SECURITIES AND EXCHANGE COMMISSION
                             Washington, D.C. 20549


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                                    FORM 11-K


                                  ANNUAL REPORT
                          PURSUANT TO SECTION 15(D) OF
                       THE SECURITIES EXCHANGE ACT OF 1934


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                   FOR THE FISCAL YEAR ENDED DECEMBER 31, 2002
                        Commission File Number 000-21923


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                         WINTRUST FINANCIAL CORPORATION
                             RETIREMENT SAVINGS PLAN
                            (Full title of the plan)


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                         WINTRUST FINANCIAL CORPORATION
                               727 NORTH BANK LANE
                              LAKE FOREST, IL 60045
           (Name of issuer of the securities held pursuant to the plan
               and the address of its principal executive office)

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



                              REQUIRED INFORMATION


ITEMS 1-3.     Omitted in accordance with Item 4.

ITEM 4.        The  Wintrust  Financial  Corporation   Retirement  Savings  Plan
               ("Plan") is subject to the Employee  Retirement  Income  Security
               Act of 1974, as amended ("ERISA").  In accordance with Item 4 and
               in lieu of the  requirements  of Items 1-3,  the  following  Plan
               financial  statements and schedules  prepared in accordance  with
               the  financial  reporting  requirements  of  ERISA  are  included
               herein:

               o    Report of Independent Auditors

               o    Statements  of  Net  Assets  Available  for  Benefits  as of
                    December 31, 2002 and 2001

               o    Statements  of Changes in Net Assets  Available for Benefits
                    for the years ended December 31, 2002 and 2001

               o    Notes to Financial Statements

               o    Supplemental Schedule

               Statements  of Net Assets  Available  for Benefits as of December
               31,  2002 and 2001,  and  Statements  of  Changes  in Net  Assets
               Available for Benefits for the years ended  December 31, 2002 and
               2001 are hereby  incorporated  by reference  to the  Registration
               Statement  on Form S-8 filed by  Wintrust  Financial  Corporation
               (Registration  No.  333-52652)  with the  Securities and Exchange
               Commission on December 22, 2000.



EXHIBITS
--------

  23.1         Consent of Independent Auditors

  99.1         Certification  of  President  and  Chief  Executive  Officer  and
               Executive Vice President and Chief Financial  Officer pursuant to
               18 U.S.C. Section 1350, as adopted pursuant to Section 906 of the
               Sarbanes-Oxley Act of 2002.


                                     - 2 -


                                   SIGNATURES

The Plan.  Pursuant to the requirements of the Securities  Exchange Act of 1934,
the trustees (or other persons who  administer  the employee  benefit plan) have
duly  caused this  annual  report to be signed on its behalf by the  undersigned
hereunto duly authorized.


Date:  June 24, 2003

                                               WINTRUST FINANCIAL CORPORATION
                                               RETIREMENT SAVINGS PLAN
                                               /s/ DAVID A. DYKSTRA
                                               -------------------------
                                               David A. Dykstra, Trustee


                                     - 3 -



Financial Statements and Supplemental Schedule

Wintrust Financial Corporation Retirement Savings Plan

Years ended December 31, 2002 and 2001
with Report of Independent Auditors

Employer Identification #36-3954651
Plan #001






             Wintrust Financial Corporation Retirement Savings Plan

                              Financial Statements
                            and Supplemental Schedule

                     Years ended December 31, 2002 and 2001




                                    CONTENTS

Report of Independent Auditors.................................................1

Financial Statements

Statements of Net Assets Available for Benefits................................2
Statements of Changes in Net Assets Available for Benefits.....................3
Notes to Financial Statements..................................................4


Supplemental Schedule

Schedule H, Line 4i - Schedule of Assets (Held
   at End of Year).............................................................8





                         Report of Independent Auditors

The Plan Administrator
Wintrust Financial Corporation
   Retirement Savings Plan

We have audited the accompanying statements of net assets available for benefits
of Wintrust  Financial  Corporation  Retirement  Savings Plan as of December 31,
2002 and 2001, and the related statements of changes in net assets available for
benefits  for  the  years  then  ended.  These  financial   statements  are  the
responsibility  of the Plan's  management.  Our  responsibility is to express an
opinion on these financial statements based on our audits.

We conducted our audits in accordance with auditing standards generally accepted
in the United States. Those standards require that we plan and perform the audit
to obtain reasonable  assurance about whether the financial  statements are free
of material misstatement. An audit includes examining, on a test basis, evidence
supporting  the amounts and  disclosures in the financial  statements.  An audit
also includes assessing the accounting principles used and significant estimates
made by  management,  as well as  evaluating  the  overall  financial  statement
presentation.  We believe  that our audits  provide a  reasonable  basis for our
opinion.

In our opinion,  the financial  statements  referred to above present fairly, in
all  material  respects,  the net assets  available  for benefits of the Plan at
December  31,  2002 and 2001,  and the changes in its net assets  available  for
benefits for the years then ended,  in  conformity  with  accounting  principles
generally accepted in the United States.

Our audits were performed for the purpose of forming an opinion on the financial
statements taken as a whole. The  accompanying  supplemental  schedule of assets
(held at end of year) as of December  31,  2002,  is  presented  for purposes of
additional  analysis and is not a required part of the financial  statements but
is  supplementary  information  required by the  Department of Labor's Rules and
Regulations for Reporting and Disclosure  under the Employee  Retirement  Income
Security Act of 1974. This  supplemental  schedule is the  responsibility of the
Plan's management.  The supplemental schedule has been subjected to the auditing
procedures  applied  in our  audits  of the  financial  statements  and,  in our
opinion,  is fairly stated in all material respects in relation to the financial
statements taken as a whole.

                                                          /s/ ERNST & YOUNG LLP

Chicago, IL
May 8, 2003


                                     - 1 -

                                                                  EIN 36-3954651
                                                                       Plan #001




             Wintrust Financial Corporation Retirement Savings Plan

                 Statements of Net Assets Available for Benefits


                                                                                   DECEMBER 31
                                                                             2002              2001
                                                                       ------------------------------------
                                                                                     
ASSETS
Cash                                                                       $  1,391,812    $      68,359
Investments, at fair value                                                    9,784,156        7,295,848
Participant contributions receivable                                             41,905            8,939
Employer matching contributions receivable                                      500,023          283,295
                                                                       ------------------------------------
Total assets                                                                 11,717,896        7,656,441

LIABILITY
Outstanding trades payable                                                    1,379,066           27,417
                                                                       ------------------------------------
Net assets available for benefits                                          $ 10,338,830    $   7,629,024
                                                                       ====================================


See notes to financial statements.

                                     - 2 -



                                                                  EIN 36-3954651
                                                                       Plan #001



             Wintrust Financial Corporation Retirement Savings Plan

           Statements of Changes in Net Assets Available for Benefits


                                                                             YEAR ENDED DECEMBER 31
                                                                             2002              2001
                                                                       ------------------------------------
                                                                                        
ADDITIONS
Investment income:
   Net realized and unrealized appreciation in fair
     value of investments                                                 $     260,609      $   585,701
   Interest and dividends                                                        79,370           86,098
                                                                       ------------------------------------
                                                                                339,979          671,799
Participant contributions - salary deferral                                   1,472,469        1,183,662
Participant contributions - rollover                                            415,810          147,190
Employer matching contributions                                                 500,023          282,924
Transfers from First Insurance
  401(k) Retirement Savings Plan                                              1,381,030                -
Transfers from Tricom Funding, Inc.
  401(k) Retirement Savings Plan                                                      -          442,635
                                                                       ------------------------------------
Total additions                                                               4,109,311        2,728,210

DEDUCTIONS
Benefits paid to participants                                                 1,399,505          202,506
Refund of excess contributions                                                        -            7,416
                                                                       ------------------------------------
Total deductions                                                              1,399,505          209,922
                                                                       ------------------------------------
Net increase in net assets available for benefits                             2,709,806        2,518,288
Net assets available for benefits:
   Beginning of year                                                          7,629,024        5,110,736
                                                                       ------------------------------------
   End of year                                                            $  10,338,830      $ 7,629,024
                                                                       ====================================


See notes to financial statements.

                                     - 3 -



                                                                  EIN 36-3954651
                                                                       Plan #001

             Wintrust Financial Corporation Retirement Savings Plan

                          Notes to Financial Statements

                     Years ended December 31, 2002 and 2001


1.  DESCRIPTION OF PLAN

The following brief description of the Wintrust Financial Corporation Retirement
Savings Plan (Plan) provides only general information. Participants should refer
to  the  Plan  Agreement  for a more  comprehensive  description  of the  Plan's
provisions.

The  Plan is a  participant-directed,  defined-contribution  plan  covering  all
eligible  employees,  as defined in the Plan, of Wintrust Financial  Corporation
and  its  eligible  subsidiaries  (the  Company).  The  Plan is  subject  to the
provisions of the Employee  Retirement  Income Security Act of 1974 (ERISA),  as
amended.

All full-time  employees who have  completed at least three months of employment
and are at least 18 years of age are eligible to participate in the Plan.

On December 31, 2002, the First  Insurance  401(k)  Retirement  Savings Plan was
merged into the Plan, and on January 1, 2001, the Tricom  Funding,  Inc.  401(k)
Retirement Savings Plan was merged into the Plan.

CONTRIBUTIONS

The Plan allows  participants  to contribute up to the maximum  allowable by the
Internal Revenue Code (Code), which during 2002 was $11,000,  plus an additional
$1,000  for  participants  over  the  age  of 50.  Prior  to  2002,  participant
contributions were also limited to the lesser of 10% of eligible compensation or
the maximum  allowable by the Code.  Participant  contributions are tax deferred
under the  provisions of Code Section  401(k),  subject to certain  limitations.
Participant contributions and earnings thereon are fully vested.

The Company may elect to make  matching  contributions  to the Plan on behalf of
all eligible participants.  Generally, participants must be employed on the last
day of the Plan year to be eligible for matching  contributions.  For 2002,  the
Company's matching contributions were 40% of a participant's contributions up to
a  maximum  of  $3,000  per  participant.   For  2001,  the  Company's  matching
contributions  were 30% of a  participant's  contributions  up to a  maximum  of
$2,000 per  participant.  Participants  are immediately  vested in the Company's
matching   contribution  and  earnings  thereon.   Additional   amounts  may  be
contributed at the discretion of the Company.

                                     - 4 -



             Wintrust Financial Corporation Retirement Savings Plan

                    Notes to Financial Statements (continued)


1.  DESCRIPTION OF PLAN (CONTINUED)

INVESTMENT OF PLAN ASSETS

A trust fund was  established  for the  purposes of holding and  investing  Plan
assets in accordance with the terms of the Trust  Agreement  between the Company
and the Trustee,  Wayne Hummer Trust Company,  N. A. (Trustee),  a subsidiary of
the Company and a party in interest.

PARTICIPANT LOANS

Participants  may borrow from their fund  account up to the lesser of $50,000 or
50%  of  their  account  balance.   Loan  terms  are  established  by  the  plan
administrator  in accordance with the Plan  Agreement.  The loans are secured by
the  balance  in  the  participant's   account  and  bear  interest  at  a  rate
commensurate   with  local   prevailing   rates,   as  determined  by  the  plan
administrator.

PARTICIPANT ACCOUNTS

Each participant's account is credited with the participant's  contributions and
allocations  of:  (a)  the  Company's  contributions,   if  any,  and  (b)  Plan
earnings/losses.  Allocations  are  based on  participant  earnings  or  account
balances,  as  defined.  The benefit to which a  participant  is entitled is the
benefit that can be provided from the participant's account.

PAYMENT OF BENEFITS

On termination of service due to death, disability, or retirement, a participant
may  elect  to  receive  either a  lump-sum  amount  equal  to the  value of the
participant's account or annual installments.  For termination of service due to
other reasons, a participant may receive the value of the participant's  account
as a lump-sum distribution.

PLAN TERMINATION

Although  it has not  expressed  any intent to do so, the  Company has the right
under the Plan to  discontinue  its  contributions,  if any,  at any time and to
terminate the Plan subject to the provisions of ERISA.

                                     - 5 -



2.  SUMMARY OF SIGNIFICANT ACCOUNTING POLICIES

BASIS OF PRESENTATION

The  accompanying  financial  statements are prepared under the accrual basis of
accounting.

INVESTMENT VALUATION AND INCOME RECOGNITION

Except for investment  contracts,  investments are reported at fair value, which
equals the quoted  market price on the last  business day of the Plan year.  The
shares of mutual funds are valued at quoted market prices,  which  represent the
net asset values of shares held by the Plan at year-end.  Loans to  participants
are reported at their outstanding balances, which approximate fair value.

Investment  contracts are recorded at their  contract  value,  which  represents
contributions and reinvested income, less any withdrawals plus accrued interest.
The fair value of the  investment  contract  approximates  contract  value.  The
crediting  interest rate for the investment  contract is reset  quarterly by the
issuer but cannot be less than zero and was 4.75% for the last  quarter of 2002,
when  the  investment  was  held  by the  Plan.  The  average  annualized  yield
approximated the crediting interest rate.

Purchases  and sales of  securities  are recorded on a trade-date  basis and are
accounted  for using the  specific  identification  method.  Interest  income is
recorded on the accrual basis.  Dividend  income is recorded on the  ex-dividend
date.

ADMINISTRATIVE EXPENSES

Administrative  expenses  of the Plan are paid from the trust fund to the extent
they are not paid by the Company.  All administrative  expenses were paid by the
Company for the years ended December 31, 2002 and 2001.

USE OF ESTIMATES

The preparation of financial statements in conformity with accounting principles
generally  accepted in the United States  requires  management to make estimates
and  assumptions  that affect amounts  reported in the financial  statements and
accompanying notes. Actual results could differ from those estimates.

                                     - 6 -


3.  INVESTMENTS

The fair value of individual investments that represent 5% or more of the Plan's
net assets available for benefits is as follows:



                                                                          DECEMBER 31
                                                                     2002             2001
                                                              ------------------------------------

                                                                                
Wintrust Financial Corporation Common Stock*                        $3,432,584        $2,872,816
Metlife Stable Value                                                 1,612,290                 -
Fidelity Advisor Equity Growth Fund                                  1,021,569         1,301,797
Fidelity Spartan 500 Index Fund                                        815,107           820,753
American Growth Funds                                                  809,444                 -
Fidelity Intermediate Government Fund                                  795,066           483,344
Janus Enterprise Fund                                                  593,661           489,577
William Blair Growth Fund                                                   **           496,080
Fidelity Spartan Money Market Fund                                           -           674,183

       *Indicates party in interest to the Plan.
     **Below 5% threshold.



The Plan's  investments  (including  gains and losses on investments  bought and
sold,  as well as held during the year)  appreciated  (depreciated)  in value as
determined by quoted market prices as follows:



                                                          YEAR ENDED DECEMBER 31
                                                          2002               2001
                                                   --------------------------------------

                                                                    
Common stock                                             $ 1,269,780      $ 1,271,669
Mutual funds                                              (1,009,171)        (685,968)
                                                   --------------------------------------
                                                         $   260,609      $   585,701
                                                   ======================================


4.  INCOME TAX STATUS

The Plan has not  received a  determination  letter  from the  Internal  Revenue
Service  stating that the Plan is qualified  under  Section  401(a) of the Code.
However,  the  plan  administrator  believes  that the  Plan is  qualified  and,
therefore, the related trust is exempt from taxation.



5.  SUBSEQUENT EVENT

During April 2003,  the Wayne Hummer Profit  Sharing and Savings Plan was merged
into the Plan.


                                     - 7 -




                              Supplemental Schedule





                                                                  EIN 36-3954651
                                                                       Plan #001



             Wintrust Financial Corporation Retirement Savings Plan

                    Schedule H, Line 4i - Schedule of Assets
                              (Held at End of Year)

                                December 31, 2002


                                                                                             CURRENT
                    DESCRIPTION OF INVESTMENT                            UNITS/SHARES         VALUE
-----------------------------------------------------------------------------------------------------------

                                                                                         
Investment contract:
   Metlife Stable Value                                                        14,728         $1,612,290

Common stock:
   Wintrust Financial Corporation*                                            109,527          3,432,584

Mutual funds:
   Fidelity Advisor Equity Growth Fund                                         29,113          1,021,569
   Fidelity Spartan 500 Index Fund                                             13,480            815,107
   American Growth Funds                                                       43,821            809,444
   Fidelity Intermediate Government Fund                                       76,596            795,066
   Janus Enterprise Fund                                                       25,868            593,661
   William Blair Growth Fund                                                   54,978            443,121
   Wayne Hummer Growth Fund                                                       881             26,293
   Ariel Growth Fund                                                              630             22,198
   Lord Abbett Mid Cap Value Fund                                               1,375             21,155
   American Funds Investment Co.                                                  744             17,465
   Wayne Hummer Income Fund*                                                      962             15,160
   Value Line Small Cap Growth Fund                                               782             13,193
   Aim Basic Value Fund                                                           204              4,452
   American Funds EuroPacific Growth Fund                                         132              3,031
   Wayne Hummer Core Portfolio Fund*                                              499              3,011

Participant loans (4.3%-9.5%)                                                                    135,356
                                                                                        -------------------
                                                                                              $9,784,156
                                                                                        ===================

*Indicates party in interest to the Plan.



                                     - 8 -