Exhibit 4.2

                    PREFERRED SECURITIES GUARANTEE AGREEMENT


                                 by and between



                         WINTRUST FINANCIAL CORPORATION


                                       and


                            WILMINGTON TRUST COMPANY




                         Dated as of September 29, 1998



                                TABLE OF CONTENTS

                                                                        Page No.
ARTICLE I
         DEFINITIONS AND INTERPRETATION........................................1
         Section 1.1.  Definitions and Interpretation..........................1

ARTICLE II
TRUST INDENTURE ACT............................................................5
         Section 2.1.  Trust Indenture Act; Application........................5
         Section 2.2.  Lists of Holders of Securities..........................5
         Section 2.3.  Reports by the Preferred Guarantee Trustee..............5
         Section 2.4.  Periodic Reports to Preferred Guarantee Trustee.........6
         Section 2.5.  Evidence of Compliance with Conditions Precedent........6
         Section 2.6.  Events of Default; Waiver...............................6
         Section 2.7.  Event of Default; Notice................................6
         Section 2.8.  Conflicting Interests...................................7

ARTICLE III
         POWERS, DUTIES AND RIGHTS OF PREFERRED GUARANTEE TRUSTEE..............7
         Section 3.1.  Powers and Duties of the Preferred Guarantee Trustee....7
         Section 3.2.  Certain Rights of Preferred Guarantee Trustee...........8
         Section 3.3.  Not Responsible for Recitals or Issuance of Guarantee..10

ARTICLE IV
         PREFERRED GUARANTEE TRUSTEE..........................................10
         Section 4.1.  Preferred Guarantee Trustee; Eligibility...............10
         Section 4.2.  Appointment, Removal and Resignation of 
                  Preferred Guarantee Trustees................................11

ARTICLE V
         GUARANTEE............................................................12
         Section 5.1.  Guarantee..............................................12
         Section 5.2.  Waiver of Notice and Demand............................12
         Section 5.3.  Obligations not Affected...............................12
         Section 5.4.  Rights of Holders......................................13
         Section 5.5.  Guarantee of Payment...................................14
         Section 5.6.  Subrogation............................................14
         Section 5.7.  Independent Obligations................................14

ARTICLE VI
         LIMITATION OF TRANSACTIONS; SUBORDINATION............................14
         Section 6.1.  Limitation of Transactions.............................14
         Section 6.2  Ranking.................................................15

                                       i


ARTICLE VII
         TERMINATION..........................................................15
         Section 7.1.  Termination............................................15

ARTICLE VIII
         INDEMNIFICATION......................................................15
         Section 8.1.  Exculpation............................................15
         Section 8.2.  Indemnification........................................16

ARTICLE IX
         MISCELLANEOUS........................................................16
         Section 9.1.  Successors and Assigns.................................16
         Section 9.2.  Amendments.............................................16
         Section 9.3.  Notices................................................16
         Section 9.4.  Benefit................................................17
         Section 9.5.  Governing Law..........................................17

                                       ii

                              CROSS REFERENCE TABLE


                Section of Trust                            Section of
                Indenture Act of                            Guarantee
                1939, as amended                            Agreement
                ----------------                            ---------

                310(a)                                      4.1(a)
                310(b)                                      4.1(c), 2.8
                310(c)                                      Not Applicable
                311(a)                                      2.2(b)
                311(b)                                      2.2(b)
                311(c)                                      Not Applicable
                312(a)                                      2.2(a)
                312(b)                                      2.2(b)
                313                                         2.3
                314(a)                                      2.4
                314(b)                                      Not Applicable
                314(c)                                      2.5
                314(d)                                      Not Applicable
                314(e)                                      1.1, 2.5, 3.2
                314(f)                                      2.1, 3.2
                315(a)                                      3.1(d)
                315(b)                                      2.7
                315(c)                                      3.1
                315(d)                                      3.1(d)
                316(a)                                      1.1, 2.6, 5.4
                316(b)                                      5.3
                317(a)                                      3.1
                317(b)                                      Not Applicable
                318(a)                                      2.1(a)
                318(b)                                      2.1
                318(c)                                      2.1(b)

                Note:  This  Cross-Reference  Table does not constitute  part of
                this Agreement and shall not affect the interpretation of any of
                its terms or provisions.

                                      iii

                    PREFERRED SECURITIES GUARANTEE AGREEMENT

         THIS  PREFERRED   SECURITIES   GUARANTEE   AGREEMENT  (this  "Preferred
Securities  Guarantee"),  dated  as of  September  29,  1998,  is  executed  and
delivered  by  WINTRUST  FINANCIAL  CORPORATION,  an Illinois  corporation  (the
"Guarantor"),  and WILMINGTON  TRUST  COMPANY,  a Delaware  banking  corporation
organized  under the laws of the State of Delaware,  as trustee (the  "Preferred
Guarantee  Trustee"),  for the benefit of the Holders (as defined  herein)  from
time to time of the Preferred Securities (as defined herein) of Wintrust Capital
Trust I, a Delaware statutory business trust (the "Trust").

                                    RECITALS

         WHEREAS,  pursuant  to an Amended and  Restated  Trust  Agreement  (the
"Trust  Agreement"),  dated as of September 29, 1998,  among the trustees of the
Trust named  therein,  the Guarantor,  as sponsor,  and the holders from time to
time of undivided  beneficial interests in the assets of the Trust, the Trust is
issuing  on the date  hereof up to  1,242,000  preferred  securities,  having an
aggregate  liquidation  amount of $31,050,000,  designated the 9.00%  Cumulative
Trust Preferred Securities (the "Preferred Securities");

         WHEREAS,  as  incentive  for the  Holders  to  purchase  the  Preferred
Securities,  the Guarantor desires  irrevocably and unconditionally to agree, to
the  extent  set forth in this  Preferred  Securities  Guarantee,  to pay to the
Holders of the Preferred  Securities the Guarantee  Payments (as defined herein)
and to make certain other payments on the terms and conditions set forth herein.

         NOW,  THEREFORE,  in  consideration  of the  purchase by each Holder of
Preferred  Securities,  which purchase the Guarantor hereby agrees shall benefit
the Guarantor,  the Guarantor  executes and delivers this  Preferred  Securities
Guarantee for the benefit of the Holders.


                                    ARTICLE I
                         DEFINITIONS AND INTERPRETATION

SECTION 1.1.  DEFINITIONS AND INTERPRETATION.

         In this Preferred  Securities  Guarantee,  unless the context otherwise
requires:

         (a) capitalized terms used in this Preferred  Securities  Guarantee but
not defined in the preamble above have the respective  meanings assigned to them
in this Section 1.1;

         (b) terms defined in the Trust Agreement as at the date of execution of
this  Preferred  Securities  Guarantee  have the same  meaning when used in this
Preferred  Securities  Guarantee,  unless  otherwise  defined in this  Preferred
Securities Guarantee;

         (c) a term defined anywhere in this Preferred  Securities Guarantee has
the same meaning throughout;


         (d) all  references to "the  Preferred  Securities  Guarantee" or "this
Preferred  Securities  Guarantee" are to this Preferred  Securities Guarantee as
modified, supplemented or amended from time to time;

         (e) all references in this Preferred  Securities  Guarantee to Articles
and  Sections  are  to  Articles  and  Sections  of  this  Preferred  Securities
Guarantee, unless otherwise specified;

         (f) a term defined in the Trust Indenture Act has the same meaning when
used in this Preferred  Securities  Guarantee,  unless otherwise defined in this
Preferred Securities Guarantee or unless the context otherwise requires; and

         (g) a reference to the singular includes the plural and vice versa.

         "Affiliate"  has the same  meaning as given to that term in Rule 405 of
the Securities Act of 1933, as amended, or any successor rule thereunder.

         "Business  Day" means any day other than a Saturday,  Sunday,  a day on
which federal or state banking institutions in New York, New York are authorized
or required by law, executive order or regulation to close or a day on which the
Corporate  Trust  Office  of the  Preferred  Guarantee  Trustee  is  closed  for
business.

         "Corporate  Trust Office"  means the office of the Preferred  Guarantee
Trustee at which the corporate trust business of the Preferred Guarantee Trustee
shall, at any particular time, be principally administered,  which office at the
date of execution  of this  Agreement is located at Rodney  Square  North,  1100
North Market Street, Wilmington, Delaware 19890-0001, Attention: Corporate Trust
Administration.

         "Covered  Person"  means any Holder or  beneficial  owner of  Preferred
Securities.

         "Debentures" means the 9.00% Subordinated  Debentures due September 30,
2028, of the Debenture Issuer held by the Property Trustee of the Trust.

         "Debenture Issuer" means Wintrust Financial Corporation,  issuer of the
Debentures under the Indenture.

         "Event of  Default"  means a  default  by the  Guarantor  on any of its
payment or other obligations under this Preferred Securities Guarantee.

         "Guarantor"   means  Wintrust   Financial   Corporation,   an  Illinois
corporation.

         "Guarantee  Payments"  means the following  payments or  distributions,
without duplication, with respect to the Preferred Securities, to the extent not
paid or made by the Trust: (i) any accrued and unpaid  Distributions (as defined
in the  Trust  Agreement)  that  are  required  to be  paid  on  such  Preferred
Securities,  to the extent the Trust shall have funds available  therefor,  (ii)
the redemption price, including all accrued and unpaid Distributions to the date
of  redemption  (the  "Redemption

                                     - 2 -

Price"), to the extent the Trust has funds available  therefor,  with respect to
any Preferred  Securities  called for redemption by the Trust,  and (iii) upon a
voluntary or  involuntary  dissolution,  winding-up or  termination of the Trust
(other than in connection with the  distribution of Debentures to the Holders in
exchange  for  Preferred  Securities  as provided in the Trust  Agreement),  the
lesser of (a) the aggregate of the liquidation amount and all accrued and unpaid
Distributions on the Preferred  Securities to the date of payment, to the extent
the Trust shall have funds available therefor (the "Liquidation  Distribution"),
and (b) the amount of assets of the Trust remaining  available for  distribution
to Holders in liquidation of the Trust.

         "Holder" shall mean any holder,  as registered on the books and records
of  the  Trust,  of  any  Preferred  Securities;  provided,  however,  that,  in
determining  whether  the  holders  of the  requisite  percentage  of  Preferred
Securities have given any request, notice, consent or waiver hereunder, "Holder"
shall not include the Guarantor, the Preferred Guarantee Trustee or any of their
respective Affiliates.

         "Indemnified   Person"  means  the  Preferred  Guarantee  Trustee,  any
Affiliate  of the  Preferred  Guarantee  Trustee,  or any  officers,  directors,
shareholders,   members,   partners,   employees,   representatives,   nominees,
custodians or agents of the Preferred Guarantee Trustee.

         "Indenture"  means the Indenture dated as of September 29, 1998,  among
the Debenture Issuer and Wilmington Trust Company, as trustee, and any indenture
supplemental  thereto pursuant to which certain  subordinated debt securities of
the Debenture Issuer are to be issued to the Property Trustee of the Trust.

         "Liquidation  Amount"  means  the  stated  value  of $25 per  Preferred
Security.

         "Liquidation  Distribution"  has the meaning  provided  therefor in the
definition of Guarantee Payments.

         "Majority in liquidation amount of the Preferred  Securities" means the
holders  of more  than 50% of the  Liquidation  Amount  of all of the  Preferred
Securities.

         "Officers'   Certificate"   means,   with  respect  to  any  Person,  a
certificate  signed by two authorized  officers of such Person,  at least one of
whom shall be the principal  executive  officer,  principal  financial  officer,
principal  accounting  officer,  treasurer or any vice president of such Person.
Any Officers'  Certificate delivered with respect to compliance with a condition
or covenant provided for in this Preferred Securities Guarantee shall include:

         (a) a statement that each officer signing the Officers' Certificate has
read the covenant or condition and the definition relating thereto;

         (b) a brief  statement  of the nature and scope of the  examination  or
investigation undertaken by each officer in rendering the Officers' Certificate;

                                     - 3 -

         (c) a statement  that each such  officer has made such  examination  or
investigation as, in such officer's opinion, is necessary to enable such officer
to express an informed  opinion as to whether or not such  covenant or condition
has been complied with; and

         (d) a  statement  as to whether,  in the opinion of each such  officer,
such condition or covenant has been complied with.

         "Person" means a legal person,  including any individual,  corporation,
estate, partnership,  joint venture,  association,  joint stock company, limited
liability  company,  trust,  unincorporated  association,  or  government or any
agency or political subdivision thereof, or any other entity of whatever nature.

         "Preferred  Guarantee Trustee" means Wilmington Trust Company,  until a
Successor  Preferred  Guarantee Trustee has been appointed and has accepted such
appointment  pursuant to the terms of this  Preferred  Securities  Guarantee and
thereafter means each such Successor Preferred Guarantee Trustee.

         "Redemption  Price" has the meaning provided therefor in the definition
of Guarantee Payments.

         "Responsible  Officer" means,  with respect to the Preferred  Guarantee
Trustee,  any  officer  within  the  Corporate  Trust  Office  of the  Preferred
Guarantee  Trustee with direct  responsibility  for the  administration  of this
Preferred  Securities  Guarantee,  including any  vice-president,  any assistant
vice-president, any assistant secretary or other officer or assistant officer of
the Preferred  Guarantee  Trustee  customarily  performing  functions similar to
those  performed by any of the above  designated  officers and also means,  with
respect to a particular  corporate trust matter,  any other officer to whom such
matter is referred  because of that officer's  knowledge of and familiarity with
the particular subject.

         "Successor  Preferred  Guarantee  Trustee" means a successor  Preferred
Guarantee Trustee  possessing the  qualifications to act as Preferred  Guarantee
Trustee under Section 4.1.

         "Trust  Indenture  Act"  means  the  Trust  Indenture  Act of 1939,  as
amended.


                                   ARTICLE II
                               TRUST INDENTURE ACT

SECTION 2.1.  TRUST INDENTURE ACT; APPLICATION.

         (a) This Preferred Securities Guarantee is subject to the provisions of
the  Trust  Indenture  Act  that  are  required  to be part  of  this  Preferred
Securities  Guarantee and shall, to the extent  applicable,  be governed by such
provisions.

                                     - 4 -

         (b)  If  and to  the  extent  that  any  provision  of  this  Preferred
Securities  Guarantee limits,  qualifies or conflicts with the duties imposed by
Section 310 to 317,  inclusive,  of the Trust Indenture Act, such imposed duties
shall control.

SECTION 2.2.  LISTS OF HOLDERS OF SECURITIES.

         (a) In the event the Preferred  Guarantee Trustee is not also acting in
the capacity of the Property  Trustee under the Trust  Agreement,  the Guarantor
shall cause to be provided to the  Preferred  Guarantee  Trustee with a list, in
such form as the Preferred  Guarantee  Trustee may  reasonably  require,  of the
names  and  addresses  of the  Holders  of the  Preferred  Securities  ("List of
Holders")  as of the date (i) within 1  Business  Day after  March 15,  June 15,
September  15 and  December  15,  and (ii) at any other  time  within 30 days of
receipt by the Guarantor of a written request for a List of Holders as of a date
no more than 15 days  before  such  List of  Holders  is given to the  Preferred
Guarantee  Trustee;  provided,  that the  Guarantor  shall not be  obligated  to
provide  such List of Holders  at any time the List of  Holders  does not differ
from the most recent List of Holders  caused to have been given to the Preferred
Guarantee Trustee by the Guarantor.  The Preferred Guarantee Trustee may destroy
any List of Holders previously given to it on receipt of a new List of Holders.

         (b) The Preferred  Guarantee  Trustee shall comply with its obligations
under Sections 311(a), 311(b) and Section 312(b) of the Trust Indenture Act.

SECTION 2.3.  REPORTS BY THE PREFERRED GUARANTEE TRUSTEE.

         On or before  July 15 of each year,  the  Preferred  Guarantee  Trustee
shall  provide to the Holders of the  Preferred  Securities  such reports as are
required by Section 313 of the Trust  Indenture  Act, if any, in the form and in
the manner  provided by Section 313 of the Trust  Indenture  Act. The  Preferred
Guarantee  Trustee shall also comply with the  requirements of Section 313(d) of
the Trust Indenture Act.

SECTION 2.4.  PERIODIC REPORTS TO PREFERRED GUARANTEE TRUSTEE.

         The Guarantor  shall provide to the  Preferred  Guarantee  Trustee such
documents,  reports and  information as required by Section 314 (if any) and the
compliance certificate required by Section 314 of the Trust Indenture Act in the
form,  in the  manner  and at the times  required  by  Section  314 of the Trust
Indenture Act.

SECTION 2.5.  EVIDENCE OF COMPLIANCE WITH CONDITIONS PRECEDENT.

         The Guarantor  shall provide to the  Preferred  Guarantee  Trustee such
evidence of compliance with any conditions  precedent,  if any,  provided for in
this Preferred  Securities Guarantee that relate to any of the matters set forth
in  Section  314(c) of the Trust  Indenture  Act.  Any  certificate  or  opinion
required to be given by an officer pursuant to Section 314(c)(1) may be given in
the form of an Officers' Certificate.

                                     - 5 -

SECTION 2.6.  EVENTS OF DEFAULT; WAIVER.

         The Holders of a Majority in liquidation amount of Preferred Securities
may, by vote, on behalf of the Holders of all of the Preferred Securities, waive
any past Event of Default and its consequences. Upon such waiver, any such Event
of Default  shall  cease to exist,  and any Event of Default  arising  therefrom
shall be  deemed  to have  been  cured,  for  every  purpose  of this  Preferred
Securities Guarantee, but no such waiver shall extend to any subsequent or other
default or Event of Default or impair any right consequent thereon.

SECTION 2.7.  EVENT OF DEFAULT; NOTICE.

         (a) The Preferred  Guarantee  Trustee  shall,  within 90 days after the
occurrence  of an Event  of  Default,  transmit  by mail,  first  class  postage
prepaid,  to the Holders of the Preferred  Securities,  notices of all Events of
Default  actually  known to a  Responsible  Officer of the  Preferred  Guarantee
Trustee,  unless such defaults have been cured before the giving of such notice;
provided,  that,  except in the case of a  default  by  Guarantor  on any of its
payment  obligations,  the  Preferred  Guarantee  Trustee  shall be protected in
withholding such notice if and so long as a Responsible Officer of the Preferred
Guarantee  Trustee in good faith  determines that the withholding of such notice
is in the interests of the Holders of the Preferred Securities.

         (b)  The  Preferred  Guarantee  Trustee  shall  not be  deemed  to have
knowledge of any Event of Default unless the Preferred  Guarantee  Trustee shall
have received written notice, or of which a Responsible Officer of the Preferred
Guarantee  Trustee charged with the  administration of the Trust Agreement shall
have obtained actual knowledge.

SECTION 2.8.  CONFLICTING INTERESTS.

         The Trust  Agreement  shall be deemed to be  specifically  described in
this Preferred  Securities Guarantee for the purposes of clause (i) of the first
proviso contained in Section 310(b) of the Trust Indenture Act.


                                   ARTICLE III
            POWERS, DUTIES AND RIGHTS OF PREFERRED GUARANTEE TRUSTEE

SECTION 3.1.  POWERS AND DUTIES OF THE PREFERRED GUARANTEE TRUSTEE.

         (a) This Preferred  Securities Guarantee shall be held by the Preferred
Guarantee  Trustee for the benefit of the Holders of the  Preferred  Securities,
and the Preferred Guarantee Trustee shall not transfer this Preferred Securities
Guarantee to any Person except a Holder of Preferred  Securities  exercising his
or her rights pursuant to Section 5.4(b) or to a Successor  Preferred  Guarantee
Trustee on  acceptance  by such  Successor  Preferred  Guarantee  Trustee of its
appointment to act as Successor  Preferred  Guarantee Trustee.  The right, title
and interest of the Preferred  Guarantee Trustee shall automatically vest in any
Successor Preferred  Guarantee Trustee,  and such vesting and cessation of 

                                     - 6 -

title  shall be  effective  whether  or not  conveyancing  documents  have  been
executed and delivered  pursuant to the appointment of such Successor  Preferred
Guarantee Trustee.

         (b) If an Event of Default  actually known to a Responsible  Officer of
the Preferred  Guarantee  Trustee has occurred and is continuing,  the Preferred
Guarantee  Trustee shall  enforce this  Preferred  Securities  Guarantee for the
benefit of the Holders of the Preferred Securities.

         (c) The Preferred Guarantee Trustee, before the occurrence of any Event
of Default and after the curing of all Events of Default that may have occurred,
shall  undertake  to perform only such duties as are  specifically  set forth in
this Preferred Securities Guarantee, and no implied covenants shall be read into
this Preferred  Securities Guarantee against the Preferred Guarantee Trustee. In
case an Event of  Default  has  occurred  (that  has not  been  cured or  waived
pursuant to Section 2.6) and is actually  known to a Responsible  Officer of the
Preferred Guarantee Trustee, the Preferred Guarantee Trustee shall exercise such
of the rights and powers vested in it by this  Preferred  Securities  Guarantee,
and use the same degree of care and skill in its exercise thereof,  as a prudent
person would  exercise or use under the  circumstances  in the conduct of his or
her own affairs.

         (d) No  provision  of this  Preferred  Securities  Guarantee  shall  be
construed to relieve the Preferred  Guarantee Trustee from liability for its own
negligent  action,  its  own  negligent  failure  to  act,  or its  own  willful
misconduct, except that:

                  (i) prior to the  occurrence of any Event of Default and after
the curing or waiving of all such Events of Default that may have occurred:

                           (A)  the  duties  and  obligations  of the  Preferred
Guarantee Trustee shall be determined  solely by the express  provisions of this
Preferred Securities Guarantee, and the Preferred Guarantee Trustee shall not be
liable  except  for  the  performance  of such  duties  and  obligations  as are
specifically set forth in this Preferred  Securities  Guarantee,  and no implied
covenants or obligations shall be read into this Preferred  Securities Guarantee
against the Preferred Guarantee Trustee; and

                           (B) in the  absence  of bad  faith on the part of the
Preferred  Guarantee Trustee,  the Preferred  Guarantee Trustee may conclusively
rely,  as to the truth of the  statements  and the  correctness  of the opinions
expressed therein,  upon any certificates or opinions furnished to the Preferred
Guarantee   Trustee  and  conforming  to  the  requirements  of  this  Preferred
Securities Guarantee;  but in the case of any such certificates or opinions that
by any  provision  hereof  are  specifically  required  to be  furnished  to the
Preferred  Guarantee Trustee,  the Preferred  Guarantee Trustee shall be under a
duty to  examine  the  same to  determine  whether  or not they  conform  to the
requirements of this Preferred Securities Guarantee;

                  (ii) the Preferred  Guarantee  Trustee shall not be liable for
any  error of  judgment  made in good  faith  by a  Responsible  Officer  of the
Preferred  Guarantee  Trustee,  unless  it shall be  proved  that the  Preferred
Guarantee  Trustee was negligent in ascertaining  the pertinent facts upon which
such judgment was made;

                                     - 7 -

                  (iii) the Preferred Guarantee Trustee shall not be liable with
respect  to any  action  taken or  omitted  to be  taken by it in good  faith in
accordance  with the  direction  of the  Holders of not less than a Majority  in
liquidation amount of the Preferred  Securities relating to the time, method and
place of conducting  any  proceeding  for any remedy  available to the Preferred
Guarantee Trustee, or exercising any trust or power conferred upon the Preferred
Guarantee Trustee under this Preferred Securities Guarantee; and

                  (iv) no provision of this Preferred Securities Guarantee shall
require  the  Preferred  Guarantee  Trustee  to  expend or risk its own funds or
otherwise  incur personal  financial  liability in the performance of any of its
duties or in the  exercise  of any of its  rights or  powers,  if the  Preferred
Guarantee Trustee shall have reasonable grounds for believing that the repayment
of such funds or  liability is not  reasonably  assured to it under the terms of
this Preferred Securities Guarantee or indemnity, reasonably satisfactory to the
Preferred  Guarantee  Trustee,  against such risk or liability is not reasonably
assured to it.

SECTION 3.2.  CERTAIN RIGHTS OF PREFERRED GUARANTEE TRUSTEE.

         (a)      Subject to the provisions of Section 3.1:

                  (i) the Preferred Guarantee Trustee may conclusively rely, and
shall be  fully  protected  in  acting  or  refraining  from  acting  upon,  any
resolution,   certificate,   statement,  instrument,  opinion,  report,  notice,
request,  direction,  consent,  order, bond, debenture,  note, other evidence of
indebtedness or other paper or document believed by it to be genuine and to have
been signed, sent or presented by the proper party or parties;

                  (ii) Any  direction or act of the  Guarantor  contemplated  by
this  Preferred  Securities  Guarantee  shall be  sufficiently  evidenced  by an
Officers' Certificate;

                  (iii)  whenever,  in  the  administration  of  this  Preferred
Securities  Guarantee,  the Preferred  Guarantee Trustee shall deem it desirable
that a matter be proved or established before taking,  suffering or omitting any
action  hereunder,  the Preferred  Guarantee  Trustee  (unless other evidence is
herein  specifically  prescribed)  may, in the absence of bad faith on its part,
request and conclusively rely upon an Officers'  Certificate which, upon receipt
of such request, shall be promptly delivered by the Guarantor;

                  (iv) the Preferred Guarantee Trustee shall have no duty to see
to any recording,  filing or registration of any instrument (or any rerecording,
refiling or registration thereof);

                  (v) the Preferred  Guarantee Trustee may consult with counsel,
and the written  advice or opinion of such counsel with respect to legal matters
shall be full and complete authorization and protection in respect of any action
taken,  suffered or omitted by it hereunder in good faith and in accordance with
such advice or opinion.  Such counsel may be counsel to the  Guarantor or any of
its  Affiliates and may include any of its  employees.  The Preferred  Guarantee
Trustee  shall have the right at any time to seek  instructions  concerning  the
administration  of  this  Preferred  Securities  Guarantee  from  any  court  of
competent jurisdiction;

                                     - 8 -

                  (vi)  the  Preferred  Guarantee  Trustee  shall  be  under  no
obligation  to  exercise  any of the  rights  or  powers  vested  in it by  this
Preferred Securities Guarantee at the request or direction of any Holder, unless
such Holder shall have provided to the Preferred Guarantee Trustee such security
and  indemnity,  reasonably  satisfactory  to the Preferred  Guarantee  Trustee,
against the costs,  expenses  (including  attorneys'  fees and  expenses and the
expenses of the Preferred  Guarantee  Trustee's agents,  nominees or custodians)
and  liabilities  that might be incurred by it in complying with such request or
direction,  including  such  reasonable  advances  as  may be  requested  by the
Preferred  Guarantee  Trustee;  provided that, nothing contained in this Section
3.2(a)(vi) shall be taken to relieve the Preferred  Guarantee Trustee,  upon the
occurrence of an Event of Default,  of its obligation to exercise the rights and
powers vested in it by this Preferred Securities Guarantee;

                  (vii) the  Preferred  Guarantee  Trustee shall not be bound to
make any  investigation  into the facts or  matters  stated  in any  resolution,
certificate, statement, instrument, opinion, report, notice, request, direction,
consent,  order, bond, debenture,  note, other evidence of indebtedness or other
paper or document,  but the Preferred Guarantee Trustee, in its discretion,  may
make such further inquiry or investigation  into such facts or matters as it may
see fit;

                  (viii) the Preferred  Guarantee Trustee may execute any of the
trusts or powers hereunder or perform any duties hereunder either directly or by
or  through  agents,  nominees,  custodians  or  attorneys,  and  the  Preferred
Guarantee  Trustee shall not be responsible  for any misconduct or negligence on
the part of any agent or attorney appointed with due care by it hereunder;

                  (ix) any action taken by the  Preferred  Guarantee  Trustee or
its agents hereunder shall bind the Holders of the Preferred Securities, and the
signature  of the  Preferred  Guarantee  Trustee  or its agents  alone  shall be
sufficient  and  effective to perform any such  action.  No third party shall be
required to inquire as to the authority of the Preferred Guarantee Trustee to so
act or as to its  compliance  with  any of the  terms  and  provisions  of  this
Preferred Securities Guarantee, both of which shall be conclusively evidenced by
the Preferred Guarantee Trustee's or its agent's taking such action;

                  (x)  whenever  in  the   administration   of  this   Preferred
Securities  Guarantee the Preferred Guarantee Trustee shall deem it desirable to
receive instructions with respect to enforcing any remedy or right or taking any
other  action  hereunder,  the  Preferred  Guarantee  Trustee  (i)  may  request
instructions  from the  Holders  of a  Majority  in  liquidation  amount  of the
Preferred  Securities,  (ii) may refrain from  enforcing such remedy or right or
taking such other action until such  instructions are received,  and (iii) shall
be  protected  in  conclusively  relying  on or acting in  accordance  with such
instructions.

         (b) No provision of this Preferred Securities Guarantee shall be deemed
to impose any duty or obligation on the Preferred  Guarantee  Trustee to perform
any act or acts or exercise any right,  power,  duty or obligation  conferred or
imposed on it in any jurisdiction in which it shall be illegal,  or in which the
Preferred  Guarantee  Trustee shall be  unqualified or incompetent in accordance
with  applicable  law, to perform  any such act or acts or to exercise  any such
right, power,

                                     - 9 -

duty or obligation.  No permissive power or authority available to the Preferred
Guarantee Trustee shall be construed to be a duty.

SECTION 3.3.  NOT RESPONSIBLE FOR RECITALS OR ISSUANCE OF GUARANTEE.

         The  Recitals  contained  in  this  Guarantee  shall  be  taken  as the
statements of the Guarantor, and the Preferred Guarantee Trustee does not assume
any responsibility for their correctness.  The Preferred Guarantee Trustee makes
no representation as to the validity or sufficiency of this Preferred Securities
Guarantee.


                                   ARTICLE IV
                           PREFERRED GUARANTEE TRUSTEE

Section 4.1.  Preferred Guarantee Trustee; Eligibility.

         (a) There shall at all times be a  Preferred  Guarantee  Trustee  which
shall:

                  (i) not be an Affiliate of the Guarantor; and

                  (ii) be a corporation  organized and doing  business under the
laws of the United States of America or any State or Territory thereof or of the
District of Columbia, or a corporation or Person permitted by the Securities and
Exchange Commission to act as an institutional trustee under the Trust Indenture
Act,  authorized  under such laws to exercise  corporate trust powers,  having a
combined capital and surplus of at least $50,000,000, and subject to supervision
or examination by Federal, State, Territorial or District of Columbia authority.
If such corporation  publishes reports of condition at least annually,  pursuant
to law or to the requirements of the supervising or examining authority referred
to above,  then,  for the  purposes of this  Section  4.1(a)(ii),  the  combined
capital  and  surplus  of such  corporation  shall be deemed to be its  combined
capital  and  surplus as set forth in its most  recent  report of  condition  so
published.

         (b) If at any time the  Preferred  Guarantee  Trustee shall cease to be
eligible to so act under Section 4.1(a),  the Preferred  Guarantee Trustee shall
immediately resign in the manner and with the effect set out in Section 4.2(c).

         (c)  If the  Preferred  Guarantee  Trustee  has or  shall  acquire  any
"conflicting  interest"  within  the  meaning  of  Section  310(b)  of the Trust
Indenture  Act,  the  Preferred  Guarantee  Trustee and  Guarantor  shall in all
respects  comply with the  provisions of Section  310(b) of the Trust  Indenture
Act.

                                     - 10 -

SECTION  4.2.  APPOINTMENT,  REMOVAL  AND  RESIGNATION  OF  PREFERRED  GUARANTEE
TRUSTEES.

         (a) Subject to Section 4.2(b),  the Preferred  Guarantee Trustee may be
appointed or removed without cause at any time by the Guarantor.

         (b) The Preferred  Guarantee Trustee shall not be removed in accordance
with  Section  4.2(a)  until a Successor  Preferred  Guarantee  Trustee has been
appointed and has accepted such  appointment by written  instrument  executed by
such Successor Preferred Guarantee Trustee and delivered to the Guarantor.

         (c) The  Preferred  Guarantee  Trustee  appointed  to office shall hold
office until a Successor  Preferred  Guarantee Trustee shall have been appointed
or until its removal or resignation.  The Preferred Guarantee Trustee may resign
from office  (without need for prior or subsequent  accounting) by an instrument
in writing  executed by the  Preferred  Guarantee  Trustee and  delivered to the
Guarantor,  which resignation shall not take effect until a Successor  Preferred
Guarantee  Trustee has been  appointed  and has  accepted  such  appointment  by
instrument in writing executed by such Successor Preferred Guarantee Trustee and
delivered to the Guarantor and the resigning Preferred Guarantee Trustee.

         (d)  If no  Successor  Preferred  Guarantee  Trustee  shall  have  been
appointed  and  accepted  appointment  as provided in this Section 4.2 within 60
days after  delivery to the  Guarantor  of an  instrument  of  resignation,  the
resigning  Preferred  Guarantee  Trustee  may  petition  any court of  competent
jurisdiction for appointment of a Successor  Preferred  Guarantee Trustee.  Such
court may  thereupon,  after  prescribing  such  notice,  if any, as it may deem
proper, appoint a Successor Preferred Guarantee Trustee.

         (e) No  Preferred  Guarantee  Trustee  shall be liable  for the acts or
omissions to act of any Successor Preferred Guarantee Trustee.

         (f) Upon termination of this Preferred  Securities Guarantee or removal
or resignation of the Preferred  Guarantee Trustee pursuant to this Section 4.2,
the Guarantor shall pay to the Preferred  Guarantee  Trustee all amounts accrued
to the date of such termination, removal or resignation.


                                    ARTICLE V
                                    GUARANTEE

SECTION 5.1.  GUARANTEE.

         The Guarantor irrevocably and unconditionally  agrees to pay in full to
the Holders the Guarantee Payments (without  duplication of amounts  theretofore
paid by the Trust), as and when due, regardless of any defense, right of set-off
or counterclaim that the Trust may have or assert. The Guarantor's obligation to
make a Guarantee  Payment may be  satisfied  by direct  payment of the  required
amounts by the  Guarantor  to the  Holders  or by causing  the Trust to pay such
amounts to the Holders.

                                     - 11 -

SECTION 5.2.  WAIVER OF NOTICE AND DEMAND.

         The Guarantor  hereby  waives  notice of  acceptance of this  Preferred
Securities  Guarantee  and of any  liability  to which it  applies or may apply,
presentment, demand for payment, any right to require a proceeding first against
the Trust or any other Person before proceeding against the Guarantor,  protest,
notice of  nonpayment,  notice of dishonor,  notice of redemption  and all other
notices and demands.

SECTION 5.3.  OBLIGATIONS NOT AFFECTED.

         The  obligations,  covenants,  agreements  and duties of the  Guarantor
under  this  Preferred  Securities  Guarantee  shall  in no way be  affected  or
impaired by reason of the happening from time to time of any of the following:

         (a) the release or waiver,  by  operation of law or  otherwise,  of the
performance  or  observance  by the Trust of any  express or implied  agreement,
covenant, term or condition relating to the Preferred Securities to be performed
or observed by the Trust;

         (b) the  extension  of time for the  payment by the Trust of all or any
portion of the Distributions,  Redemption Price, Liquidation Distribution or any
other sums payable under the terms of the Preferred  Securities or the extension
of time for the performance of any other obligation under, arising out of, or in
connection with, the Preferred  Securities  (other than an extension of time for
payment of Distributions,  Redemption Price,  Liquidation  Distribution or other
sum payable that results from the  extension of any interest  payment  period on
the Debentures or any extension of the maturity date of the Debentures permitted
by the Indenture);

         (c) any  failure,  omission,  delay or lack of diligence on the part of
the Holders to enforce, assert or exercise any right, privilege, power or remedy
conferred on the Holders pursuant to the terms of the Preferred  Securities,  or
any action on the part of the Trust  granting  indulgence  or  extension  of any
kind;

         (d) the voluntary or involuntary liquidation,  dissolution, sale of any
collateral, receivership,  insolvency, bankruptcy, assignment for the benefit of
creditors, reorganization,  arrangement, composition or readjustment of debt of,
or other similar  proceedings  affecting,  the Trust or any of the assets of the
Trust;

         (e) any  invalidity  of, or  defect or  deficiency  in,  the  Preferred
Securities;

         (f) any  failure or  omission  to receive  any  regulatory  approval or
consent  required in  connection  with the Preferred  Securities  (or the common
equity  securities  issued by the Trust),  including  the failure to receive any
approval of the Board of Governors of the Federal  Reserve  System  required for
the redemption of the Preferred Securities;

                                     - 12 -

         (g) the settlement or compromise of any obligation guaranteed hereby or
hereby incurred; or

         (h) any other circumstance whatsoever that might otherwise constitute a
legal or equitable  discharge or defense of a guarantor,  it being the intent of
this  Section  5.3 that the  obligations  of the  Guarantor  hereunder  shall be
absolute and unconditional under any and all circumstances.

         There  shall be no  obligation  of the  Holders  to give  notice to, or
obtain  consent of, the  Guarantor  with respect to the  happening of any of the
foregoing.

SECTION 5.4.  RIGHTS OF HOLDERS.

         (a) Subject to Section 5.4(b), the Holders of a Majority in liquidation
amount of the Preferred Securities have the right to direct the time, method and
place of conducting of any proceeding for any remedy  available to the Preferred
Guarantee  Trustee  in  respect  of  this  Preferred   Securities  Guarantee  or
exercising  any trust or power  conferred upon the Preferred  Guarantee  Trustee
under this Preferred Securities Guarantee.

         (b) Any Holder of Preferred  Securities  may  institute and prosecute a
legal proceeding directly against the Guarantor to enforce its rights under this
Preferred  Securities  Guarantee,  without first  instituting a legal proceeding
against the Trust, the Preferred Guarantee Trustee or any other Person.

SECTION 5.5.  GUARANTEE OF PAYMENT.

         This Preferred  Securities Guarantee creates a guarantee of payment and
not of collection.

SECTION 5.6.  SUBROGATION.

         The Guarantor shall be subrogated to all (if any) rights of the Holders
of Preferred Securities against the Trust in respect of any amounts paid to such
Holders by the Guarantor under this Preferred  Securities  Guarantee;  provided,
however,  that the  Guarantor  shall  not  (except  to the  extent  required  by
mandatory  provisions  of law) be entitled to enforce or exercise any right that
it may acquire by way of subrogation or any  indemnity,  reimbursement  or other
agreement,  in all cases as a result of payment under this Preferred  Securities
Guarantee,  if, at the time of any such payment,  any amounts are due and unpaid
under this Preferred  Securities  Guarantee.  If any amount shall be paid to the
Guarantor in violation of the preceding  sentence,  the Guarantor agrees to hold
such amount in trust for the Holders and to pay over such amount to the Holders.

                                     - 13 -

SECTION 5.7.  INDEPENDENT OBLIGATIONS.

         The  Guarantor   acknowledges   that  its  obligations   hereunder  are
independent  of the  obligations  of the Trust  with  respect  to the  Preferred
Securities,  and that the  Guarantor  shall be liable as principal and as debtor
hereunder to make  Guarantee  Payments  pursuant to the terms of this  Preferred
Securities Guarantee  notwithstanding the occurrence of any event referred to in
subsections (a) through (h), inclusive, of Section 5.3 hereof.


                                   ARTICLE VI
                    LIMITATION OF TRANSACTIONS; SUBORDINATION

SECTION 6.1.  LIMITATION OF TRANSACTIONS.

         So long as any Preferred Securities remain outstanding,  if there shall
have occurred an Event of Default under this Preferred Securities Guarantee,  an
event of  default  under the Trust  Agreement  or  during an  Extended  Interest
Payment Period (as defined in the  Indenture),  then (a) the Guarantor shall not
declare or pay any  dividend  on,  make any  distributions  with  respect to, or
redeem, purchase,  acquire or make a liquidation payment with respect to, any of
its capital stock (other than as a result of a  reclassification  of its capital
stock for another class of its capital  stock) and (b) the  Guarantor  shall not
make any payment of interest or principal on or repay,  repurchase or redeem any
debt securities  issued by the Guarantor which rank pari passu with or junior to
the Debentures.

SECTION 6.2  RANKING.

         This  Preferred  Securities  Guarantee  will  constitute  an  unsecured
obligation  of the Guarantor  and will rank  subordinate  and junior in right of
payment to all Senior Debt, Subordinated Debt and Additional Senior Obligations,
as defined in the Indenture,  of the Guarantor,  to the extent and in the manner
set forth in the Indenture,  and the applicable provisions of the Indenture will
apply, in all relevant respects, to the obligations of the Guarantor hereunder.


                                   ARTICLE VII
                                   TERMINATION

SECTION 7.1.  TERMINATION.

         This  Preferred  Securities  Guarantee  shall  terminate  upon (i) full
payment of the  Redemption  Price of all  Preferred  Securities,  (ii) upon full
payment of the  amounts  payable in  accordance  with the Trust  Agreement  upon
liquidation of the Trust,  or (iii) upon  distribution  of the Debentures to the
Holders  of  the  Preferred  Securities.  Notwithstanding  the  foregoing,  this
Preferred  Securities  Guarantee  shall  continue  to be  effective  or shall be
reinstated,  as the  case  may  be,  if at any  time  any  Holder  of  Preferred
Securities must restore payment of any sums paid under the Preferred  Securities
or under this Preferred Securities Guarantee.

                                     - 14 -

                                  ARTICLE VIII
                                 INDEMNIFICATION

SECTION 8.1.  EXCULPATION.

         (a) No Indemnified  Person shall be liable,  responsible or accountable
in damages or  otherwise to the  Guarantor  or any Covered  Person for any loss,
damage or claim  incurred by reason of any act or omission  performed or omitted
by such  Indemnified  Person in good  faith in  accordance  with this  Preferred
Securities  Guarantee and in a manner that such  Indemnified  Person  reasonably
believed to be within the scope of the authority  conferred on such  Indemnified
Person  by  this  Preferred  Securities  Guarantee  or by  law,  except  that an
Indemnified  Person shall be liable for any such loss,  damage or claim incurred
by reason of such  Indemnified  Person's  negligence or willful  misconduct with
respect to such acts or omissions.

         (b) An Indemnified  Person shall be fully  protected in relying in good
faith upon the records of the  Guarantor  and upon such  information,  opinions,
reports or statements presented to the Guarantor by any Person as to matters the
Indemnified   Person   reasonably   believes  are  within  such  other  Person's
professional or expert competence and who has been selected with reasonable care
by or on behalf of the Guarantor,  including information,  opinions,  reports or
statements  as to the value  and  amount of the  assets,  liabilities,  profits,
losses,  or any other facts pertinent to the existence and amount of assets from
which Distributions to Holders of Preferred Securities might properly be paid.

SECTION 8.2.  INDEMNIFICATION.

         The Guarantor agrees to indemnify each  Indemnified  Person for, and to
hold each Indemnified  Person harmless against,  any loss,  liability or expense
incurred  without  negligence  or bad  faith on its part,  arising  out of or in
connection  with  the  acceptance  or  administration  of the  trust  or  trusts
hereunder, including the costs and expenses (including reasonable legal fees and
expenses) of defending itself against, or investigating,  any claim or liability
in connection  with the exercise or  performance  of any of its powers or duties
hereunder.  The  obligation  to indemnify as set forth in this Section 8.2 shall
survive the termination of this Preferred Securities Guarantee.


                                   ARTICLE IX
                                  MISCELLANEOUS

SECTION 9.1.  SUCCESSORS AND ASSIGNS.

         All guarantees and  agreements  contained in this Preferred  Securities
Guarantee  shall  bind  the  successors,   assigns,   receivers,   trustees  and
representatives  of the  Guarantor and shall inure to the benefit of the Holders
of the Preferred Securities then outstanding.

                                     - 15 -

SECTION 9.2.  AMENDMENTS.

         Except with  respect to any changes  that do not  materially  adversely
affect  the rights of  Holders  (in which  case no  consent  of Holders  will be
required),  this  Preferred  Securities  Guarantee  may only be amended with the
prior  approval of the Holders of at least a Majority in  Liquidation  Amount of
the Preferred  Securities.  The provisions of Article VI of the Trust  Agreement
with  respect to meetings of Holders of the  Preferred  Securities  apply to the
giving of such approval.

SECTION 9.3.  NOTICES.

         All notices provided for in this Preferred  Securities  Guarantee shall
be in  writing,  duly  signed  by the party  giving  such  notice,  and shall be
delivered, telecopied or mailed by registered or certified mail, as follows:

         (a) If given  to the  Preferred  Guarantee  Trustee,  at the  Preferred
Guarantee  Trustee's  mailing  address set forth below (or such other address as
the  Preferred  Guarantee  Trustee  may give  notice  of to the  Holders  of the
Preferred Securities):

                           Wilmington Trust Company
                           Rodney Square North
                           1100 North Market Street
                           Wilmington, Delaware  19890-0001
                           Attention:  Corporate Trust Administrator

         (b) If given to the Guarantor,  at the Guarantor's  mailing address set
forth below (or such other  address as the  Guarantor  may give notice of to the
Holders of the Preferred Securities):

                           Wintrust Financial Corporation
                           727 North Bank Lane
                           Lake Forest, Illinois 60045
                           Attention:  David A. Dykstra, Chief Financial Officer

         (c) If given to any Holder of Preferred Securities,  at the address set
forth on the books and records of the Trust.

         All such  notices  shall be deemed to have been given when  received in
person,  telecopied  with  receipt  confirmed,  or mailed by first  class  mail,
postage prepaid except that if a notice or other document is refused delivery or
cannot be delivered  because of a changed  address of which no notice was given,
such notice or other document shall be deemed to have been delivered on the date
of such refusal or inability to deliver.

                                     - 16 -

SECTION 9.4.  BENEFIT.

         This  Preferred  Securities  Guarantee is solely for the benefit of the
Holders of the  Preferred  Securities  and,  subject to Section  3.1(a),  is not
separately transferable from the Preferred Securities.

SECTION 9.5.  GOVERNING LAW.

         THIS PREFERRED SECURITIES GUARANTEE SHALL BE GOVERNED BY, AND CONSTRUED
AND INTERPRETED IN ACCORDANCE WITH, THE LAWS OF THE STATE OF ILLINOIS.

         This Preferred  Securities Guarantee is executed as of the day and year
first above written.

                                      WINTRUST FINANCIAL CORPORATION,
                                      as Guarantor

                                      By:_______________________________________
                                      Its:______________________________________


                                      WILMINGTON TRUST COMPANY
                                      as Preferred Guarantee Trustee

                                      By:_______________________________________
                                      Its:______________________________________