<PAGE>


                                  SCHEDULE 14A

          PROXY STATEMENT PURSUANT TO SECTION 14(a) OF THE SECURITIES
                     EXCHANGE ACT OF 1934 (AMENDMENT NO.  )

     Filed by the registrant [X]

     Filed by a party other than the registrant [ ]

     Check the appropriate box:

     [ ] Preliminary proxy statement.       [ ] Confidential, for use of the
                                                Commission only (as permitted by
                                                Rule 14a-6(e)(2)).

     [X] Definitive proxy statement.

     [ ] Definitive additional materials.

     [ ] Soliciting material pursuant to Section 240.14a-12

                             CHESTER BANCORP, INC.
--------------------------------------------------------------------------------
                (Name of Registrant as Specified in Its Charter)

--------------------------------------------------------------------------------
    (Name of Person(s) Filing Proxy Statement if Other Than the Registrant)

Payment of filing fee (check the appropriate box):

     [X] No fee required.

     [ ] Fee computed on table below per Exchange Act Rules 14a-6(i)(1) and
         0-11.

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

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

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

     (4) Proposed maximum aggregate value of transaction:
         NA
--------------------------------------------------------------------------------

     (5) Total fee paid:
         NA
--------------------------------------------------------------------------------

     [ ] Fee paid previously with preliminary materials.
--------------------------------------------------------------------------------

     [ ] Check box if any part of the fee is offset as provided by Exchange Act
         Rule 0-11(a)(2) and identify the filing for which the offsetting fee
         was paid previously. Identify the previous filing by registration
         statement number, or the form or schedule and the date of its filing.

     (1) Amount Previously Paid:
         NA
--------------------------------------------------------------------------------

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

     (3) Filing Party:
         NA
--------------------------------------------------------------------------------

     (4) Date Filed:
         NA
--------------------------------------------------------------------------------





<PAGE>
                                  March 1, 2002






Dear Stockholder:

         You are cordially invited to attend the Annual Meeting of Stockholders
of Chester Bancorp, Inc. to be held at the American Legion Hall located at 500
E. Opdyke St., Chester, Illinois, on Friday, April 5, 2002, at 10:00 a.m., local
time.

         The Notice of the Annual Meeting of Stockholders and Proxy Statement
appearing on the following pages describe the formal business to be transacted
at the meeting. During the meeting, we will also report on the operations of the
Corporation.

         IT IS IMPORTANT THAT YOUR SHARES ARE REPRESENTED AT THIS MEETING,
WHETHER OR NOT YOU ATTEND THE MEETING IN PERSON AND REGARDLESS OF THE NUMBER OF
SHARES YOU OWN. TO MAKE SURE YOUR SHARES ARE REPRESENTED, WE URGE YOU TO
COMPLETE AND MAIL THE ENCLOSED PROXY CARD. IF YOU ATTEND THE MEETING, YOU MAY
VOTE IN PERSON EVEN IF YOU HAVE PREVIOUSLY MAILED A PROXY CARD.

         We look forward to seeing you at the meeting.

                                      Sincerely,

                                      /s/ Michael W. Welge

                                      Michael W. Welge
                                      Chairman of the Board, President and Chief
                                      Financial Officer


<PAGE>
                              CHESTER BANCORP, INC.
                                1112 STATE STREET
                             CHESTER, ILLINOIS 62233
                                 (618) 826-5038

--------------------------------------------------------------------------------
                    NOTICE OF ANNUAL MEETING OF STOCKHOLDERS
                           TO BE HELD ON APRIL 5, 2002
--------------------------------------------------------------------------------

         NOTICE IS HEREBY GIVEN that the Annual Meeting of Stockholders of
Chester Bancorp, Inc. ("Corporation") will be held at the American Legion Hall
located at 500 E. Opdyke St., Chester, Illinois, on Friday, April 5, 2002, at
10:00 a.m., local time, for the following purposes:

         (1)  To elect two directors to serve for three year terms; and

         (2)  To consider and act upon such other matters as may properly come
              before the meeting or any adjournments thereof.

         NOTE: The Board of Directors is not aware of any other business to come
before the meeting.

         Any action may be taken on the foregoing proposals at the meeting on
the date specified above or on any date or dates to which, by original or later
adjournment, the meeting may be adjourned. Stockholders of record at the close
of business on February 15, 2002 are entitled to notice of and to vote at the
meeting and any adjournments or postponements thereof.

         You are requested to complete and sign the enclosed form of proxy,
which is solicited by the Board of Directors, and to mail it promptly in the
enclosed envelope. The proxy will not be used if you attend the meeting and vote
in person.

                                           BY ORDER OF THE BOARD OF DIRECTORS




                                           EDWARD K. COLLINS
                                           SECRETARY


Chester, Illinois
March 1, 2002


--------------------------------------------------------------------------------
IMPORTANT: THE PROMPT RETURN OF PROXIES WILL SAVE THE CORPORATION THE EXPENSE OF
FURTHER REQUESTS FOR PROXIES IN ORDER TO ENSURE A QUORUM. A SELF-ADDRESSED
ENVELOPE IS ENCLOSED FOR YOUR CONVENIENCE. NO POSTAGE IS REQUIRED IF MAILED IN
THE UNITED STATES.
--------------------------------------------------------------------------------

<PAGE>
--------------------------------------------------------------------------------
                                 PROXY STATEMENT
                                       OF
                              CHESTER BANCORP, INC.
                                1112 STATE STREET
                             CHESTER, ILLINOIS 62233
--------------------------------------------------------------------------------

                         ANNUAL MEETING OF STOCKHOLDERS
                                  APRIL 5, 2002

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

         This Proxy Statement is furnished in connection with the solicitation
of proxies by the Board of Directors of Chester Bancorp, Inc. ("Corporation"),
the holding company for Chester National Bank and Chester National Bank of
Missouri (together the "Banks"), to be used at the Annual Meeting of
Stockholders of the Corporation ("Annual Meeting"). The Annual Meeting will be
held at the American Legion Hall located at 500 E. Opdyke St., Chester, Illinois
on Friday, April 5, 2002, at 10:00 a.m., local time. This Proxy Statement and
the enclosed proxy card are being mailed to stockholders on or about March 1,
2002.

--------------------------------------------------------------------------------
                           VOTING AND PROXY PROCEDURE
--------------------------------------------------------------------------------

         Stockholders of record as of the close of business on February 15, 2002
are entitled to one vote for each share of common stock ("Common Stock") of the
Corporation then held. As of December 31, 2001, the Corporation had 977,970
shares of Common Stock issued and outstanding. The presence, in person or by
proxy, of at least a majority of the total number of outstanding shares of
Common Stock entitled to vote is necessary to constitute a quorum at the Annual
Meeting. Abstentions will be counted as shares present and entitled to vote at
the Annual Meeting for purposes of determining the existence of a quorum. Broker
non-votes will not be considered shares present and will not be included in
determining whether a quorum is present.

         The Board of Directors solicits proxies so that each stockholder has
the opportunity to vote on the proposals to be considered at the Annual Meeting.
When a proxy card is returned properly signed and dated, the shares represented
thereby will be voted in accordance with the instructions on the proxy card.
Where no instructions are indicated, proxies will be voted FOR the nominees for
directors set forth below. If a stockholder attends the Annual Meeting, he or
she may vote by ballot. If a stockholder does not return a signed proxy card or
does not attend the Annual Meeting and vote in person, his or her shares will
not be voted.

         Stockholders who execute proxies retain the right to revoke them at any
time. Proxies may be revoked by written notice delivered in person or mailed to
the Secretary of the Corporation or by filing a later proxy prior to a vote
being taken on a particular proposal at the Annual Meeting. Attendance at the
Annual Meeting will not automatically revoke a proxy, but a stockholder in
attendance may request a ballot and vote in person, thereby revoking a prior
granted proxy.

         The two directors to be elected at the Annual Meeting will be elected
by a plurality of the votes cast by stockholders present in person or by proxy
and entitled to vote. Stockholders are not permitted to cumulate their votes for
the election of directors. With respect to the election of directors, votes may
be cast for or withheld from each nominee. Votes that are withheld and broker
non-votes will have no effect on the outcome of the election because directors
will be elected by a plurality of votes cast.


<PAGE>


--------------------------------------------------------------------------------
         SECURITY OWNERSHIP OF CERTAIN BENEFICIAL OWNERS AND MANAGEMENT
--------------------------------------------------------------------------------

         Persons and groups who beneficially own in excess of 5% of the
Corporation's Common Stock are required to file certain reports disclosing such
ownership pursuant to the Securities Exchange Act of 1934, as amended ("Exchange
Act"). Based on such reports, the following table sets forth, as of December 31,
2001, certain information as to those persons who were beneficial owners of more
than 5% of the outstanding shares of Common Stock. Management knows of no
persons other than those set forth below who beneficially owned more than 5% of
the outstanding shares of Common Stock at December 31, 2001. The following table
also sets forth, as of December 31, 2001, information as to the shares of Common
Stock beneficially owned by each director, by the named executive officers of
the Corporation, and by all executive officers and directors of the Corporation
as a group.

<TABLE>
<CAPTION>
                                                Number of Shares                         Percent of Shares
Name                                         Beneficially Owned (1)(2)                       Outstanding
----                                         ------------------                          --------------------
<S>                                          <C>                                         <C>
DIRECTORS AND BENEFICIAL
OWNERS OF MORE THAN 5%

Chester National Bank Employee Stock Ownership Plan and Trust
     1112 State Street
     Chester, Illinois 62233                         171,343(3)                               17.52%

Michael W. Welge                                     187,646(3)(4)                            18.45%
Allen R. Verseman                                     64,100(5)                                6.31%
John R. Beck, M.D.                                    62,217                                   6.31%
James C. McDonald                                     31,671                                   3.21%
Thomas E. Welch, Jr.                                  19,389(3)                                1.98%
Carl H. Welge                                         19,973                                   2.02%

NAMED EXECUTIVE OFFICERS(6)
Edward K. Collins                                     68,289(3)                                6.72%

All Executive Officers and
 Directors as a Group (7 persons)                    453,295                                  41.61%
</TABLE>

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

(1)  In accordance with Rule 13d-3 under the Exchange Act, a person is deemed to
     be the beneficial owner, for purposes of this table, of any shares of
     Common Stock if he or she has voting or investment power with respect to
     such security. The table includes shares owned by spouses, other immediate
     family members in trust, shares held in retirement accounts or funds for
     the benefit of the named individuals, and other forms of ownership, over
     which shares the persons named in the table may possess voting and/or
     investment power.

(2)  Includes the following shares which are not presently owned but could be
     acquired by such persons within 60 days after December 31, 2001, upon
     exercise of employee stock options or director non-qualified stock options:
     38,988 shares for each of Mr. M. Welge and Mr. Collins; and 8,729 shares
     for each of Messrs. Beck, Verseman, McDonald and C. Welge.

(3)  Shares held in accounts under the Corporation's ESOP, as to which the
     holders have voting power but not investment power, are included as
     follows: Mr. Collins, 4,817 shares, Mr. M. Welge, 2,602 shares, and Mr.
     Welch, 1,597 shares.

(4)  Includes 93,856 shares over which Mr. M. Welge has sole voting and
     investment power, 52,200 shares over which Mr. M. Welge has shared
     investment and voting power, options to acquire 38,988 shares and 2,602
     shares held in the ESOP.

(5)  Includes 51,396 shares over which Mr. Verseman has sole voting and
     investment power and 1,500 shares over which Mr. Verseman has shared
     investment and voting power.

(6)  Under SEC regulations, the term "named executive officer" is defined to
     include the chief executive officer, regardless of compensation level, and
     the four most highly compensated executive officers, other than the chief
     executive officer, whose total annual salary and bonus for the last
     completed fiscal year exceeded $100,000. Edward K. Collins was the
     Corporation's only "named executive officer" for the fiscal year ended
     December 31, 2001. He is also a director of the Corporation.


                                        2
<PAGE>


--------------------------------------------------------------------------------
                       PROPOSAL I -- ELECTION OF DIRECTORS
--------------------------------------------------------------------------------

         The Corporation's Board of Directors consists of seven members and is
divided into three classes with three-year staggered terms, with approximately
one-third of the directors elected each year. Two directors will be elected at
the Annual Meeting to serve for a three year period, or until their respective
successors have been elected and qualified. The nominees for election this year
are Michael W. Welge and Edward K. Collins. The nominees are current members of
the Boards of Directors of the Corporation and the Banks.

         It is intended that the proxies solicited by the Board of Directors
will be voted for the election of the above named nominees. If any nominee is
unable to serve, the shares represented by all valid proxies will be voted for
the election of such substitute as the Board of Directors may recommend or the
Board of Directors may adopt a resolution to amend the Bylaws and reduce the
size of the Board. At this time the Board of Directors knows of no reason why
any nominee might be unavailable to serve.

         THE BOARD OF DIRECTORS RECOMMENDS A VOTE "FOR" THE ELECTION OF MESSRS.
WELGE AND COLLINS.

         The following table sets forth certain information regarding the
nominees for election at the Annual Meeting, as well as information regarding
those directors continuing in office after the Annual Meeting.

<TABLE>
<CAPTION>
                                                              Year First
                                                               Elected                       Term to
    Name                            Age(1)                    Director(2)                    Expire(3)
    ----                            ---                       --------                       ------
<S>                            <C>                           <C>                            <C>
                                                BOARD NOMINEES

Michael W. Welge(4)                   61                        1980                           2005
Edward K. Collins                     57                        1996                           2005


                                        DIRECTORS CONTINUING IN OFFICE


Thomas E. Welch, Jr.                  62                        1990                           2003
John R. Beck, M.D.                    67                        1989                           2003
James C. McDonald                     72                        1990                           2003
Carl H. Welge(4)                      58                        1980                           2004
Allen R. Verseman                     67                        1992                           2004
</TABLE>
--------------

(1)  As of December 31, 2001.
(2)  Includes prior service on the Board of Directors of Chester Savings Bank.
(3)  Assuming the individual is re-elected.
(4)  Michael W. Welge and Carl H. Welge are second cousins.

         The present principal occupation and other business experience during
the last five years of each nominee for election and each director continuing in
office is set forth below:

         Michael W. Welge is Chairman of the Board of Directors, President and
Chief Financial Officer. He has responsibility for various management functions,
including financial management and investment portfolio management,
determination of all employee compensation and employment decisions. Mr. Welge
has been employed for the past 40 years at Gilster-Mary Lee Corporation where he
currently serves as its Executive Vice President, Secretary and Treasurer. He
has been active in civic affairs as a past President of both the Chester Chamber
of Commerce and the Chester School Board, an Alderman of the City Council of
Chester for 20 years and the President and a director of several local
corporations and clubs.

                                       3
<PAGE>

         Edward K. Collins is Secretary, Treasurer and Chief Executive Officer
of the Corporation and has been Chief Executive Officer of Chester National Bank
since January 1995. He is responsible for Chester National Bank's supervisions
and performance of operations and lending. Prior to his employment at Chester
National Bank, Mr. Collins was Executive Vice President and Senior Loan Officer
of Union Bank of Illinois from August 1991 to December 1994 and was President,
Chief Executive Officer and a Director of First National Bank & Trust, Syracuse,
Nebraska, from August 1988 to August 1991. Mr. Collins is a member of the Board
of Directors of the Chester Chamber of Commerce.

         Carl H. Welge has been employed for 12 years at Gilster-Mary Lee
Corporation and currently serves as Accounts Receivable Supervisor. He is a
member of the Memorial Hospital Board of Directors and a member of the Friends
of Chester Public Library.

         John R. Beck, M.D. is a self-employed physician. He is a member of the
Hospital staff of Memorial Hospital, Chester, Illinois, and a director of Home
Health Care.

         James C. McDonald retired after being employed for over 40 years at the
U.S. Postal Service. He is a Trustee of the Presbyterian Church, Sparta,
Illinois, and is a member of the Sparta Building Commission and the Sparta
Senior Citizen Board.

         Thomas E. Welch, Jr. was employed as an officer of Chester National
Bank since 1990 when Heritage Federal was acquired by Chester National Bank. Mr.
Welch retired from employment as the Senior Vice President and Compliance
Officer for Chester National Bank and manager of the Sparta branch in March of
2000.

         Allen R. Verseman has been employed for 33 years at Gilster-Mary Lee
Corporation and currently serves as Plant Superintendent.

--------------------------------------------------------------------------------
                  MEETINGS AND COMMITTEES OF THE BOARD OF DIRECTORS
--------------------------------------------------------------------------------

         The Boards of Directors of the Corporation and the Banks conduct their
business through meetings of the Boards and through their committees. During the
fiscal year ended December 31, 2001, the Board of Directors of the Corporation
held 12 meetings, the Board of Directors of Chester National Bank held 12
meetings, and the Board of Directors of Chester National Bank of Missouri held
12 meetings. No director of the Corporation or the Banks attended fewer than 75%
of the total meetings of the Boards and committees on which such person served
during this period.

         Each year an Audit Committee is appointed, and consists of at least
four directors who are not officers or employees of the Company. The purpose of
this Committee is to review financial data of the Company and retain the
Company's independent auditor. During the fiscal year ended December 31, 2001,
the Audit Committee met 12 times.

         The Executive Committee consists of Directors M. Welge, and Collins,
the Secretary and two rotating Directors. The Executive Committee meets weekly,
and the committee has full authority of the Board of Directors in order to
conduct business in a timely manner. The Executive Committee also functions as
the Banks' Loan Committee and Asset Liability Committee. All actions of the
Executive Committee are subsequently ratified by the full Board of Directors.
The Executive Committee met 52 times during the fiscal year ended December 31,
2001.

         The Board of Directors of the Corporation acts as a nominating
committee for selecting the nominees for election as directors. During the
fiscal year ended December 31, 2001, the Board of Directors met once in its
capacity as nominating committee to select nominees for election at the Annual
Meeting.

--------------------------------------------------------------------------------
                             DIRECTORS' COMPENSATION
--------------------------------------------------------------------------------

DIRECTORS' COMPENSATION

         BOARD AND COMMITTEE FEES. Directors received a fee of $800 per month
during the year ended December 31, 2001, with no additional fees paid for
committee meetings, except for the rotating Directors who serve on the

                                       4
<PAGE>

Executive Committee who receive $50 per meeting attended. Director's fees
totaled $67,450 for the year ended December 31, 2001.

--------------------------------------------------------------------------------
                             EXECUTIVE COMPENSATION
--------------------------------------------------------------------------------

SUMMARY COMPENSATION TABLE

<TABLE>
<CAPTION>
                                                                           Annual Compensation
                                                       ------------------------------------------------------
Name and                                                                                         Other Annual
Position                                               Year     Salary($)     Bonus($)        Compensation($)(1)
--------                                               ----     ---------     --------        ---------------
<S>                                                    <C>      <C>           <C>             <C>
Edward K. Collins                                      2001     $ 84,000          --             $    --
Secretary, Treasurer and Chief Executive               2000     $ 83,500          --             $    --
  Officer of the Corporation, Chief Executive          1999     $ 80,000          --             $    --
  Officer and Director of Chester National Bank
</TABLE>

---------------------
(1)   Does not include perquisites which, in the aggregate, did not exceed the
      lesser of $50,000 or 10% of salary and bonus.

EMPLOYMENT AGREEMENTS

         The Corporation and the Banks have entered into a three-year employment
agreement with Mr. Collins. Under the agreement, the salary level for Mr.
Collins is $80,000, which amount will be paid by Chester National Bank and may
be increased at the discretion of the Board of Directors or an authorized
committee of the Board. On each anniversary of the commencement date of the
agreement, the term of the agreement may be extended for an additional year. The
current term of the agreement has been extended to January 1, 2005. The
agreement is terminable by the Employers at any time or upon the occurrence of
certain events specified by federal regulations.

         The employment agreement provides for severance payments and other
benefits in the event of involuntary termination of employment in connection
with any change in control of the Employers. Severance payments also will be
provided in connection with a voluntary termination of employment where,
subsequent to a change in control, Mr. Collins is assigned duties inconsistent
with his position, duties, responsibilities and status immediately prior to such
change in control. The term "change in control" is defined in the agreement as
having occurred when, among other things, (a) a person other than the
Corporation purchases shares of Common Stock pursuant to a tender or exchange
offer for such shares, (b) any person is or becomes the beneficial owner,
directly or indirectly, of securities of the Corporation representing 25% or
more of the combined voting power of the Corporation's then outstanding
securities, (c) the membership of the Board of Directors changes as the result
of a contested election, or (d) stockholders of the Corporation approve a
merger, consolidation, sale or disposition of all or substantially all of the
Corporation's assets, or a plan of partial or complete liquidation.

         The severance payments from the Employers will equal 2.99 times Mr.
Collins' average annual compensation during the five-year period preceding the
change in control. Such amount will be paid in a lump sum within 10 business
days following the termination of employment. Assuming that a change in control
had occurred at December 31, 2001, Mr. Collins would be entitled to severance
payments of approximately $240,000. Section 280G of the Internal Revenue Code of
1986, as amended ("Code"), states that severance payments that equal or exceed
three times the base compensation of the individual are deemed to be "excess
parachute payments" if they are contingent upon a change in control. Individuals
receiving excess parachute payments are subject to a 20% excise tax on the
amount of such excess payments, and the Employers would not be entitled to
deduct the amount of such excess payments.

         The agreement restricts Mr. Collins' right to compete against the
Employers for a period of one year from the date of termination of the agreement
if he voluntarily terminates his employment, except in the event of a change in
control. The Board of Directors of the Corporation or the Banks may, from time
to time, also extend employment agreements to other senior executive officers.


                                       5
<PAGE>

COMPENSATION COMMITTEE INTERLOCKS AND INSIDER PARTICIPATION

         The entire Board of Directors of the Corporation acts as the
Compensation Committee which determines the compensation for Mr. Collins and the
other officers of the Corporation. The Committee met once in 2001.

         Notwithstanding anything to the contrary set forth in any of the
Corporation's previous filings under the Securities Act or the Exchange Act that
might incorporate future filings, including this Proxy Statement, in whole or in
part, the following Report of the Compensation Committee and Performance Graph
shall not be incorporated by reference into any such filings.

REPORT OF THE COMPENSATION COMMITTEE

         Under the rules established by the SEC, the Corporation is required to
provide certain data and information in regard to the compensation and benefits
provided to the Corporation's Chief Executive Officer and other executives
officers of the Corporation. The disclosure requirements for the Chief Executive
Officer and other executive officers include the use of tables and a report
explaining the rationale and considerations that led to the fundamental
executive compensation decisions affecting those individuals. Insofar as no
separate compensation is currently payable by the Corporation, the Committee,
acting on behalf of Chester National Bank, has prepared the following report for
inclusion in this proxy statement.

         The Committee's duties are to administer policies that govern executive
compensation for the Corporation. The Committee evaluates executive
performances, compensation policies and salaries and makes determinations
concerning the compensation of each named executive officer and other executive
officers. The Committee establishes the compensation levels for the coming year.
The executive compensation policy of the Corporation is designed to establish an
appropriate relationship between executive pay and the Corporation's annual and
long-term performance, long-term growth objectives, and the Corporation's
ability to attract and retain qualified executive officers. Although the
Committee did not establish executive compensation levels on the basis of
whether specific financial goals had been achieved by the Corporation, the
Committee considered the overall profitability of the Corporation when making
their decisions. The Committee believes that management compensation levels, as
a whole, appropriately reflect the application of the Corporation's executive
compensation policy and the progress of the Corporation. During the year ended
December 31, 2001, the base compensation for Edward K. Collins was $80,000,
which did not represent an increase from the previous year.

REPORT OF THE AUDIT COMMITTEE

         The audit committee is comprised of Messrs. Welch, Beck, McDonald,
Verseman and C. Welge, five directors who are not officers or employees of the
Company. Four of the five are considered independent as that term is defined by
NASD listing standards. Mr. Welch is not considered independent because he was
formerly an employee of Chester National Bank, however, with respect to Mr.
Welch the independence requirement as been waived in accordance with NASD
listing standards. The board of directors has adopted a written charter for the
audit committee.

         The audit committee reviews our financial reporting process on behalf
of the board of directors. In fulfilling its responsibilities, the committee has
reviewed and discussed the audited financial statements contained in the 2001
Annual Report on SEC Form 10-K with our management and the independent auditors.
Management is responsible for the financial statements and the reporting
process, including the system of internal controls. The independent auditors are
responsible for expressing an opinion on the conformity of those audited
financial statements with accounting principles generally accepted in the United
States.

         The audit committee discussed with the independent auditors, the
matters required to be discussed by Statement on Auditing Standards No. 61,
Communication with Audit Committees, as amended. In addition, the audit
committee has discussed with the independent auditors, the auditors'
independence from the Corporation and its management including the matters in
the written disclosures required by Independence Standards Board Standard No. 1,
Independence Discussions with Audit Committees.


                                       6
<PAGE>

         In reliance on the reviews and discussions referred to above, the audit
committee recommended to the Board of Directors (and the Board has approved)
that the audited financial statements be included in the Corporation's Annual
Report on SEC Form 10-K for the year ended December 31, 2001, for filing with
the Securities Exchange Commission.

Audit Fees

         As of February 1, 2002, the aggregate fees billed for professional
services rendered for the audit of the Corporation's annual financial statements
for the 2001 fiscal year were $25,000, and additional fees for such audit are
expected to be approximately $17,300. Audit fees include the entire amount of
the audit fees associated with the year-end audit, whether or not they have been
billed, and also includes fees related to review of press releases, 10-Q's, the
Annual Report and Form 10-K, including proofing the printer's copy. All
procedures performed in connection with the year-end audit are performed by
individuals who are full-time, permanent employees of McGladrey & Pullen, LLP or
RSM McGladrey, Inc.

All Other Fees.

         The aggregate fees billed for professional services rendered for by the
Corporation's principal accountants for services other than the audit of the
Corporation's annual financial statements and the review of the Corporation's
Forms 10-Q were $15,375 for the fiscal year ending December 31, 2001. The audit
committee has determined that the provision of these services is compatible with
the maintaining the principal accountant's independence.


                                       7
<PAGE>
PERFORMANCE GRAPH

         Set forth hereunder is a performance graph comparing (a) the total
return of the Corporation's common stock for the five (5) year period beginning
December 31, 1996 through December 31, 2002, (b) the cumulative total return on
stocks included in the Russell 2000 Index over such period, and (c) the
cumulative total return on stocks included in the SNL Bank - less than $250M -
Asset-Size Index. The cumulative total return on the Corporation's common stock
was computed assuming the reinvestment of cash dividends.

                              [PERFORMANCE GRAPH]

<TABLE>
<CAPTION>
     -------------------------------------------------------------------------------------------------------
                                                                    PERIOD ENDING
     -------------------------------------------------------------------------------------------------------
     INDEX                               12/31/96    12/31/97    12/31/98    12/31/99    12/31/00   12/31/01
     -------------------------------------------------------------------------------------------------------
<S>                                      <C>         <C>         <C>         <C>        <C>         <C>
     Chester Bancorp, Inc.                100.00      138.36      132.25      133.37     137.36      157.40
     -------------------------------------------------------------------------------------------------------
     Russell 2000                         100.00      122.36      119.25      144.60     140.23      143.71
     -------------------------------------------------------------------------------------------------------
     SNL <$250M Bank Index                100.00      163.18      155.12      136.21     134.86      168.15
     -------------------------------------------------------------------------------------------------------
</TABLE>

                                       8

<PAGE>
--------------------------------------------------------------------------------
                COMPLIANCE WITH SECTION 16(a) OF THE EXCHANGE ACT
--------------------------------------------------------------------------------

         Section 16(a) of the Exchange Act requires the Corporation's executive
officers and directors, and persons who own more than 10% of any registered
class of the Corporation's equity securities, to file reports of ownership and
changes in ownership with the SEC. Executive officers, directors and greater
than 10% stockholders are required by regulation to furnish the Corporation with
copies of all Section 16(a) forms they file.

         Based solely on its review of the copies of such forms it has received
and written representations provided to the Corporation by the above referenced
persons, the Corporation believes that, during the 2001 fiscal year, all filing
requirements applicable to its reporting officers, directors and greater than
10% stockholders were properly and timely complied with.

--------------------------------------------------------------------------------
                          TRANSACTIONS WITH MANAGEMENT
--------------------------------------------------------------------------------
         Current law requires that all loans or extensions of credit to
executive officers and directors must be made on substantially the same terms,
including interest rates and collateral, as those prevailing at the time for
comparable transactions with other persons and does not involve more than the
normal risk of repayment or present other unfavorable features. The Banks are
prohibited from making any new loans or extensions of credit to the Banks'
executive officers and directors at different rates or terms than those offered
to the general public, and has adopted a policy to this effect. The aggregate
amount of loans by the Banks to its executive officers and directors was
$428,860 at December 31, 2001.

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                                    AUDITORS
--------------------------------------------------------------------------------

         McGladrey and Pullen, LLP was the auditor for the fiscal year ending
December 31, 2001. The Board of Directors has appointed McGladrey & Pullen, LLP,
independent public accountants, to serve as the Corporation's auditors for the
fiscal year ending December 31, 2002.

         On July 11, 2000, the Corporation dismissed KPMG LLP as the Company's
independent accountants and appointed McGladrey & Pullen, LLP as its new
independent accountants. The decision to change accountants was approved by the
Audit Committee of the Board of Directors of the Company.

         During 1999, the opinion of KPMG LLP did not contain any adverse
opinion or a disclaimer of opinion and was not qualified or modified as to
uncertainty, audit scope or accounting principles. During 1999 (and the
subsequent interim period) the Company had no disagreements with KPMG LLP on any
matter of accounting principles or practices, financial statement disclosure or
auditing scope or procedure, which disagreement(s), if not resolved to the
satisfaction of KPMG LLP, would have caused it to make reference to the subject
matter of the disagreement(s) in connection with its report. None of the events
described at Item 304(a)(1)(v) of Regulation S-K took place in 1999 nor in the
subsequent interim period.

         McGladrey & Pullen, LLP's appointment is effective July 11, 2000.
During 1999 and the subsequent interim period prior to such appointment, the
Company did not consult with McGladrey & Pullen, LLP regarding the application
of accounting principles generally accepted in the United States of America to a
specific transaction, either proposed or completed, or the type of audit opinion
that might be rendered on the Company's financial statements. Because there were
no disagreements or reportable events (as defined in Item 304(a)(2) of
Regulation S-K), the Company did not consult McGladrey & Pullen, LLP in respect
to those matters during that time.

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                                  OTHER MATTERS
--------------------------------------------------------------------------------

         The Board of Directors is not aware of any business to come before the
Annual Meeting other than those matters described above in this Proxy Statement.
However, if any other matters should properly come before the

                                       9

<PAGE>

Annual Meeting, it is intended that proxies in the accompanying form will be
voted in respect thereof in accordance with the judgment of the person or
persons voting the proxies.

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                                  MISCELLANEOUS
--------------------------------------------------------------------------------

         The cost of solicitation of proxies will be borne by the Corporation.
The Corporation will reimburse brokerage firms and other custodians, nominees
and fiduciaries for reasonable expenses incurred by them in sending proxy
materials to the beneficial owners of the Common Stock. In addition to
solicitations by mail, directors, officers and regular employees of the
Corporation may solicit proxies personally or by telecopier or telephone without
additional compensation.

         The Corporation's 2001 Annual Report to Stockholders, including
consolidated financial statements, has been mailed to all stockholders of record
as of the close of business on February 15, 2002. Any stockholder who has not
received a copy of the Annual Report may obtain a copy by writing to the
Corporation. The Annual Report is not to be treated as part of the proxy
solicitation material or having been incorporated herein by reference.

         A COPY OF THE CORPORATION'S FORM 10-K FOR THE FISCAL YEAR ENDED
DECEMBER 31, 2001, AS FILED WITH THE SEC, WILL BE FURNISHED WITHOUT CHARGE TO
STOCKHOLDERS OF RECORD AS OF FEBRUARY 15, 2002, UPON WRITTEN REQUEST TO MICHAEL
W. WELGE, PRESIDENT, CHESTER BANCORP, INC., 1112 STATE STREET, CHESTER, ILLINOIS
62233.

--------------------------------------------------------------------------------
                              STOCKHOLDER PROPOSALS
--------------------------------------------------------------------------------

         Proposals of stockholders intended to be presented at the Corporation's
annual meeting to be held in April 2003 must be received by the Corporation no
later than October 1, 2002 to be considered for inclusion in the proxy
solicitation materials and form of proxy relating to such meeting. Any such
proposals shall be subject to the requirements of the proxy solicitation rules
adopted under the Exchange Act.

                                         BY ORDER OF THE BOARD OF DIRECTORS

                                         EDWARD K. COLLINS
                                         SECRETARY

Chester, Illinois
March 1, 2002



                                       10
<PAGE>

                                 REVOCABLE PROXY
                              CHESTER BANCORP, INC.

<TABLE>
<S><C>
[X]      PLEASE MARK VOTES
         AS IN THIS EXAMPLE
                                                                                                                     For All   With-
            ANNUAL MEETING OF STOCKHOLDERS                                                                    For    Except    hold
                     APRIL 5, 2002                                 1.     The election as directors of the
                                                                          nominees listed (except as marked   [ ]      [ ]     [ ]
                                                                          to the contrary below):
     The undersigned hereby appoints the official Proxy
Committee of the Board of Directors of Chester Bancorp, Inc.                     MICHAEL W. WELGE    EDWARD K. COLLINS
("Corporation") with full powers of substitution to act as
attorneys and proxies for the undersigned, to vote all shares of   INSTRUCTION:  TO WITHHOLD AUTHORITY TO VOTE FOR ANY
Common Stock of the Corporation which the undersigned is           INDIVIDUAL NOMINEE, MARK "FOR ALL EXCEPT" AND WRITE THAT
entitled to vote at the Annual Meeting of Stockholders, to be      NOMINEE'S NAME IN THE SPACE PROVIDED BELOW.
held at the American Legion Hall, 500 E. Opdyke St., Chester,
Illinois on Friday, April 5, 2002 at 10:00 a.m., local time, and           --------------------------------------------------------
at any and all adjournment thereof, as follows:

                                                                   2.     In their discretion, upon such other matters as may
                                                                      properly come before the meeting.


THIS PROXY WILL BE VOTED AS DIRECTED, BUT IF NO INSTRUCTIONS ARE
SPECIFIED THIS PROXY WILL BE VOTED FOR THE PROPOSITIONS STATED.             THIS PROXY IS SOLICITED BY THE BOARD OF DIRECTORS
IF ANY OTHER BUSINESS IS PRESENTED AT SUCH MEETING, THIS PROXY
WILL BE VOTED BY THE BOARD OF DIRECTORS IN ITS BEST JUDGMENT. AT
THE PRESENT TIME, THE BOARD OF DIRECTORS KNOWS OF NO OTHER
BUSINESS TO BE PRESENTED AT THE ANNUAL MEETING. THIS PROXY ALSO
CONFERS DISCRETIONARY AUTHORITY ON THE BOARD OF DIRECTORS TO
VOTE WITH RESPECT TO THE ELECTION OF ANY PERSONS AS DIRECTOR
WHERE THE NOMINEES ARE UNABLE TO SERVE OR FOR GOOD CAUSE WILL
NOT SERVE AND MATTERS INCIDENT TO THE CONDUCT OF THE ANNUAL
MEETING.

                                      ---------------------------
Please be sure to sign and date          Date
    this Proxy in the box below.
-----------------------------------------------------------------


 Stockholder sign above                       Co-holder (if any)
                        ----------------------
                             sign above
-----------------------------------------------------------------
</TABLE>

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

   DETACH ABOVE CARD, SIGN, DATE AND MAIL IN POSTAGE PAID ENVELOPE PROVIDED.

                              CHESTER BANCORP, INC.

--------------------------------------------------------------------------------
    Should the above signed be present and elect to vote at the Annual Meeting
or at any adjournment thereof and after notification to the Secretary of the
Corporation at the Annual Meeting of the stockholder's decision to terminate
this proxy, then the power of said attorneys and proxies shall be deemed
terminated and of no further force and effect.

    The above signed acknowledges receipt from the Corporation prior to the
execution of this proxy of the Notice of Annual Meeting of Stockholders, a Proxy
Statement for the Annual Meeting, dated March 1, 2002 and the Annual Report to
Stockholders.

    Please sign exactly as your name appears on the enclosed card. When signing
as attorney, executor, administrator, trustee or guardian, please give your full
title. If shares are held jointly, each holder should sign.

            PLEASE COMPLETE, DATE, SIGN, AND MAIL THIS PROXY PROMPTLY
                    IN THE ENCLOSED POSTAGE-PREPAID ENVELOPE.
--------------------------------------------------------------------------------