                              EXCHANGE ACT OF 1934


Filed by the Registrant {x} Filed by a Party other than the Registrant { } Check
the appropriate box: { } Preliminary  Proxy Statement { } Confidential,  for use
of the Commission Only (as permitted by Rule
     14a-6(e)(2))
{X} Definitive Proxy Statement
{ } Definitive  Additional Materials
{ } Soliciting Material Pursuant to 240.14a-11(c) or 240.14a-12

                         WINTRUST FINANCIAL CORPORATION

- --------------------------------------------------------------------------------
                (Name of Registrant as Specified in its Charter)


- --------------------------------------------------------------------------------
    (Name of Person(s) Filing Proxy Statement, if other than the Registrant)

Payment of Filing Fee (Check the appropriate box):
{X} No fee required.
{ } Fee  computed on table below per Exchange  Act Rules  14a-6(i)(1)  and 0-11

        (1) Title of each class of securities to which transaction applies:

        (2) Aggregate number of securities to which transaction applies:

        (3) Per unit price or other  underlying  value of  transaction  computed
            pursuant  to  Exchange  Act Rule 0-11 (set forth the amount on which
            the filing fee is calculated and state how it was determined):

        (4) Proposed maximum aggregate value of transaction:

        (5) Total fee paid:

{ } Fee paid previously with preliminary materials:
{ } Check box if any part of the fee is offset as  provided  by  Exchange  Act
    Rule  0-11(a)(2)  and identify the filing for which the  offsetting  fee was
    paid  previously.  Identify the previous  filing by  registration  statement
    number, or Form or Schedule and the date of its filing.

        (1) Amount Previously Paid:

        (2) Form, Schedule or Registration Statement No.:

        (3) Filing Party:

        (4) Date Filed:


                         WINTRUST FINANCIAL CORPORATION
                    NOTICE OF ANNUAL MEETING OF SHAREHOLDERS
                                  MAY 24, 2001


         The 2001 Annual Meeting of Shareholders of Wintrust Financial
Corporation will be held at the Hyatt Deerfield Hotel, 1750 Lake Cook Road,
Deerfield, Illinois 60015, on Thursday, May 24, 2001, at 10:00 a.m. local time,
for the following purposes:

     1.   To elect eight  Class II  directors  to hold  office for a  three-year
          term;

     2.   To consider a proposal to approve the Wintrust  Financial  Corporation
          Directors Deferred Fee and Stock Plan;

     3.   To  transact  such other  business  as may  properly  come  before the
          Meeting and any adjournment thereof.

The record date for determining shareholders entitled to notice of, and to vote
at, the Meeting is the close of business on April 3, 2001. To make it easier for
you to vote, we are again providing the options of internet and telephone
voting. The instructions printed on your proxy card describe how to use these
convenient services. Of course, if you prefer, you can vote by mail by
completing your proxy card and returning it in the enclosed postage-paid
envelope.

                                             By order of the Board of Directors,


                                             /s/ David A. Dykstra
                                             David A. Dykstra
                                             Secretary

April 27, 2001


WHETHER OR NOT YOU PLAN TO ATTEND THE ANNUAL  MEETING,  IT IS IMPORTANT THAT YOU
VOTE BY ONE OF THE METHODS NOTED ABOVE.



                         WINTRUST FINANCIAL CORPORATION
                               727 North Bank Lane
                           Lake Forest, Illinois 60045

                                 PROXY STATEMENT
                         FOR THE 2001 ANNUAL MEETING OF
                 SHAREHOLDERS TO BE HELD THURSDAY, MAY 24, 2001


          These  proxy   materials  are   furnished  in   connection   with  the
solicitation by the Board of Directors of Wintrust  Financial  Corporation  (the
"Company"),  an Illinois  corporation,  of proxies to be used at the 2001 Annual
Meeting of Shareholders of the Company and at any adjournment of such meeting.

          You are cordially  invited to attend the Company's  Annual  Meeting of
Shareholders to be held on May 24, 2001, at 10:00 a.m., at the Hyatt  Deerfield,
1750 Lake Cook Road, Deerfield, Illinois 60015.

PROXIES, OUTSTANDING VOTING SECURITIES, AND SHAREHOLDERS ENTITLED TO VOTE

          The Board of  Directors  has fixed the close of  business  on April 3,
2001 as the record date for determining  shareholders entitled to notice of, and
to vote at, the Annual Meeting.  On the record date, the Company had outstanding
8,616,976  shares  without  par value of Common  Stock  ("Common  Stock").  Each
outstanding   share  of  Common   Stock   entitles   the  holder  to  one  vote.
Representation at the meeting of a majority of shares will constitute a quorum.

          Proxies received from shareholders in proper form will be voted at the
meeting  and, if  specified,  as directed by the  shareholder.  Unless  contrary
instructions  are given, the proxy will be voted at the meeting FOR the election
of each of the nominees  for Class II Director as set forth below,  FOR approval
of the Directors  Deferred Fee and Stock Plan and, in  accordance  with the best
judgment of the persons  voting the proxies,  with respect to any other business
which may  properly  come before the meeting and is  submitted  to a vote of the
shareholders.  Under  Illinois  law and the  Company's  By-laws,  directors  are
elected by a plurality  of votes cast.  Approval of Proposal  No. 2 requires the
affirmative vote of a majority of the shares present in person or represented by
proxy at the meeting and entitled to vote.  Therefore  abstentions will have the
effect of  voting  against  Proposal  No. 2. With  respect  to  brokers  who are
prohibited from  exercising  discretionary  authority for beneficial  owners who
have not returned  proxies to the brokers,  those shares WILL NOT be included in
                                                         --------
the vote totals,  although both  abstentions and broker non-votes are counted as
shares present for the purpose of determining  whether the shares represented at
the meeting constitute a quorum. A proxy may be revoked at any time prior to its
exercise by means of a written  revocation or submission of a properly  executed
proxy bearing a later date.  Shareholders of record having executed and returned
a proxy who attend the meeting and desire to vote in person are  requested to so
notify the  Secretary of the Company  prior to or at the time of a vote taken at
the meeting.

          YOUR VOTE IS IMPORTANT.  Because many  shareholders  cannot personally
          -----------------------
attend the Annual Meeting, it is necessary that a large number be represented by
proxy.  Whether or not you plan to attend the meeting in person,  prompt  voting
will be  appreciated.  Registered  shareholders  can vote  their  shares via the
Internet or by using a toll-free telephone number.  Instructions for using these
convenient  services  are provided on the proxy card.  Of course,  you may still
vote your shares on the proxy card.  To do so, we ask that you  complete,  sign,
date and return the enclosed proxy card promptly in the postage-paid envelope.

          This Proxy Statement is being mailed to shareholders on or about April
27, 2001.


COST OF PROXY SOLICITATION

          The  cost  of  soliciting  proxies  will  be  borne  by  the  Company.
Directors,  officers, employees and agents of the Company may solicit proxies in
person or by mail, telephone, facsimile transmission and other means. Directors,
officers and employees will receive no additional  compensation for solicitation
services. Brokerage houses, nominees, fiduciaries and other custodians have been
requested to forward soliciting  materials to the beneficial owners of shares of
record held by them and will be reimbursed for their expenses.

INTEREST OF CERTAIN PERSONS IN MATTERS TO BE ACTED UPON

          Directors,  and Director Nominees if elected,  are eligible to receive
awards pursuant to the Director  Deferred Fee and Stock Plan which  shareholders
are being asked to approve in Proposal 2.

                                 PROPOSAL NO. 1
                              ELECTION OF DIRECTORS

          The By-laws of the Company  provide  that three  classes of  Directors
will be elected to hold office for  staggered  three-year  terms.  Each year the
shareholders  elect members of one class of Directors for a term of three years.
The term of office of those persons currently serving as Class II Directors will
expire  at this  Annual  Meeting  of  Shareholders.  The term of  those  persons
currently  serving as Class III  Directors  expires  at the  Annual  Shareholder
Meeting  to be held in 2002;  and the term of Class I  Directors  expires at the
Annual Shareholder Meeting to be held in 2003.

          The eight  persons  named below have been  nominated  for  election as
Class II directors for a term to end at the Annual  Meeting of  Shareholders  in
the year 2004 or until their  successors are elected and  qualified.  All of the
nominees  currently serve as Class II directors  except nominees Getz and Perry.
Each nominee has  indicated a willingness  to serve,  and the Board of Directors
has no reason to believe  that any of the  nominees  will not be  available  for
election. However, if any of the nominees is not available for election, proxies
may be  voted  for the  election  of  other  persons  selected  by the  Board of
Directors.  Proxies  cannot,  however,  be voted for a greater number of persons
than  the  number  of  nominees  named.  Shareholders  of the  Company  have  no
cumulative voting rights with respect to the election of directors.

          The  following  sections set forth the names of  nominees,  continuing
directors  of each  class,  their  ages,  a brief  description  of their  recent
business  experience,  including  present  occupation  and  employment,  certain
directorships  held by each, and the year in which they became  directors of the
Company.  Director  positions in the Company's  subsidiaries are included in the
biographical  information set forth below. Such subsidiaries include Lake Forest
Bank & Trust  Company  ("Lake  Forest  Bank"),  Hinsdale  Bank &  Trust  Company
("Hinsdale  Bank"),  North Shore  Community  Bank & Trust Company  ("North Shore
Bank"), Libertyville Bank & Trust Company ("Libertyville Bank"), Barrington Bank
& Trust Company,  N.A.  ("Barrington Bank"),  Crystal Lake Bank & Trust Company,
N.A. ("Crystal Lake Bank"), Northbrook Bank & Trust Company ("Northbrook Bank"),
Crabtree  Capital  Corporation  ("Crabtree"),   First  Insurance  Funding  Corp.
("FIFC"),  Wintrust Asset Management Company, N.A. ("WAMC"), and Tricom, Inc. of
Milwaukee ("Tricom").

            NOMINEES TO SERVE AS CLASS II DIRECTORS UNTIL THE ANNUAL
                    MEETING OF SHAREHOLDERS IN THE YEAR 2004

BRUCE K. CROWTHER (49), DIRECTOR SINCE 1998 Mr. Crowther has served as President
and  Chief  Executive  Officer  of  Northwest  Community  Healthcare,  Northwest
Community  Hospital and certain of its affiliates  since January 1992.  Prior to
that time he served as Executive Vice President and Chief Operating Officer from
1989 to 1991. He is a Fellow of the American  College of Healthcare  Executives.
Mr.  Crowther is the past  Chairman of the Board of  Directors  of the  Illinois
Hospital  and Health  Systems  Association  as well as a member of the boards of
directors of the Chicago Hospital Risk Pooling Program and Dianon Systems,  Inc.
Mr. Crowther is a Director of Barrington Bank.

                                     - 2 -

BERT A. GETZ,  JR. (33),  DIRECTOR  NOMINEE Mr. Getz is executive vice president
and a director  of Globe  Corporation  where he has  worked  since  1991.  Globe
Corporation  is  a  diversified   investment  company  focused  on  real  estate
investment and  development,  asset  management and private equity  investments.
Founded in 1901, Globe Corporation is currently managed by the fourth generation
of Getz  family  members.  He serves as a Trustee  of the  Brookfield  Zoo and a
Director  of  Children's  Memorial  Hospital.  Mr.  Getz serves as a Director of
Libertyville Bank and WAMC.

WILLIAM C. GRAFT (39), DIRECTOR SINCE 1997 Since December 1999, Mr. Graft is the
founding managing partner of Graft,  Sciaccotta & Associates,  a law firm with a
practice  concentrated  in general  corporate  matters,  commercial  litigation,
finance and complex commercial real estate law. From April 1996 to December 1999
he was the sole  shareholder and President of his law firm. Until December 1995,
Mr. Graft was a partner in the national law firm of Keck Mahin & Cate. Mr. Graft
is also a  principal  and  general  partner of several  real  estate  investment
partnerships  and  corporations  actively  owning and developing  commercial and
medical  real estate  facilities.  He serves as  Chairman  of the Good  Shepherd
Hospital  Development  Council,  is  President  of the Board of Directors of the
Barrington Area Arts Council,  a member of the Creighton  University  College of
Arts and Sciences  Board of Advisors  and serves as a director of several  other
private business enterprises. Mr. Graft is a Director of Barrington Bank.

MARGUERITE  SAVARD MCKENNA (58),  DIRECTOR SINCE 1996 Ms. McKenna is an attorney
who  has  practiced  law in  Wilmette  since  1983  with  an  emphasis  in  real
estate/construction.  She has served as  President  of the  Wilmette  Chamber of
Commerce and the New Trier High School  Parents  Association,  organizations  in
which she  continues  active  membership.  She is also a member of the  Wilmette
Harbor  Rotary Club and the North  Suburban Bar  Association.  Ms.  McKenna is a
Director of North Shore Bank.

ALBIN F. MOSCHNER (48),  DIRECTOR  SINCE 1996 Since December 1999, Mr.  Moschner
has been President and Chief  Executive  Officer of One Point  Services,  LLC, a
telecommunications  company.  From September 1997 to November 1999, he served as
President and Chief Executive  Officer of Millecom,  LLC, a developmental  stage
internet  communications  company. From August 1996 to August 1997, he served as
Vice  Chairman and director and an officer of Diba,  Inc., a  development  stage
internet  technology  company.  Mr.  Moschner  served as President and CEO and a
director of Zenith Electronics,  Glenview, Illinois, from 1991 to July 1996. Mr.
Moschner  is  also  a  director  of  Polaroid   Corporation  and  Pella  Windows
Corporation. Mr. Moschner serves as a Director of Lake Forest Bank.

CHRISTOPHER  J. PERRY (45),  DIRECTOR  NOMINEE Mr. Perry is  currently  Managing
Director and President of Continental Illinois Venture  Corporation,  a position
he has held since 1994, and is also a Managing  Member of CIVC Partners LLC, the
General Partner of the CIVC Fund, L.P. Mr. Perry has been at Bank of America or,
prior to its merger with Bank of America,  Continental  Bank,  since 1985. Prior
positions with Bank of America or Continental Bank include Managing Director and
head of  Mezzanine  Investments  Group  and  Managing  Director  and head of the
Chicago Structured  Finance Group. Prior to joining  Continental Bank, Mr. Perry
was in the Corporate Finance Department of Northern Trust. Mr. Perry also serves
as a Director of TransWestern  Publishing  Company,  L.P. and a variety of other
corporate and  charitable  boards of directors.  Mr. Perry serves as Director of
North Shore Bank.

INGRID S.  STAFFORD  (47),  DIRECTOR  SINCE 1998 Ms.  Stafford  has held various
positions  since  1977 with  Northwestern  University,  where  she is  currently
Associate Vice President for Finance and Controller.  She has been a Director of
Wittenberg  University  since 1993 and serves as its Vice Chair. She is a member
of the National  Association of College and University  Business  Officers.  Ms.
Stafford is the Chair of Leadership  Evanston and a board member of the Evanston
Community Foundation. She is also the former President of the Board of Directors
of  Childcare  Network of Evanston and former chair of the Board of Directors of
the Evanston McGaw YMCA. Ms. Stafford is a Director of North Shore Bank.

                                     - 3 -

KATHARINE V.  SYLVESTER  (61),  DIRECTOR  SINCE 1996 Since  November  1997,  Ms.
Sylvester has been the Office Manager for Fibrex Sales,  Ltd. Ms.  Sylvester has
been active in civic affairs in the Hinsdale area for many years.  She is on the
Board of Trustees of the Hinsdale  Community  House, is a member of the Board of
Directors  of King  Bruwaert  House and is an  Associate  Member of the  Women's
Auxiliary of the Robert Crown Center for Health  Education.  Ms.  Sylvester is a
Director of Hinsdale Bank and Tricom.


           CLASS I - CONTINUING DIRECTORS SERVING UNTIL THE YEAR 2003

JAMES B. MCCARTHY (49),  DIRECTOR SINCE 1996 From 1991 to present,  Mr. McCarthy
has been Chairman and Chief Executive Officer of Gemini Consulting Group,  Inc.,
Oak Brook,  Illinois,  an international  holding company that specializes in the
development of ambulatory surgery center joint ventures.  Mr. McCarthy serves as
Vice  Chairman of the Board of Trustees of Lake  Forest  Academy,  Lake  Forest,
Illinois  and is a member of the Board of  Directors  of the Robert Crown Center
for Health Education, Hinsdale, Illinois. Mr. McCarthy is a Director of Hinsdale
Bank.

JOHN W. LEOPOLD (57), DIRECTOR SINCE 2000 From 1989 to present,  Mr. Leopold has
been President of Tricom, Inc. of Milwaukee,  a financial services subsidiary of
the Company. Additionally, Mr. Leopold serves as President of Techstaff, Inc., a
national franchise of technical placement offices for the staffing industry. Mr.
Leopold is a Director of Tricom.

DOROTHY M. MUELLER (46),  DIRECTOR SINCE 2000 For the past 23 years, Ms. Mueller
has been Vice President of Mark I Construction, Crystal Lake, Illinois, a custom
home building company. Ms. Mueller is a Director of Crystal Lake Bank.

THOMAS J. NEIS (52), DIRECTOR SINCE 1999 Mr. Neis is the owner of Neis Insurance
Agency, Inc., Longaker Insurance Agency and Neis Insurance Consultants, Inc. and
is an independent insurance agent with these companies.  He serves as a chairman
of the Crystal  Lake Sister City  organization  and is a director of the McHenry
County Foundation and several other charitable and fraternal organizations.  Mr.
Neis is a Director of Crystal Lake Bank.

J.  CHRISTOPHER  REYES (47),  DIRECTOR SINCE 1996 Mr. Reyes is Chairman of Reyes
Holdings which owns businesses in beverage  distribution,  food distribution and
processing with  headquarters in Lake Forest,  IL. Mr. Reyes serves on the board
of directors  of Dean Foods Co.,  the Boys & Girls Clubs of Chicago,  Children's
Memorial  Hospital,  Northwestern  Memorial  Foundation,  Museum of Science  and
Industry,  Steppenwolf  Theatre Company and Lake Forest Academy.  Mr. Reyes is a
Director of Lake Forest Bank.

PETER P. RUSIN (48),  DIRECTOR  SINCE 1997 Since 1994,  Mr.  Rusin has served as
Executive Director of Health World, a not for profit children's health education
center and museum,  located in Barrington,  Illinois. Mr. Rusin is a Director of
Barrington Bank.

EDWARD J. WEHMER (47), DIRECTOR SINCE 1996 Since May 1998, Mr. Wehmer has served
as President  and Chief  Executive  Officer of Wintrust  Financial  Corporation.
Prior to May 1998,  he served as President  and Chief  Operating  Officer of the
Company  since its  formation in 1996. He served as the President of Lake Forest
Bank from 1991 to 1998.  He was one of the  principal  organizers of each of the
banking  subsidiaries  and serves as Chairman or Vice Chairman and a Director of
each of the  subsidiary  Banks,  FIFC,  WAMC and  Tricom.  Prior to joining  the
Company,  Mr.  Wehmer  was,  from 1985 to 1991,  Senior  Vice  President,  Chief
Financial  Officer,  and a director of River Forest Bancorp,  Inc. (now known as
Corus  Bankshares,  Inc.),  Chicago,  Illinois.  Mr.  Wehmer is also a certified
public  accountant  and  earlier  in his  career  spent  seven  years  with  the
accounting  firm of Ernst & Young  LLP  specializing  in the  banking  field and
particularly  in the  area of bank  mergers  and  acquisitions.  Mr.  Wehmer  is
involved in several charitable and fraternal organizations.

                                     - 4 -

          CLASS III - CONTINUING DIRECTORS SERVING UNTIL THE YEAR 2002

JOSEPH ALAIMO (70),  DIRECTOR  SINCE 1997 Since  September  1998, Mr. Alaimo has
been the  President of WAMC.  Immediately  prior  thereto,  Mr. Alaimo served as
Director of Trust  Investments at Lake Forest Bank since December 1994. Prior to
joining Lake Forest Bank, he was employed for more than 30 years by  Continental
Bank,  where he served most  recently as  Director  of Investor  Relations.  Mr.
Alaimo held various senior positions in the trust department at Continental Bank
before he became their Director of Investor Relations. Mr. Alaimo also currently
serves as a trustee of Loomis Sayles Funds. Mr. Alaimo is a Director of WAMC.

PETER D. CRIST (49),  DIRECTOR  SINCE 1996 Since  December  1999,  Mr. Crist has
served as Vice  Chairman of  Korn/Ferry,  International,  the largest  executive
search firm in the world.  Previously he was President of Crist Partners,  Ltd.,
an  executive   search  firm  he  founded  in  1995  and  sold  to   Korn/Ferry,
International in 1999. Immediately prior thereto he was Co-Head of North America
and the Managing Director of the Chicago office of Russell Reynolds  Associates,
Inc., the largest  executive  search firm in the Midwest,  where he was employed
for more than 18 years.  Mr.  Crist also  serves as a director  of  Northwestern
Memorial Corporation. He is a Director of Hinsdale Bank.

KATHLEEN R. HORNE (57),  DIRECTOR SINCE 1997 Mrs.  Horne is a former  elementary
school  teacher.  For 14  years  she was  Vice  President  of the  International
Creative Group - London/Chicago  Ltd., a  creative-marketing  consultancy.  From
1995 to 1997,  she  served as  President  of the  Woman's  Board of the  Chicago
Horticultural  Society  and as a  member  of the  Board  of  Directors  of  that
organization.  In 2000, Mrs. Horne represented the United States in two honorary
floral  exhibitions  in  Ireland  and  England.  Mrs.  Horne  is a  Director  of
Barrington Bank.

JOHN S.  LILLARD  (70),  DIRECTOR  SINCE  1996 Mr.  Lillard  has  served  as the
Company's  Chairman  since May 1998. He spent more than 15 years as an executive
with JMB Institutional Realty Corporation,  a real estate investment firm, where
he served as President  from 1979 to 1991 and as Chairman - Founder from 1992 to
1994. Mr. Lillard was a general partner of Scudder Stevens & Clark until joining
JMB in 1979.  He is a Life  Trustee of the  Chicago  Symphony  Orchestra,  and a
Trustee of Lake Forest College.  Mr. Lillard  currently  serves as a director of
Stryker Corporation. Mr. Lillard is a Director of Lake Forest Bank and WAMC.

HOLLIS W. RADEMACHER (65),  DIRECTOR SINCE 1996 Mr.  Rademacher is self-employed
as a business  consultant  and  private  investor.  He has  participated  in the
organization of six of the seven Banks.  From 1957 to 1993, Mr.  Rademacher held
various  positions,  including  Officer in Charge,  U.S. Banking  Department and
Chief Credit Officer,  of Continental Bank, N.A.,  Chicago,  Illinois,  and from
1988 to 1993 held the position of Chief Financial  Officer.  Mr. Rademacher is a
director of Schawk, Inc., CTN Media Group and The Restaurant Company, as well as
several other private business enterprises. Mr. Rademacher currently serves as a
Director of each of the subsidiary Banks, FIFC, WAMC and Tricom.

JOHN N. SCHAPER (49),  DIRECTOR  SINCE 1996 Since 1991,  Mr.  Schaper has been a
general agent for American  United Life  Insurance  Company.  He also  currently
serves as the  president  of the College of Lake County  Foundation  Board.  Mr.
Schaper is a Director of Libertyville Bank.

JOHN J. SCHORNACK (70),  DIRECTOR SINCE 1996 Since 1999 Mr. Schornack has served
as  Chairman  of Strong Arm  Products,  LLC.  Mr.  Schornack  is also the former
Chairman and CEO of KraftSeal Corporation,  Lake Forest, Illinois, a position he
held  from  1991 to 1997,  and  retired  Chairman  of Binks  Sames  Corporation,
Chicago,  Illinois.,  where he served from 1996 to 1998.  From 1955 to 1991, Mr.
Schornack was with Ernst & Young LLP, serving most recently as Vice Chairman and
Managing  Partner of the  Midwest  Region.  He is a Life  Trustee of the Chicago
Symphony  Orchestra,  a  trustee  of the Kohl  Children's  Museum  and The Night
Ministry.  He also is the  retired  Chairman  of the Board of  Trustees of Barat
College, Lake Forest,  Illinois. Mr. Schornack is a Director of North Shore Bank
and several other private business enterprises.

                                     - 5 -

LARRY V. WRIGHT (61), DIRECTOR SINCE 1996 Mr. Wright serves as the president and
director of Milbank Corporation, Chicago, Illinois, an investment advisory firm.
Mr. Wright was appointed  President in 2000 and before that served 35 years as a
vice president of Milbank Corporation.


                    RETIRING DIRECTORS AND DIRECTOR EMERITUS

MAURICE F. DUNNE, JR. (74), DIRECTOR SINCE 1996 Mr. Dunne has been the President
of Maurice F. Dunne Ltd., an educational  consulting firm, since September 1991.
Prior  thereto,  he served as  President of the Lake Forest  Graduate  School of
Management,  Lake Forest, Illinois for more than 25 years. Mr. Dunne also served
as the chief operating  officer of the Northern  Illinois  Business  Association
from  September  1991 to June 1993.  Mr. Dunne is a Director of Lake Forest Bank
and North Shore Bank.  Effective at the Annual Meeting,  Mr. Dunne will become a
Director  Emeritus  for a one  year  term  that  is  renewable  at  the  Board's
discretion and will be available to consult with the Board.

JAMES E. MAHONEY (63), DIRECTOR SINCE 1996 From 1978 to present, Mr. Mahoney has
been the owner and  President  of  Heidi's  Cheese  Products,  Inc.,  Mundelein,
Illinois.  In December  2000,  Mr. James E.  Mahoney  resigned his position as a
Class I  member  of the  Board  of  Directors.  Mr.  Mahoney  is a  Director  of
Libertyville Bank.

JANE R. STEIN  (56),  DIRECTOR  SINCE 1996 Since  1983,  Ms.  Stein has been the
Executive Director of the Lake County Medical Society, Lake Forest,  Illinois, a
not-for-profit  professional  association  for physicians in Lake County.  Since
February,  1999, she has been the Executive  Director of the Illinois Society of
Oral and  Maxillofacial  Surgeons.  Ms. Stein also serves as President of Marble
House,  Ltd., a management  education and consulting  firm. She is also the past
president of the Chicago  Association of Healthcare  Executives.  Ms. Stein is a
Director of Libertyville Bank.

LEMUEL H. TATE, JR. (74),  DIRECTOR  1996-2000 For the past four years, Mr. Tate
has,  from  time  to  time  served  as a  consultant  to  the  Company  and  its
subsidiaries regarding real estate leasing and acquisition matters in connection
with  expansion  activities.  From 1982 to 1988,  Mr. Tate was an executive with
Northwestern  Telecommunication Services (now known as Northwestern Technologies
Group) which is a venture partnership  jointly owned by Northwestern  University
and  Northwestern  Memorial  Hospital  Group.  He retired as President and Chief
Operating  Officer of the  company in 1988.  Since  1988,  he has been active in
volunteer work in the local Chicago area. He is a member of the Evanston  Rotary
Club and is active  in the  International  Executive  Service  Corps.  Since its
inception  in 1994,  Mr.  Tate has been  Chairman  and a Director of North Shore
Bank. In May 2000, Mr. Tate became a Director  Emeritus for a one year renewable
term. The Board has renewed Mr. Tate's Emeritus status for another one year term
that is  renewable  at the Board's  discretion.  Mr. Tate will be  available  to
consult with the Board.

BOARD OF DIRECTORS' COMMITTEES AND COMPENSATION

BOARD OF DIRECTORS' COMMITTEES

          Members of the  Company's  Board of Directors  have been  appointed to
serve on various  committees of the Board of  Directors.  The Board of Directors
has established four committees:  (i) the Compensation and Nominating Committee;
(ii) the Audit  Committee;  (iii) the Risk  Management  Committee;  and (iv) the
Executive Committee.

          Compensation and Nominating Committee. The Compensation and Nominating
Committee is composed  entirely of outside  directors  who are not now, and have
never been, officers of the Company.  Currently, the members of the Compensation
and  Nominating  Committee  are Messrs.  Crist  (Chairman),  Lillard,  McCarthy,
Moschner,  Neis,  Rademacher and Reyes and Ms.  McKenna.  The  Compensation  and
Nominating  Committee is  responsible  for reviewing the Company's  compensation
policies and  administering  the Company's  employee benefit and stock incentive
programs,   and   reports  to  the  Board   regarding   executive   compensation
recommendations.  This  Committee  also  functions as a nominating  committee to
propose to the full Board a slate of nominees  for  election as  directors.  Any
nominations  for  director,  other than the slate  proposed  by the Board,  must
comply with the procedures set forth in the Company's  By-Laws (See "Shareholder
Proposals"). During 2000, four Compensation Committee meetings were held.

                                     - 6 -

          Audit Committee.  The Audit Committee is composed  entirely of outside
independent  directors  who are not now,  and have never  been,  officers of the
Company.  Currently,  the members of the Audit  Committee are Messrs.  Schornack
(Chairman),  Crowther,  Dunne,  and Graft and Ms. Stein and Ms.  Sylvester.  The
Audit  Committee  is  responsible  for  oversight of the  Company's  accounting,
reporting and financial controls practices, reports to the Board regarding audit
activities  and  examinations,   and  annually  reviews  the  qualifications  of
independent auditors.  Additional  information regarding the functions performed
by the Committee is set forth in the "Report of the Audit  Committee,"  included
in this  annual  proxy  statement.  A written  charter  approved by the Board of
Directors  governs the Audit  Committee.  A copy of this  charter is included in
Appendix A. During 2000, six Audit Committee meetings were held.

          Risk Management  Committee.  The Risk Management  Committee  currently
consists of Messrs. Rademacher (Chairman), Moschner, Rusin, and Schaper, and Ms.
Horne,  Ms.  Mueller  and  Ms.  Stafford.   The  Risk  Management  Committee  is
responsible  for  monitoring and  overseeing  the Company's  insurance  program,
interest rate risk and credit risk exposure on a  consolidated  basis and at the
subsidiaries.   This  Committee  is  also   responsible   for   development  and
implementation  of the Company's overall  asset/liability  management and credit
policies. During 2000, four Risk Management Committee meetings were held.

          Executive  Committee.  The Executive  Committee  currently consists of
Messrs. Rademacher (Chairman), Crist, Lillard, Reyes, Schornack, and Wehmer, and
Ms. Stafford.  The Executive  Committee is authorized to exercise certain powers
of the  Board,  and  meets as  needed,  usually  in  situations  where it is not
feasible to take action by the full Board. No Executive  Committee meetings were
held during 2000.

BOARD OF DIRECTORS' COMPENSATION

          Non-employee  members of the Board of Directors are compensated by the
Company at the rate of $500 for each Board of  Directors  meeting  attended  and
$200 for each committee meeting attended.  There were four meetings of the Board
of Directors  during 2000. In addition to regular  board and  committee  meeting
fees, the Company pays  retainers to the Chairman of the Board,  the chairman of
the Risk  Management  Committee,  the  chairman of the Audit  Committee  and the
chairman  of the  Compensation  and  Nominating  Committee.  During  2000,  such
retainers were $50,000, $30,000, $3,000 and $3,000, respectively, and are set to
be $52,500, $35,000, $10,000 and $5,000, respectively, in 2001. Employee members
of the  Board  of  Directors  receive  no Board of  Director  compensation.  All
non-employee  directors who serve on the subsidiary boards of directors are also
entitled to compensation  for such service.  For the period during 2000 in which
they served,  all of the directors  attended at least 75% of the total number of
meetings held of the Board and those Committees on which they served, except for
Directors Crowther, Mahoney, Reyes, Rusin and Wright.

DEFERRED COMPENSATION FOR NON-EMPLOYEE DIRECTORS

          The Wintrust Financial  Corporation  Deferred Director Fee Plan allows
non-employee  Directors to elect to defer receipt of director fees and retainers
due such Directors.  The deferred director fees and retainers are payable at the
Director's  option as a lump sum or in installments  over a period not to exceed
ten years. Cumulative deferred amounts bear interest at the 91-day Treasury Bill
discount rate, adjusted monthly,  until paid. Payments under the plan, which are
unfunded obligations of the Company, begin at the date specified by the Director
or upon  cessation of service as a Director.  If the Directors  Deferred Fee and
Stock Plan  described in Proposal  No. 2 of this Proxy  Statement is approved by
the shareholders at the Annual Meeting, the Deferred Director Fee Plan currently
in effect will be superseded.

                                     - 7 -

                        EXECUTIVE OFFICERS OF THE COMPANY

          The Company's Executive Officers are elected annually by the Company's
Board of  Directors  at the first  meeting  of the Board  following  the  Annual
Meeting of Shareholders.  Certain information regarding those persons serving as
the Company's Executive Officers is set forth below.

Edward J. Wehmer (47) --  President  and Chief  Executive  Officer - Mr.  Wehmer
serves as the  Company's  President  and  performs  the  functions  of the Chief
Executive Officer.  Accordingly,  he is responsible for overseeing the execution
of the  Company's  day-to-day  operations  and  strategic  initiatives.  See the
description  above under  "Election of Directors"  for  additional  biographical
information.

David A. Dykstra (40) -- Executive  Vice  President,  Chief  Financial  Officer,
Secretary and Treasurer - Mr.  Dykstra serves as the Company's  Chief  Financial
Officer and oversees all financial  affairs of the Company,  including  internal
and external financial  reporting.  Prior thereto, Mr. Dykstra was employed from
1990 to 1995 by River  Forest  Bancorp,  Inc.  (now  known as Corus  Bankshares,
Inc.),  Chicago,  Illinois,  most  recently  holding the position of Senior Vice
President  and Chief  Financial  Officer.  Prior to his  association  with River
Forest  Bancorp,  Mr.  Dykstra  spent seven years with KPMG LLP,  most  recently
holding the position of Audit Manager in the banking practice.  Mr. Dykstra is a
Director of Libertyville Bank, Northbrook Bank, FIFC and Tricom.

Lloyd M. Bowden (47) --  Executive  Vice  President --  Technology - Mr.  Bowden
serves  as  Executive  Vice  President  -  Technology  for  the  Company  and is
responsible  for  planning,  implementing  and  maintaining  all  aspects of the
subsidiary  banks' internal data processing  systems and technology  designed to
service the  subsidiary  banks'  customer base. Mr. Bowden joined the Company in
April  1996 to serve as the  Director  of  Technology  with  responsibility  for
implementing technological improvements to enhance customer service capabilities
and operational efficiencies.  Prior thereto, he was employed by Electronic Data
Systems,  Inc. in various  capacities  since 1982, most recently in an executive
management  position with the Banking  Services  Division and  previously in the
Banking Group of the Management Consulting Division.

Robert F. Key (46) -- Executive  Vice President -- Marketing - Mr. Key serves as
the  Executive  Vice  President  -  Marketing  for the  Company  and directs all
advertising  and marketing  programs for each of the subsidiary  banks and WAMC.
Mr. Key joined the Company in March 1996 to serve as Executive Vice President of
Marketing.  From 1978 through March 1996,  Mr. Key was a Vice  President/Account
Director at Leo Burnett Company.

Barbara A. Kilian (42) -- Senior Vice  President -- Finance - Ms.  Kilian serves
as the Senior Vice  President - Finance for the Company and is  responsible  for
the management of all accounting,  auditing, financial and tax activities of the
Company and its  subsidiaries.  Ms.  Kilian  joined the Company in October 2000.
Previously  Ms.  Kilian  was  employed  from  1995 to 2000 as Vice  President  -
Corporate Acquisitions at FBOP Corporation, Oak Park, Illinois, and from 1986 to
1995 at First Colonial Bankshares Corporation,  Chicago, Illinois, most recently
holding the position of Senior Vice President and Chief Financial Officer. Prior
to her association with First Colonial,  Ms. Kilian spent 7 years with KPMG LLP,
in various audit and tax positions serving the financial institutions industry.

David J. Galvan (40) -- Vice President -- Investments - Mr. Galvan has served as
the Vice  President of  Investments  since June 1999. He directs all  securities
investment activity, wholesale funding and interest rate risk management for the
Company.  Previously,  Mr. Galvan was employed for 16 years at Amcore Financial,
Inc., Rockford, Illinois, where he served as Vice President and Funds Manager.

                                     - 8 -

    SECURITY OWNERSHIP OF CERTAIN BENEFICIAL OWNERS, DIRECTORS AND MANAGEMENT

          The following table sets forth the beneficial  ownership of the Common
Stock as of the Annual  Meeting  Record Date,  with respect to (i) each Director
and each Named  Executive  Officer of the Company;  and (ii) all  Directors  and
executive  officers of the Company as a group. No shareholders are known to hold
in excess of 5% of any class of the Company's voting securities.



                                                     Amount of             Currently               Total
                                                   Common Shares          Exercisable            Amount of             Total
                                                    Beneficially            Options &            Beneficial         Percentage
                                                      Owned(1)            Warrants (1)          Ownership(1)         Ownership
                                                   -------------          ------------          ------------        ----------
                                                                                                         
        DIRECTORS
        ---------
        Joseph Alaimo..........................           7,395                24,673                 32,068              *
        Peter D. Crist.........................          28,884                 2,672                 31,556              *
        Bruce Crowther.........................             645                   255                    900              *
        Maurice F. Dunne, Jr...................          45,902                 9,415                 55,317              *
        William C. Graft.......................          13,300                   340                 13,640              *
        Kathleen R. Horne......................             500                   306                    806              *
        John W. Leopold........................         188,442                    --                188,442          2.19%
        John S. Lillard........................         119,760                 4,507                124,267          1.44%
        James B. McCarthy......................          13,840                 2,551                 16,391              *
        Marguerite Savard McKenna..............          15,074                 4,156                 19,230              *
        Albin F. Moschner......................           8,869                    --                  8,869              *
        Dorothy M. Mueller.....................             150                    --                    150              *
        Thomas J. Neis.........................             617                    --                    617              *
        Hollis W. Rademacher...................          51,007                10,136                 61,143              *
        J. Christopher Reyes...................         163,940                 4,005                167,945          1.95%
        Peter P. Rusin.........................           1,000                   187                  1,187              *
        John N. Schaper........................           1,207                 1,208                  2,415              *
        John J. Schornack......................           9,500                 3,804                 13,304              *
        Ingrid Stafford........................           2,992                 3,887                  6,879              *
        Jane R. Stein..........................              --                 1,208                  1,208              *
        Katharine V. Sylvester.................           3,120                 2,793                  5,913              *
        Edward J. Wehmer**.....................         147,000               177,076                324,076          3.69%
        Larry V. Wright(2).....................         358,865                28,492                387,357          4.48%

        DIRECTOR NOMINEES NOT CURRENTLY SERVING
        ---------------------------------------
        Bert A. Getz, Jr.......................             500                 1,208                  1,708              *
        Christopher J. Perry(3)................         324,173                    --                324,173          3.76%

        OTHER NAMED EXECUTIVE OFFICERS
        ------------------------------
        Lloyd M. Bowden........................          15,641                28,803                 44,444              *
        David A. Dykstra.......................          19,074                60,611                 79,685              *
        Robert F. Key..........................          25,651                40,700                 66,351              *
        Barbara A. Kilian .....................             200                    --                    200              *

        TOTAL EXISTING DIRECTORS, & EXECUTIVE
        -------------------------------------
            OFFICERS (28 PERSONS)  ............       1,244,375               413,085              1,657,460         18.35%
            ---------------------

        TOTAL CONTINUING DIRECTORS, NOMINEES
        ------------------------------------
            & EXECUTIVE OFFICERS (28 PERSONS)         1,523,146               403,670              1,926,816         21.36%
            ---------------------------------

- ------------------------------------------

<FN>
*       Less than 1%
**      Denotes person serving as Director and as an executive officer.
(1)     Beneficial  ownership and  percentages are calculated in accordance with
        SEC Rule 13d-3 promulgated under the Securities Exchange Act of 1934.

                                     - 9 -

(2)     Includes  (i) 21,433  shares and 4,667 shares  subject to Warrants  held
        directly by Larry Wright;  (ii) 3,000 shares held by Milbank Corporation
        ("Milbank")  of  which  Mr.  Wright  is an  officer,  director  and sole
        shareholder and with respect to which shares he exercises  shared voting
        and  investment  power;  (iii) 8,721 shares and 1,092 shares  subject to
        Warrants  held by an  employee  retirement  plan of Milbank of which Mr.
        Wright is a trustee  with  shared  voting  and  investment  power;  (iv)
        320,884  shares and 22,733  shares  subject to Warrants held in Deerpath
        Investments LLP, a limited  partnership  ("Deerpath"),  to which Milbank
        serves as  investment  advisor  and with  respect  to which  Mr.  Wright
        exercises shared voting and investment  power; and (v) 4,827 shares held
        in certain  family trusts of another  officer of Milbank with respect to
        which Mr. Wright acts as co-trustee  and exercises  shared voting power.
(3)     Includes (i) 30,055  shares held directly by Mr. Perry and his immediate
        family;  and (ii)  294,118  shares held by CIVC Fund,  L.P. of which Mr.
        Perry is a Managing  Member of the general  partner and with  respect to
        which shares he exercises shared voting and investment power.
</FN>


                             EXECUTIVE COMPENSATION

SUMMARY COMPENSATION TABLE

          The following table  summarizes the  compensation  paid by the Company
and its subsidiaries to those persons serving as Chief Executive Officer and the
four other most highly  compensated  executive  officers  (the "Named  Executive
Officers")  during 2000,  1999 and 1998. In determining  the level of bonuses in
1999,  the  Company's  Compensation  Committee  evaluated  the  bonus  amount in
conjunction with stock incentive awards. See further discussion of the Company's
overall  compensation  philosophy  in  the  "Compensation  Committee  Report  on
Executive Compensation" contained later in this Proxy Statement.



                                                            SUMMARY COMPENSATION TABLE
                               -------------------------------------------------------------------------------------
                                                                                         LONG-TERM
                                                                                       COMPENSATION
                                                    ANNUAL COMPENSATION                    AWARDS
                                                ------------------------------------   -------------

                                                                       OTHER ANNUAL    SECURITIES      ALL OTHER
                                                                          COMPEN-      UNDERLYING       COMPEN-
           NAME AND                              SALARY        BONUS     SATION(1)      OPTIONS/       SATION(2)
      PRINCIPAL POSITION            YEAR            ($)         ($)          ($)         SARS (#)           ($)
      ------------------            ----           -----       -----        -----        --------          -----

                                                                                       
Edward J. Wehmer                     2000       470,000         50,000      8,499              --        84,900
President & Chief                    1999       450,000         11,000      9,446          14,667           900
   Executive Officer                 1998       450,000         45,000      9,895              --         1,200

David A. Dykstra                     2000       250,000         50,000      7,484              --           600
Executive Vice President &           1999       225,000          8,000      6,911          10,667            --
    Chief Financial Officer          1998       206,000         30,000      6,517              --            --

Robert F. Key                        2000       200,000         20,000      5,558              --           720
Executive Vice President &           1999       190,000          4,500      6,003           5,600           720
   Director of Marketing             1998       180,000         18,000      6,482              --           469

Lloyd M. Bowden                      2000       160,000         19,500      2,405              --           450
Executive Vice President &           1999       150,500          4,000      2,222           5,333           450
   Director of Technology            1998       140,500         18,000      2,523              --           332

Barbara A. Kilian                    2000(3)     35,000         19,000      1,437           7,500            --
Senior Vice President - Finance

- --------------------------------------------
<FN>
(1)       Other annual compensation represents the value of certain perquisites,
          including the use of a Company car and/or the payment of club dues.

(2)       Represents the aggregate life insurance  premium paid on behalf of the
          named  executive  officer by the Company  and/or  other  miscellaneous
          benefits.  For Mr.  Wehmer,  the amount  includes  $84,000  related to
          interest  forgiven in early 2001 for interest  accrued in 2000 related
          to a term  loan  agreement.  See  "Transactions  with  Management  and
          Others".

(3)       Reflects  compensation  for partial  year service  during  executive's
          initial year of employment with the Company.  The 2000 base salary for
          Ms.  Kilian was  $140,000.  The 2000 bonus  amount  includes a signing
          bonus of $15,000.
</FN>



                                     - 10 -

OPTION/SAR GRANTS IN LAST FISCAL YEAR

         The table on the following page summarizes for each Named Executive
Officer certain information about options which were granted by the Company
under the 1997 Stock Incentive Plan with respect to the executives' service in
2000. All options were granted at per share exercise prices equal to the fair
market value per share on the date of grant.



                      OPTION/SAR GRANTS IN LAST FISCAL YEAR

                                             % OF TOTAL                                  POTENTIAL REALIZABLE
                              NUMBER OF       OPTIONS/                                     VALUE AT ASSUMED
                                SHARES          SARS                                        ANNUAL RATES OF
                              UNDERLYING     GRANTED TO    EXERCISE                           STOCK PRICE
                               OPTIONS/       EMPLOYEES     OR BASE                          APPRECIATION
                                 SARS         IN FISCAL      PRICE     EXPIRATION        FOR OPTION/SAR TERM
           NAME                 GRANTED           YEAR      ($/SH)          DATE                5%       10%
           ----                 --------          -----     -------         -----          --------  --------


                                                                                      
Edward J. Wehmer ..........           --             --         --             --             --             --
David A. Dykstra ..........           --             --         --             --             --             --
Robert F. Key .............           --             --         --             --             --             --
Lloyd M. Bowden ...........           --             --         --             --             --             --
Barbara A. Kilian (1)......        7,500          5.45%     $16.88       10/02/10         79,594        201,708
- -------------------------------------------------
<FN>
(1)       Pursuant to the terms of the option  award,  the  options  vest in 20%
          annual increments beginning on October 2, 2001.
</FN>



AGGREGATED OPTION/SAR EXERCISES AND YEAR-END VALUES

     The following table summarizes for each Named Executive Officer the number
of shares of Common Stock subject to outstanding Options/SARs and the value of
such Options/SARs that were unexercised at December 31, 2000. None of the Named
Executive Officers had Option/SAR exercises during 2000.



             AGGREGATED OPTION/SAR EXERCISES IN LAST FISCAL YEAR AND FISCAL YEAR-END OPTION/SAR VALUES

                                                                     NUMBER OF
                                                               SECURITIES UNDERLYING       VALUE OF UNEXERCISED
                               SHARES                               UNEXERCISED                IN-THE-MONEY
                           ACQUIRED ON           VALUE            OPTIONS/SARS AT            OPTIONS/SARS AT
           NAME           EXERCISE (#)       REALIZED ($)      DECEMBER 31, 2000 (#)      DECEMBER 31, 2000 ($)
           ----           ------------       ------------      ---------------------      ---------------------
                                                                    EXERCISABLE/               EXERCISABLE/
                                                                  UNEXERCISABLE(1)           UNEXERCISABLE(1)
                                                                 -----------------           ----------------

                                                                                     
Edward J. Wehmer..........       --               --           153,938 /     12,000      $1,212,100 /  $      0
David A. Dykstra..........       --               --            55,571 /     10,800         171,613 /         0
Robert F. Key.............       --               --            38,700 /      6,000          88,573 /         0
Lloyd M. Bowden...........       --               --            27,203 /      4,800          57,565 /         0
Barbara A. Kilian.........       --               --                 0 /      7,500               0 /         0
- ----------------------------------------
<FN>
(1)  The numbers and amounts represent shares of Common Stock subject to
     outstanding Options/SARs granted by the Company or its predecessors that
     were unexercised as of December 31, 2000.
</FN>


                                     - 11 -

EMPLOYMENT AGREEMENTS

          In 1998,  the Company  entered into a new employment  agreements  with
Edward J. Wehmer, David A. Dykstra,  Robert F. Key, and Lloyd M. Bowden, as well
as certain other  officers of the Company and its  subsidiaries.  The employment
agreements   contain   confidentiality   agreements  and  two-year   non-compete
provisions in the event of termination of employment for any reason, and provide
for up to 24 months of severance pay at an annual rate equal to the  executive's
current base salary and prior year bonus amount in the event of (i)  termination
without cause, (ii) a material reduction in duties and  responsibilities,  (iii)
permanent  disability (as defined in the  agreement),  or (iv) reduction in base
annual  compensation  to  less  than  75% of  the  executive's  "Adjusted  Total
Compensation",  as defined in the  agreement to be the aggregate of current base
salary plus the dollar value of all perquisites  for the preceding  twelve month
period. "Adjusted Total Compensation" excludes any bonus payments paid or earned
by the executives. The severance amounts payable under the agreement are subject
to reduction  for any income  earned from other  employment  during the two-year
period  or,  in the  case of  disability,  any  long-term  disability  insurance
benefits from policies  maintained or paid for by the Company.  In addition,  in
the event of the executive's  death resulting in termination of employment,  the
executive's  beneficiaries  are  entitled  to a lump  sum  payment  equal to the
aggregate  severance pay amount,  reduced by any life  insurance  benefits under
policies paid for by the Company.  The "Adjusted Total  Compensation"  as of the
respective dates of such agreements for Messrs. Wehmer, Dykstra, Key, and Bowden
were $469,000, $214,000, $190,000 and $149,000, respectively. In addition to any
increases  in base  salaries  that  may be  agreed  to from  time to  time,  the
executives  are entitled to  participate  in any employee  insurance  and fringe
benefit  programs that may be established by the Company for its employees.  The
current  annual base salaries of Messrs.  Wehmer,  Dykstra,  Key, and Bowden are
$480,000, $275,000, $208,000 and $168,000, respectively.

          The employment  agreements  also provide for a lump sum payment in the
event the executive's  employment is terminated without cause (or constructively
terminated  due to a  material  reduction  in duties and  responsibilities  or a
reduction in Adjusted Total  Compensation  as described  above) within 12 months
following a change in control (as defined in the agreement) of the Company. Such
change in control payment shall be equal to two times the sum of the executive's
base annual  salary plus prior  year's  bonus,  subject to  reduction in certain
circumstances if the amount payable under the agreement  together with any other
amounts  payable by the Company to the  executive is deemed to result in "excess
parachute  payments"  under  Section  280G of the  Internal  Revenue  Code.  The
agreement  does not  require the amount to be scaled back to satisfy the Section
280G limit,  however,  if the  contractual  change in control  payment minus the
excise  taxes that would be payable by the  executive  would be greater than the
reduced amount.

          Pursuant to an amendment made to Mr. Wehmer's employment  agreement in
January  2000,  he is also  entitled to certain  special  bonus  payments to pay
interest on a loan made to him by the Company. See "Transactions with Management
and Others".

COMPENSATION AND NOMINATING COMMITTEE INTERLOCKS AND INSIDER PARTICIPATION

          The Committee that determines executive compensation consists entirely
of  non-employee  Directors,  although  Edward J.  Wehmer,  President  and Chief
Executive  Officer  of the  Company,  makes  recommendations  to  the  Committee
regarding  compensation of officers other than himself. Mr. Wehmer serves on the
compensation  committees of each of the Company's  subsidiaries,  including WAMC
and Tricom which are responsible for determining the  compensation of the senior
officers  of those  subsidiaries.  Joseph  Alaimo  and John W.  Leopold,  senior
officers of WAMC and Tricom, respectively, are Directors of the Company.

                                     - 12 -

COMPENSATION COMMITTEE REPORT ON EXECUTIVE COMPENSATION

          OVERALL  COMPENSATION  PHILOSOPHY:  The  Compensation  and  Nominating
Committee of the Board of Directors (the "Committee") has the  responsibility to
monitor and implement the overall executive compensation program of the Company.
The objectives of the Company's compensation policies are to enhance shareholder
value;  to create  and  sustain  high  performance;  to  attract  and  retain as
executives  individuals who can contribute  substantially to the Company's short
and long term goals;  and to align the interests of executives with those of the
shareholders  of the Company.  The  philosophy  is to provide  competitive  base
salaries which reflect  individual  levels of  responsibility  and  performance,
annual  bonuses  based upon personal  achievement  and  contributions  to annual
corporate performance,  and stock-based incentive awards. The combined result is
a  strengthening  of  the  mutuality  of  interest  in the  Company's  long-term
performance between its executive officers and the Company's shareholders.

          BASE SALARIES: Base salaries for executive officers were determined at
the time of hire by comparing  responsibilities  of the  position  with those of
other  similar   executive   officer   positions  in  the  marketplace  and  the
individual's  experience.  Annual salary adjustments have been determined giving
consideration to the Company's performance and the individual's  contribution to
that   performance.   While  there  are  no  specific   performance   weightings
established,  the salary  recommendations are based on performance criteria such
as:

     o    financial  performance of the Company with a balance  between long and
          short term growth in earnings, revenue and asset growth;
     o    role in development and implementation of long term strategic plans;
     o    responsiveness  to changes in the financial  institution  marketplace;
          and
     o    growth and diversification of the Company.

          In the  absence  of  similar  de novo bank  holding  companies,  it is
difficult to identify  appropriate peer group  comparisons for the base salaries
of the  Company's  executives.  In addition,  the  Company's  strategy is to pay
executives very  competitive  salaries in an effort to attract and retain highly
qualified,  well-experienced  individuals  which,  given  the  relatively  young
history of the Company,  currently  may be higher than those paid by  comparably
sized financial  institutions.  However, as the Company continues to mature, the
Committee believes that increases to total compensation  should  increasingly be
more heavily  weighted toward the bonus and stock incentive  components than the
base  salary  component.  This  philosophy  is  intended  to  ensure  a pay  for
performance compensation framework which is aligned with shareholder value.

          BONUSES:  Executives  may  earn  annual  cash  bonuses  based  upon  a
pay-for-performance philosophy which are determined at year-end. In recommending
bonuses,  the Committee considers the achievements of each executive officer for
that  year,  as well  as the  Company's  performance.  The  achievements  may be
quantitative or qualitative.  Qualitative factors include but are not limited to
commitment, dedication,  demonstration of the entrepreneurial spirit, creativity
and  initiative,  and  attention  to personnel  relations.  The  Committee  also
evaluates the bonus amount in conjunction with stock incentive awards, if any.

          Given the size of the Company,  the Committee  believes it is feasible
to evaluate the  different  individual  contributions  of each of the  Company's
executive  officers,  and,  as a matter of policy,  there has not been a defined
bonus plan  established.  However,  the Committee did evaluate the attainment of
certain  specific  Company and individual  objectives in  determining  the bonus
amounts  awarded  to  executives.  The  primary  objectives  were based upon net
income, deposit growth, loan growth, certain financial performance measures such
as net interest margin and net overhead ratios, and tailored personal objectives
for  each  executive.  The  Committee  used  these  measurable  objectives  as a
guideline to establish  executive  bonuses,  but the end  determination  of such
bonuses was ultimately a discretionary decision. Accordingly, the policy used by
the Board to set cash bonuses is considered subjective.  The bonuses for each of
the executive  officers  other than the President and CEO were set at the levels
recommended by management.

                                     - 13 -

          STOCK  OPTIONS:  To ensure a direct  connection  between the executive
officer  interests and the shareholders of the Company,  the Company has awarded
and intends to continue to award stock-based incentives which are longer term in
nature than the base salary and annual bonus components of overall compensation.
The  incentives  have been  primarily  in the form of stock  options  granted at
exercise  prices  at or  above  fair  market  value on the  date of  grant.  The
intention is to incentivize  employees to create shareholder value over the long
term  since the full  benefit of the  compensation  package  cannot be  realized
unless an  appreciation  in the share price  occurs  over a specified  number of
years. The Company did not award equity incentives for 1998 or 2000 to any named
executive officers other than Ms. Kilian upon the commencement of her employment
in 2000.  In 1999,  the Company  granted  non-qualified  stock options to senior
management as part of their overall  compensation  package and in lieu of larger
cash bonuses.  The equity  incentives  were  determined in the fourth quarter of
1999.  Such stock  options were granted at exercise  prices equal to fair market
value on the date of grant,  were fully  exercisable as of December 31, 1999 and
have a term of ten years.

          CHIEF  EXECUTIVE  OFFICER  COMPENSATION:  Mr.  Edward  J.  Wehmer  was
appointed Chief Executive Officer, in addition to his role as President,  in May
1998. Mr.  Wehmer's base salary for 1999 was established by the Committee at the
beginning of the year and his salary level for 2000 was increased by $20,000, or
4.4%,  to  $470,000.  The  Committee  determined  that the base salary level was
appropriate and that Mr. Wehmer's  compensation  level should be influenced more
heavily by incentive-based compensation than by base salary increases.

          The  2000  bonus  amount  awarded  to  Mr.  Wehmer  was  based  on the
recognition  by the members of the Committee of his dedication to the success of
the Company as exhibited through long-term vision,  entrepreneurial spirit, hard
work ethic, knowledge of the financial services industry, strong operational and
financial  control  knowledge and his ability to recruit a management  team with
similar  characteristics.  In addition,  the Committee  considered the following
corporate achievements:

      (1)   The  continued  growth of the  Company as one of the largest de novo
            banking operations in the Midwest area.

      (2)   The increase in the profitability of the Company to $11.2 million in
            2000 from $9.4 million in 1999.

      (3)   The growth of the Company's  assets,  deposits and loans during 2000
            of $423 million,  $363 million and $280 million,  respectively.  The
            increases  show  growth in these  categories  in the range of 21% to
            26%.

      (4)   The Company's net revenues increased 38% in 2000 over the prior year
            level.

      (5)   The  successful  opening  of  four  additional  banking  facilities,
            including the Company's seventh  separately  chartered de novo bank.
            These additional  facilities  expanded the geographical reach of the
            organization  and enlarged  the platform  utilized by the Company to
            effectuate continued growth.

      (6)   The successful  completion of a trust preferred  securities offering
            during the year that  provided for  continued  growth of the Company
            while maintaining an efficient capital structure.

      (7)   The  reduction  in  the  net  overhead   ratio   (exclusive  of  the
            non-recurring  charge in 2000) to 1.90% in 2000  from  2.00% in 1999
            despite the opening of the four  additional  banking  facilities  in
            2000.

      (8)   The  improvement  in the Company's  net interest  margin to 3.66% in
            2000 from 3.54% in 1999 and his  commitment  to improving the margin
            through the  effective  execution  of the  Company's  strategy to be
            "asset driven" through a diverse set of earning asset portfolios.

      (9)   The successful  integration  of the 1999  acquisition of the Tricom,
            Inc. business into the Wintrust family.

      (10)  The continuing  stability in the manageable level of  non-performing
            assets.

                                     - 14 -

         SECTION 162(M): The Compensation and Nominating Committee does not
believe that the provisions of Section 162(m) of the Internal Revenue Code of
1986, as amended (the "Code"), relating to the deductibility of compensation
paid to the Named Executive Officers, will limit the deductibility of the
executive compensation currently expected to be paid by the Company. The
Compensation and Nominating Committee will continue to evaluate the impact of
such provisions and to consider compensation policies and programs appropriate
for an organization of the Company's size and history in an effort to address
the potential impact, if any, in the future.

         CONCLUSION: The Compensation Committee believes the executive officers'
individual compensation packages are designed in a manner which is consistent
with the Company's overall compensation philosophy.

        PETER D. CRIST (Chairman of the Committee)      ALBIN F. MOSCHNER
        JOHN S. LILLARD                                 THOMAS J. NEIS
        JAMES B MCCARTHY                                HOLLIS W. RADEMACHER
        MARGUERITE SAVARD MCKENNA                       J. CHRISTOPHER REYES

PERFORMANCE GRAPH

         The following performance graph compares the percentage change in the
Company's cumulative shareholder return on common stock compared with the
cumulative total return on composites of (1) all Nasdaq National Market stocks
for United States companies (broad market index) and (2) all Nasdaq National
Market bank stocks (peer group index). Cumulative total return is computed by
dividing the sum of the cumulative amount of dividends for the measurement
period and the difference between the Company's share price at the end and the
beginning of the measurement period by the share price at the beginning of the
measurement period. The Nasdaq National Market for United States companies index
comprises all domestic common shares traded on the Nasdaq National Market and
the Nasdaq Small-Cap Market. The Nasdaq National Market bank stocks index
comprises all banks traded on the Nasdaq National Market and the Nasdaq
Small-Cap Market.



                              1/24/97   6/30/97    12/31/97   6/30/1998 12/31/1998  6/30/1999 12/31/1999 6/30/2000 12/31/2000
- ------------------------------------------------------------------------------------------------------------------------------
                                                                                            
Wintrust Financial Corporation     100     112.50     113.33     131.67    130.83      117.50     101.67    103.25     106.91
Nasdaq - Total US                  100     104.49     114.36     137.54    161.28      197.86     299.71    292.45     180.33
Nasdaq - Bank Index                100     118.50     158.60     164.36    157.58      162.35     151.48    133.17     172.97
- ------------------------------------------------------------------------------------------------------------------------------


          The Company  became  subject to reporting its  cumulative  shareholder
returns as of January 24, 1997 when the Company  became a  registrant  under the
Securities Exchange Act of 1934. Accordingly,  the graph presents the cumulative
shareholder  returns from January 24, 1997 through December 31, 2000 based on an
assumed investment of $100 on January 24, 1997.

                                     - 15 -

REPORT OF THE AUDIT COMMITTEE

          The report of the Audit Committee shall not be deemed  incorporated by
reference  by any  general  statement  incorporating  by  reference  this  Proxy
Statement  into  any  other  filing  under  the  Securities  Act of  1933 or the
Securities  Exchange  Act  of  1934  except  to  the  extent  that  the  Company
specifically incorporates this information by reference, and shall not otherwise
be deemed filed under such acts.

          The Audit Committee oversees the Company's financial reporting process
on behalf of the Board of Directors.  Management has the primary  responsibility
for the financial  statements and the reporting process including the systems of
internal  controls.  In  fulfilling  its oversight  responsibilities,  the Audit
Committee reviewed and discussed the audited financial  statements in the Annual
Report with  management  including a  discussion  of the  quality,  not just the
acceptability,  of the accounting principles,  the reasonableness of significant
judgments, and the clarity of disclosures in the financial statements.

          The Committee  reviewed and discussed with the  independent  auditors,
who are responsible for expressing an opinion on the conformity of those audited
financial  statements  with  generally  accepted  accounting  principles,  their
judgments as to the quality,  and not just the  acceptability,  of the Company's
accounting  principles  and such other  matters as are  required to be discussed
with the  Audit  Committee  under  generally  accepted  auditing  standards.  In
addition,  the Audit Committee has discussed with the  independent  auditors the
auditors'  independence from management and the Company including the matters in
the  written  disclosures  required  by the  Independence  Standards  Board  and
considered  the   compatibility   of  non-audit   services  with  the  auditors'
independence.

          The Audit Committee discussed with the Company's  independent auditors
the  overall  scope  and  plan  for the  audit.  The  Committee  meets  with the
independent  auditors,  with and  without  management  present,  to discuss  the
results  of their  examination,  their  evaluations  of the  Company's  internal
controls and the overall quality of the Company's financial reporting.

          In  reliance on the reviews  and  discussions  referred to above,  the
Audit  Committee  recommended  to the  Board of  Directors  (and the  Board  has
approved) that the audited financial statements be included in the Annual Report
on Form 10-K for the year ended December 31, 2000 for filing with the Securities
and Exchange  Commission.  The Audit  Committee and the Board have also approved
the  selection of Ernst and Young LLP as the Company's  independent  auditor for
2001.

        JOHN J. SCHORNACK  (Chairman of the Committee)  WILLIAM C. GRAFT
        BRUCE K. CROWTHER                               JANE R. STEIN
        MAURICE F. DUNNE, JR.                           KATHARINE V. SYLVESTER

TRANSACTIONS WITH MANAGEMENT AND OTHERS

          Some of the  executive  officers and Directors of the Company are, and
have been during the  preceding  year,  customers  of the Bank,  and some of the
officers and  Directors  of the Company are direct or indirect  owners of 10% or
more of the stock of corporations which are, or have been in the past, customers
of the Bank.  As such  customers,  they have had  transactions  in the  ordinary
course of business of the Bank, including borrowings,  all of which transactions
are or were on  substantially  the same  terms  (including  interest  rates  and
collateral on loans) as those prevailing at the time for comparable transactions
with nonaffiliated persons. In the opinion of management of the Company, none of
the  transactions  involved  more  than the  normal  risk of  collectibility  or
presented any other  unfavorable  features.  At December 31, 2000, the Banks had
$30.5 million in loans outstanding to certain  Directors and executive  officers
of the  Company  and  certain  executive  officers  of the Banks,  which  amount
represented 29.8% of total shareholders' equity as of that date.

                                     - 16 -

          During the organization of the Company's predecessor companies, Edward
J. Wehmer,  President and Chief Executive  Officer,  purchased various shares of
Company stock using  borrowed  funds.  Mr. Wehmer  maintained  the loan for such
purchases at an  unaffiliated  bank. In January 2000, the Company entered into a
term note agreement with Mr. Wehmer and his spouse and loaned them $1,200,000 in
order for Mr. Wehmer to retire the debt at the unaffiliated bank. The note has a
maturity  date of January 31,  2005 and bears  interest at an annual rate of 7%,
compounded annually.  Interest is payable annually. The note is full recourse to
the borrowers and is also secured by a pledge of 100,000 shares of the Company's
common stock.  If Mr. Wehmer's  employment  with the Company  terminates for any
reason, the Company has the right to immediately  accelerate the maturity of the
Note if the  principal  and  accrued  interest  on the  Note is not paid in full
within 90 days of the date of termination.  The Company also agreed to amend Mr.
Wehmer's  employment  agreement to provide for a special annual bonus to be paid
to Mr. Wehmer in the amount equal to the accrued  interest on the note,  payable
one  business  day prior to each  anniversary  of the date of the  Note.  If Mr.
Wehmer is terminated  without  cause,  or if he resigns for any reason within 18
months  following  a change of  control,  he is  entitled  to  receive a special
severance payment equal to accumulated interest through his termination date.

SECTION 16(A) BENEFICIAL OWNERSHIP REPORTING COMPLIANCE

          Section  16(a) of the  Securities  Exchange  Act of 1934  requires the
Company's  Directors  and  executive  officers to file  reports of holdings  and
transactions in the Company's  Common Stock with the the Securities and Exchange
Commission.  Based upon its review of copies of such  reports  and of trading in
the Company's  common stock, the Company is not aware of any late filings during
2000 with the following exceptions: (1) Director Neis should have filed a Form 4
by September 10, 2000 to report purchases  totaling 517 shares in August,  2000.
Mr. Neis'  reported such  purchases in February,  2001;  and (2) Director  Graft
reported an April 25, 2000  purchase of 1,000  shares in early June,  2000.  Mr.
Graft's purchase should have been reported by May 10, 2000.


                                 PROPOSAL NO. 2

                        SHAREHOLDER APPROVAL OF DIRECTORS
                           DEFERRED FEE AND STOCK PLAN

          Introduction.  At the  Annual  Meeting,  there  will  be  submitted  a
proposal to approve the Wintrust  Financial  Corporation  Directors Deferred Fee
and Stock Plan (the  "Plan").  The Board of Directors  adopted the Plan on April
26,  2001,  subject  to  shareholder  approval.   The  Plan  is  effective  upon
shareholder approval.

          The following description of the Plan sets forth the material terms of
the Plan; however,  it is a summary,  and does not purport to be complete and is
qualified in its entirety by reference to the  provisions of the Plan. A copy of
the Plan is attached hereto as Appendix B.

          Purpose.  The purpose of the Plan is to allow directors of the Company
and its  subsidiaries  to choose  payment of  directors  fees in either  cash or
Common  Stock of the Company and to  facilitate  deferral of receipt of fees for
income tax  purposes,  both in cash or Common  Stock.  In addition,  the Plan is
designed to encourage stock  ownership by directors by facilitating  the receipt
of Common Stock in lieu of directors  fees.  The Plan will supersede and replace
cash deferred  compensation  plans  currently  maintained by the Company and its
subsidiaries for directors.

          Participants.  The  Plan  is  open  to all  members  of the  Board  of
Directors   of  the  Company  and  its   subsidiaries.   Currently,   there  are
approximately 84 persons who are eligible to participate in the Plan.

          Authorization.  The Company has reserved  150,000  shares for issuance
under the Plan. The shares may be newly issued shares or treasury shares.

                                     - 17 -

          Administration.  The Board of Directors  of the Company has  delegated
the  administration  of the Plan to the Company's  Chief Financial  Officer.  As
administrator,  the Chief Financial Officer is authorized to interpret the Plan,
to  prescribe  and  modify  its  rules  and  procedures,  and to make all  other
determinations  necessary for its administration,  including employing agents to
assist in plan administration.

          Compensation  Elections.  Eligible  directors  who  do  not  elect  to
participate  in  the  Plan  will  continue  to  receive  cash  compensation  for
attendance at Board of Directors or committee  meetings.  Eligible directors who
elect  to  participate  in  the  Plan  must  choose  from  the  following  three
compensation options:


          1.   Fees Paid in  Stock.  If so  elected  by the  director,  the fees
          payable  to such  director  will be paid in  shares  of the  Company's
          Common  Stock.  The number of shares of Common Stock to be issued will
          be determined by dividing the fees earned during a calendar quarter by
          the fair market  value (as defined in the Plan) of the Common Stock on
          the last trading day of the  preceding  quarter.  The shares of Common
          Stock to be paid will be issued once a year on or about  January 15th,
          or more frequently if so determined by the administrator. Once issued,
          the shares will be entitled to full dividend and voting rights.

          2.   Deferral of Common Stock.  If a director  elects to defer receipt
          of the Common Stock,  the Company will maintain on its books  deferred
          stock units  ("Units")  representing  an obligation to issue shares of
          Common Stock to the  director.  The number of Units  credited  will be
          equal to the number of shares  that would have been issued but for the
          deferral election.

               Additional  Units will be credited at the time dividends are paid
          on the Common  Stock.  The number of  additional  Units to be credited
          each quarter will be computed by dividing the amount of the  dividends
          that would have been received if the Units were outstanding  shares by
          the fair market  value of the Common  Stock on the last trading day of
          the preceding quarter.

               Because  Units  represent a right to receive  Common Stock in the
          future,  and not actual shares,  there are no voting rights associated
          with  them.   In  the  event  of  an   adjustment   in  the  Company's
          capitalization  or a merger or other  transaction  that  results  in a
          conversion of the Common Stock, corresponding adjustments will be made
          to the Units. The director will be a general unsecured creditor of the
          Company for purposes of the Common Stock to be paid in the future.

               The  shares  of Common  Stock  represented  by the Units  will be
          issued on or about January 15th in the year  specified by the director
          in  his  participation  agreement  or in  annual  installments  over a
          specified period not to exceed ten years.


          3.   Deferral  of Cash.  If a  director  elects  to defer  receipt  of
          directors  fees in cash,  the  Company  will  maintain  on its books a
          deferred  compensation  account  representing an obligation to pay the
          director cash in the future. The amount of the director's fees will be
          credited to this account as of the date such fees  otherwise  would be
          payable to the director.

               All  amounts  credited  to  a  director's  deferred  compensation
          account  will accrue  interest  based on to the 91-day  Treasury  Bill
          discount rate, adjusted  quarterly,  until paid. Accrued interest will
          be credited at the end of each calendar quarter.

               No funds will  actually be set aside for payment to the  director
          and the director will be a general  unsecured  creditor of the Company
          for purposes of the amount in his deferred compensation account.

                                     - 18 -

               The amount in the deferred  compensation  account will be paid to
          the  director on or about  January  15th in the year  specified by the
          director in his participation agreement or in annual installments over
          a specified period not to exceed ten years.

          Adjustments.  In the  event  there is any  change  in the  outstanding
shares  of  Common   Stock  as  a  result  of  any  stock   dividend  or  split,
recapitalization,  merger, consolidation combination,  share exchange or similar
corporate  change,  the number of shares of Common Stock  available for issuance
under the Plan will be adjusted accordingly.

          Amendments  and  Termination.  The Board of Directors  may at any time
amend or terminate the Plan to the extent permitted by law;  provided,  however,
that no such action may  adversely  affect a  director's  rights with respect to
fees already earned but not yet paid in cash,  common stock or units without the
director's written consent.

          Federal Income Tax Considerations. The following discussion summarizes
the federal income tax  consequences to participants in the Plan. The discussion
is based upon  interpretations  of the Code in effect as of January 1, 2001, and
the regulations promulgated thereunder as of such date.

          Taxes  Related to the Receipt of Stock.  The fair market  value of the
shares of Common Stock  received  under the Plan is taxed as ordinary  income in
the year received.  If a director elects to receive  compensation in the form of
Common Stock on a current basis,  he or she will be taxed currently on the value
of the shares on the date issued to the director, as if such value had been paid
in cash. If a director  elects to defer  receipt of the Common Stock,  he or she
will not be taxed currently, but instead will be taxed at the time in the future
when the shares of Common Stock are actually issued.  At that time, the director
will recognize ordinary income equal to the value of the shares determined as of
the future date of  issuance.  The Company  will be entitled to a tax  deduction
equal to the amount of ordinary income recognized by the director at that time.

          Taxes Related to the Deferral of Cash.  Cash  received  under the Plan
will be  taxed  as  ordinary  income  in the year  received.  Accordingly,  if a
director  elects to defer receipt of fees to be paid in cash, he or she will not
be  taxed  currently,  but  will be taxed in the  future  on the  director  fees
deferred and the accrued interest when the cash is actually  received.  The cash
will be taxed as  ordinary  income and the  Company  will be  entitled  to a tax
deduction equal to the amount of ordinary income recognized.

          Plan  Benefits.  For the year ended December 31, 2000, the Company and
its  subsidiaries  expensed a total of  approximately  $620,000 for non-employee
directors  attendance at Board of Directors and committee meetings.  If the Plan
were in  existence  during  2000,  all of such  directors  could have elected to
receive their compensation  pursuant to the terms of the Plan. Directors who are
employees  of the  Company or its  subsidiaries  are not  currently  eligible to
receive director fees and therefore are not currently eligible to participate in
the Plan.

          THE BOARD OF DIRECTORS  RECOMMENDS  SHAREHOLDERS  VOTE FOR APPROVAL OF
THE WINTRUST FINANCIAL CORPORATION DIRECTORS DEFERRED FEE AND STOCK PLAN.

                              INDEPENDENT AUDITORS

          Ernst and Young LLP served as the  Company's  independent  auditor for
2000. Ernst and Young's fees for the last fiscal year's audit were: Annual audit
of  $181,500,  audit  related  services  of $133,300  and all other  services of
$141,750.  Audit related  services  generally  include fees for the benefit plan
audits,  Securities and Exchange Commission registration statements and internal
audit  services.  All other  services  generally  include fees for review of tax
returns  and other tax  services.  Ernst and  Young LLP  provided  no  financial
information systems or design and implementation services during 2000. The audit
committee  has  considered  whether the  provision of non-audit  services by the
Company's auditor is compatible with maintaining auditor independence.

                                     - 19 -

          One or more  representatives of Ernst and Young LLP will be present at
the meeting and will have the  opportunity to make a statement if they desire to
do so and will be available at the meeting to respond to appropriate questions.


                              SHAREHOLDER PROPOSALS

          Shareholders' proposals intended to be presented at the Company's 2002
Annual Meeting of  Shareholders  must be received in writing by the Secretary of
the Company no later than  December  28,  2001,  in order to be  considered  for
inclusion in the proxy material for that meeting.  Any such  proposals  shall be
subject to the  requirements  of the proxy rules  adopted  under the  Securities
Exchange  Act of 1934  (the  "Exchange  Act").  Furthermore,  in  order  for any
shareholder  to properly  propose any  business  for  consideration  at the 2001
Annual  Meeting,  including  the  nomination  of any  person for  election  as a
director,  or any other matter  raised other than  pursuant to Rule 14a-8 of the
proxy rules adopted under the Exchange Act, written notice of the  shareholder's
intention to make such  proposal  must be furnished to the Company in accordance
with the By-laws.  Under the  provisions  of the By-laws,  the deadline for such
notice is March 24, 2002.


                                 OTHER BUSINESS

          The  Company is  unaware  of any other  matter to be acted upon at the
annual  meeting for  shareholder  vote.  In case of any matter  properly  coming
before the meeting for shareholder vote, unless discretionary authority has been
denied the proxy holders named in the proxy  accompanying  this statement  shall
vote them in accordance with their best judgment.


                                              BY ORDER OF THE BOARD OF DIRECTORS



                                              /s/ David A. Dykstra
                                              David A. Dykstra
                                              Secretary


                                     - 20 -

                                   APPENDIX A
                         WINTRUST FINANCIAL CORPORATION

                    Audit Committee of the Board of Directors

                                COMMITTEE CHARTER
                   [(approved by the Board on April 18, 2000)]


COMPOSITION:        The  Audit  Committee  shall be  comprised  of not less than
- ------------
                    three  members  of the  Board  as may  be  appointed  to the
                    Committee from time to time by a majority of the Board, each
                    of whom shall not be an officer or  employee  of the Company
                    or its subsidiaries,  shall not have any relationship which,
                    in the  opinion  of the  Board,  would  interfere  with  the
                    exercise  of  independent   judgment  in  carrying  out  the
                    responsibilities of a director,  and shall otherwise satisfy
                    the applicable  membership  requirements  under the rules of
                    the National  Association  of Securities  Dealers,  Inc. All
                    members  shall be  financially  literate  and at  least  one
                    member shall have accounting or related financial management
                    experience.  The Chairman of the Committee  shall be elected
                    by  the  Board  out  of  those  members   appointed  to  the
                    Committee.  The  Chairman  shall  preside at meetings of the
                    Committee.

COMMITTEE ROLE AND
SCOPE OF AUTHORITY: The Audit Committee shall provide assistance to the Board in
- -------------------
                    fulfilling   their   oversight    responsibility    to   the
                    shareholders,   potential   shareholders,   the   investment
                    community,  and others  relating to the  Company"  financial
                    statements and the financial  reporting  process  (including
                    the establishment and adequacy of appropriate reserves), the
                    systems of internal accounting and financial  controls,  the
                    internal audit function, the annual independent audit of the
                    Company's  financial  statements,  and legal  compliance and
                    ethics programs as established by management and the Board.

                    The  primary  responsibility  of the Audit  Committee  is to
                    oversee the Company's  financial reporting process on behalf
                    of the Board and report the results of their  activities  to
                    the Board.  Management  is  responsible  for  preparing  the
                    Company's financial statements, and the independent auditors
                    are responsible for auditing those financial statements.

                    The Committee shall have a clear  understanding with Company
                    management and the independent auditors that the independent
                    auditors  are  ultimately   accountable  to  the  Board  and
                    Committee as representatives of the Company's shareholders.



                    The duties of the Audit Committee shall include (in addition
                    to any other specific responsibilities expressly assigned to
                    the Committee by resolution of the Board) the following:

                    1.   the ultimate authority and  responsibility,  along with
                         the Board, to select,  evaluate and, where appropriate,
                         replace  the  independent  auditors.   The  review  and
                         recommendation   to  the  Board  of  the  selection  of
                         independent auditors shall be done on an annual basis;

                    2.   discuss   with   the    independent    auditors   their
                         independence  from  management  and the Company and the
                         matters included in the written disclosures required by
                         the Independence Standards Board;

                    3.   meet  with  the  independent   auditors  and  financial
                         management  of the  Company  to review the scope of the
                         proposed  audit for the current year, the related audit
                         fees and the audit  procedures  to be utilized,  and at
                         the conclusion  thereof,  review such audit,  including
                         any  comments  or  recommendations  of the  independent
                         auditors;

                    4.   review with the  independent  auditors,  the  Company's
                         internal  auditor (if  appointed),  and  financial  and
                         accounting personnel, the adequacy and effectiveness of
                         the  accounting  and financial  controls of the Company
                         including  the  Company's  system to monitor and manage
                         business   risk  and  legal  and   ethical   compliance
                         programs,   and  elicit  any  recommendations  for  the
                         improvement  of such  internal  control  procedures  or
                         particular areas where new or more detailed controls or
                         procedures are desirable. Particular emphasis should be
                         given to the  adequacy  of such  internal  controls  to
                         expose any payments,  transactions,  or procedures that
                         might be deemed illegal or otherwise improper;

                    5.   periodically   review  Company  policy   statements  to
                         determine adherence to an appropriate corporate code of
                         conduct;

                    6.   review  the  internal  audit  function  of the  Company
                         including  the   independence   and  authority  of  its
                         reporting obligations, the proposed audit plans for the
                         coming year,  and the  coordination  of such plans with
                         the independent auditors;

                                     - 2 -

                    7.   receive  prior to each  meeting,  a summary of findings
                         from completed internal audits and a progress report on
                         the proposed internal audit plan, with explanations for
                         any deviations from the original plan;

                    8.   review the interim financial statements with management
                         and the independent auditors prior to the filing of the
                         Company's Quarterly Report on Form 10-Q and discuss the
                         results of the  quarterly  review and any other matters
                         required to be communicated by the independent auditors
                         under  generally  accepted  auditing   standards.   The
                         Chairman may  represent  the entire  Committee  for the
                         purposes of this timely review;

                    9.   review the  financial  statements to be included in the
                         Company's  Annual  Report on Form 10-K with  management
                         and the  independent  auditors  including a  discussion
                         with the  independent  auditors about the quality,  not
                         just  acceptability,   of  accounting  principles,  the
                         reasonableness of significant judgments,  the degree of
                         aggressiveness  or  conservatism,  the  clarity  of the
                         disclosures  in  the  financial  statements,   and  the
                         results  of the  annual  audit  and any  other  matters
                         required  to be  communicated  to the  Committee  under
                         generally accepted auditing standards;

                    10.  provide  sufficient  opportunity  for the  internal and
                         independent  auditors  to meet with the  members of the
                         Committee without members of management  present (items
                         to  be   discussed   are  the   independent   auditors'
                         evaluation of the Company's financial,  accounting, and
                         auditing personnel, and the cooperation the independent
                         auditors received during the course of the audit);

                    11.  review  accounting  and financial  human  resources and
                         succession  planning  related to those functions within
                         the Company; and

                    12.  empowered  to  investigate  any  matter  brought to its
                         attention  within  the  scope of its  duties  with full
                         access  to  all  books,  records,  facilities,  Company
                         personnel and independent  counsel or other experts for
                         this purpose if, in its judgment, that is appropriate.

                                     - 3 -

                    In  carrying  out  its  duties  and  responsibilities,   the
                    Committee shall maintain free and open communication between
                    the directors,  independent auditors, internal auditors, and
                    management of the Company.

FORMAL REPORTING:   Beginning  with the 2001 Annual Proxy  Statement,  the Audit
- -----------------
                    Committee must annually include a report therein that states
                    whether the  Committee  has: 1) reviewed the annual  audited
                    financial statements with management;  2) discussed with the
                    independent  auditors the matters required by SAS No. 61; 3)
                    received from the independent  auditors the required written
                    communication  and  discussed  with them their  independence
                    and,  based  on  the  above  reviews  and  discussions,   4)
                    recommended   to  the  Board  that  the  audited   financial
                    statements be included in the Company's Form 10-K for filing
                    with the  Securities  and  Exchange  Commission.  The report
                    shall  also state that it is  governed  by a formal  written
                    charter and must disclose if the Committee has determined to
                    allow a non-independent  director to serve on the Committee.
                    Once every three years, beginning with the 2001 Annual Proxy
                    Statement,  the  Committee  must also  include a copy of its
                    charter.

MANNER OF ACTING:   A majority of the members of the Audit Committee present (in
- -----------------
                    person or by  telephone)  at any  meeting  of the  Committee
                    shall  constitute a quorum and approval by a majority of the
                    quorum is necessary for Committee  action.  Minutes shall be
                    recorded of each meeting held. When appropriate,  action may
                    be taken by  written  consent  in lieu of a  meeting  of the
                    Committee.

REPORTS:            The Chairman of the Audit  Committee (or in his absence such
- --------
                    other  Committee  member as the  Committee may select) shall
                    report on behalf of the  Committee to the full Board at each
                    regularly  scheduled  meeting  thereof  with  respect to any
                    action  taken  by  the  Committee  if  any  meetings  of the
                    Committee have been held (or action  otherwise  taken) since
                    the date of the previous Board meeting.  In lieu of any such
                    report,  the  minutes of  meetings  held or other  record of
                    action taken may be submitted to the Board of Directors  for
                    review.

REVIEW OF CHARTER:  The  Audit  Committee,  on at least an annual  basis,  shall
- ------------------
                    review and  reassess  its  charter and  subsequently  obtain
                    approval of its charter from the Board of Directors.

                                     - 4 -



                                   APPENDIX B




                         WINTRUST FINANCIAL CORPORATION




                      DIRECTORS DEFERRED FEE AND STOCK PLAN

                                    * * * * *



                                TABLE OF CONTENTS

                                                                            Page

1.       Establishment; Purpose................................................1

2.       Participation.........................................................1

3.       Election to Participate...............................................1

4.       Cash Deferral Election................................................1

5.       Fees Paid in Stock....................................................2

6.       Deferred Stock Units..................................................2

7.       Available Shares......................................................3

8.       Shares................................................................3

9.       Treatment of Prior Deferred Compensation Accounts.....................3

10.      Securities Law Compliance.............................................3

11.      Adjustment in Capitalization..........................................3

12.      Nonassignment.........................................................3

13.      Designation of Beneficiary............................................3

14.      Administration........................................................4

15.      Federal Tax Withholding...............................................4

16.      Amendment.............................................................4

17.      Governing Law.........................................................4


                                     - i -

                         WINTRUST FINANCIAL CORPORATION
                      DIRECTORS DEFERRED FEE AND STOCK PLAN


1.        ESTABLISHMENT; PURPOSE. Wintrust Financial Corporation (the "Company")
          establishes this Wintrust Financial Corporation Directors Deferred Fee
          and Stock Plan (the  "Plan"),  for the benefit of the directors of the
          Company  and  the  directors  of  the  Company's  subsidiaries,  to be
          administered  by the  Chief  Financial  Officer  of the  Company  (the
          "Administrator").  The  purpose  of the  Plan  is to  provide  a means
          whereby  directors of the Company and its  subsidiaries  may defer, to
          some future  date,  the fees payable to the director for services as a
          director,  as well as to provide an  incentive  to such  directors  to
          remain as  directors,  increase  their  efforts for the success of the
          Company,  and encourage them to own additional  shares of Common Stock
          of the Company ("Common Stock"), thereby aligning their interests more
          closely with the  interests of the  shareholders  of the Company.  The
          Plan is  intended  as a means  of  maximizing  the  effectiveness  and
          flexibility of the Company's  compensation  arrangements for directors
          and as an aid in attracting  and retaining  individuals of outstanding
          abilities to serve as  directors.  This Plan shall be  effective  upon
          approval by the Company's shareholders and supersedes and replaces all
          prior deferred  compensation plans maintained by the Company or any of
          its subsidiaries for the benefit of directors.

2.        PARTICIPATION.  An eligible  director may become a participant  in the
          Plan by making an  election  pursuant to  paragraph  3 hereof.  In the
          event a participant no longer meets the requirements for participation
          in  this  Plan,  he or  she  shall  become  an  inactive  participant,
          retaining all the rights  described under this Plan,  except the right
          to make any  further  deferrals,  until  the time that he or she again
          becomes an active participant.

3.        ELECTION  TO  PARTICIPATE.  Any  director of the Company or any of its
          subsidiaries  may  elect  to  participate  in the  Plan by  filing  an
          election with the Administrator.  Elections to participate shall apply
          at a minimum to a one-year  period  commencing on July 1 and ending on
          June 30. Once an election has been filed with the  Administrator,  the
          director shall participate in the Plan for the entire year in which he
          or she has initially  elected to  participate  and for all  subsequent
          years until the  director  files a notice of  revocation  or change of
          such election with the Administrator.  To be effective,  any election,
          revocation or change under this  paragraph 3 must be filed by the June
          30th immediately preceding the July 1st on which it is to take effect;
          provided,  however,  a newly eligible  director may, within 30 days of
          the  date  he or she  first  becomes  an  eligible  director,  make an
          election  which  relates  to  fees  otherwise  payable  to  him or her
          provided such fees relate to future services.


                                     - 1 -

4.        CASH DEFERRAL ELECTION. Commencing as of July 1 of the year a director
          elects to defer  receipt of his or her  director's  fees in cash,  all
          director  fees  earned  by the  director  shall be  maintained  by the
          Company  in  a  deferred  compensation  account.  The  amount  of  the
          director's  fees shall be credited to this account as of the date such
          fees otherwise would be payable.  No funds shall actually be set aside
          for  payment  under  the Plan and any  director  to whom an  amount is
          credited under the Plan shall be deemed a general,  unsecured creditor
          of the Company.  Director fees for this purpose shall be all fees paid
          to a  director  by reason of his or her being a member of the Board of
          Directors of the Company or any of its  subsidiaries  or any committee
          of any thereof. All dollar amounts credited to a deferred compensation
          account  maintained in the name of a director shall accrue interest at
          the rate per annum equal to the 91-day  Treasury Bill  discount  rate,
          adjusted quarterly,  until paid. Accrued interest shall be credited to
          deferred  compensation  accounts  as of the last day of each  calendar
          quarter.

5.        FEES PAID IN  STOCK.  Commencing  as of July 1 of the year a  director
          elects to  receive  his or her  director's  fees  currently  in Common
          Stock,  all  director  fees  earned by the  director  shall be paid in
          shares of Common  Stock until the  director  shall cease to serve as a
          member of the  Company's  Board of  Directors  or until June 30 of the
          year in which the director  shall file a notice of  revocation of such
          election, whichever first occurs. Director fees for this purpose shall
          be all fees paid to a director  by reason of his or her being a member
          of the Board of Directors of the Company or any of its subsidiaries or
          any committee of any thereof.  The number of shares of Common Stock to
          be paid to a director  shall be computed  quarterly  by  dividing  the
          total amount of fees earned by the director in the quarter by the fair
          market value of one share of Common Stock as of the last  business day
          on which  trades in Common  Stock were  reported  during the  calendar
          quarter  immediately  preceding  the  quarter  in which  the fees were
          earned. Fair market value as of any date means the average of the high
          and low sales  prices of the Common  Stock as  reported  on the Nasdaq
          National  Market on that  date.  The  number of shares to be paid to a
          director shall be issued, and shares delivered to the director,  on an
          annual basis,  on or about  January  15th,  or more  frequently as the
          administrator shall determine.

6.        DEFERRED  STOCK UNITS.  Commencing as of July 1 of the year a director
          elects to receive his or her  director's  fees in Common  Stock and to
          defer receipt of such Common Stock,  the Company shall maintain on its
          books deferred  stock units  ("Units")  representing  an obligation to
          issue shares of Common Stock to such director. Units shall be credited
          to the  director  at the time and in the amount  that shares of Common
          Stock  would  otherwise  have  been  determined  to be  payable  under
          paragraph 5 in the absence of an election to defer.  Additional  Units
          shall be credited at the time  dividends are paid on the Common Stock,
          as if such  dividends  were  director  fees  subject to this Plan.  No
          Common Stock shall  actually be set aside for payment  under the Units
          and any  director to whom Units are  credited  under the Plan

                                     - 2 -

          shall be deemed a general, unsecured creditor of the Company. Director
          fees for this  purpose  shall be all fees paid to a director by reason
          of his or her being a member of the Board of  Directors of the Company
          and any of its subsidiaries or any committee of any thereof.

7.        AVAILABLE  SHARES.  Subject to paragraph  10 (relating to  adjustments
          upon changes in capitalization),  as of any date the maximum number of
          shares of Common  Stock  issued and  issuable  under the Plan shall be
          150,000.

8.        SHARES.  Shares  paid to  directors  under the Plan shall be paid with
          newly issued shares of Common Stock of the Company or treasury  shares
          of Common Stock held by the  Company.  No  fractional  shares shall be
          issued.  Whenever the  computation  of the number of shares to be paid
          results in a  fractional  amount of one-half  or greater,  such amount
          shall be rounded up to the next greater  whole number of shares and in
          all other  cases such amount  shall be rounded  down to the next lower
          whole number of shares.

9.        TREATMENT OF PRIOR  DEFERRED  COMPENSATION  ACCOUNTS.  Dollar  amounts
          accrued  through June 30, 2001, to deferred  compensation  accounts of
          directors under plans previously  maintained by the Corporation or any
          of its subsidiaries will be transferred and credited to the directors'
          respective deferred compensation accounts under the Plan as of July 1,
          2001; provided, however, at the discretion of the Administrator,  such
          amounts may be credited on such date in Units on the basis of the fair
          market  value of the Common  Stock on June 30, 2001 for any  directors
          who  have  submitted  participation  agreements  prior  to  such  date
          electing to defer  director fees under the Plan and to receive  Common
          Stock.

10.       SECURITIES  LAW  COMPLIANCE.   The   Administrator   may  impose  such
          requirements  and  restrictions  with  respect to any shares of Common
          Stock  acquired  under  the Plan as it may deem  advisable  including,
          without   limitation,   (a)  legends   and/or   stop-transfer   orders
          restricting   transferability,    and   (b)   investment   and   other
          representations from directors.

11.       ADJUSTMENT  IN  CAPITALIZATION.  In the event  that any  change in the
          outstanding  shares  of  Common  Stock  occurs  by  reason  of a stock
          dividend,  stock  split,   recapitalization,   merger,  consolidation,
          combination,  share  exchange  or similar  corporate  change,  (i) the
          number of shares of Common  Stock which may be issued  under this Plan
          shall be  appropriately  adjusted,  and (ii) the Units credited to any
          participant's  deferred  compensation  account shall be  appropriately
          adjusted.

12.       NONASSIGNMENT. Neither a director, during his or her lifetime, nor his
          or her duly  designated  beneficiary  shall  have any right to assign,
          transfer,  pledge or otherwise  convey the right to receive any Common
          Stock or Units hereunder, and any such attempted assignment, transfer,
          other conveyance shall not be recognized by the Company.

13.       DESIGNATION OF  BENEFICIARY.  A director may designate the beneficiary
          which is to receive any unpaid  Common Stock or Common  Stock  payable
          with  respect  to  Units  credited  at  the  director's   death.  Such
          designation  shall be effective by filing a written  notification with
          the  Administrator  and may be  changed  from time to time by  similar
          action. If no such designation is made by a director, any such balance
          shall be paid to the director's estate.

                                     - 3 -

14.       ADMINISTRATION.  The Administrator  shall establish the procedures and
          maintain  all books  and  records  in  connection  with the Plan.  The
          Administrator   may,  in  his  sole  discretion,   delegate  any  plan
          administration  responsibilities  to one or more  agents  as he  deems
          advisable.

15.       FEDERAL TAX  WITHHOLDING.  If the  Company or any of its  subsidiaries
          becomes  obligated  to make  federal  tax  withholding  payments  with
          respect to  directors  fees paid,  the  Company  shall be  entitled to
          withhold such amounts from the amounts payable to directors regardless
          of whether the directors have elected to be paid in cash or stock.  If
          amounts are to be withheld out of shares  issuable to a director,  the
          reduction in the number of shares  issuable shall be determined  based
          on the fair market value of the Company's  Common Stock on the date of
          issuance.  With respect to fees payable in stock,  in lieu of reducing
          the number of shares to be issued,  the Company may in its  discretion
          require  participants  to pay cash to the Company in the amount of the
          tax withholding due prior to releasing the shares.

16.       AMENDMENT. The Plan may be amended or terminated at any time by action
          of the Board of  Directors  of the  Company,  but no  amendment  shall
          adversely  affect a director's  rights with respect to fees earned but
          not yet  paid in  either  cash,  Common  Stock or  Units  without  the
          director's written consent.  Upon termination of the Plan, the Company
          may make immediate  distributions  of all amounts credited to deferred
          compensation accounts.

17.       GOVERNING  LAW.  This  Plan  shall be  governed  by and  construed  in
          accordance with Illinois law. 1.

                                     - 4 -

The Directors and Officers of

Wintrust  Financial  Corporation
cordially invite you to attend our
2001 Annual Meeting of Shareholders
Thursday,  May 24, 2001, 10:00 a.m.
Hyatt-Deerfield
1750 Lake Cook Road
Deerfield, Illinois


   YOU CAN VOTE IN ONE OF THREE WAYS: 1) BY MAIL, 2) BY PHONE, 3) BY INTERNET.
              See the reverse side of this sheet for instructions.


IF YOU ARE NOT VOTING BY TELEPHONE OR BY  INTERNET,  COMPLETE  BOTH SIDES OF THE
           ---
        PROXY CARD, DETACH HERE AND RETURN IN THE ENCLOSED ENVELOPE TO:

                           Illinios Stock Transfer Co.
                      209 West Jackson Boulevard, Suite 903
                             Chicago, Illinois 60606


                                   IMPORTANT
                                   ---------
           Please complete both sides of the PROXY CARD, sign, date,
                  detach and return in the enclosed envelope.

- --------------------------------------------------------------------------------
THIS PROXY IS SOLICITED ON BEHALF OF THE BOARD OF  DIRECTORS.  IF NOT  OTHERWISE
SPECIFIED ON THE REVERSE SIDE,  THIS PROXY WILL BE VOTED FOR ALL NOMINEES LISTED
AND FOR PROPOSAL 2. THE UNDERSIGNED REVOKES ALL PROXIES HERETOFORE GIVEN TO VOTE
AT SUCH MEETING AND ALL ADJOURNMENTS OR POSTPONEMENTS.






Dated _____________________

___________________________

___________________________
(Please sign here)


Please sign your name as it appears above. If executed by a corporation,  a duly
authorized officer should sign. Executors, administrators,  attorneys, guardians
and trustees  should so indicate  when signing.  If shares are held jointly,  at
least one holder must sign.

- --------------------------------------------------------------------------------

Wintrust Financial Corporation

If you  personally  plan to attend the Annual  Meeting of  Shareholders,  please
check the box below and list the names of attendees on reverse side.

Return this stub in the enclosed envelope with your completed proxy card.


I/We do plan to attend
the 2001 meeting         ________




                                 TO VOTE BY MAIL

To vote by mail, complete both sides, sign and date the proxy card below. Detach
the card below and return it in the envelope provided.

                              TO VOTE BY TELEPHONE

Your telephone vote is quick, confidential and immediate. Just follow these easy
steps:

1. Read the accompanying Proxy Statement.
2. Using a Touch-Tone  telephone,  call Toll Free  1-800-555-8140 and follow the
instructions.
3. When asked for your Voter Control Number, enter the number printed just above
your name on the front of the proxy card below.  Please note that all votes cast
by telephone  must be submitted  prior to midnight  Central Time,  May 22, 2001.
Your telephone vote authorizes the named proxies to vote your shares to the same
extent as if you marked, signed, dated and returned the proxy card.

      If You Vote By TELEPHONE Please Do Not Return Your Proxy Card By Mail

                               TO VOTE BY INTERNET

Your  internet  vote  is  quick,  confidential  and  your  vote  is  immediately
submitted. Just follow the se easy steps:

1. Read the accompanying Proxy Statement.

2. Visit our Internet  voting Site at  HTTP://WWW.EPROXYVOTE.COM/IST-WFCCM/  and
follow the instructions on the screen.

3. When prompted for your Voter Control  Number,  enter the number  printed just
above your name on the front of the proxy card.  Please note that all votes cast
by internet must be submitted prior to midnight Central Time, May 22, 2001. Your
Internet  vote  authorizes  the named  proxies  to vote your  shares to the same
extent as if you marked, signed, dated and returned the proxy card.

THIS IS A "SECURED" WEB PAGE SITE. YOUR SOFTWARE  AND/OR INTERNET  PROVIDER MUST
BE ENABLED TO ACCESS THIS SITE.  PLEASE CALL YOUR SOFTWARE OR INTERNET  PROVIDER
FOR FURTHER INFORMATION.

      If You Vote By Internet, Please Do Not Return Your Proxy Card By Mail

- --------------------------------------------------------------------------------


Wintrust Financial Corporation
REVOCABLE PROXY

THIS PROXY IS SOLICITED ON BEHALF OF THE BOARD OF DIRECTORS

The undersigned  hereby appoints John S. Lillard and Edward J. Wehmer and either
of them as Proxies,  each with the power to appoint his  substitute,  and hereby
authorizes  each them to represent  and to vote, as  designated  below,  all the
shares of Common Stock of Wintrust  Financial  Corporation which the undersigned
is entitled to vote at the Annual Meeting of  Shareholders to be held on May 24,
2001 or any  adjournment  thereof.  If any other  business is  presented  at the
Annual Meeting, including whether or not to adjourn the meeting, this proxy will
be voted,  to the extent  legally  permissable,  by those named in this proxy in
their best judgement.

      PROPOSAL 1 -  ELECTION  OF  DIRECTORS  (To  be  designated  as  Class  II
                   Directors with term ending in 2004.)
                   [   ]    FOR ALL NOMINEES LISTED BELOW
                            (Except as marked to the contrary below).

                   [   ]    WITHHOLD AUTHORITY to vote for all nominees below.
                            (INSTRUCTIONS: TO WITHHOLD AUTHORITY TO VOTE FOR
                            ANY INDIVIDUAL NOMINEE, STRIKE A LINE THROUGH THE
                            NOMINEE'S NAME).

        01   Bruce K. Crowther                  05   Albin F. Moschner
        02   Bert A. Getz, Jr.                  06   Christopher J. Perry
        03   William C. Graft                   07   Ingrid S. Stafford
        04   Marguerite Savard McKenna          08   Katharine V. Sylvester


     PROPOSAL 2 - APPROVAL OF DIRECTORS DEFERRED FEE AND STOCK PLAN
                  AS DESCRIBED IN THE PROXY STATEMENT

                  [   ] FOR   [   ] AGAINST   [   ] ABSTAIN


                        (To be signed on the other side)