May, 2001




Dear Shareholders,

         This  letter  provides  a brief  update  on our  financial  performance
through  the  first  quarter  of  2001  and  other  news of  Wintrust  Financial
Corporation.  Our April 20, 2001 news  release of our  earnings  for the quarter
ended March 31, 2001 is also attached for your information.

HIGHLIGHTS FOR FIRST QUARTER OF 2001

     We again  achieved  record  earnings  for this  quarter  while  assets also
increased  to record  levels.  Here is a summary of our  financial  results  and
accomplishments for the three months ending March 31, 2001:

     o    Net  income of $3.9  million  for the  quarter  ended  March 31,  2001
          increased 25% over the first quarter of 2000;

     o    On a per share  basis,  net income  totaled  $0.44 per diluted  common
          share for the first  quarter of 2001,  a 26%  increase  as compared to
          year ago;

     o    Excluding a required  charge for a change in an accounting  principle,
          net income  increased 33% over the prior year and earnings per diluted
          common share increased 34%;

     o    Return on average equity increased to 15.39% from 13.32% for the prior
          year quarter;

     o    Total assets rose to $2.17  billion as of March 31, 2001,  an increase
          of $395 million, or 22%, compared to a year ago;

     o    Total deposits were $1.92 billion as of March 31, 2001, an increase of
          $383 million, or 25%, compared to a year ago;

     o    Total loans grew to $1.66 billion as of March 31, 2001, an increase of
          $348 million, or 27%, compared to a year ago;

     o    Net  overhead  ratio  declined  to 1.75%  from 1.84% in the prior year
          quarter; and

     o    In February  2001, we opened a new branch in McHenry,  Illinois  under
          the name, McHenry Bank & Trust. This gives Crystal Lake Bank & Trust a
          total of four facilities in the fast growing McHenry County area. MB&T
          is also off to a very fast start as folks from  McHenry are  beginning
          to experience community banking the way it ought to be.

                                     - 1 -

INCOME AND EARNINGS

         Although the interest rate  environment was quite volatile in the first
quarter with  substantial rate cuts by the Federal Reserve Bank, we were able to
maintain  a  relatively  stable net  interest  margin  and net  interest  income
increased 25% as compared to the prior year.

         Non-interest  income  showed a sharp  increase in the first quarter and
totaled $6.9 million, an increase of 60% over the prior year. The growth in this
category  was  mainly a result of a higher  level of fees from  originating  and
selling  residential  mortgage loans into the secondary  market and enhanced fee
income  received  from  covered call option  transactions  which are designed to
increase the returns on certain U.S.  Treasury and agency securities held in the
Company's investment portfolio.

         Non-interest  expenses  totaled  $16.0 million for the first quarter of
2001  representing  an  increase  of 32% over a year ago.  These  increases  are
attributable  to the general  growth of the  Company's  balance  sheet and costs
associated with supporting our additional fee revenue.

         Also, the first quarter of 2001 earnings  included a cumulative  effect
of a change in  accounting  principle  for interest  rate cap  contracts,  which
resulted in an after-tax  charge of $254,000.  Without this  required  change in
accounting  practice,  our  earnings per share would have been $0.03 higher on a
diluted share basis. This change in accounting  principle was simply a change in
the timing of recognizing the cost of our interest rate cap contracts and not an
economic loss to the Company.

YEAR-TO-DATE PERFORMANCE VERSUS GOAL

         At Wintrust,  we set  aggressive  goals and  evaluate  our  performance
versus those goals.  Reaching these financial goals over the next few years will
make our Company a high performing bank relative to its peers. We have made good
progress towards achieving most of these goals and expect continued  improvement
as  our  young   franchises--  the  de  novo  community  banks,  and  our  other
subsidiaries   Wintrust   Asset   Management,   First   Insurance   Funding  and
Tricom--mature. The following performance statistics indicate that we are making
overall improvement in these areas.



                                                                        QUARTER ENDED
                                              -------------------------------------------------------------------
                                                MARCH        DEC.        SEPT.      JUNE    MARCH 31,    DEC.
                                                 31,          31,         30,       30,                   31,
                                     GOAL        2001        2000       2000(1)     2000      2000       1999
                                     ----        ----        ----       ----        ----      ----       ----





                                                                                   
Core Net Interest Margin (2)       4 - 4.5%     3.94%        3.93%       3.92%     3.94%      3.84%      3.75%

Net Overhead Ratio                 1.5 - 2%     1.75%        1.90%       1.90%     1.89%      1.84%      1.89%

Return on Average Equity           20 - 25%    15.39%       15.44%      14.74%    13.86%     13.32%     12.66%

Return on Average Assets               1.5%     0.75%        0.75%       0.75%     0.75%      0.73%      0.68%

Earnings per diluted
   Common share                                 $0.44        $0.43       $0.41     $0.37      $0.35      $0.32

Non-Performing Assets
   as a percent of total assets                 0.64%        0.46%       0.35%     0.33%      0.41%      0.41%
- ----------------------------
<FN>
(1)  Excludes  the impact of a one-time  charge of to $2.7  million to its third
     quarter earnings.

(2)  By definition, our Core Net Interest Margin excludes the impact of interest
     expense associated with the Company's Trust Preferred Securities offerings.
</FN>


                                     - 2 -

NON-PERFORMING ASSETS

         Relative to the  problems  some other  banks are having,  our core loan
portfolio is very solid. The level of non-performing  assets in our core banking
loan portfolio remained low and very manageable at $2.5 million, or 0.22% of the
core banking loan  portfolio.  The  non-performing  assets in the indirect  auto
portfolio remained fairly constant at approximately  $600,000,  or 0.31% of that
portfolio.  The  Tricom  finance  receivable  portfolio  had  only  $112,000  of
non-performing assets.

         Non-performing  premium finance receivables increased to $10.7 million,
or 3.22% of that  portfolio.  The  increase in  non-performing  premium  finance
receivables  over the  course  of recent  quarters  is  primarily  a result of a
proportionately large number of delinquent accounts associated with new business
derived  from a marketing  arrangement  entered into in July,  1999.  Management
identified  the issue in the  second  half of 2000 and began to take  corrective
measures to eliminate a significant  number of these new business  relationships
that were generating  disproportionately high delinquencies.  Specifically,  the
Company has eliminated more than 1,300  relationships with insurance agents that
were  referring  new business to our premium  finance  subsidiary.  These agents
represented  about 30% of our  transactions  but only  accounted  for 13% of the
total  dollar  amount of our premium  finance  loan  volume.  The volume of work
associated with those small balance  accounts placed an increased  burden on the
collection efforts of the premium finance  subsidiary.  The impact of this prior
business is still reflected in the non-performing asset totals as these accounts
customarily take 60-150 days to convert the collateral held by insurance company
into cash  collections.  Because of the  longer-term  nature of  converting  the
collateral to cash, we believe our  corrective  actions and increased  resources
devoted to  collections  should  result in  significant  improvement  during the
second  quarter of 2001 and that the  non-performing  totals have reached  their
peak  in the  first  quarter.  As  such,  the  delinquency  levels  should  show
improvement over the next two quarters.

DE NOVO EXPANSION ACTIVITIES

         Our seventh separately chartered de novo bank, Northbrook Bank & Trust,
is off to a terrific  start after  opening in November  2000.  At the writing of
this  report,  they have assets over $45 million and are ahead of their  earning
goals as well.  That's  remarkable  given that they are  operating out of a very
small temporary  facility with no  drive-through  location.  NB&T recently broke
ground on their new permanent main bank facility with an attached  drive-through
at the  corner of  Shermer  Road and  Waukegan  Road.  Their  grand  opening  is
scheduled for early 2002.

     We have  also  made  good  progress  on a number  of new  branches  for our
existing banks.

     o    Renovation  of a new  facility in  Winnetka,  which will be an upgrade
          from the current branch, is coming along fine. That facility should be
          opened during the summer.

     o    Construction  has started on Hoffman Estates  Community Bank, a branch
          of Barrington  Bank & Trust.  This beautiful  facility is scheduled to
          open in the latter half of 2001.

     o    As noted  above,  in  February,  we opened a new  facility in McHenry,
          Illinois.

     o    Wauconda  Community Bank, a branch of Libertyville  Bank & Trust,  has
          just  broken  ground on a new  permanent  main bank and  drive-through
          facility on our property  centrally located across the street from the
          big bank competitor in town.

                                     - 3 -

NEW INVESTOR RELATIONS WEB SITE

         Check  out our new  state-of-the-art  investor  relations  web  site at
www.wintrust.com.  It is powered by PR Newswire,  the same firm that distributes
financial press  releases.  We created a new look and utilized some advanced web
navigation  features  that are  befitting a  progressive  company like  Wintrust
Financial  Corporation.  The new site also  allows  for  e-mail  alerts for news
releases  and stock  price  targets.  Hope you like it.  Please  let us know any
comments you might have.

ANNUAL MEETING

         The 2001 Annual Meeting of Shareholders  will be held on Thursday,  May
24,  2001 at 10:00 a.m. at the Hyatt  Deerfield  Hotel at 1750 Lake Cook Road in
Deerfield, Illinois. You should have already received your 2000 Annual Report to
Shareholders and proxy statement. If you have not done so already, please return
the proxy card or vote via the telephone or the internet.  We hope to see you at
our annual  meeting.  We will look  forward  to  providing  you with  additional
details about our improving  results and  presenting to you our strategy for the
future.

SUMMARY

         In summary,  we are very pleased with the continued  growth in earnings
and assets in the first  quarter.  We are working  diligently  to  continue  our
unique growth story while improving our earnings  level.  We remain  comfortable
that we will be able to meet or exceed the analysts' consensus earnings estimate
for 2001 of $1.84 per share.

                                  Yours truly,




     /s/ John S. Lillard                         /s/ Edward J. Wehmer
     ---------------------                       -----------------------
         John S. Lillard                             Edward J. Wehmer
         Chairman                                    President and CEO




- --------------------------------------------------------------------------------
FORWARD-LOOKING STATEMENTS
- --------------------------------------------------------------------------------
This  letter  contains  forward-looking  statements  related  to  the  Company's
financial  performance  that are based on  estimates.  The Company  intends such
forward-looking  statements  to be covered  by the safe  harbor  provisions  for
forward-looking statements contained in the Private Securities Litigation Reform
Act of 1995, and is including this statement for purposes of invoking these safe
harbor  provisions.  Actual results could differ materially from those addressed
in the  forward-looking  statements  due to factors  such as changes in economic
conditions,  competition,  or other factors that may  influence the  anticipated
growth rate of loans and  deposits,  the quality of the loan  portfolio and loan
and deposit  pricing,  unanticipated  changes in interest rates that  negatively
impact net interest  income,  future  events that may cause  unforeseen  loan or
lease losses,  slower than anticipated  development and growth of Tricom and the
new  trust and  investment  business,  unanticipated  changes  in the  temporary
staffing industry, the ability to adapt successfully to technological changes to
compete  effectively  in the  marketplace,  the  ability to  attract  and retain
experienced senior management,  and the ability to recover on the loss resulting
from the  fraudulent  loan  scheme  perpetrated  against the  Company's  premium
finance  subsidiary.  Therefore,  there can be no assurances  that future actual
results will correspond to these forward-looking statements.
- --------------------------------------------------------------------------------

                                     - 4 -

                         Wintrust Financial Corporation
                727 North Bank Lane, Lake Forest, Illinois 60045


NEWS RELEASE

FOR IMMEDIATE RELEASE                                             April 20, 2001
- ---------------------

FOR MORE INFORMATION CONTACT:
Edward J. Wehmer, President & Chief Executive Officer
David A. Dykstra, Executive Vice President & Chief Financial Officer
(847) 615-4096
Website address:  www.wintrust.com


                     WINTRUST FINANCIAL CORPORATION REPORTS
                     --------------------------------------
             RECORD FIRST QUARTER EARNINGS AHEAD 25% OVER PRIOR YEAR
             -------------------------------------------------------


         LAKE FOREST,  ILLINOIS -- Wintrust Financial  Corporation  ("Wintrust")
(Nasdaq:  WTFC)  announced  record  quarterly net income of $3.9 million for the
quarter  ended March 31, 2001,  an increase of $782,000,  or 25%,  over the $3.1
million  recorded in the first quarter of 2000. On a per share basis, net income
for the first  quarter of 2001 totaled $0.44 per diluted  common share,  a $0.09
per share, or 26%, increase as compared to the 2000 first quarter total of $0.35
per diluted common share. Included in the first quarter of 2001, is a cumulative
effect of a change in accounting  for interest rate caps,  which  resulted in an
after-tax charge of $254,000,  or $0.03 per diluted share. The return on average
equity for the first  quarter of 2001  increased  to 15.39%  from 13.32% for the
prior year quarter.

         Total assets rose to $2.17  billion at March 31,  2001,  an increase of
$395 million,  or 22%,  compared to $1.77 billion a year ago, and an increase of
$64 million, or 3%, since December 31, 2000. Total deposits as of March 31, 2001
were $1.92  billion,  an increase of $383 million,  or 25%, as compared to $1.53
billion at March 31, 2000, and an increase of $90 million, or 5%, since year-end
2000. Total loans grew to $1.66 billion as of March 31, 2001, a $348 million, or
27%,  increase  over the  $1.31  billion  balance  as of a year  ago,  and a $98
million, or 6%, increase since December 31, 2000.

         For the first  quarter  of 2001,  net  interest  income  totaled  $17.3
million  and  increased  $3.4  million,  or 25%,  as  compared to the prior year
quarterly total of $13.9 million.  Non-interest  income totaled $6.9 million for
the first  quarter of 2001 and increased  $2.6  million,  or 60%, over the first
quarter of 2000.  The  increase  was mainly a result of  increases  in fees from
originating and selling residential mortgage loans into the secondary market and
from
                                      - 5 -


fees from ongoing transactions  designed to increase the returns on certain U.S.
Treasury and agency securities in the Company's investment portfolio.  Partially
offsetting these increases was a decline in gains on the sale of premium finance
receivables. Non-interest expense totaled $16.0 million for the first quarter of
2001 and  increased  $3.9  million,  or 32%,  over the  first  quarter  of 2000.
Increases are attributable to the general growth of the Company's  balance sheet
and fee-based businesses. The net overhead ratio declined to 1.75% from 1.84% in
the prior year quarter.

         "We are very pleased with the  continued  growth in earnings and assets
in the first quarter," commented Edward J. Wehmer, President and Chief Executive
Officer.  "We are working  diligently  to continue our unique growth story while
improving our earnings level and we remain  comfortable  that we will be able to
meet or exceed the analysts'  consensus  earnings estimate for 2001 of $1.84 per
share."

         Wintrust's key operating  measures  continue to show impressive  growth
rates in 2001 as compared to the prior year as evidenced by the table below:



                                                                  Quarter            Quarter
                                                                   Ended              Ended             Percent
        In thousands, except per share data                       3/31/01            3/31/00          Improvement
        -----------------------------------                       -------            -------          -----------

                                                                                                
        Net income                                                  $  3,904           $  3,122          25.1%
        Net income per common share - Diluted                       $   0.44           $   0.35          25.7%

        Net revenues                                                $ 24,126           $ 18,146          33.0%
        Net interest income                                         $ 17,276           $ 13,868          24.6%

        Net interest margin                                            3.67%              3.65%           0.5%
        Core net interest margin(1)                                    3.94%              3.84%           2.6%
        Net overhead ratio                                             1.75%              1.84%           4.9%
        Return on average assets                                       0.75%              0.73%           2.7%
        Return on average equity                                      15.39%             13.32%          15.5%

        Total assets                                              $2,166,630         $1,771,891          22.3%
        Total loans, net of unearned income                       $1,655,543         $1,307,796          26.6%
        Total deposits                                            $1,916,756         $1,533,661          25.0%

        Book value per common share                                 $  12.29           $  10.83          13.5%

<FN>
(1)  Core net interest  margin  excludes  interest  expense  associated with the
     Company's Trust Preferred Securities.
</FN>


                                      - 6 -

         Wintrust is a financial  services holding company whose common stock is
traded on the Nasdaq Stock Market(R).  Its seven suburban Chicago community bank
subsidiaries,  each of which was founded as a de novo bank since  December 1991,
are located in high income retail  markets -- Lake Forest Bank & Trust  Company,
Hinsdale Bank & Trust  Company,  North Shore  Community  Bank & Trust Company in
Wilmette,  Libertyville  Bank & Trust Company,  Barrington Bank & Trust Company,
Crystal Lake Bank & Trust Company and Northbrook Bank & Trust Company. The banks
also operate facilities in Lake Bluff, Highwood,  Glencoe,  Winnetka,  Clarendon
Hills, Western Springs,  Skokie, Wauconda and McHenry,  Illinois.  Additionally,
the Company  operates  three  non-bank  subsidiaries.  First  Insurance  Funding
Corporation,  one of the largest commercial  insurance premium finance companies
operating in the United States,  serves commercial loan customers throughout the
country. Wintrust Asset Management Company, a trust subsidiary,  allows Wintrust
to service  customers'  trust and  investment  needs at each  banking  location.
Tricom, Inc. of Milwaukee provides short-term accounts receivable  financing and
value-added  out-sourced  administrative  services,  such as data  processing of
payrolls,  billing and cash management  services,  to temporary staffing service
clients located  throughout the United States.  Currently,  Wintrust  operates a
total of 29  banking  offices  and is in the  process  of  constructing  several
additional  branch  facilities.  All of the Company's  banking  subsidiaries are
locally  managed  with  large  local  boards of  directors.  Wintrust  Financial
Corporation has been one of the fastest growing de novo bank groups in Illinois.

                                     - 7 -

WINTRUST FINANCIAL CORPORATION
SELECTED FINANCIAL HIGHLIGHTS
(DOLLARS IN THOUSANDS, EXCEPT PER SHARE DATA)


- ------------------------------------------------------------------------------------------------------------------
                                                                                       THREE MONTHS
                                                                                      ENDED MARCH 31,
                                                                                  2001                2000
- ------------------------------------------------------------------------------------------------------------------
                                                                                                
SELECTED FINANCIAL CONDITION DATA
  (AT END OF PERIOD):
  Total assets                                                                    $ 2,166,630         $ 1,771,891
  Total deposits                                                                    1,916,756           1,533,661
  Total loans, net of unearned income                                               1,655,543           1,307,796
  Notes payable                                                                        38,875              14,050
  Long-term debt - trust preferred securities                                          51,050              31,050
  Total shareholders' equity                                                          105,872              94,835
- ------------------------------------------------------------------------------------------------------------------

SELECTED STATEMENTS OF INCOME DATA:
  Net interest income                                                               $  17,276           $  13,868
  Net revenues                                                                         24,126              18,146
  Income before taxes and cumulative effect of accounting change                        6,517               4,896
  Net income before cumulative effect of accounting change                              4,158               3,122
  Net income                                                                            3,904               3,122
  Net income per common share - Basic                                                    0.45                0.35
  Net income per common share - Diluted                                                  0.44                0.35
- ------------------------------------------------------------------------------------------------------------------

SELECTED FINANCIAL RATIOS AND OTHER DATA:
Performance Ratios:
  Net interest margin                                                                   3.67%               3.65%
  Core net interest margin (1)                                                          3.94%               3.84%
  Non-interest income to average assets                                                 1.32%               1.01%
  Non-interest expense to average assets                                                3.07%               2.85%
  Net overhead ratio                                                                    1.75%               1.84%
  Return on average assets                                                              0.75%               0.73%
  Return on average equity                                                             15.39%              13.32%

  Average total assets                                                            $ 2,110,058         $ 1,708,494
  Average shareholders' equity                                                        102,851              94,281
  Average loan-to-average deposit ratio                                                 87.1%               88.4%

Common Share Data at end of period:
  Market price per common share                                                      $  18.63            $  14.25
  Book value per common share                                                           12.29               10.83
  Common shares outstanding                                                         8,616,976           8,752,643

Other Data at end of period:
  Number of:
    Bank subsidiaries                                                                       7                   6
    Non-bank subsidiaries                                                                   3                   3
    Banking offices                                                                        29                  25

- ------------------------------------------------------------------------------------------------------------------
<FN>
(1)  The core net interest margin excludes the interest expense  associated with
     the Company's Trust Preferred Securities.
</FN>


                                      - 8 -

WINTRUST FINANCIAL CORPORATION AND SUBSIDIARIES
CONSOLIDATED STATEMENTS OF CONDITION (UNAUDITED)


(In thousands)


                                                                        MARCH 31,           December 31,           March 31,
                                                                          2001                  2000                 2000
- ---------------------------------------------------------------------------------------------------------------------------------
                                                                                                             
ASSETS
Cash and due from banks                                                     $  48,152             $  65,413            $  42,664
Federal funds sold and securities purchased under resale agreements           170,696               164,641               97,099
Interest-bearing deposits with banks                                               74                   182                  288
Available-for-Sale securities, at fair value                                  168,365               193,105              210,825
Loans, net of unearned income                                               1,655,543             1,558,020            1,307,796
    Less: Allowance for possible loan losses                                   11,067                10,433                9,359
- ---------------------------------------------------------------------------------------------------------------------------------
    Net loans                                                               1,644,476             1,547,587            1,298,437
Premises and equipment, net                                                    87,717                86,386               74,891
Accrued interest receivable and other assets                                   36,558                34,722               36,382
Goodwill and other intangible assets, net                                      10,592                10,770               11,305
- ---------------------------------------------------------------------------------------------------------------------------------

    Total assets                                                          $ 2,166,630            $2,102,806           $1,771,891
=================================================================================================================================


Liabilities and Shareholders' Equity
Deposits:
  Non-interest bearing                                                      $ 182,364             $ 198,319            $ 155,507
  Interest bearing                                                          1,734,392             1,628,257            1,378,154
- ---------------------------------------------------------------------------------------------------------------------------------
    Total  deposits                                                         1,916,756             1,826,576            1,533,661

Short-term borrowings                                                          14,727                43,639               68,721
Notes payable                                                                  38,875                27,575               14,050
Long-term debt - trust preferred securities                                    51,050                51,050               31,050
Accrued interest payable and other liabilities                                 39,350                51,690               29,574
- ---------------------------------------------------------------------------------------------------------------------------------

    Total liabilities                                                       2,060,758             2,000,530            1,677,056
- ---------------------------------------------------------------------------------------------------------------------------------

Shareholders' equity:
  Preferred stock                                                                   -                     -                    -
  Common stock                                                                  8,859                 8,857                8,838
  Surplus                                                                      83,745                83,710               83,487
  Common stock warrants                                                           100                   100                  100
  Treasury stock, at cost                                                      (3,863)               (3,863)              (1,306)
  Retained earnings                                                            17,137                13,835                6,235
  Accumulated other comprehensive loss                                           (106)                 (363)              (2,519)
- ---------------------------------------------------------------------------------------------------------------------------------
    Total shareholders' equity                                                105,872               102,276               94,835
- ---------------------------------------------------------------------------------------------------------------------------------

    Total liabilities and shareholders' equity                            $ 2,166,630           $ 2,102,806          $ 1,771,891
=================================================================================================================================


                                      - 9 -

WINTRUST FINANCIAL CORPORATION AND SUBSIDIARIES
CONSOLIDATED STATEMENTS OF INCOME (UNAUDITED)


(IN THOUSANDS, EXCEPT PER SHARE DATA)
                                                                   THREE MONTHS ENDED
                                                                       MARCH 31,
                                                                   2001         2000
- -----------------------------------------------------------------------------------------
                                                                          
INTEREST INCOME
  Interest and fees on loans                                       $ 36,863     $ 28,738
  Interest bearing deposits with banks                                    2           16
  Federal funds sold and securities purchased under resale agreements 1,122          247
  Securities                                                          3,795        3,308
- -----------------------------------------------------------------------------------------
    Total interest income                                            41,782       32,309
- -----------------------------------------------------------------------------------------

INTEREST EXPENSE
   Interest on deposits                                              22,172       16,599
   Interest on short-term borrowings and notes payable                1,046        1,107
   Interest on long-term debt - trust preferred securities            1,288          735
- -----------------------------------------------------------------------------------------
     Total interest expense                                          24,506       18,441
- -----------------------------------------------------------------------------------------

NET INTEREST INCOME                                                  17,276       13,868
Provision for possible loan losses                                    1,638        1,141
- -----------------------------------------------------------------------------------------

Net interest income after provision for possible loan losses         15,638       12,727
- -----------------------------------------------------------------------------------------

NON-INTEREST INCOME
  Fees on mortgage loans sold                                         1,524          483
  Service charges on deposit accounts                                   547          469
  Trust fees                                                            450          472
  Gain on sale of premium finance receivables                           942        1,241
  Administrative services revenue                                     1,021        1,013
  Net securities gains                                                  286            3
  Other                                                               2,080          597
- -----------------------------------------------------------------------------------------
    Total non-interest income                                         6,850        4,278
- -----------------------------------------------------------------------------------------

NON-INTEREST EXPENSE
  Salaries and employee benefits                                      8,478        6,335
  Occupancy, net                                                      1,244        1,010
  Equipment expense                                                   1,484        1,149
  Data processing                                                       830          680
  Advertising and marketing                                             307          249
  Professional fees                                                     531          295
  Amortization of intangibles                                           178          178
  Other                                                               2,919        2,213
- -----------------------------------------------------------------------------------------
    Total non-interest expense                                       15,971       12,109
- -----------------------------------------------------------------------------------------

Income before taxes and cumulative effect of accouting change         6,517        4,896
Income tax expense                                                    2,359        1,774
- -----------------------------------------------------------------------------------------

Income before cumulative effect of accounting change                  4,158        3,122
Cumulative effect of accounting change, net of tax                      254            -
- -----------------------------------------------------------------------------------------

NET INCOME                                                          $ 3,904      $ 3,122
=========================================================================================

BASIC EARNINGS PER SHARE:
  Income before cumulative effect of accounting change               $ 0.48       $ 0.35
  Cumulative effect of accounting change, net of tax                   0.03            -
- -----------------------------------------------------------------------------------------
NET INCOME PER COMMON SHARE - BASIC                                  $ 0.45       $ 0.35
=========================================================================================

DILUTED EARNINGS PER SHARE:
  Income before cumulative effect of accounting change               $ 0.47       $ 0.35
  Cumulative effect of accounting change, net of tax                   0.03            -
- -----------------------------------------------------------------------------------------
NET INCOME PER COMMON SHARE - DILUTED                                $ 0.44       $ 0.35
=========================================================================================

- -----------------------------------------------------------------------------------------
CASH DIVIDENDS DECLARED PER COMMON SHARE                             $ 0.07       $ 0.05
=========================================================================================

Weighted average common shares outstanding                            8,615        8,798
Dilutive potential common shares                                        303          213
- -----------------------------------------------------------------------------------------
Average common shares and dilutive common shares                      8,918        9,011
=========================================================================================


                                     - 10 -

NET INTEREST INCOME

The following  tables present a summary of the Company's net interest income and
related net interest margins,  calculated on a fully  tax-equivalent  basis, for
the three-month periods ended March 31, 2001 and 2000:



                                                        FOR THE QUARTER ENDED                       For the Quarter Ended
                                                            MARCH 31, 2001                              March 31, 2000
                                             -----------------------------------------    ---------------------------------------
(dollars in thousands)                            AVERAGE      INTEREST       RATE            Average       Interest      Rate
- ----------------------                       ---------------- ------------- ----------    --------------- ------------- ---------

                                                                                                          
Liquidity management assets (1) (2)            $   319,028     $   4,933         6.27%       $ 228,838     $   3,548        6.24%
Loans, net of unearned income (2)                1,612,617        37,054         9.32          1,309,355      28,844        8.86
                                             ---------------- ------------- ----------    --------------- ------------- ---------
   Total earning assets                          1,931,645        41,987         8.82%       1,538,193        32,392        8.47%
                                             ---------------- ------------- ----------    --------------- ------------- ---------

Interest-bearing deposits                        1,669,942        22,172         5.38%       1,333,012        16,598        5.01%
Short-term borrowings and notes payable             67,897         1,046         6.25           74,048         1,108        6.02
Long-term debt - trust preferred securities         51,050         1,288        10.09           31,050           735        9.47
                                             ---------------- ------------- ----------    --------------- ------------- ---------
   Total interest-bearing liabilities            1,788,889        24,506         5.56%       1,438,110        18,441        5.16%
                                             ---------------- ------------- ----------    --------------- ------------- ---------

Tax-equivalent net interest income                              $ 17,481                                    $ 13,951
                                                              =============                               =============
Net interest margin                                                              3.67%                                      3.65%
                                                                            ==========                                  =========
Core net interest margin (3)                                                     3.94%                                      3.84%
                                                                            ==========                                  =========

- -------------------------------
<FN>
(1)  Liquidity  management assets include securities,  interest earning deposits
     with banks and federal funds sold.
(2)  Interest  income  on  tax-advantaged   loans  and  securities   reflects  a
     tax-equivalent adjustment based on a marginal federal corporate tax rate of
     35%. The total  adjustments  for the quarters ended March 31, 2001 and 2000
     were $205,000 and $83,000, respectively.
(3)  The  core  net  interest  margin  excludes  the  impact  of  the  Company's
     Cumulative Trust Preferred Securities.
</FN>


Net interest income, which is the difference between interest income and fees on
earning  assets and interest  expense on deposits and  borrowings,  is the major
source of earnings for the Company.  Tax-equivalent  net interest income for the
quarter ended March 31, 2001 totaled $17.5 million, an increase of $3.5 million,
or 25%, as compared to the $14.0  million  recorded in the same quarter of 2000.
This  increase  mainly  resulted  from loan growth and  management's  ability to
control funding costs. Tax-equivalent interest and fees on loans for the quarter
ended March 31, 2001 totaled $37.1 million, an increase of $8.2 million, or 28%,
over  the  prior  year  quarterly  total  of  $28.8  million.  This  growth  was
predominantly due to a $303 million, or 23%, increase in average total loans.

Net  interest  margin  represents  net interest  income as a  percentage  of the
average earning assets during the period. For the first quarter of 2001, the net
interest  margin was 3.67%, an increase of two basis points when compared to the
margin of 3.65% in the prior year quarter.  The core net interest margin,  which
excludes  the  interest   expense  related  to  the  Company's  Trust  Preferred
Securities,  was 3.94% for the first  quarter of 2001,  and  increased ten basis
points when compared to the prior year quarterly core margin of 3.84%.

The rate paid on interest-bearing  deposits averaged 5.38% for the first quarter
of 2001  versus  5.01% for the same  quarter of 2000,  an  increase  of 37 basis
points. The rate in the first quarter of 2001 reflects a 39 basis

                                     - 11 -

point decrease from the rate on interest-bearing  deposits in the fourth quarter
of 2000. This increase in rate over the same period last year reflects continued
increases in market rates  throughout most of 2000 and the decrease in rate over
the fourth  quarter of 2000 reflects the decreases in market rates  beginning in
the fourth quarter of 2000 and continuing through the first quarter of 2001. The
rate paid on short-term  borrowings and notes payable  increased to 6.25% in the
first quarter of 2001 as compared to 6.02% in the same quarter of 2000. The rate
on the trust  preferred  securities  in the first  quarter  of 2001 was  10.09%,
compared  to 9.47% in the same  period  of  2000.  The  increase  was due to the
issuance of $20.0 million of 10.5% trust preferred securities in June 2000.

The yield on total  earning  assets  for the first  quarter of 2001 was 8.82% as
compared to 8.47% in 2000, an increase of 35 basis points. The yield on earnings
assets is heavily  dependent on the yield on loans since average loans comprised
approximately  83% of average earning assets.  During the first quarter 2001 the
yield on loans was 9.32%,  a 46 basis point  increase when compared to the prior
year quarterly  yield of 8.86%.  The average prime lending rate was 8.62% during
the first  quarter  of 2001  versus  8.69% for the first  quarter  of 2000.  The
Company's loan portfolio does not re-price in a parallel fashion to increases in
the prime rate due to a portion of the portfolio  being  longer-term  fixed rate
loans.

NON-INTEREST INCOME

For the first  quarter of 2001,  non-interest  income  totaled  $6.9 million and
increased $2.6 million over the prior year quarter.  Significant  increases were
realized  in fees  from the  origination  and sale of  mortgage  loans  into the
secondary  market and income from certain covered call option  transactions  and
were  partially  offset by a decrease in gains from the sale of premium  finance
receivables.

Fees on  mortgage  loans  sold  include  income  from  originating  and  selling
residential real estate loans into the secondary  market.  For the quarter ended
March 31, 2001, these fees totaled $1.5 million, an increase of $1.0 million, or
216%, from the prior year quarter. This increase was due to significantly higher
levels of  mortgage  origination  volumes,  particularly  refinancing  activity,
caused by the recent decreases in mortgage  interest rates.  Management  expects
continuation  of higher  refinancing  activity to continue at least  through the
next quarter.

The administrative  services revenue contributed by Tricom added $1.0 million to
total  non-interest  income  in the  first  quarter  of 2001 and was  relatively
consistent  with the level of revenue in the prior year  quarter.  This  revenue
comprises  income  from  administrative  services,  such as data  processing  of
payrolls,  billing and cash management  services,  to temporary staffing service
clients located throughout the United States. Tricom also earns interest and fee
income from  providing  short-term  accounts  receivable  financing to this same
client base, which is included in the net interest income category.

As  a  result  of  continued   strong  loan   originations  of  premium  finance
receivables,  the Company sold  approximately  $51 million of  receivables to an
unrelated  third  party in the first  quarter  of 2001 and  recognized  gains of
$942,000  related to this activity,  compared to the sale of  approximately  $74
million  of  premium  finance  receivables  in the  first  quarter  of 2000 that
resulted in gains of $1.2 million.  The Company has a philosophy of  maintaining
its  average  loan-to-deposit  ratio in the range of  85-90%.  During  the first
quarter of 2001, the ratio was approximately 87%. Accordingly,  the Company sold
excess premium finance  receivables volume to an unrelated third party financial
institution.  Consistent  with Wintrust's  strategy to be  asset-driven  and the
desire to maintain our loan-to-deposit  ratio in the aforementioned range, it is
probable that similar  sales of premium  finance  receivables  will occur in the
future.

                                     - 12 -

Service charges on deposit  accounts  totaled  $547,000 for the first quarter of
2001, an increase of $78,000, or 17%, when compared to the same quarter of 2000.
This  increase was mainly due to a higher  deposit  base and a larger  number of
accounts at the banking  subsidiaries.  The majority of deposit  service charges
relate to customary fees on overdrawn  accounts and returned items. The level of
service charges received is substantially  below peer group levels as management
believes in the philosophy of providing high quality service without encumbering
that service with numerous activity charges.

Trust fees  totaled  $450,000 for the first  quarter of 2001,  a $22,000,  or 5%
decrease  over the first  quarter of 2000.  This  decrease is  reflective of the
decrease  in  value of  assets  under  management  as a  result  of  significant
decreases  in the overall  stock  market.  Wintrust is  committed to growing the
trust and  investment  business  in order to better  service its  customers  and
create a more diversified revenue stream.

Other non-interest income for the first quarter of 2001 totaled $2.1 million and
increased  $1.5 million over the prior year  quarterly  total of $597,000.  This
increase was due  primarily to a $1.3  million  increase in premium  income from
certain  covered call option  transactions.  The Company  routinely  enters into
these  transactions  with  the  goal of  enhancing  its  overall  return  on its
investment  portfolio.  The Company  generally  writes the call options  against
certain U.S.  Treasury and agency issues held in its portfolio for liquidity and
other purposes.  Also contributing to the increase in other non-interest  income
was a $150,0000  increase in rental income from equipment leased through the MMF
Leasing division of Lake Forest Bank.


NON-INTEREST EXPENSE

Non-interest  expense for the first  quarter of 2001 totaled  $16.0  million and
increased  $3.9  million,  or 32%,  from the first  quarter  2000 total of $12.1
million. The continued growth and expansion of the de novo banks with additional
branches,  the opening of the Company's  seventh de novo bank (Northbrook Bank &
Trust) in November 2000 and the growth in the premium  finance  business are the
major causes for this increase.  Since March 31, 2000,  total deposits and total
loans have  increased  25% and 27%,  respectively,  requiring  higher  levels of
staffing and other costs to both attract and service the larger customer base.

Salaries and  employee  benefits  totaled $8.5 million for the first  quarter of
2001, an increase of $2.1 million, or 34%, as compared to the prior year's first
quarter total of $6.3 million. This increase was primarily due to the opening of
Northbrook  Bank & Trust and three  additional  branch  offices  since the first
quarter  of  2000  and  increased  staffing  at the  Company's  premium  finance
subsidiary.

Other categories of non-interest  expense,  such as occupancy  costs,  equipment
expense and data  processing,  also  increased over the prior year first quarter
due to the  general  growth of the  Company.  Amortization  expense  related  to
goodwill and other  intangibles  totaled $178,000 for the first quarters of 2001
and  2000.   Other   non-interest   expense,   which   includes  loan  expenses,
correspondent bank service charges, postage, insurance, stationery and supplies,
telephone,  directors  fees,  and other sundry  expenses,  also  increased  when
compared to the prior year quarter due mainly to the factors mentioned earlier.

                                     - 13 -

ASSET QUALITY

Allowance for Possible Loan Losses
A  reconciliation  of the activity in the balance of the  allowance for possible
loan  losses  for the three  months  ended  March 31,  2001 and 2000 is shown as
follows (dollars in thousands):



                                                                       THREE MONTHS ENDED MARCH 31,
                                                                     2001                    2000
                                                              --------------------    --------------------

                                                                                           
  Balance at beginning of period                                        $  10,433                $  8,783

 Provision for possible loan losses                                         1,638                   1,141

 Charge-offs
  Core banking loans                                                          108                     128
  Indirect automobile loans                                                   286                     311
  Tricom finance receivables                                                   --                       2
  Premium finance receivables                                                 712                     201
                                                              --------------------    --------------------
     Total charge-offs                                                      1,106                     642
                                                              --------------------    --------------------

 Recoveries
  Core banking loans                                                            2                       8
  Indirect automobile loans                                                    54                      43
  Tricom finance receivables                                                   --                      --
  Premium finance receivables                                                  46                      26
                                                              --------------------    --------------------
      Total recoveries                                                        102                      77
                                                              --------------------    --------------------
  Net charge-offs                                                          (1,004)                  (565)
                                                              --------------------    --------------------
  Balance at March 31                                                   $  11,067                $  9,359
                                                              --------------------    --------------------
  Loans at March 31                                                    $1,655,543              $1,307,796
                                                              --------------------    --------------------
  Allowance as a percentage of loans                                        0.67%                   0.72%
                                                              --------------------    --------------------
  Annualized net charge-offs as a percentage of average:
        Core banking loans                                                   0.04%                   0.06%
        Indirect automobile loans                                            0.47%                   0.43%
        Tricom finance receivables                                              --                   0.04%
        Premium finance receivables                                          0.77%                   0.29%
                                                              --------------------    --------------------
            Total loans                                                      0.25%                   0.17%
                                                              --------------------    --------------------

        Annualized provision for
            possible loan losses                                            61.29%                  49.52%
                                                              --------------------    --------------------


The  provision  for  possible  loan losses  totaled  $1.6  million for the first
quarter  of 2001,  an  increase  of  $497,000  from a year  earlier.  The higher
provision was due to a $348 million,  or 27%, increase in loan balances compared
to March  31,  2000 and a higher  level  of net  charge-offs,  primarily  in the
premium finance portfolio. For the quarter ended March 31, 2001, net charge-offs
totaled $1.0 million and increased from the $565,000 of

                                     - 14 -

net  charge-offs  recorded in the same  period of 2000.  On a ratio  basis,  net
charge-offs as a percentage of average loans increased  slightly to 0.25% in the
first  quarter of 2001 from 0.17% in the same  period in 2000 and from 0.24% for
the  full  year  2000.  This  increase  is  the  result  of a  higher  level  of
delinquencies  in the  premium  finance  receivables  portfolio.  Management  is
actively monitoring and pursuing methods to reduce the level of delinquencies in
the  indirect  auto and premium  finance  portfolios.  Management  believes  the
allowance for possible loan losses is adequate to provide for inherent losses in
the portfolio. There can be no assurances,  however, that future losses will not
exceed the amounts provided for, thereby affecting future results of operations.
The amount of future additions to the allowance for possible loan losses will be
dependent upon the economy,  changes in real estate values,  interest rates, the
regulatory  environment,  the level of past-due and  non-performing  loans,  and
other factors.

Past Due Loans and Non-performing Assets
- ----------------------------------------
The following table sets forth the Company's  non-performing assets at the dates
indicated.  The information in the table should be read in conjunction  with the
detailed discussion following the table (dollars in thousands).



                                                           MARCH 31,             December 31,             March 31,
                                                              2001                   2000                    2000
                                                              ----                   ----                    ----
                                                                                                       
      Past Due greater than 90 days
           and still accruing:
            Core banking loans                                 $  1,778                  $  651                 $  362
            Indirect automobile loans                               350                     397                    466
            Tricom finance receivables                               --                      --                     --
            Premium finance receivables                           4,881                   4,306                  2,273
                                                      ---------------------  ----------------------  ---------------------
                Total                                             7,009                   5,354                  3,101
                                                      ---------------------  ----------------------  ---------------------

      Non-accrual loans:
            Core banking loans                                      720                     770                  1,582
            Indirect automobile loans                               234                     221                    266
            Tricom finance receivables                              112                      --                     --
            Premium finance receivables                           5,872                   3,338                  2,334
                                                      ---------------------  ----------------------  ---------------------
                Total non-accrual loans                           6,938                   4,329                  4,182
                                                      ---------------------  ----------------------  ---------------------

      Total non-performing loans:
            Core banking loans                                    2,498                   1,421                  1,944
            Indirect automobile loans                               584                     618                    732
            Tricom finance receivables                              112                      --                     --
            Premium finance receivables                          10,753                   7,644                  4,607
                                                      ---------------------  ----------------------  ---------------------
                Total non-performing loans                       13,947                   9,683                  7,283
                                                      ---------------------  ----------------------  ---------------------

      Other real estate owned                                        --                      --                     --
                                                      ---------------------  ----------------------  ---------------------

      Total non-performing assets                              $ 13,947                 $ 9,683                $ 7,283
                                                      =====================  ======================  =====================


                                     - 15 -



                                                           MARCH 31,             December 31,             March 31,
                                                              2001                   2000                    2000
                                                              ----                   ----                    ----
                                                                                                           
      Total non-performing  loans by category as
        a percent of its own respective category:
            Core banking loans                                       0.22%                   0.14%                  0.24%
            Indirect automobile loans                                0.31%                   0.30%                  0.29%
            Tricom finance receivables                               0.60%                      --                     --
            Premium finance receivables                              3.22%                   2.44%                  2.04%
                                                      ---------------------  ----------------------  ---------------------
               Total non-performing loans                            0.84%                   0.62%                  0.56%
                                                      ---------------------  ----------------------  ---------------------

      Total non-performing assets as a
          percentage of total assets                                 0.64%                   0.46%                  0.41%

      Allowance for possible loan losses as
        a percentage of non-performing loans                        79.35%                 107.75%                128.50%



Non-performing Core Banking Loans

Total  non-performing  loans for the Company's  core banking  business were $2.5
million,  or 0.22%,  of the  Company's  core banking loans as of March 31, 2001,
compared  to 0.14%  and  0.24% as of  December  31,  2000 and  March  31,  2000,
respectively.  Non-performing  core banking loans  consist  primarily of a small
number of commercial  and real estate loans which  management  believes are well
secured and in the process of  collection.  In fact,  the loans  comprising  the
non-performing  core loan category  total less than 30 individual  credits.  The
small number of such  non-performing  loans  allows  management  to  effectively
monitor the status of these credits and work with the borrowers to resolve these
problems.


Non-performing Premium Finance Receivables

The table below presents the level of non-performing premium finance receivables
as of March  31,  2001 and  2000,  and the  amount  of net  charge-offs  for the
quarters then ended.




                                                                                     MARCH 31,                 March 31,
                                                                                       2001                       2000
                                                                                --------------------      ---------------------

                                                                                                         
     Non-performing premium finance receivables                                         $10,753,000            $4,607,000
        - as a percent of premium finance receivables                                          3.22%                 2.04%


     Net charge-offs of premium finance receivables                                       $ 666,000             $ 175,000
     - annualized as a percent of premium finance  receivables                                 0.77%                 0.29%



                                     - 16 -

The increase in  non-performing  premium finance  receivables over the course of
recent  quarters is  primarily  a result of a  proportionately  large  number of
delinquent  accounts  associated  with new  business  derived  from a  marketing
arrangement entered into in July, 1999.  Management  identified the issue in the
second  half of 2000 and  began  to take  corrective  measures  to  eliminate  a
significant  number of these new  business  relationships  that were  generating
disproportionately high delinquencies.  Specifically, the Company has eliminated
more than 1,300  relationships  with  insurance  agents that were  referring new
business to our premium  finance  subsidiary.  The volume  associated  with this
business  includes  a large  number of small  balance  accounts  which  place an
increased  burden on the collection  efforts of the premium finance  subsidiary.
The impact of this prior business is still reflected in the non-performing asset
totals as these accounts  customarily take 60-150 days to convert the collateral
held by insurance  company  into cash  collections.  Because of the  longer-term
nature of converting the  collateral to cash, we believe our corrective  actions
and increased  resources  devoted to  collections  should result in  significant
improvement during the second quarter of 2001 and that the non-performing totals
have reached their peak in the first quarter.  As such, the  delinquency  levels
should show improvement over the next two quarters.

The ratio of non-performing  premium finance receivables  fluctuates  throughout
the year due to the nature  and  timing of  canceled  account  collections  from
insurance  carriers.  Due  to the  nature  of  collateral  for  premium  finance
receivables,  it customarily  takes 60-150 days to convert the  collateral  into
cash  collections.  Accordingly,  the level of  non-performing  premium  finance
receivables is not necessarily indicative of the loss inherent in the portfolio.
In the event of  default,  the  Company  has the power to cancel  the  insurance
policy and  collect  the  unearned  portion of the  premium  from the  insurance
carrier.  In the event of  cancellation,  the cash  returned  in  payment of the
unearned  premium by the insurer  should  generally be  sufficient  to cover the
receivable  balance,  the  interest and other  charges due. Due to  notification
requirements  and processing time by most insurance  carriers,  many receivables
will become delinquent beyond 90 days while the insurer is processing the return
of the unearned premium.  Management continues to accrue interest until maturity
as the unearned  premium is  ordinarily  sufficient  to pay-off the  outstanding
balance and contractual interest due.


Non-performing Indirect Automobile Loans

Total non-performing  indirect automobile loans were $584,000 at March 31, 2001,
decreasing  from  $618,000 at December  31, 2000 and $732,000 at March 31, 2000.
The ratio of these  non-performing  loans to total indirect automobile loans has
increased slightly to 0.31% of total indirect automobile loans at March 31, 2001
from 0.30% at December 31, 1999 and 0.29% at March 31, 2000. The increase in the
ratios despite a decrease in the amount of non-performing loans is reflective of
the runoff in this portfolio. As noted in the Allowance for Possible Loan Losses
table, net charge-offs as a percent of total indirect automobile loans increased
slightly  from 0.43% in the first  quarter of 2000 to 0.47% in the first quarter
of 2001.  These ratios  continue to be below standard  industry  ratios for this
type of loan category.

                                     - 17 -

FORWARD-LOOKING STATEMENTS

This press release contains forward-looking  statements related to the Company's
financial  performance  that are based on  estimates.  The Company  intends such
forward-looking  statements  to be  covered  by the safe  harbor  provision  for
forward-looking statements contained in the Private Securities Litigation Reform
Act of 1995, and is including this statement for purposes of invoking these safe
harbor  provisions.  Actual results could differ materially from those addressed
in the  forward-looking  statements  due to factors  such as changes in economic
conditions,  competition,  or other factors,  that may influence the anticipated
growth rate of loans and  deposits,  the quality of the loan  portfolio and loan
and deposit  pricing,  unanticipated  changes in interest rates that  negatively
impact net interest  income,  future  events that may cause  unforeseen  loan or
lease losses,  slower than anticipated  development and growth of Tricom and the
new  trust and  investment  business,  unanticipated  changes  in the  temporary
staffing industry, the ability to adapt successfully to technological changes to
compete  effectively in the  marketplace,  and the ability to attract and retain
experienced senior management. Therefore, there can be no assurances that future
actual results will correspond to these forward-looking statements.

                                     - 18 -