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


NEWS RELEASE

FOR IMMEDIATE RELEASE                                           October 19, 1999
- ---------------------

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 THIRD QUARTER 1999 RESULTS
                        ---------------------------------

         LAKE FOREST,  ILLINOIS -- Wintrust Financial  Corporation  ("Wintrust")
(Nasdaq: WTFC) announced record net income of $2.5 million for the quarter ended
September  30,  1999,  an increase of  $373,000,  or 17%,  over the $2.2 million
recorded in the third quarter of 1998. On a per share basis,  net income for the
third quarter of 1999 totaled $0.30 per diluted common share, a $0.05 per share,
or 20%,  increase  as  compared  to the 1998  third  quarter  total of $0.25 per
diluted common share. The return on average equity for the third quarter of 1999
increased to 12.46% from 11.80% for the prior year  quarter.  Pre-tax  operating
earnings for the third quarter of 1999 totaled $3.8 million and  increased  $1.5
million, or 68%, over the prior year quarter; a more representative indicator of
improved  operating  results  due  to  the  impact  of  tax  benefits  from  the
recognition of prior years' net operating tax losses.

         For the nine months ended  September 30, 1999,  net income totaled $6.6
million, or $0.78 per diluted common share, an increase of $2.5 million, or 59%,
and $0.29 per diluted common share, when compared to the same period in 1998. On
a pre-tax  basis,  year-to-date  operating  earnings  totaled  $9.9  million and
increased $6.8 million, or 217%, over the 1998 year-to-date total. The return on
average  equity for the nine  months  ended  September  30,  1999 rose to 11.29%
versus 7.83% in the 1998 period.

         "Our earnings  improvement  in the third quarter of 1999 was mainly the
result of solid  loan  growth in both the core and niche loan  portfolios  and a
decline in deposit funding  costs,"  commented  Edward J. Wehmer,  President and
Chief  Executive  Officer.  Mr.  Wehmer  added,  "We are also  pleased  with the
improvement in our net overhead ratio,  which was 1.91% for the third quarter of
1999 and is now within the range of our previously  stated  performance  goal of
1.50% - 2.00%."
                                    - more -


         For the third  quarter  of 1999,  net  interest  income  totaled  $12.2
million  and  increased  $2.3  million,  or 24%,  as  compared to the prior year
quarterly  total of $9.9  million.  In addition,  solid loan growth in the niche
premium finance portfolio  necessitated the sale of approximately $20 million of
new volume to an  unrelated  third party,  resulting in a third  quarter gain of
$377,000.  These earnings  increases were partially offset by a $790,000 decline
in fees on  mortgage  loans  sold due  mainly to the rise in  mortgage  interest
rates, which caused a significant drop in refinancing activity.

         Total assets rose to $1.56  billion at September  30, 1999, an increase
of $321 million,  or 26%,  compared to $1.24 billion a year ago, and an increase
of $217  million,  or 16%,  from $1.35  billion as of December 31,  1998.  Total
deposits  as of  September  30,  1999 were $1.39  billion,  an  increase of $265
million,  or 24%, as compared to $1.12 billion as of September 30, 1998,  and an
increase of $159  million,  or 13%,  from the December 31, 1998 balance of $1.23
billion.  Total loans grew to $1.20  billion as of  September  30,  1999, a $294
million,  or 32%,  increase over the $908 million balance a year earlier,  and a
$210 million,  or 21%, increase over the $992 million balance as of December 31,
1998.

         Third quarter 1999 results were also impacted by the  additional  costs
associated  with  establishing  two new branch  facilities.  In  September,  the
Crystal Lake Bank subsidiary  opened a branch located in south Crystal Lake and,
in October,  the North Shore  Community  Bank  subsidiary  opened a full service
branch located in Skokie,  Illinois.  Wintrust continues with its plan to expand
through additional de novo bank and branch locations and possible acquisitions.

         Wintrust is a financial  services holding company whose common stock is
traded on the Nasdaq Stock Market(R).  Its six 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 and Trust Company,
Hinsdale Bank and Trust Company, North Shore Community Bank and Trust Company in
Wilmette,  Libertyville  Bank and  Trust  Company,  Barrington  Bank  and  Trust
Company,  N.A.,  and Crystal Lake Bank and Trust  Company,  N.A.. The banks also
operate facilities in Lake Bluff,  Glencoe,  Winnetka,  Clarendon Hills, Western
Springs and Skokie, Illinois. The Company's finance subsidiary,  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,  N.A., a new trust
subsidiary,  allows Wintrust to service customers' trust and investment needs at
each  banking  location.  Currently,  Wintrust  operates  a total of 24  banking
offices and is in the process of constructing  one additional  branch  facility.
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.
                                      # # #



WINTRUST FINANCIAL CORPORATION
SELECTED FINANCIAL HIGHLIGHTS
(DOLLARS IN THOUSANDS, EXCEPT PER SHARE DATA)
- --------------------------------------------------------------------------------------------------------------------
                                                            THREE MONTHS                     NINE MONTHS
                                                         ENDED SEPTEMBER 30,              ENDED SEPTEMBER 30,
                                                        1999             1998            1999             1998
- --------------------------------------------------------------------------------------------------------------------
                                                                                            
SELECTED FINANCIAL CONDITION DATA
  (AT END OF PERIOD):
  Total assets                                        $ 1,564,879       $ 1,243,556    $ 1,564,879      $ 1,243,556
  Total deposits                                        1,388,442         1,123,756      1,388,442        1,123,756
  Total loans, net of unearned income                   1,202,256           908,276      1,202,256          908,276
  Long-term debt and notes payable                         38,400            30,703         38,400           30,703
  Total shareholders' equity                               80,854            73,155         80,854           73,155
- --------------------------------------------------------------------------------------------------------------------

SELECTED STATEMENTS OF INCOME DATA:
  Net interest income                                    $ 12,222          $  9,873       $ 34,636        $  26,787
  Net revenues                                             14,239            11,882         41,079           32,468
  Income before income taxes                                3,819             2,272          9,878            3,119
  Net income                                                2,527             2,154          6,621            4,159
  Net income per common share - Basic                        0.31              0.26           0.81             0.51
  Net income per common share - Diluted                      0.30              0.25           0.78             0.49
- --------------------------------------------------------------------------------------------------------------------

SELECTED FINANCIAL RATIOS AND OTHER DATA:
Performance Ratios:
  Core net interest margin (1)                              3.59%             3.61%          3.64%            3.46%
  Net interest margin                                       3.47%             3.61%          3.53%            3.46%
  Net interest spread                                       3.17%             3.19%          3.21%            3.03%
  Non-interest income to average assets                     0.52%             0.67%          0.59%            0.67%
  Non-interest expense to average assets                    2.43%             2.87%          2.63%            3.07%
  Net overhead ratio                                        1.91%             2.20%          2.03%            2.40%
  Return on average assets                                  0.65%             0.72%          0.61%            0.49%
  Return on average equity                                 12.46%            11.80%         11.29%            7.83%

  Average total assets                                $ 1,540,530       $ 1,193,210    $ 1,450,608      $ 1,133,615
  Average shareholders' equity                             80,440            72,429         78,417           71,002
  Average loan-to-average deposit ratio                    86.85%            82.47%         86.27%           79.29%

Common Share Data at end of period:
  Market price per common share                          $  17.25          $  17.25
  Book value per common share                                9.89              8.98

Other Data at end of period:
  Number of:
    Bank subsidiaries                                           6                 6
    Banking offices                                            23                19

- --------------------------------------------------------------------------------------------------------------------
<FN>
(1)  The core net interest margin excludes the net impact of the Company's 9.00%
     Cumulative Trust Preferred  Securities  offering and certain  discretionary
     investment leveraging transactions.
</FN>


                                     - 1 -



WINTRUST FINANCIAL CORPORATION AND SUBSIDIARIES
CONSOLIDATED STATEMENTS OF CONDITION (UNAUDITED)
(In thousands)
                                                                        September 30,       December 31,       September 30,
                                                                             1999               1998               1998
- ------------------------------------------------------------------------------------------------------------------------------
                                                                                                           
ASSETS
Cash and due from banks-non-interest bearing                                  $  38,391          $  33,924          $  28,048
Federal funds sold                                                               59,161             18,539             18,250
Interest-bearing deposits with banks                                              3,746              7,863             10,231
Available-for-Sale securities, at fair value                                    164,747            209,119            193,037
Held-to-Maturity securities, at amortized cost                                        -              5,000              5,000
Loans, net of unearned income                                                 1,202,256            992,062            908,276
    Less: Allowance for possible loan losses                                      8,200              7,034              6,500
- ------------------------------------------------------------------------------------------------------------------------------
    Net loans                                                                 1,194,056            985,028            901,776
Premises and equipment, net                                                      68,257             56,964             53,165
Accrued interest receivable and other assets                                     35,213             30,082             32,451
Goodwill and organizational costs                                                 1,308              1,529              1,598
- ------------------------------------------------------------------------------------------------------------------------------

    TOTAL ASSETS                                                            $ 1,564,879         $1,348,048         $1,243,556
==============================================================================================================================


LIABILITIES AND SHAREHOLDERS' EQUITY
Deposits:
 Non-interest bearing                                                         $ 125,870          $ 131,309          $ 106,090
 Interest bearing                                                             1,262,572          1,097,845          1,017,666
- ------------------------------------------------------------------------------------------------------------------------------
    Total  deposits                                                           1,388,442          1,229,154          1,123,756

Short-term borrowings                                                            40,025                  -                  -
Notes payable                                                                     7,350                  -              3,203
Long-term debt - trust preferred securities                                      31,050             31,050             27,500
Accrued interest payable and other liabilities                                   17,158             12,639             15,942
- ------------------------------------------------------------------------------------------------------------------------------

    TOTAL LIABILITIES                                                         1,484,025          1,272,843          1,170,401
- ------------------------------------------------------------------------------------------------------------------------------

SHAREHOLDERS' EQUITY:
  Preferred stock                                                                     -                  -                  -
  Common stock                                                                    8,174              8,150              8,150
  Surplus                                                                        73,165             72,878             72,878
  Common stock warrants                                                             100                100                100
  Retained earnings (deficit)                                                       749             (5,872)            (7,958)
  Accumulated other comprehensive loss                                           (1,334)               (51)               (15)
- ------------------------------------------------------------------------------------------------------------------------------
    TOTAL SHAREHOLDERS' EQUITY                                                   80,854             75,205             73,155
- ------------------------------------------------------------------------------------------------------------------------------

    TOTAL LIABILITIES AND SHAREHOLDERS' EQUITY                              $ 1,564,879        $ 1,348,048        $ 1,243,556
==============================================================================================================================


                                     - 2 -



WINTRUST FINANCIAL CORPORATION AND SUBSIDIARIES
CONSOLIDATED STATEMENTS OF INCOME (UNAUDITED)
(In thousands, except per share data)
                                                                    THREE MONTHS ENDED              NINE MONTHS ENDED
                                                                       SEPTEMBER 30,                  SEPTEMBER 30,
                                                                    1999           1998            1999           1998
- ----------------------------------------------------------------------------------------------------------------------------
                                                                                                       
INTEREST INCOME
  Interest and fees on loans                                           $24,990       $20,045        $ 69,993       $ 54,645
  Interest bearing deposits with banks                                      44           378             165          2,159
  Federal funds sold                                                       504           542           1,074          1,801
  Securities                                                             2,546         1,976           7,244          5,683
- ----------------------------------------------------------------------------------------------------------------------------
    Total interest income                                               28,084        22,941          78,476         64,288
- ----------------------------------------------------------------------------------------------------------------------------

INTEREST EXPENSE
   Interest on deposits                                                 14,401        12,562          40,167         36,166
   Interest on short-term borrowings and notes payable                     727           506           1,470          1,335
   Interest on long-term debt - trust preferred securities                 734             -           2,203              -
- ----------------------------------------------------------------------------------------------------------------------------
     Total interest expense                                             15,862        13,068          43,840         37,501
- ----------------------------------------------------------------------------------------------------------------------------

NET INTEREST INCOME                                                     12,222         9,873          34,636         26,787
Provision for possible loan losses                                         990           971           2,707          3,311
- ----------------------------------------------------------------------------------------------------------------------------

Net interest income after provision for possible loan losses            11,232         8,902          31,929         23,476
- ----------------------------------------------------------------------------------------------------------------------------

NON-INTEREST INCOME
  Fees on mortgage loans sold                                              533         1,323           2,750          3,902
  Service charges on deposit accounts                                      399           293           1,080            747
  Trust fees                                                               295           210             770            578
  Gain on sale of premium finance receivables                              377             -             640              -
  Net securities gains                                                      15             -              15              -
  Other                                                                    398           183           1,188            454
- ----------------------------------------------------------------------------------------------------------------------------
    Total non-interest income                                            2,017         2,009           6,443          5,681
- ----------------------------------------------------------------------------------------------------------------------------

NON-INTEREST EXPENSE
  Salaries and employee benefits                                         4,984         4,565          15,256         14,353
  Occupancy, net                                                           743           589           2,088          1,765
  Equipment expense                                                        796           550           2,126          1,576
  Data processing                                                          551           440           1,544          1,234
  Advertising and marketing                                                309           358           1,041          1,114
  Professional fees                                                        242           455             828          1,203
  Other                                                                  1,805         1,682           5,611          4,793
- ----------------------------------------------------------------------------------------------------------------------------
    Total non-interest expense                                           9,430         8,639          28,494         26,038
- ----------------------------------------------------------------------------------------------------------------------------

Income before income taxes                                               3,819         2,272           9,878          3,119
Income tax expense (benefit)                                             1,292           118           3,257         (1,040)
- ----------------------------------------------------------------------------------------------------------------------------

NET INCOME                                                             $ 2,527       $ 2,154         $ 6,621        $ 4,159
- ----------------------------------------------------------------------------------------------------------------------------
NET INCOME PER COMMON SHARE - BASIC                                     $ 0.31        $ 0.26          $ 0.81         $ 0.51
- ----------------------------------------------------------------------------------------------------------------------------
NET INCOME PER COMMON SHARE - DILUTED                                   $ 0.30        $ 0.25          $ 0.78         $ 0.49
- ----------------------------------------------------------------------------------------------------------------------------

Weighted average common shares outstanding                               8,173         8,150           8,166          8,141
Dilutive potential common shares                                           310           384             322            358
- ----------------------------------------------------------------------------------------------------------------------------
Average common shares and dilutive common shares                         8,483         8,534           8,488          8,499
============================================================================================================================


                                     - 3 -


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 taxable  equivalent basis,
for the quarterly and nine-month periods ended September 30, 1999 and 1998:



                                                      FOR THE QUARTER ENDED                       FOR THE QUARTER ENDED
                                                        SEPTEMBER 30, 1999                          SEPTEMBER 30, 1998
                                             -----------------------------------------    ---------------------------------------
(dollars in thousands)                            AVERAGE      INTEREST       RATE            AVERAGE       INTEREST      RATE
- ----------------------                       ---------------- ------------- ----------    --------------- ------------- ---------

                                                                                                         
Liquidity management assets (1) (2)              $ 231,273       $ 3,096         5.31%       $ 204,915       $ 2,896       5.61%
Loans, net of unearned income (2)                1,173,278        25,065         8.48          883,515        20,068       9.01
                                             ---------------- ------------- ----------    --------------- ------------- ---------
   Total earning assets                          1,404,551        28,161         7.95%       1,088,430        22,964       8.37%
                                             ---------------- ------------- ----------    --------------- ------------- ---------

Interest-bearing deposits                        1,225,090        14,401         4.66%         969,591        12,562       5.14%
Short-term borrowings and notes payable             59,315           727         4.86           30,447           506       6.59
Long-term debt - trust preferred securities         31,050           734         9.46                -             -          -
                                             ---------------- ------------- ----------    --------------- ------------- ---------
   Total interest-bearing liabilities            1,315,455        15,862         4.78%       1,000,038        13,068       5.18%
                                             ---------------- ------------- ----------    --------------- ------------- ---------

Tax-equivalent net interest income                              $ 12,299                                     $ 9,896
                                                              =============                               =============
Net interest margin                                                              3.47%                                     3.61%
                                                                            ==========                                  =========
Core net interest margin (3)                                                     3.59%                                     3.61%
                                                                            ==========                                  =========






                                                    FOR THE NINE MONTHS ENDED                   FOR THE NINE MONTHS ENDED
                                                        SEPTEMBER 30, 1999                          SEPTEMBER 30, 1998
                                             -----------------------------------------    ---------------------------------------
(dollars in thousands)                            AVERAGE      INTEREST       RATE            AVERAGE       INTEREST      RATE
- ----------------------                       ---------------- ------------- ----------    --------------- ------------- ---------

                                                                                                         
Liquidity management assets (1) (2)              $ 216,047       $ 8,490         5.25%       $ 228,340       $ 9,643       5.65%
Loans, net of unearned income (2)                1,103,881        70,154         8.50          808,009        54,711       9.05
                                             ---------------- ------------- ----------    --------------- ------------- ---------
   Total earning assets                          1,319,928        78,644         7.97%       1,036,349        64,354       8.30%
                                             ---------------- ------------- ----------    --------------- ------------- ---------

Interest-bearing deposits                        1,157,076        40,167         4.64%         924,048        36,166       5.23%
Short-term borrowings and notes payable             44,439         1,470         4.42           26,559         1,335       6.72
Long-term debt - trust preferred securities         31,050         2,203         9.46                -             -          -
                                             ---------------- ------------- ----------    --------------- ------------- ---------
   Total interest-bearing liabilities            1,232,565        43,840         4.76%         950,607        37,501       5.27%
                                             ---------------- ------------- ----------    --------------- ------------- ---------

Tax-equivalent net interest income                              $ 34,804                                    $ 26,853
                                                              =============                               =============
Net interest margin                                                              3.53%                                     3.46%
                                                                            ==========                                  =========
Core net interest margin (3)                                                     3.64%                                     3.46%
                                                                            ==========                                  =========
- -------------------------------
<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
     34%. This total  adjustment for the quarters  ended  September 30, 1999 and
     1998 was $77,000 and $23,000,  respectively, and for the nine-month periods
     ended September 30, 1999 and 1998 was $168,000 and $66,000, respectively.
(3)  The core net interest margin excludes the net impact of the Company's 9.00%
     Cumulative Trust Preferred  Securities  offering and certain  discretionary
     investment leveraging transactions.
</FN>


                                     - 4 -

Tax-equivalent  net interest  income for the quarter  ended  September  30, 1999
totaled $12.3 million,  an increase of $2.4 million,  or 24%, as compared to the
$9.9 million  recorded in the same quarter of 1998. This increase was mainly the
result of loan  growth  coupled  with a decline in deposit  funding  cost rates.
Tax-equivalent  interest and fees on loans for the quarter  ended  September 30,
1999 totaled $25.1 million,  an increase of $5.0 million, or 25%, over the prior
year quarterly total of $20.1 million.  This growth was  predominantly  due to a
$290 million, or 33%, increase in average total loans.

For the third quarter of 1999,  the net interest  margin was 3.47%, a decline of
14 basis points when  compared to the margin of 3.61% in the prior year quarter.
This  decline  was due  mainly to the net impact of the 9.00%  Cumulative  Trust
Preferred Securities offering and certain  discretionary  investment  leveraging
transactions.  The core net interest margin,  which excludes the impact of these
items, was 3.59% for the third quarter of 1999, and declined only 2 basis points
when compared to the prior year quarterly margin of 3.61%.

The rate paid on interest-bearing  deposits averaged 4.66% for the third quarter
of 1999 versus 5.14% for the same quarter in 1998, a decline of 48 basis points.
This  decline  was  caused by a general  market  decline in rates  coupled  with
management's  decision to be less  aggressive on its deposit pricing at the more
mature banks. The rate paid on short-term  borrowings and notes payable declined
to 4.86% in the third  quarter of 1999 as compared to 6.59% in the same  quarter
of 1998. A change in composition of this category coupled with a general decline
in market rates were the primary  factors  causing this 173 basis point decline.
In 1998,  most of the average  balance  comprised  notes payable under a line of
credit  agreement with an  unaffiliated  bank at an interest rate indexed at 125
basis points over the LIBOR rate. In 1999, the average balance  comprised mainly
short-term repurchase agreements, which generally have lower rates when compared
to the terms of the line of credit agreement.

The yield on total  earning  assets  for the third  quarter of 1999 was 7.95% as
compared to 8.37% in 1998,  a decline of 42 basis  points due to lower yields on
both  loans  and  liquidity  management  assets,  offset  somewhat  by a  higher
proportion of average loans to average  earning  assets.  The third quarter 1999
loan yield of 8.48%  declined 53 basis  points  when  compared to the prior year
quarterly yield of 9.01% and was due primarily to a higher prime lending rate of
8.50% during the entire third  quarter of 1998 versus an average  prime  lending
rate of 8.10% for the third quarter of 1999.

For the nine months ended September 30, 1999, tax-equivalent net interest income
totaled $34.8 million and increased $8.0 million, or 30%, over the $26.9 million
recorded  in the same  period of 1998.  This  increase  was  primarily  due to a
combination  of loan growth and lower  funding cost rates.  Interest and fees on
loans,  on a  tax-equivalent  basis,  totaled $70.2  million for the  nine-month
period ended  September 30, 1999 and increased  $15.4 million,  or 28%, over the
same period of 1998.  Average  loans for the  nine-month  period of 1999 totaled
$1.10  billion  and grew $296  million,  or 37%,  over the  average for the same
period of 1998. The net interest  margin for the nine months ended September 30,
1999 was 3.53%,  an increase of 7 basis points when  compared to the same period
in 1998.  The core net  interest  margin for the  nine-month  period of 1999 was
3.64% and  increased  18 basis  points  over the same  margin in the prior  year
period.  These margin increases were directly the result of a decline in funding
cost rates and loan growth.  The total  deposit  funding  cost rate  declined 59
basis points since the prior year nine-month period and was 4.64% for nine-month
period of 1999. The growth in loans caused a higher  proportion of average loans
to average total earning  assets,  and increased  from 78% in the 1998 period to
84% in the 1999  period.  This  improved  loan  proportion  creates a higher net
interest  margin,  as loans earn  interest at a higher  rate than other  earning
assets. The year-to-date loan yield declined 55 basis points to 8.50%, which was
due to a lower  average  prime  lending rate of 7.87% in the  year-to-date  1999
period versus and average  prime lending rate of 8.50% in the 1998  year-to-date
period.

                                     - 5 -

NON-INTEREST INCOME

For the third  quarter of 1999,  non-interest  income  totaled  $2.0 million and
increased  $8,000  over the prior year  quarter.  Gains from the sale of premium
finance  receivables and increases in trust fees,  deposit  services charges and
leased  equipment  rental  income  were offset by a lower level of fees from the
sale of mortgage loans.

Fees on mortgage  loans  sold,  the largest  category  of  non-interest  income,
includes income from originating and selling  residential real estate loans into
the  secondary  market.  For the quarter ended  September  30, 1999,  these fees
totaled  $533,000,  a decline of $790,000,  or 60%, from the prior year quarter.
This  decline  was due  mainly to lower  mortgage  volumes  caused by the recent
increases in mortgage interest rates. Accordingly, future fee income on mortgage
loans sold is not expected to be at the levels that were experienced in the last
half of 1998.

During the third quarter of 1999,  approximately  $20 million of premium finance
receivables  were  sold  to  an  unrelated  third  party  and  resulted  in  the
recognition  of a $377,000  gain.  It is possible  that similar  future sales of
premium  finance  receivables  may occur  depending  on the level of new  volume
growth in relation to the capacity within the subsidiary banks' loan portfolios.

Service charges on deposit  accounts  totaled  $399,000 for the third quarter of
1999,  an increase of  $106,000,  or 36%,  when  compared to the same quarter of
1998.  This  increase was due to a higher  deposit  base and a larger  number of
accounts at both the more mature banks and the newer de novo banks. 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  $295,000 for the third quarter of 1999, an $85,000,  or 40%,
increase  over the same quarter of 1998.  This increase was mainly the result of
new business  development  efforts  generated from a larger staff of experienced
trust  officers.  Wintrust  is  committed  to growing  the trust and  investment
business in order to better service its customers and create a more  diversified
revenue stream.  However,  as the  introduction of expanded trust and investment
services  continues to unfold,  it is expected that overhead levels will be high
when  compared to the initial fee income that is  generated.  This overhead will
consist   primarily  of  the  salaries   and  benefits  of   experienced   trust
professionals.  It is anticipated that trust fees will eventually  increase to a
level sufficient to absorb this overhead within a few years.

Other  non-interest  income for the third  quarter of 1999 totaled  $398,000 and
increased   $215,000   over  the  prior  year   quarterly   total  of  $183,000.
Approximately  $105,000  of this  increase  resulted  from  rental  income  from
equipment leased through the Medical and Municipal  Funding division of the Lake
Forest Bank, a business that was acquired in mid-1998.  The remaining difference
primarily  relates to income and fees earned from various bank services provided
to a growing customer base.

For the nine months ended September 30, 1999, total non-interest income was $6.4
million and  increased  $762,000,  or 13%,  when  compared to the same period in
1998.  This  increase was mainly the result of a $640,000  gain from the sale of
premium finance receivables, a $333,000 increase in deposit service charges, the
recognition of $249,000 in premium income from certain call option transactions,
a $192,000  increase  in trust fees and  $212,000  of rental  income from leased
equipment.  These  increases were partially  offset by a $1.2 million decline in
fees  from the sale of  mortgage  loans  due  principally  to the  increases  in
mortgage loan interest  rates,  which caused a significant  drop in  refinancing
activity.

                                     - 6 -

NON-INTEREST EXPENSE

Non-interest  expense for the third  quarter of 1999  totaled  $9.4  million and
increased  $791,000,  or 9%, from the third  quarter 1998 total of $8.6 million.
The continued  growth and expansion of the de novo banks and the  development of
the new  trust  and  investment  subsidiary  were the  primary  causes  for this
increase. Since September 30, 1998, total deposits have grown 24% and total loan
balances have risen 32%,  requiring higher levels of staffing and other costs to
both attract and service the larger customer base.

Salaries  and  employee  benefits  expense  totaled  $5.0  million for the third
quarter of 1999,  an increase of $419,000,  or 9%, as compared to the prior year
quarter total of $4.6 million. As mentioned earlier, this increase was primarily
due to the  hiring  of  experienced  trust  professionals  for the new trust and
investment subsidiary.

Other categories of non-interest  expense,  such as occupancy  costs,  equipment
expense and data  processing,  also increased over the prior year quarter due to
the  general  growth of the  Company  and the  opening  of several  new  banking
facilities.  Other  non-interest  expense,  which includes the  amortization  of
intangible assets, loan expenses,  correspondent bank service charges,  postage,
insurance,  stationary  and supplies and other sundry  expenses,  also increased
when  compared to the prior year  quarter  due mainly to the  factors  mentioned
earlier.

For the nine-month period ended September 30, 1999, non-interest expense totaled
$28.5 million and increased $3.5 million,  or 14%, over the same period of 1998,
excluding  the second  quarter 1998  non-recurring  charge  mentioned in earlier
reports. This increase was predominantly due to the continued growth of loan and
deposit  accounts and the start-up of the new trust and  investment  subsidiary.
Despite  this  growth  and the  related  increases  in many of the  non-interest
expense  categories,  Wintrust's ratio of non-interest  expense to total average
assets  declined from 2.95% for the nine-month  period ended September 30, 1998,
exclusive of the previously  mentioned  non-recurring  charge,  to 2.63% for the
1999 period,  and is favorable to the Company's most recent peer group ratio. In
addition,  the net overhead  ratio for the first nine months of 1999 declined to
2.03%  as  compared  to the 1998  year-to-date  ratio of  2.28%,  excluding  the
non-recurring  charge.  The  improvement  in this  ratio  has  caused  this  key
indicator  of  overhead  to  reach  the  upper  end  of  the  previously  stated
performance goal range of 1.50% - 2.00%.

                                     - 7 -

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 and nine months ended  September  30, 1999 and 1998 is
shown as follows (dollars in thousands):



                                                        Three Months Ended                           Nine Months Ended
                                                           September 30,                               September 30,
                                                    1999                  1998                  1999                 1998
                                             -------------------     ----------------     -----------------     ----------------

                                                                                                         
 Balance at beginning of period                     $  7,677              $ 5,856                $7,034              $ 5,116

 Provision for possible loan losses                      990                  971                 2,707                3,311

 Charge-offs
  Core banking loans                                     190                  235                   593                1,508
  Indirect automobile loans                              156                  115                   795                  380
  Premium finance receivables                            193                   62                   383                  359
                                             -------------------     ----------------     -----------------     ----------------
     Total charge-offs                                   539                  412                 1,771                2,247
 Recoveries
  Core banking loans                                       9                   14                    19                  176
  Indirect automobile loans                               33                   19                    61                   32
  Premium finance receivables                             30                   52                   150                  112
                                             -------------------     ----------------     -----------------     ----------------
      Total recoveries                                    72                   85                   230                  320
                                             -------------------     ----------------     -----------------     ----------------

  Net charge-offs                                       (467)                (327)               (1,541)              (1,927)
                                             -------------------     ----------------     -----------------     ----------------

  Balance at September 30                           $  8,200              $ 6,500                $8,200              $ 6,500
                                             ===================     ================     =================     ================

  Loans at September 30                                                                      $1,202,256            $ 908,276
                                                                                          =================     ================

  Allowance as a percentage of loans                                                                  0.68%              0.72%
                                                                                          =================     ================

  Annualized net charge-offs as a percentage of average:
        Core banking loans                                                                            0.12%              0.36%
        Indirect automobile loans                                                                     0.42%              0.29%
        Premium finance receivables                                                                   0.15%              0.21%
                                                                                          -----------------     ----------------
            Total loans                                                                               0.19%              0.32%
                                                                                          =================     ================
        Annualized provision for
            possible loan losses                                                                     56.93%             58.20%
                                                                                          =================     ================


The provision for possible loan losses totaled $990,000 for the third quarter of
1999, a slight increase from a year earlier.  For the first nine months of 1999,
the  provision  totaled $2.7 million and declined  $604,000  from the prior year
total.  The higher  provision  in 1998 was  necessary  to cover  increased  loan
charge-offs  that  occurred at one banking  office in early 1998.  For the first
nine months of 1999, net charge-offs totaled $1.5 million and were down from the
$1.9 million of net charge-offs  recorded in 1998. On a ratio basis,  annualized
net  charge-offs as a percentage of average loans declined to 0.19% in 1999 from
0.32% in 1998.

                                     - 8 -

Management  believes  the  allowance  for  possible  loan  losses is adequate to
provide  for  potential  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).



                                                         September 30,           December 31,           September 30,
                                                              1999                   1998                    1998

                                                                                                        
      Past Due greater than 90 days
           and still accruing:
            Core banking loans                                   $  997                  $  800                  $ 686
            Indirect automobile loans                               354                     274                    167
            Premium finance receivables                           1,337                   1,214                    778
                                                      ---------------------  ----------------------  ---------------------
                Total                                             2,688                   2,288                  1,631
                                                      ---------------------  ----------------------  ---------------------

      Non-accrual loans:
            Core banking loans                                    1,139                   1,487                  3,387
            Indirect automobile loans                               369                     195                    129
            Premium finance receivables                           1,726                   1,455                    875
                                                      ---------------------  ----------------------  ---------------------
                Total non-accrual loans                           3,234                   3,137                  4,391
                                                      ---------------------  ----------------------  ---------------------

      Total non-performing loans:
            Core banking loans                                    2,136                   2,287                  4,073
            Indirect automobile loans                               723                     469                    296
            Premium finance receivables                           3,063                   2,669                  1,653
                                                      ---------------------  ----------------------  ---------------------
                Total non-performing loans                        5,922                   5,425                  6,022
                                                      ---------------------  ----------------------  ---------------------

      Other real estate owned                                         -                     587                      -
                                                      ---------------------  ----------------------  ---------------------

      Total non-performing assets                               $ 5,922                 $ 6,012                $ 6,022
                                                      =====================  ======================  =====================

      Total non-performing  loans by category as a percent of its own respective
        category:
            Core banking loans                                       0.29%                   0.38%                  0.75%
            Indirect automobile loans                                0.28%                   0.22%                  0.16%
            Premium finance receivables                              1.42%                   1.50%                  0.95%
                                                      ---------------------  ----------------------  ---------------------
               Total non-performing loans                            0.49%                   0.55%                  0.66%
                                                      ---------------------  ----------------------  ---------------------

      Total non-performing assets as a
          percentage of total assets                                 0.38%                   0.45%                  0.48%

      Allowance for possible loan losses as
        a percentage of non-performing loans                       138.47%                 129.66%                107.94%


                                     - 9 -


Non-performing Core Banking Loans

Total  non-performing  loans for the Company's  core banking  business were $2.1
million, or 0.29%, of the Company's core banking loans as of September 30, 1999,
and were down from the ratios of 0.38% as of December  31,  1998,  and 0.75% one
year ago.  Although the outstanding core loan portfolio has increased 34% from a
year ago,  the amount of  non-performing  core loans has  declined  48% from the
prior year totals.  Non-performing  core banking  loans  consist  primarily of a
small number of commercial and real estate loans, of which  management  believes
are well secured and in the process of  collection.  In fact,  about $455,000 of
the total relates to two residential real estate loans with appropriate  advance
ratios  that  protect  the  Company   from  loss.   The  small  number  of  such
non-performing  loans allows  management the  opportunity to monitor closely the
status of these credits and work with the  borrowers to resolve  these  problems
effectively.

Non-performing Premium Finance Receivables

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  premium finance receivables were $3.1 million, or
1.42% of total premium finance receivables, as of September 30, 1999. This ratio
compares  favorably  with the ratio of 1.50% at  December  31,  1998.  The ratio
fluctuates  throughout the year due to the nature and timing of canceled account
collections from insurance  carriers.  It is important to note that the ratio of
losses is substantially  less than the ratio of non-performing  assets indicated
above.  Please  refer to the  Allowance  for  Possible  Loan Losses  table where
annualized net  charge-offs for the first nine months of 1999 were only 0.15% of
average premium finance receivables.

Non-performing Indirect Automobile Loans

Total  non-performing  indirect  automobile loans were $723,000 at September 30,
1999. The ratio of these non-performing loans has increased slightly to 0.28% of
total indirect automobile loans at September 30, 1999 from 0.22% at December 31,
1998 and 0.16% at  September  30,  1998.  Despite  the  increase in the level of
non-performing  loans, the ratios continue to be below standard  industry ratios
for this type of loan category.

FORWARD-LOOKING STATEMENTS

This press release contains forward-looking  statements related to the Company's
financial  performance that are based on estimates.  Actual results could differ
materially from those addressed in the forward-looking statements due to factors
such as changes in economic conditions,  unanticipated changes in interest rates
that negatively impact net interest income,  competition and the related pricing
of loan and deposit  products,  future events that may cause  unforeseen loan or
lease losses,  slower than  anticipated  development and growth of the new trust
and investment  business,  the ability to adapt  successfully  to  technological
changes to compete  effectively in the marketplace,  the Company's success,  and
that of its outside data processing providers,  in testing and implementing Year
2000 compliant  hardware,  software and systems,  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.

                                     - 10 -