<PAGE>   1
    AS FILED WITH THE SECURITIES AND EXCHANGE COMMISSION ON JANUARY 26, 2000
                                                     REGISTRATION NO. 333-
================================================================================

                                  UNITED STATES
                       SECURITIES AND EXCHANGE COMMISSION
                             WASHINGTON, D.C. 20549

                                    FORM S-8
             REGISTRATION STATEMENT UNDER THE SECURITIES ACT OF 1933

                              QUOTESMITH.COM, INC.
             (Exact name of registrant as specified in its charter)

                DELAWARE                                58-1521612
(State of incorporation or organization)    (I.R.S. Employer Identification No.)

            8205 SOUTH CASS AVENUE, SUITE 102, DARIEN, ILLINOIS 60561
                    (Address of Principal Executive Offices)

   QUOTESMITH.COM, INC. 1997 STOCK OPTION PLAN (AS AMENDED ON MARCH 29, 1999)
             QUOTESMITH.COM, INC. 1999 EMPLOYEE STOCK PURCHASE PLAN
                            (Full title of the plans)

                           BURKE A. CHRISTENSEN, ESQ.
            VICE PRESIDENT AND GENERAL COUNSEL, QUOTESMITH.COM, INC.
            8205 SOUTH CASS AVENUE, SUITE 102, DARIEN, ILLINOIS 60561
                   (630) 515-0170 (PHONE) (630) 515-0276 (FAX)
           (Name, Address, and Telephone Number of Agent for Service)

                                 WITH A COPY TO:
                             GORDON P. PAULSON, ESQ.
                             CYNTHIA A. LANCE, ESQ.
 FREEBORN & PETERS, 311 SOUTH WACKER DRIVE, SUITE 3000, CHICAGO, ILLINOIS 60606
                  (312) 360-6602 (PHONE) (312) 360-6574 (FAX)

APPROXIMATE DATE OF COMMENCEMENT OF PROPOSED SALE TO THE PUBLIC: As soon as
practicable after the effective date of this Registration Statement. The
securities that are being registered on this Form are to be offered on a delayed
or continuous basis pursuant to Rule 415 under the Securities Act of 1933.

<TABLE>
<CAPTION>
------------------------------------------------------------------------------------------------------------------------------------
                                                  CALCULATION OF REGISTRATION FEE
                Title Of Securities                         Amount To Be       Offering Price    Maximum Aggregate      Amount Of
                 To Be Registered                            Registered       Per Share (1)(2)    Offering Price    Registration Fee
------------------------------------------------------------------------------------------------------------------------------------
<S>                                                          <C>                   <C>              <C>                 <C>
[1997 Stock Option Plan]
     Common Stock $.001 par value per share.............     1,500,000             $11.25           $16,875,000         $   4,455
[1999 Stock Purchase Plan]
    Common Stock $.001 par value per share (3)..........       250,000             $ 9.56           $ 2,390,000         $  630.96
                                                                                   TOTAL FEE                            $5,085.96
------------------------------------------------------------------------------------------------------------------------------------
</TABLE>

(1)  The Offering Price Per Share has been estimated in accordance with Rule
     457(h) under the Securities Act of 1933 as to the 1,500,000 shares of
     Common Stock authorized for issuance pursuant to the 1997 Stock Plan,
     solely for the purpose of calculating the registration fee. The computation
     is based upon the average of the high and low price of the Common Stock as
     reported on the Nasdaq National Market on January 21, 2000.

(2)  The Offering Price Per Share has been estimated in accordance with Rule
     457(h) under the Securities Act of 1933 solely for the purpose of
     calculating the registration fee. The computation is based upon 85% of the
     average of the high and low price of the Common Stock as reported on the
     Nasdaq National Market on January 21, 2000.

(3)  Includes registration of any interests in the 1999 Stock Purchase Plan
     acquired during any purchase period.


<PAGE>   2

                                     PART II

               INFORMATION REQUIRED IN THE REGISTRATION STATEMENT

ITEM 3.    INFORMATION INCORPORATED BY REFERENCE.

           The following documents filed by Quotesmith.com, Inc. with the
Securities and Exchange Commission (the "Commission") are incorporated by
reference:

           (a)      The Quotesmith.com Prospectus filed with the Commission on
                    August 3, 1999 pursuant to Rule 424(b) under the Securities
                    Act of 1933, as amended (the "Securities Act").

           (b)      Quotesmith.com's Quarterly Report on form 10-Q for the
                    quarter ended September 30, 1999 and filed with the
                    Commission on November 15, 1999.

           (c)      The description of the Common Stock, $.001 par value per
                    share, contained in the Quotesmith.com Registration
                    Statement on Form 8-A filed on July 21, 1999 pursuant to
                    Section 12(g) of the Securities Exchange Act of 1943, as
                    amended (the "Exchange Act").

           (d)      All documents filed by Quotesmith.com pursuant to Sections
                    13(a), 13(c), 14 and 15(d) of the Exchange Act, subsequent
                    to the filing of this Registration Statement and prior to
                    the filing of a post-effective amendment which indicates
                    that all securities offered have been sold, or which
                    deregisters all securities then remaining unsold, shall be
                    deemed to be incorporated by reference in this Registration
                    Statement and to be part hereof from the date of filing of
                    such documents.

ITEM 4.    DESCRIPTION OF SECURITIES.

           Not applicable.

ITEM 5.    INTERESTS OF NAMED EXPERTS AND COUNSEL.

            Not applicable.

ITEM 6.    INDEMNIFICATION OF DIRECTORS AND OFFICERS.

           The Quotesmith.com Certificate of Incorporation: (a) eliminates the
personal liability of the Quotesmith.com directors and officers for monetary
damages arising from a breach of their fiduciary duties under certain
circumstances; and (b) authorizes Quotesmith.com to indemnify its directors and
officers to the fullest extent permitted by the Delaware General Corporation
Law. The limitation of liability in the Certificate of Incorporation does not
affect the availability of equitable remedies such as injunctive relief or
rescission, and does not apply to liabilities arising under the federal
securities laws. The Quotesmith.com Bylaws: (a) allow for the indemnity of the
Quotesmith.com directors and officers to the fullest extent permitted by the
Delaware General Corporation Law; and (b) require, under certain circumstances,
Quotesmith.com to advance expenses to its directors and officers in connection
with a legal proceeding.

         Quotesmith.com has also entered into indemnification agreements with
its directors which allow for the indemnification of directors for most
expenses, including attorneys' fees, judgments, fines and settlement amounts
incurred by them in any action or proceeding, including any action brought by or
in the right of Quotesmith.com, or any other company or enterprise to which the
person provides services at the request of Quotesmith.com. Under


<PAGE>   3
these agreements, Quotesmith.com is also required to advance expenses to its
directors under certain circumstances.

ITEM 7.    EXEMPTION FROM REGISTRATION CLAIMED.
           Not applicable.

ITEM 8.    EXHIBITS.

           The exhibits listed on the accompanying Index to Exhibits are a part
of this Registration Statement. (See Exhibit Index below).

ITEM 9.    UNDERTAKINGS.

           (a)    Quotesmith.com undertakes:

                  (1)     to file, during any period in which offers or sales
                          are being made, a post-effective amendment to this
                          Registration Statement:

                         (i)     To include any prospectus required by
                                 Section 10(a)(3) of the Securities Act;

                         (ii)    To reflect in the prospectus any facts or
                                 events arising after the effective date of the
                                 Registration Statement (or the most recent
                                 post-effective amendment thereof) which,
                                 individually or in the aggregate, represent a
                                 fundamental change in the information set forth
                                 in the Registration Statement. Notwithstanding
                                 the foregoing, any increase or decrease in
                                 volume of securities offered (if the total
                                 dollar value of securities offered would not
                                 exceed that which was registered) and any
                                 deviation from the low or high end of the
                                 estimated maximum offering range may be
                                 reflected in the form of a prospectus filed
                                 with the Commission pursuant to Rule 424(b) if,
                                 in the aggregate, the changes in volume and
                                 price represent no more than a 20% change in
                                 the maximum aggregate offering price set forth
                                 in the "Calculation of Registration Fee" table
                                 in the effective Registration Statement;

                         (iii)   To include any material information with
                                 respect to the plan of distribution not
                                 previously disclosed in the Registration
                                 Statement or any material change to such
                                 information in the Registration Statement;

                  Provided, however, that paragraphs (1)(i) and (1)(iii) do not
           apply if the information required to be included in a post-effective
           amendment by those paragraphs is contained in periodic reports filed
           with or furnished to the Commission by the Registrant pursuant to
           Section 13 or Section 15(d) of the Exchange Act that are incorporated
           by reference in the Registration Statement.

           (2)    That, for the purpose of determining any liability under the
                  Securities Act, each such post-effective amendment shall be
                  deemed to be a new registration statement relating to the
                  securities offered therein, and the offering of such
                  securities at that time shall be deemed to be the initial bona
                  fide offering thereof.

           (3)    To remove from registration by means of a post-effective
                  amendment any of the securities being registered which remain
                  unsold at the termination of the offering.




<PAGE>   4

           (b)    Quotesmith.com undertakes that, for purposes of determining
                  any liability under the Securities Act, each filing of the
                  annual report of Quotesmith.com pursuant to Section 13(a) or
                  Section 15(d) of the Exchange Act (and, where applicable, each
                  filing of an employee benefit plan's annual report pursuant to
                  Section 15(d) of the Exchange Act) that is incorporated by
                  reference in the Registration Statement, shall be deemed to be
                  a new registration statement relating to the securities
                  offered therein, and the offering of such securities at that
                  time shall be deemed to be an initial bona fide offering
                  thereof.

           (c)    Insofar as indemnification for liabilities arising under the
                  Securities Act may be permitted to directors, officers and
                  controlling persons of Quotesmith.com pursuant to the
                  foregoing provisions, or otherwise, Quotesmith.com has been
                  advised that in the opinion of the Commission such
                  indemnification is against public policy as expressed in the
                  Securities Act and is, therefore, unenforceable. In the event
                  that a claim for indemnification against such liabilities
                  (other than the payment by Quotesmith.com of expenses incurred
                  or paid by a director, officer or controlling person of
                  Quotesmith.com in the successful defense of any action, suit
                  or proceeding) is asserted by such director, officer or
                  controlling person in connection with the securities being
                  registered, Quotesmith.com will, unless in the opinion of its
                  counsel the matter has been settled by controlling precedent,
                  submit to a court of appropriate jurisdiction the question
                  whether such indemnification by it is against public policy as
                  expressed in the Securities Act and will be governed by the
                  final adjudication of such issue.



<PAGE>   5

                                   SIGNATURES

         Pursuant to the requirements of the Securities Act of 1933, as amended,
Quotesmith.com certifies that it has reasonable grounds to believe that it meets
all of the requirements for filing on Form S-8 and has duly caused this
Registration Statement to be signed on its behalf by the undersigned, thereunto
duly authorized in the City of Darien, State of Illinois on January 20, 2000.

                                       QUOTESMITH.COM, INC.

                                       By: /s/ Robert S. Bland
                                          -----------------------------------
                                              Robert S. Bland
                                              Chairman, President and Chief
                                              Executive Officer

                                POWER OF ATTORNEY

         KNOW ALL PERSONS BY THESE PRESENTS, that each person whose signature
appears below constitutes and appoints Robert S. Bland and William V. Thoms,
jointly and severally, his attorneys-in-fact, each with the power of
substitution, for him in any and all capacities, to sign any amendments to this
Registration Statement on Form S-8, and to file the same, with exhibits thereto
and other documents in connection therewith, with the Securities and Exchange
Commission, hereby ratifying and confirming all that each of said
attorneys-in-fact, or his substitute or substitutes, may do or cause to be done
by virtue hereof.

         Pursuant to the requirements of the Securities Act of 1933, as amended,
this Registration Statement has been signed by the following persons in the
capacities indicated on January 20, 2000.


/s/ Robert S. Bland               Chairman, President and Chief Executive
------------------------------    Officer (Principal Executive Officer)
         Robert S. Bland

/s/ William V. Thoms              Executive Vice President and Director
------------------------------
         William V. Thoms

/s/ David I. Vickers              Senior Vice President, Chief Financial Officer
------------------------------    and Secretary (Principal Financial and
         David I. Vickers         Accounting Officer)


/s/ Bruce J. Reuben               Director
------------------------------
         Bruce J. Reuben

/s/ Timothy F. Shannon            Director
------------------------------
         Timothy F. Shannon

/s/ John McCartney                Director
------------------------------
         John McCartney

/s/ Richard F. Gretsch            Director
------------------------------
         Richard F. Gretsch

/s/ Jeremiah A. Denton, Jr.       Director
------------------------------
         Jeremiah A. Denton, Jr.


<PAGE>   6

                                  EXHIBIT INDEX

Exhibit    Description
-------    -----------

4.1*      Certificate of Incorporation of Quotesmith.com
4.2*      Bylaws of Quotesmith.com
4.3*      Quotesmith.com, Inc. 1997 Stock Option Plan (As Amended March 29,1999)
4.4*      Quotesmith.com, Inc. 1999 Stock Purchase Plan
5.1       Opinion of Freeborn & Peters (Counsel to Quotesmith.com)
23.1      Consent of Ernst & Young LLP (Independent Auditors)
23.2      Consent of Freeborn & Peters (contained in Exhibit 5.1 hereto)
24.1      Power of Attorney (contained on Signature Page)


*  Incorporated by reference from the Company's Registration Statement on Form
   S-1, as amended, effective August 2, 1999
[{"type": "S-8", "sequence": "1", "description": "REGISTRATION STATEMENT", "secsgml_size_bytes": 17266}]
{"company-data": {"conformed-name": "QUOTESMITH COM INC", "cik": "0001079996", "assigned-sic": "7374", "irs-number": "581521612", "state-of-incorporation": "DE", "fiscal-year-end": "1231"}, "filing-values": {"form-type": "S-8", "act": "33", "file-number": "333-95411", "film-number": "513469"}, "business-address": {"street1": "8205 SOUTH CASS AVE", "street2": "SUITE 102", "city": "DARIEN", "state": "IL", "zip": "60561", "phone": "6305150170"}, "mail-address": {"street1": "8205 SOUTH CASS AVENUE", "city": "DARIEN", "state": "IL", "zip": "60561"}}
1
    AS FILED WITH THE SECURITIES AND EXCHANGE COMMISSION ON JANUARY 26, 2000
                                                     REGISTRATION NO. 333-
================================================================================

                                  UNITED STATES
                       SECURITIES AND EXCHANGE COMMISSION
                             WASHINGTON, D.C. 20549

                                    FORM S-8
             REGISTRATION STATEMENT UNDER THE SECURITIES ACT OF 1933

                              QUOTESMITH.COM, INC.
             (Exact name of registrant as specified in its charter)

                DELAWARE                                58-1521612
(State of incorporation or organization)    (I.R.S. Employer Identification No.)

            8205 SOUTH CASS AVENUE, SUITE 102, DARIEN, ILLINOIS 60561
                    (Address of Principal Executive Offices)

   QUOTESMITH.COM, INC. 1997 STOCK OPTION PLAN (AS AMENDED ON MARCH 29, 1999)
             QUOTESMITH.COM, INC. 1999 EMPLOYEE STOCK PURCHASE PLAN
                            (Full title of the plans)

                           BURKE A. CHRISTENSEN, ESQ.
            VICE PRESIDENT AND GENERAL COUNSEL, QUOTESMITH.COM, INC.
            8205 SOUTH CASS AVENUE, SUITE 102, DARIEN, ILLINOIS 60561
                   (630) 515-0170 (PHONE) (630) 515-0276 (FAX)
           (Name, Address, and Telephone Number of Agent for Service)

                                 WITH A COPY TO:
                             GORDON P. PAULSON, ESQ.
                             CYNTHIA A. LANCE, ESQ.
 FREEBORN & PETERS, 311 SOUTH WACKER DRIVE, SUITE 3000, CHICAGO, ILLINOIS 60606
                  (312) 360-6602 (PHONE) (312) 360-6574 (FAX)

APPROXIMATE DATE OF COMMENCEMENT OF PROPOSED SALE TO THE PUBLIC: As soon as
practicable after the effective date of this Registration Statement. The
securities that are being registered on this Form are to be offered on a delayed
or continuous basis pursuant to Rule 415 under the Securities Act of 1933.
------------------------------------------------------------------------------------------------------------------------------------
                                                  CALCULATION OF REGISTRATION FEE
                Title Of Securities                         Amount To Be       Offering Price    Maximum Aggregate      Amount Of
                 To Be Registered                            Registered       Per Share (1)(2)    Offering Price    Registration Fee
------------------------------------------------------------------------------------------------------------------------------------
[1997 Stock Option Plan]
     Common Stock $.001 par value per share.............     1,500,000             $11.25           $16,875,000         $   4,455
[1999 Stock Purchase Plan]
    Common Stock $.001 par value per share (3)..........       250,000             $ 9.56           $ 2,390,000         $  630.96
                                                                                   TOTAL FEE                            $5,085.96
------------------------------------------------------------------------------------------------------------------------------------
(1)  The Offering Price Per Share has been estimated in accordance with Rule
     457(h) under the Securities Act of 1933 as to the 1,500,000 shares of
     Common Stock authorized for issuance pursuant to the 1997 Stock Plan,
     solely for the purpose of calculating the registration fee. The computation
     is based upon the average of the high and low price of the Common Stock as
     reported on the Nasdaq National Market on January 21, 2000.

(2)  The Offering Price Per Share has been estimated in accordance with Rule
     457(h) under the Securities Act of 1933 solely for the purpose of
     calculating the registration fee. The computation is based upon 85% of the
     average of the high and low price of the Common Stock as reported on the
     Nasdaq National Market on January 21, 2000.

(3)  Includes registration of any interests in the 1999 Stock Purchase Plan
     acquired during any purchase period.
2

                                     PART II

               INFORMATION REQUIRED IN THE REGISTRATION STATEMENT

ITEM 3.    INFORMATION INCORPORATED BY REFERENCE.

           The following documents filed by Quotesmith.com, Inc. with the
Securities and Exchange Commission (the "Commission") are incorporated by
reference:

           (a)      The Quotesmith.com Prospectus filed with the Commission on
                    August 3, 1999 pursuant to Rule 424(b) under the Securities
                    Act of 1933, as amended (the "Securities Act").

           (b)      Quotesmith.com's Quarterly Report on form 10-Q for the
                    quarter ended September 30, 1999 and filed with the
                    Commission on November 15, 1999.

           (c)      The description of the Common Stock, $.001 par value per
                    share, contained in the Quotesmith.com Registration
                    Statement on Form 8-A filed on July 21, 1999 pursuant to
                    Section 12(g) of the Securities Exchange Act of 1943, as
                    amended (the "Exchange Act").

           (d)      All documents filed by Quotesmith.com pursuant to Sections
                    13(a), 13(c), 14 and 15(d) of the Exchange Act, subsequent
                    to the filing of this Registration Statement and prior to
                    the filing of a post-effective amendment which indicates
                    that all securities offered have been sold, or which
                    deregisters all securities then remaining unsold, shall be
                    deemed to be incorporated by reference in this Registration
                    Statement and to be part hereof from the date of filing of
                    such documents.

ITEM 4.    DESCRIPTION OF SECURITIES.

           Not applicable.

ITEM 5.    INTERESTS OF NAMED EXPERTS AND COUNSEL.

            Not applicable.

ITEM 6.    INDEMNIFICATION OF DIRECTORS AND OFFICERS.

           The Quotesmith.com Certificate of Incorporation: (a) eliminates the
personal liability of the Quotesmith.com directors and officers for monetary
damages arising from a breach of their fiduciary duties under certain
circumstances; and (b) authorizes Quotesmith.com to indemnify its directors and
officers to the fullest extent permitted by the Delaware General Corporation
Law. The limitation of liability in the Certificate of Incorporation does not
affect the availability of equitable remedies such as injunctive relief or
rescission, and does not apply to liabilities arising under the federal
securities laws. The Quotesmith.com Bylaws: (a) allow for the indemnity of the
Quotesmith.com directors and officers to the fullest extent permitted by the
Delaware General Corporation Law; and (b) require, under certain circumstances,
Quotesmith.com to advance expenses to its directors and officers in connection
with a legal proceeding.

         Quotesmith.com has also entered into indemnification agreements with
its directors which allow for the indemnification of directors for most
expenses, including attorneys' fees, judgments, fines and settlement amounts
incurred by them in any action or proceeding, including any action brought by or
in the right of Quotesmith.com, or any other company or enterprise to which the
person provides services at the request of Quotesmith.com. Under
3
these agreements, Quotesmith.com is also required to advance expenses to its
directors under certain circumstances.

ITEM 7.    EXEMPTION FROM REGISTRATION CLAIMED.
           Not applicable.

ITEM 8.    EXHIBITS.

           The exhibits listed on the accompanying Index to Exhibits are a part
of this Registration Statement. (See Exhibit Index below).

ITEM 9.    UNDERTAKINGS.

           (a)    Quotesmith.com undertakes:

                  (1)     to file, during any period in which offers or sales
                          are being made, a post-effective amendment to this
                          Registration Statement:

                         (i)     To include any prospectus required by
                                 Section 10(a)(3) of the Securities Act;

                         (ii)    To reflect in the prospectus any facts or
                                 events arising after the effective date of the
                                 Registration Statement (or the most recent
                                 post-effective amendment thereof) which,
                                 individually or in the aggregate, represent a
                                 fundamental change in the information set forth
                                 in the Registration Statement. Notwithstanding
                                 the foregoing, any increase or decrease in
                                 volume of securities offered (if the total
                                 dollar value of securities offered would not
                                 exceed that which was registered) and any
                                 deviation from the low or high end of the
                                 estimated maximum offering range may be
                                 reflected in the form of a prospectus filed
                                 with the Commission pursuant to Rule 424(b) if,
                                 in the aggregate, the changes in volume and
                                 price represent no more than a 20% change in
                                 the maximum aggregate offering price set forth
                                 in the "Calculation of Registration Fee" table
                                 in the effective Registration Statement;

                         (iii)   To include any material information with
                                 respect to the plan of distribution not
                                 previously disclosed in the Registration
                                 Statement or any material change to such
                                 information in the Registration Statement;

                  Provided, however, that paragraphs (1)(i) and (1)(iii) do not
           apply if the information required to be included in a post-effective
           amendment by those paragraphs is contained in periodic reports filed
           with or furnished to the Commission by the Registrant pursuant to
           Section 13 or Section 15(d) of the Exchange Act that are incorporated
           by reference in the Registration Statement.

           (2)    That, for the purpose of determining any liability under the
                  Securities Act, each such post-effective amendment shall be
                  deemed to be a new registration statement relating to the
                  securities offered therein, and the offering of such
                  securities at that time shall be deemed to be the initial bona
                  fide offering thereof.

           (3)    To remove from registration by means of a post-effective
                  amendment any of the securities being registered which remain
                  unsold at the termination of the offering.
4

           (b)    Quotesmith.com undertakes that, for purposes of determining
                  any liability under the Securities Act, each filing of the
                  annual report of Quotesmith.com pursuant to Section 13(a) or
                  Section 15(d) of the Exchange Act (and, where applicable, each
                  filing of an employee benefit plan's annual report pursuant to
                  Section 15(d) of the Exchange Act) that is incorporated by
                  reference in the Registration Statement, shall be deemed to be
                  a new registration statement relating to the securities
                  offered therein, and the offering of such securities at that
                  time shall be deemed to be an initial bona fide offering
                  thereof.

           (c)    Insofar as indemnification for liabilities arising under the
                  Securities Act may be permitted to directors, officers and
                  controlling persons of Quotesmith.com pursuant to the
                  foregoing provisions, or otherwise, Quotesmith.com has been
                  advised that in the opinion of the Commission such
                  indemnification is against public policy as expressed in the
                  Securities Act and is, therefore, unenforceable. In the event
                  that a claim for indemnification against such liabilities
                  (other than the payment by Quotesmith.com of expenses incurred
                  or paid by a director, officer or controlling person of
                  Quotesmith.com in the successful defense of any action, suit
                  or proceeding) is asserted by such director, officer or
                  controlling person in connection with the securities being
                  registered, Quotesmith.com will, unless in the opinion of its
                  counsel the matter has been settled by controlling precedent,
                  submit to a court of appropriate jurisdiction the question
                  whether such indemnification by it is against public policy as
                  expressed in the Securities Act and will be governed by the
                  final adjudication of such issue.
5

                                   SIGNATURES

         Pursuant to the requirements of the Securities Act of 1933, as amended,
Quotesmith.com certifies that it has reasonable grounds to believe that it meets
all of the requirements for filing on Form S-8 and has duly caused this
Registration Statement to be signed on its behalf by the undersigned, thereunto
duly authorized in the City of Darien, State of Illinois on January 20, 2000.

                                       QUOTESMITH.COM, INC.

                                       By: /s/ Robert S. Bland
                                          -----------------------------------
                                              Robert S. Bland
                                              Chairman, President and Chief
                                              Executive Officer

                                POWER OF ATTORNEY

         KNOW ALL PERSONS BY THESE PRESENTS, that each person whose signature
appears below constitutes and appoints Robert S. Bland and William V. Thoms,
jointly and severally, his attorneys-in-fact, each with the power of
substitution, for him in any and all capacities, to sign any amendments to this
Registration Statement on Form S-8, and to file the same, with exhibits thereto
and other documents in connection therewith, with the Securities and Exchange
Commission, hereby ratifying and confirming all that each of said
attorneys-in-fact, or his substitute or substitutes, may do or cause to be done
by virtue hereof.

         Pursuant to the requirements of the Securities Act of 1933, as amended,
this Registration Statement has been signed by the following persons in the
capacities indicated on January 20, 2000.

/s/ Robert S. Bland               Chairman, President and Chief Executive
------------------------------    Officer (Principal Executive Officer)
         Robert S. Bland

/s/ William V. Thoms              Executive Vice President and Director
------------------------------
         William V. Thoms

/s/ David I. Vickers              Senior Vice President, Chief Financial Officer
------------------------------    and Secretary (Principal Financial and
         David I. Vickers         Accounting Officer)

/s/ Bruce J. Reuben               Director
------------------------------
         Bruce J. Reuben

/s/ Timothy F. Shannon            Director
------------------------------
         Timothy F. Shannon

/s/ John McCartney                Director
------------------------------
         John McCartney

/s/ Richard F. Gretsch            Director
------------------------------
         Richard F. Gretsch

/s/ Jeremiah A. Denton, Jr.       Director
------------------------------
         Jeremiah A. Denton, Jr.
6

                                  EXHIBIT INDEX

Exhibit    Description
-------    -----------

4.1*      Certificate of Incorporation of Quotesmith.com
4.2*      Bylaws of Quotesmith.com
4.3*      Quotesmith.com, Inc. 1997 Stock Option Plan (As Amended March 29,1999)
4.4*      Quotesmith.com, Inc. 1999 Stock Purchase Plan
5.1       Opinion of Freeborn & Peters (Counsel to Quotesmith.com)
23.1      Consent of Ernst & Young LLP (Independent Auditors)
23.2      Consent of Freeborn & Peters (contained in Exhibit 5.1 hereto)
24.1      Power of Attorney (contained on Signature Page)

*  Incorporated by reference from the Company's Registration Statement on Form
   S-1, as amended, effective August 2, 1999