<PAGE>

                                                                     Exhibit 4.2

                             COOLSAVINGS.COM INC.

                         REGISTRATION RIGHTS AGREEMENT

          REGISTRATION RIGHTS AGREEMENT, dated as of July 30, 2001 (this
"Agreement"), among Landmark Ventures VII, LLC and any affiliates or transferee
 ---------
thereof ("Landmark"), the investors listed on Schedule I hereto (the "Current
          --------                                                    -------
Investors", and, together with Landmark, the "Investors") and coolsavings.com
---------                                     ---------
inc., a Michigan corporation (the "Company").
                                   -------

                                R E C I T A L S
                                - - - - - - - -

          WHEREAS, the Current Investors own shares of Series C Convertible
Preferred Stock, with no par value per share, of the Company (the "Series C
                                                                   --------
Preferred Stock"), and/or shares of Common Stock, with no par value per share,
---------------
of the Company (the "Common Stock"); and
                     ------------

          WHEREAS, Landmark has, pursuant to the terms of the Securities
Purchase Agreement, dated as of July 30, 2001, between Landmark and the Company
(the "Purchase Agreement"), agreed to purchase shares of Series B Convertible
      ------------------
Preferred Stock, with no par value per share, of the Company (the "Series B
                                                                   --------
Preferred Stock" and, together with the Series C Preferred Stock, the "Preferred
---------------                                                        ---------
Stock"), warrants to purchase Common Stock (the "Warrants") and a Senior Secured
-----                                            --------
Note of the Company (the "Note"); and
                          ----

          WHEREAS, the shares of Preferred Stock and the Warrants purchased by
Landmark are convertible into shares of Common Stock; and

          WHEREAS, the Current Investors have previously been granted certain
registration rights under that certain Shareholders Agreement, dated June 1,
1998 between the Company and the Holders as defined and listed therein (the
Current Investors that are parties to such Shareholders Agreement are
hereinafter collectively referred to as the "1998 Holders", and are listed on
                                             ------------
Schedule II hereto), and the Registration Rights Agreement, dated as of March 1,
2001 by and among the Company and the purchasers of its 8% senior subordinated
convertible promissory notes (the Current Investors that are parties to such
Registration Rights Agreement are hereinafter collectively referred to as the
"2001 Holders", and are listed on Schedule III hereto), and
 ------------

          WHEREAS, the Company has agreed, as a condition precedent to
Landmark's obligations under the Purchase Agreement, to grant the Investors
certain registration rights; and

          WHEREAS, the Company and the Investors desire to define the
registration rights of the Investors on the terms and subject to the conditions
herein set forth.
<PAGE>

          NOW, THEREFORE, in consideration of the foregoing premises and for
other good and valuable consideration, the parties hereby agree as follows:

          SECTION 1. DEFINITIONS

          As used in this Agreement, the following terms have the respective
meaning set forth below.  Capitalized terms used but not defined herein shall
have the meaning set forth in the Purchase Agreement.

          Exchange Act: shall mean the Securities Exchange Act of 1934, as
          ------------
amended;

          Holder: shall mean any holder of Registrable Securities;
          ------

          Initiating Holder:  shall mean Landmark and any of its successors or
          -----------------
assigns who in the aggregate are Holders of more than 15% of the then
outstanding Registrable Securities and the 2001 Holders subject to the
restrictions set forth in Section 2(a)(3).

          Person:  shall mean an individual, partnership, joint-stock company,
          ------
corporation, trust or unincorporated organization, and a government or agency or
political subdivision thereof;

          Register, Registered and Registration: shall mean a registration
          --------  ----------     ------------
effected by preparing and filing a registration statement in compliance with the
Securities Act (and any post-effective amendments filed or required to be filed)
and the declaration or ordering of effectiveness of such registration statement;

          Registrable Securities: shall mean (A) shares of Common Stock
          ----------------------
issuable upon conversion of the Preferred Stock or exercise of the Warrants, (B)
any additional shares of Common Stock acquired or held as of the date hereof by
the Investors, (C) with respect to Landmark, any additional shares of Common
Stock acquired after the date hereof, and (D) any stock of the Company issued as
a dividend or other distribution with respect to, or in exchange for or in
replacement of, the shares of Preferred Stock, the Warrants or Common Stock
referred to in clause (A) or (B). As to any particular Registrable Securities,
such securities will cease to be Registrable Securities on the earliest of the
following dates: (a) the date such securities have been sold to the public
pursuant to an offering registered under the Securities Act, or (b) the date
such securities have been sold to the public in a transaction exempt from the
registration and prospectus delivery requirements of the Securities Act;

          Registration Expenses: shall mean all expenses incurred by the
          ---------------------
Company in compliance with Section 2(a), (b) and (c) hereof, including, without
limitation, all registration and filing fees, printing expenses, fees and
disbursements of counsel for the Company, fees and expenses of one counsel for
all the Holders in an amount not to exceed $25,000 (provided that if such fees
and expenses of the Holders' counsel are incurred by the Company in connection
with a registration pursuant to Section 2(b) or 2(c), such fees and expenses
shall not exceed $15,000), blue sky fees and expenses and the expense of any
special audits incident to or required by any such registration (but excluding
the compensation of regular employees of the Company, which shall be paid in any
event by the Company);

                                      -2-
<PAGE>

          SEC: shall mean the Securities and Exchange Commission, or any
          ---
successor commission or agency having similar powers;

          Security, Securities: shall have the meaning set forth in Section
          --------------------
2(1) of the Securities Act;

          Securities Act: shall mean the Securities Act of 1933, as amended, and
          --------------
the rules and regulations promulgated thereunder; and

          Selling Expenses: shall mean all underwriting discounts and selling
          ----------------
commissions applicable to the sale of Registrable Securities, all transfer taxes
relating to the sale or disposition of the Registrable Securities and all fees
and disbursements of counsel for each of the Holders other than fees and
expenses of one counsel for all the Holders in an amount not to exceed $25,000
(provided that if such fees and expenses of the Holders' counsel are incurred by
the Company in connection with a registration pursuant to Section 2(b) or 2(c),
such fees and expenses shall not exceed $15,000).

          SECTION 2.    REGISTRATION RIGHTS

     (a)  Requested Registration.
          ----------------------

          (i)  Request for Registration.  If the Company shall receive from an
               ------------------------
     Initiating Holder, at any time, a written request that the Company effect
     any registration with respect to all or a part of the Registrable
     Securities, the Company will:

               (1)  promptly give written notice of the proposed registration,
          qualification or compliance to all other Holders; and

               (2)  as soon as practicable, use its diligent best efforts to
          effect such registration (including, without limitation, the execution
          of an undertaking to file post-effective amendments, appropriate
          qualification under applicable blue sky or other state securities laws
          and appropriate compliance with applicable regulations issued under
          the Securities Act) as may be so requested and as would permit or
          facilitate the sale and distribution of all or such portion of such
          Registrable Securities as are specified in such request, together with
          all or such portion of the Registrable Securities of any Holder or
          Holders joining in such request as are specified in a written request
          received by the Company within 10 business days after written notice
          from the Company is given under Section 2(a)(i)(1) above except as set
          forth in Section 2(a)(ii) below; provided that the Company shall not
                                           --------
          be obligated to effect, or take any action to effect, any such
          registration pursuant to this Section 2(a):

                    (A)  In any particular jurisdiction (x) in which the Company
               would be required to execute a general consent to service of
               process in effecting such registration, qualification or
               compliance, unless the Company is already subject to service in
               such jurisdiction and except as

                                      -3-
<PAGE>

               may be required by the Securities Act or applicable rules or
               regulations thereunder, or (y) where expressions of investment
               interest are not sufficient in such jurisdiction to reasonably
               justify the registration or qualification in such jurisdiction;

                    (B)  After the Company has effected five (5) such
               registrations pursuant to this Section 2(a) and such
               registrations have been declared or ordered effective and the
               sales of such Registrable Securities shall have closed;

                    (C)  If the Registrable Securities requested by all Holders
               to be registered pursuant to such request have an anticipated
               aggregate public offering price (before any underwriting
               discounts and commissions) of less than $5,000,000;

                    (D)  If the Company shall furnish to the Initiating Holder a
               certificate signed by the President of the Company stating that
               in the good faith judgment of the Board of Directors it would be
               seriously detrimental to the Company or its stockholders for a
               registration statement to be filed in the near future, in which
               case the Company's obligation to use its best efforts to comply
               with this Section 2 shall be deferred for a period not to exceed
               ninety (90) days from the date of receipt of written request from
               the Initiating Holder; provided, however, that the Company shall
                                      --------  -------
               not exercise such right more than once in any 360 day period.

               (3)  Notwithstanding anything to the contrary set forth herein,
     Landmark may initiate a total of three (3) requested registrations as an
     Initiating Holder and the 2001 Holders may initiate a total of one (1)
     requested registration under this Section 2(a). The 2001 Holders may only
     initiate such requested registration as an Initiating Holder under the
     following conditions:

                    (A)  The 2001 Holders (or their permitted transferees) shall
     have requested such registration prior to March 1, 2005;

                    (B)  Such request constitutes a request by the holder or
     holders of at least 75% of Registrable Securities held by the 2001 Holders
     (or their permitted transferees); and

                    (C)  Landmark shall have consented in writing to such
     requested registration by the 2001 Holders (or their permitted
     transferees); provided, however, that such written consent from Landmark
                   --------  -------
     shall not be required if either (a) Landmark does not own any Registrable
     Securities and the Company has no outstanding indebtedness of any kind to
     Landmark, or (b) each of the conditions under Section 2(l) have been
     satisfied.

                                      -4-
<PAGE>

          If any of the other Holders request such inclusion, the registration
     statement filed pursuant to the request of the Initiating Holder may,
     subject to the provisions of Section 2(a)(ii) below, include Registrable
     Securities held by such Holders.  In the event any Initiating Holder
     requests a registration pursuant to this Section 2(a) in connection with a
     distribution of Registrable Securities to its affiliates, the registration
     shall provide for the resale by such affiliates, if requested by such
     Initiating Holder.

          (ii) Underwriting.
               ------------

               (1)  If the Initiating Holder intends to distribute the
          Registrable Securities covered by its request by means of an
          underwriting, it shall so advise the Company as a part of its request
          made pursuant to Section 2(a).

               (2)  If any of the other Holders request such inclusion, the
          Initiating Holder shall offer to include the securities of such
          Holders in the underwriting and may condition such offer on their
          acceptance of the further applicable provisions of this Section 2. The
          Holders whose shares are to be included in such registration and the
          Company shall enter into an underwriting agreement (together with such
          other documents as may be required by such underwriting agreement) in
          customary form with the representative of the underwriter or
          underwriters selected for such underwriting by Landmark and reasonably
          acceptable to the Company.

               (3)  Notwithstanding any other provision of this Section 2(a), if
          the representative of the underwriter(s) advises the Holders in
          writing that marketing factors require a limitation on the number of
          shares to be underwritten, the Company shall include in such
          registration (A) first, all of the Registrable Securities requested to
          be included therein by the Initiating Holder, (B) second, the
          Registrable Securities requested to be included therein by Landmark
          (or its successors or assigns), and (C) third, the Registrable
          Securities requested to be included therein by Holders (including the
          2001 Holders) other than Landmark, pro rata among such Holders (based
          on the number of shares held by each such Holder) by such minimum
          number of shares as is necessary to comply with such request. If a
          limitation on the number of shares is still required (even after all
          other Holders have been reduced down to zero), then and only then
          shall the securities held by Landmark be reduced on a pro rata basis
          (based on the number of shares held by Landmark) by such minimum
          number of shares as is necessary to comply with such request. No
          Registrable Securities or any other securities excluded from the
          underwriting by reason of the underwriter's marketing limitation shall
          be included in such registration.

               (4)  If any Holder who has requested inclusion in such
          registration as provided above disapproves of the terms of the
          underwriting, such person may elect to withdraw therefrom by written
          notice to the Company, the underwriter and the Initiating Holder. The
          securities so withdrawn shall also be withdrawn from registration.

                                      -5-
<PAGE>

               (5)  If the underwriter has not limited the number of Registrable
          Securities or other securities to be underwritten, the Company and
          officers and directors of the Company may include its or their
          securities for its or their own account in such registration if the
          representative of the underwriter(s) so agrees and if the number of
          Registrable Securities and other securities which would otherwise have
          been included in such registration and underwriting will not thereby
          be limited.

     (b)  Company Registration.
          --------------------

          (i)  If the Company shall determine to register any of its equity
     securities for its own account, other than a registration relating solely
     to employee benefit plans, or a registration relating solely to an SEC Rule
     145 transaction, or a registration on any registration form which does not
     permit secondary sales or does not include substantially the same
     information as would be required to be included in a registration statement
     covering the sale of Registrable Securities, then the Company will in
     connection with each such registration:

               (1)  promptly give to each of the Holders a written notice
          thereof (which shall include a list of the jurisdictions in which the
          Company intends to attempt to qualify such securities under the
          applicable blue sky or other state securities laws); and

               (2)  include in such registration (and any related qualification
          under blue sky laws or other compliance), and in any underwriting
          involved therein, all the Registrable Securities specified in a
          written request or requests, made by the Holders within fifteen (15)
          days after receipt of the written notice from the Company described in
          clause (1) above, except as set forth in Section 2(b)(ii) below. Such
          written request may specify all or a part of the Holders' Registrable
          Securities. In the event any Holder requests inclusion in a
          registration pursuant to this Section 2(b) in connection with a
          distribution of Registrable Securities to its affiliates, the
          registration shall provide for the resale by such affiliates, if
          requested by such Holder.

          (ii) Underwriting.
               ------------

               (1)  If the registration of which the Company gives notice is for
          a registered public offering involving an underwriting, the Company
          shall so advise each of the Holders as a part of the written notice
          given pursuant to Section 2(b)(i)(1).

               (2)  If any of the Holders request such inclusion, the Company
          shall offer to include the securities of such Holders in the
          underwriting and may condition such offer on their acceptance of the
          further applicable provisions of this Section 2. The Holders whose
          shares are to be included in such registration shall (together with
          the Company) enter into an underwriting agreement (together

                                      -6-
<PAGE>

          with such other documents as may be required by such underwriting
          agreement) in customary form with the representative of the
          underwriter or underwriters selected for underwriting by the Company
          and reasonably acceptable to the Holders.

                (3)  Notwithstanding any other provision of this Section 2(b),
          if the representative of the underwriter(s) determines that marketing
          factors require a limitation on the number of shares to be
          underwritten, the representative may (subject to the allocation
          priority set forth below) limit the number of Registrable Securities
          to be included in the registration and underwriting. The Company shall
          so advise all Holders requesting registration, and the number of
          shares of securities that are entitled to be included in the
          registration and underwriting shall be allocated in the following
          manner: (i) first, the Company shall include in such registration the
          securities that the Company proposes to sell, (ii) second, the Company
          shall include in such registration the Registrable Securities
          requested to be included therein by Landmark (or its successors or
          assigns), (iii) third, the Company shall include in such registration
          the Registrable Securities requested to be included therein by Holders
          (including the 2001 Holders) other than Landmark, pro rata among such
          Holders (based on the number of shares held by each such Holder), and
          (iv) fourth, the Company shall include in such registration the
          securities of the Company held by officers and directors of the
          Company (other than Registrable Securities) requested to be included
          therein by such officers and directors.

                (4)  If any of the Holders or any officer or director
          disapproves of the terms of any such underwriting, he may elect to
          withdraw therefrom by written notice to the Company and the
          underwriter. Any Registrable Securities or other securities excluded
          or withdrawn from such underwriting shall be withdrawn from such
          registration.

          (iii) Notwithstanding the foregoing, the rights of the 1998 Holders
     and the 2001 Holders shall be limited in the following manner.

                (1)  All rights of the 1998 Holders under this Agreement shall
          terminate on May 19, 2005.

                (3)  All rights of the 2001 Holders under this Agreement shall
          terminate on March 1, 2005.

     (c)  Form S-3.
          --------

          (i)   The Company shall use its best efforts to qualify for
     registration on Form S-3 for secondary sales. After the Company has
     qualified for the use of Form S-3, each of Landmark, the 1998 Holders and
     the 2001 Holders shall have the right to request registrations on Form S-3
     (such requests shall be in writing and shall state the number of shares of
     Registrable Securities to be disposed of and the intended method of
     disposition

                                      -7-
<PAGE>

     of shares by such holders); provided that the Company shall not be
                                 --------
     obligated to effect, or take any action to effect, any such registration
     pursuant to this Section 2(c):

                 (1)  Unless Landmark, the 1998 Holders or the 2001 Holders
           requesting registration proposes to dispose of shares of Registrable
           Securities having an aggregate price to the public (before deduction
           of underwriting discounts and expenses of sale) of more than
           $2,000,000;

                 (2)  Within 180 days of the effective date of the most recent
           registration pursuant to this Section 2(c) in which securities held
           by Landmark, the 1998 Holders or the 2001 Holders could have been
           included for sale or distribution;

                 (3)  In any particular jurisdiction (x) in which the Company
           would be required to execute a general consent to service of process
           in effecting such registration, qualification or compliance, unless
           the Company is already subject to service in such jurisdiction and
           except as may be required by the Securities Act or applicable rules
           or regulations thereunder, or (y) where expressions of investment
           interest are not sufficient in such jurisdiction to reasonably
           justify the registration or qualification in such jurisdiction;

                 (4)  If the Company shall furnish to Landmark, the 1998 Holders
           or the 2001 Holders, as applicable, a certificate signed by the
           President of the Company stating that in the good faith judgment of
           the Board of Directors it would be seriously detrimental to the
           Company or its stockholders for a registration statement to be filed
           in the near future, in which case the Company's obligation to use its
           best efforts to comply with this Section 2(c) shall be deferred for a
           period not to exceed ninety (90) days from the date of receipt of
           written request from Landmark, the 1998 Holders or the 2001 Holders;
           provided, however, that the Company shall not exercise such right
           --------  -------
           more than once in any 360 day-period.

           (ii)  The Company shall give written notice to all Holders of the
     receipt of a request for registration pursuant to this Section 2(c) and
     shall provide a reasonable opportunity for other Holders to participate in
     the registration, provided that if the registration is for an underwritten
                       --------
     offering, the terms of Section 2(a)(ii) shall apply to all participants in
     such offering.  Subject to the foregoing, the Company will use its best
     efforts to effect promptly the registration of all shares of Registrable
     Securities on Form S-3 to the extent requested by Landmark, the 1998
     Holders or the 2001 Holders thereof for purposes of disposition.  In the
     event Landmark, the 1998 Holders or the 2001 Holders requests a
     registration pursuant to this Section 2(c) in connection with a
     distribution of Registrable Securities to its affiliates, the registration
     shall provide for the resale by such affiliates, if requested by Landmark,
     the 1998 Holders or the 2001 Holders, as applicable.

           (iii) Notwithstanding anything to the contrary set forth herein,
     Landmark shall have the right to request an unlimited number of Form S-3
     registrations, the 1998 Holders shall collectively only have the right to
     request two (2) Form S-3 registrations under this

                                      -8-
<PAGE>

     section 2(c) and the 2001 Holders shall collectively only have the right to
     request three (3) Form S-3 registrations under this Section 2(c). The 1998
     Holders and the 2001 Holders may only initiate such requested registration
     if Landmark shall have consented in writing to such requested registration
     prior to the Company granting such request for registration; provided,
                                                                  --------
     however, that such written consent from Landmark shall not be required if
     -------
     either (A) Landmark does not own any Registrable Securities and the Company
     has no outstanding indebtedness of any kind to Landmark, or (B) each of the
     conditions under Section 2(l) have been satisfied.

     (d)  Expenses of Registration.  All Registration Expenses incurred in
          ------------------------
connection with any registration, qualification or compliance pursuant to this
Section 2 shall be borne by the Company, and all Selling Expenses shall be borne
by the holders of the securities so registered pro rata on the basis of the
number of their shares so registered.

     (e)  Registration Procedures.  In the case of each registration effected
          -----------------------
by the Company pursuant to this Section 2, the Company will keep the Holders, as
applicable, advised in writing as to the initiation of each registration and as
to the completion thereof. At its expense, the Company will:

          (i)    keep such registration effective for a period of one hundred
     twenty (120) days or until the Holders (or in the case of a distribution to
     the affiliates of such Holder, such affiliates), as applicable, have
     completed the distribution described in the registration statement relating
     thereto, whichever first occurs; provided, however, that in the case of any
                                      --------  -------
     registration of Registrable Securities on Form S-3 which are intended to be
     offered on a continuous or delayed basis, such 120-day period shall be
     extended until all such Registrable Securities are sold, provided that Rule
                                                              --------
     415, or any successor rule under the Securities Act, permits an offering on
     a continuous or delayed basis, and provided further that applicable rules
                                        ----------------
     under the Securities Act governing the obligation to file a post-effective
     amendment permit, in lieu of filing a post-effective amendment which (y)
     includes any prospectus required by Section 10(a) of the Securities Act or
     (z) reflects facts or events representing a material or fundamental change
     in the information set forth in the registration statement, the
     incorporation by reference of information required to be included in (y)
     and (z) above to be contained in periodic reports filed pursuant to Section
     12 or 15(d) of the Exchange Act in the registration statement;

          (ii)   furnish such number of prospectuses and other documents
     incident thereto as each of the Holders, as applicable, from time to time
     may reasonably request;

          (iii)  notify each Holder of Registrable Securities covered by such
     registration at any time when a prospectus relating thereto is required to
     be delivered under the Securities Act of the happening of any event as a
     result of which the prospectus included in such registration statement, as
     then in effect, includes an untrue statement of a material fact or omits to
     state a material fact required to be stated therein or necessary to make
     the statements therein not misleading in the light of the circumstances
     then existing; and

          (iv)   furnish, on the date that such Registrable Securities are
     delivered to the underwriters for sale, if such securities are being sold
     through underwriters (1) an

                                      -9-
<PAGE>

     opinion, dated as of such date, of the counsel representing the Company for
     the purposes of such registration, in form and substance as is customarily
     given to underwriters in an underwritten public offering and reasonably
     satisfactory to a majority in interest of the Holders participating in such
     registration, addressed to the underwriters and (2) a letter, dated as of
     such date, from the independent certified public accountants of the
     Company, in form and substance as is customarily given by independent
     certified public accountants to underwriters in an underwritten public
     offering and reasonably satisfactory to a majority in interest of the
     Holders participating in such registration, addressed to the underwriters.

          Each Holder agrees that, upon receipt of any notice from the Company
     of the happening of any event of the kind described in subsection (iii)
     above, such Holder shall forthwith discontinue disposition of shares of
     Common Stock pursuant to a Registration until receipt of an appropriate
     supplement or amendment to the prospectus of such Registration.

     (f)  Indemnification.
          ---------------

          (i)  The Company will indemnify each of the Holders, as applicable,
     each of its officers, directors and partners, and each person controlling
     each of the Holders, with respect to each registration which has been
     effected pursuant to this Section 2, and each underwriter, if any, and each
     person who controls any underwriter, against all claims, losses, damages
     and liabilities (or actions in respect thereof) arising out of or based on
     any untrue statement (or alleged untrue statement) of a material fact
     contained in any prospectus, offering circular or other document (including
     any related registration statement, notification or the like) incident to
     any such registration, qualification or compliance, or based on any
     omission (or alleged omission) to state therein a material fact required to
     be stated therein or necessary to make the statements therein not
     misleading, or any violation by the Company of the Securities Act or the
     Exchange Act or any rule or regulation thereunder applicable to the Company
     and relating to action or inaction required of the Company in connection
     with any such registration, qualification or compliance, and will reimburse
     each of the Holders, each of its officers, directors and partners, and each
     person controlling each of the Holders, each such underwriter and each
     person who controls any such underwriter, for any legal and any other
     expenses reasonably incurred in connection with investigating and defending
     any such claim, loss, damage, liability or action; provided, however, that
                                                        --------  -------
     the Company will not be liable in any such case to the extent that any such
     claim, loss, damage, liability or expense arises out of or is based on (1)
     any untrue statement or omission based upon written information furnished
     to the Company by the Holders or underwriter and stated to be specifically
     for use therein, or (2) a Holder's, or underwriter's, failure to deliver a
     copy of the registration statement or prospectus or any amendments or
     supplements thereto after the Company has furnished such Holder with a
     sufficient number of copies of the same.

          (ii) Each of the Holders will, if Registrable Securities held by it
     are included in the securities as to which such registration, qualification
     or compliance is being effected, severally and not jointly indemnify the
     Company, each of its directors and officers and each underwriter, if any,
     of the Company's securities covered by such a

                                      -10-
<PAGE>

     registration statement, each person who controls the Company or such
     underwriter, each other Holder and each of their officers, directors and
     partners, and each person controlling such other Holder against all claims,
     losses, damages and liabilities (or actions in respect thereof) arising out
     of or based on any untrue statement (or alleged untrue statement) of a
     material fact contained in any such registration statement, prospectus,
     offering circular or other document made by such Holder, or any omission
     (or alleged omission) to state therein a material fact required to be
     stated therein or necessary to make the statements by such Holder therein
     not misleading, and will reimburse the Company and such other Holders,
     directors, officers, partners, persons, underwriters or control persons for
     any legal or any other expenses reasonably incurred in connection with
     investigating or defending any such claim, loss, damage, liability or
     action, in each case to the extent, but only to the extent, that such
     untrue statement (or alleged untrue statement) or omission (or alleged
     omission) is made in such registration statement, prospectus, offering
     circular or other document in reliance upon and in conformity with written
     information furnished to the Company by such Holder and stated to be
     specifically for use therein and then only to the extent that any loss,
     damages or other liability of any kind result from such alleged untrue
     statement; provided, however, that the obligations of each of the Holders
                --------  -------
     hereunder shall be limited to an amount equal to the net proceeds to such
     Holder of securities sold as contemplated herein.

          (iii)  Each party entitled to indemnification under this Section 2(f)
     (the "Indemnified Party") shall give notice to the party required to
           -----------------
     provide indemnification (the "Indemnifying Party") promptly after such
                                   ------------------
     Indemnified Party has actual knowledge of any claim as to which indemnity
     may be sought, and shall permit the Indemnifying Party to assume the
     defense of any such claim or any litigation resulting therefrom; provided
                                                                      --------
     that counsel for the Indemnifying Party, who shall conduct the defense of
     such claim or any litigation resulting therefrom, shall be approved by the
     Indemnified Party (whose approval shall not unreasonably be withheld) and
     the Indemnified Party may participate in such defense at such party's
     expense (unless the Indemnified Party shall have reasonably concluded that
     there may be a conflict of interest between the Indemnifying Party and the
     Indemnified Party in such action, in which case the reasonable fees and
     expenses of one counsel shall be at the expense of the Indemnifying Party),
     and provided further that the failure of any Indemnified Party to give
         -------- -------
     notice as provided herein shall not relieve the Indemnifying Party of its
     obligations under this Section 2 unless the Indemnifying Party is
     materially prejudiced thereby. No Indemnifying Party, in the defense of any
     such claim or litigation shall, except with the consent of each Indemnified
     Party (whose consent shall not be unreasonably withheld), consent to entry
     of any judgment or enter into any settlement which does not include as an
     unconditional term thereof the giving by the claimant or plaintiff to such
     Indemnified Party of a release from all liability in respect to such claim
     or litigation. Each Indemnified Party shall furnish such information
     regarding itself or the claim in question as an Indemnifying Party may
     reasonably request in writing and as shall be reasonably required in
     connection with the defense of such claim and litigation resulting
     therefrom.

          (iv)   If the indemnification provided for in this Section 2(f) is
     held by a court of competent jurisdiction to be unavailable to an
     Indemnified Party with respect to any loss,

                                      -11-
<PAGE>

     liability, claim, damage or expense referred to herein, then the
     Indemnifying Party, in lieu of indemnifying such Indemnified Party
     hereunder, shall contribute to the amount paid or payable by such
     Indemnified Party as a result of such loss, liability, claim, damage or
     expense (solely to the extent such amount is required pursuant to Section
     2(f)) in such proportion as is appropriate to reflect the relative fault of
     the Indemnifying Party on the one hand and of the Indemnified Party on the
     other in connection with the statements or omissions which resulted in such
     loss, liability, claim, damage or expense, as well as any other relevant
     equitable considerations including without limitation the relative fault of
     other Indemnifying Parties. The relative fault of the Indemnifying Party
     and of the Indemnified Party shall be determined by reference to, among
     other things, whether the untrue (or alleged untrue) statement of a
     material fact or the omission (or alleged omission) to state a material
     fact relates to information supplied by the Indemnifying Party or by the
     Indemnified Party and the parties' relative intent, knowledge, access to
     information and opportunity to correct or prevent such statement or
     omission. The foregoing notwithstanding, no Indemnifying Party will be
     required to contribute any amount in excess of the public offering price of
     all Registrable Securities offered by it pursuant to the registration
     statement, and no person or entity guilty of fraudulent misrepresentation
     (within the meaning of Section 11(f) of the Securities Act) will be
     entitled to contribution from any person or entity who was not guilty of
     such fraudulent misrepresentation.

          (v)   Notwithstanding the foregoing, to the extent that the provisions
     on indemnification and contribution contained in the underwriting agreement
     entered into in connection with any underwritten public offering
     contemplated by this Agreement are in conflict with the foregoing
     provisions, the provisions in such underwriting agreement shall be
     controlling.

          (vi)  The foregoing indemnity agreement of the Company and Holders is
     subject to the condition that, insofar as they relate to any loss, claim,
     liability or damage arising out of a statement made in or omitted from a
     preliminary prospectus but eliminated or remedied in the amended prospectus
     on file with the Commission at the time the registration statement in
     question becomes effective or the amended prospectus filed with the
     Commission pursuant to Commission Rule 424(b) (the "Final Prospectus"),
                                                         ----------------
     such indemnity or contribution agreement shall not inure to the benefit of
     any underwriter or Holder if a copy of the Final Prospectus was furnished
     to the underwriter and was not furnished to the person asserting the loss,
     liability, claim or damage at or prior to the time such action is required
     by the Securities Act.

     (g)  Information by the Holders.
          --------------------------

          (i)   Each of the Holders holding securities included in any
     registration shall furnish to the Company such information regarding such
     Holder and the distribution proposed by such Holder as the Company may
     reasonably request in writing and as shall be reasonably required in
     connection with any registration, qualification or compliance referred to
     in this Section 2.

                                      -12-
<PAGE>

          (ii)   In the event that, either immediately prior to or subsequent to
     the effectiveness of any registration statement, any Holder shall
     distribute Registrable Securities to its affiliates, such Holder shall so
     advise the Company and provide such information as shall be necessary to
     permit an amendment to such registration statement to provide information
     with respect to such affiliates, as selling securityholders. Promptly
     following receipt of such information, the Company shall file an
     appropriate amendment to such registration statement reflecting the
     information so provided. Any incremental expense to the Company resulting
     from such amendment shall be borne by such Holder.

     (h)  Rule 144 Reporting.
          ------------------

          With a view to making available the benefits of certain rules and
regulations of the SEC which may permit the sale of restricted securities to the
public without registration, the Company agrees to:

          (i)    make and keep public information available as those terms are
     understood and defined in Rule 144 under the Securities Act ("Rule 144");
                                                                   --------

          (ii)   use its best efforts to file with the SEC in a timely manner
     all reports and other documents required of the Company under the
     Securities Act and the Exchange Act; and

          (iii)  so long as the Holder owns any Registrable Securities, furnish
     to the Holder upon request a written statement by the Company as to its
     compliance with the reporting requirements of Rule 144 and of the
     Securities Act and the Exchange Act, a copy of the most recent annual or
     quarterly report of the Company, and such other reports and documents so
     filed as the Holder may reasonably request in availing itself of any rule
     or regulation of the SEC allowing the Holder to sell any such securities
     without registration.

     (i)  Assignment.  The registration rights set forth in this Section 2 may
          ----------
be assigned, in whole or in part, to any transferee of Registrable Securities
(who shall be bound by all obligations of this Agreement).

     (j)  Additional Agreements.  Without the written consent of Landmark and
          ---------------------
the holders of a majority of the Registrable Securities held by the Current
Investors, the Company shall not enter into any additional registration rights
agreements.

     (k)  Termination of Prior Agreements.  The 2001 Holders and the Company
          -------------------------------
hereby terminate that certain Registration Rights Agreement, dated as of March
1, 2001, which is hereby declared null and void and of no further force or
effect. The Current Investors hereby irrevocably waive all of their rights under
that certain: (1) Shareholders Agreement, dated June 1, 1998, by and among the
Company and certain of its stockholders; (2) Registration Rights Agreement,
dated May 28, 1999, by and among the Company and the purchasers of its 1999
Unsecured Convertible Subordinated Promissory Notes; and (3) Registration Rights
Agreement, dated

                                      -13-
<PAGE>

December 21, 1999, by and among the Company and its Series A Preferred
stockholders.

     (l)  Requested Registrations Not Subject to Landmark Consent.  The rights
          -------------------------------------------------------
of the 2001 Holders to request registrations pursuant to Sections 2(a) and 2(c)
and the rights of the 1998 Holders to request registrations pursuant Section
2(c) shall not be subject to the written consent of Landmark if such request for
registration (a "Section 2(l) Request") is made after December 31, 2003, and as
                 --------------------
of the date of the Section 2(l) Request the following conditions have been
satisfied:

          (i)    no event of default has occurred and is continuing under that
     certain Amended and Restated Loan and Security Agreement, dated as of
     July 30, 2001, by and between the Company and Landmark Communications,
     Inc. (the "Loan Agreement");
                ---------------

          (ii)   the Company has paid all accrued dividends on the Company's
     Series B Preferred Stock and issued all PIK Warrants (as defined in the
     Loan Agreement) required under the Loan Agreement;

          (iii)  for each of the past four (4) fiscal quarters immediately
     preceding such Section 2(l) Request, the Company has had positive net
     earnings of at least $500,000 and positive earnings before interest, taxes,
     depreciation and amortization ("EBITDA") of at least $1,000,000, and each
                                     ------
     such determination of net earnings and EBITDA has been calculated according
     to generally accepted accounting principles;

          (iv)   the Company has positive Working Capital (as that term is
     defined in the Loan Agreement) of at least $3,000,000;

          (v)    the applicable 1998 or 2001 Holder making a Section 2(l)
     Request provides the Company with a written letter addressed to the Company
     by a nationally recognized investment banking firm which confirms that, as
     of the date of such request for registration, the current market conditions
     and financial condition of the Company are satisfactory for granting such
     Section 2(l) Request taking into account solely the number of shares to be
     issued thereunder;

          (vi)   the Company is listed on a nationally recognized stock exchange
     or is quoted on the automated quotation system of a national securities
     association; and

          (vii)  the Company has not granted a Section 2(l) Request from a 2001
     Holder or 1998 Holder without the written consent of Landmark in the twelve
     (12) months immediately preceding such Section 2(l) Request.

          SECTION 3.  MISCELLANEOUS

                                      -14-
<PAGE>

     (a)  Directly or Indirectly.  Where any provision in this Agreement refers
          ----------------------
to action to be taken by any Person, or which such Person is prohibited from
taking, such provision shall be applicable whether such action is taken directly
or indirectly by such Person.

     (b)  Governing Law.  This Agreement shall be governed by and construed in
          -------------
accordance with the laws of the State of New York applicable to contracts made
and to be performed entirely within such State.

     (c)  Section Headings.  The headings of the sections and subsections of
          ----------------
this Agreement are inserted for convenience only and shall not be deemed to
constitute a part thereof.

     (d)  Notices.
          -------

          (i)    All communications under this Agreement shall be in writing and
     shall be delivered by hand or facsimile or mailed by overnight courier or
     by registered or certified mail, postage prepaid:

                 (1)  if to the Company, to 360 N. Michigan Avenue, Chicago,
          Illinois 60601, Attention: CEO (facsimile: (312) 853-0456), or at such
          other address as it may have furnished in writing to the Holders, with
          a copy to Jaffe, Raitt, Heuer & Weiss, One Woodward Avenue, Suite
          2400, Detroit, Michigan 48226 (facsimile: (313) 961-8358), Attention:
          Peter Sugar.

                 (2)  if to Landmark, at Landmark Communications, Inc., 150 W.
          Brambleton Avenue Norfolk, VA 23510, Facsimile: (757) 664-2164,
          Attention: Guy R. Friddell III, Executive Vice President and General
          Counsel, or at such other address or facsimile number as may have been
          furnished the Company in writing, with copies to Willcox and Savage,
          1800 Bank of America Center, One Commercial Place, Norfolk, Virginia
          23510-2197 (facsimile (757 628-5566), Attention Thomas Inglima, Esq.
          and Willkie Farr & Gallagher, 787 Seventh Avenue, New York, NY 10019
          (facsimile: (212) 728-8111), Attention: William J. Grant, Jr.

                 (3)  if to the Current Investors, at the address or facsimile
          number listed on Schedule II hereto, or at such other address or
          facsimile number as may have been furnished the Company in writing.

          (ii)   Any notice so addressed shall be deemed to be given: if
     delivered by hand or facsimile, on the date of such delivery; if mailed by
     courier, on the first business day following the date of such mailing; and
     if mailed by registered or certified mail, on the third business day after
     the date of such mailing.

     (e)  Reproduction of Documents.  This Agreement and all documents relating
          -------------------------
thereto, including, without limitation, any consents, waivers and modifications
which may hereafter be executed may be reproduced by the parties by any
photographic, photostatic, microfilm, microcard, miniature photographic or other
similar process and the parties may destroy any

                                      -15-
<PAGE>

     original document so reproduced.  The parties hereto agree and stipulate
     that any such reproduction shall be admissible in evidence as the original
     itself in any judicial or administrative proceeding (whether or not the
     original is in existence and whether or not such reproduction was made by
     the parties in the regular course of business) and that any enlargement,
     facsimile or further reproduction of such reproduction shall likewise be
     admissible in evidence.

          (f)  Successors and Assigns. This Agreement shall inure to the benefit
               ----------------------
     of and be binding upon the successors and assigns of each of the parties.

          (g)  Entire Agreement; Amendment and Waiver. This Agreement
               --------------------------------------
     constitutes the entire understanding of the parties hereto and supersedes
     all prior understanding among such parties. This Agreement may be amended,
     and the observance of any term of this Agreement may be waived, with (and
     only with) the written consent of the Company, Landmark and the Holders
     holding a majority of the then outstanding Registrable Securities held by
     the Current Investors.

          (h)  Severability. In the event that any part or parts of this
               ------------
     Agreement shall be held illegal or unenforceable by any court or
     administrative body of competent jurisdiction, such determination shall not
     affect the remaining provisions of this Agreement which shall remain in
     full force and effect.

          (i)  Counterparts. This Agreement may be executed in one or more
               ------------
     counterparts, each of which shall be deemed an original and all of which
     together shall be considered one and the same agreement.

                                      -16-
<PAGE>

     IN WITNESS WHEREOF, the undersigned have executed this Agreement as of the
date first set forth above.


                              COOLSAVINGS.COM INC.



                              By: /s/ Matthew Moog
                                 --------------------------------------
                                 Name: Matthew Moog
                                 Title: President & CEO



                              LANDMARK VENTURES VII, LLC



                              By: /s/ Richard A. Fraim
                                 --------------------------------------
                                 Name: Richard A. Fraim
                                 Title: VP/Sec/Treasurer



                              LEND LEASE INTERNATIONAL PTY.
                                LIMITED [ACN# 000489109]



                              By: /s/ Mark Skinner
                                 --------------------------------------
                                 Name: Mark Skinner
                                 Title: Power of Attorney

                        [Registration Rights Agreement]

<PAGE>

                              STEVEN M. GOLDEN



                              /s/ Steven M. Golden
                              -----------------------------------------

                              STEVEN M. GOLDEN REVOCABLE LIVING
                                   TRUST DATED 3/3/98



                              By: /s/ Steven M. Golden
                                 --------------------------------------
                                 Name: Steven M. Golden
                                 Title: Trustee


                              STEVEN M. GOLDEN L.L.C.



                              By: /s/ Steven M. Golden
                                 --------------------------------------
                                 Name: Steven M. Golden
                                 Title: member


                              MATTHEW MOOG


                              /s/ Matthew Moog
                              -----------------------------------------



                              RICHARD H. ROGEL


                              /s/ Richard H. Rogel
                              -----------------------------------------

                              RICHARD H. ROGEL REVOCABLE LIVING
                                   TRUST DATED 3/21/90



                              By: /s/ Richard H. Rogel
                                 --------------------------------------
                                 Name: Richard H. Rogel
                                 Title:

                        [Registration Rights Agreement]

<PAGE>

                              RICHARD ROGEL -- CHARITABLE
                                   REMAINDER TRUST



                              By: /s/ RICHARD H. ROGEL
                                 --------------------------------------
                                 Name: RICHARD H. ROGEL
                                 Title:


                              HUGH R. LAMLE


                              /s/ HUGH R. LAMLE
                              -----------------------------------------



                              HLBL FAMILY PARTNERS LP



                              By: /s/ HUGH R. LAMLE
                                 --------------------------------------
                                 Name:
                                 Title: Managing G.P.


                              RONALD G. ZACK, M.D.


                              /s/ Ronald Zack
                              -----------------------------------------

                        [Registration Rights Agreement]

<PAGE>

                                   SCHEDULE I

                               CURRENT INVESTORS
<TABLE>
<CAPTION>

Investor Name                                    Investor Address
------------------------------------------------------------------------------------------------
<S>                                              <C>
Lend Lease International Pty. Limited            Level 44 Australia Square
[ACN# 000489109]                                 Sydney, Australia 2000

Steven M. Golden                                 360 N. Michigan Ave., 19/th/ Floor
                                                 Chicago, Illinois 60601

Steven M. Golden Revocable Living Trust dated    360 N. Michigan Ave., 19/th/ Floor
3/3/98; Steven M. Golden as Trustee              Chicago, Illinois 60601

Steven M. Golden L.L.C.                          360 N. Michigan Ave., 19/th/ Floor
                                                 Chicago, Illinois 60601

Matthew Moog                                     360 N. Michigan Ave., 19/th/ Floor
                                                 Chicago, Illinois 60601

Richard H. Rogel                                 416 Shooting Star
                                                 P.O. Box 1659
                                                 Avon, Colorado 81620

Richard H. Rogel Revocable Living Trust dated    416 Shooting Star
3/31/90                                          P.O. Box 1659
                                                 Avon, Colorado 81620

Richard Rogel -- Charitable Remainder Trust      416 Shooting Star
                                                 P.O. Box 1659
                                                 Avon, Colorado 81620

Hugh R. Lamle                                    M.D. Sass Investor Services, Inc.
                                                 1185 Avenue of the Americas
                                                 New York, New York 10036-2699

HLBL Family Partners LP                          M.D. Sass Investor Services, Inc.
                                                 1185 Avenue of the Americas
                                                 New York, New York 10036-2699

Ronald G. Zack, M.D.                             18211 W. Twelve Mile Road
                                                 Lathrup Village, MI 48076

------------------------------------------------------------------------------------------------
</TABLE>

<PAGE>

                                  SCHEDULE II

                                 1998 Holders

<TABLE>
<CAPTION>
-----------------------------------------------------------------------------------
Investor Name                             Investor Address
-----------------------------------------------------------------------------------
<S>                                       <C>
Lend Lease International Pty Limited      Level 44 Australia Square
[ACN# 000489109]                          Sydney, Australia 2000

-----------------------------------------------------------------------------------
Steven M. Golden Revocable Living Trust   360 N. Michigan Avenue, 19/th/ Floor
dated 3/3/98; Steven M. Golden as         Chicago, Illinois 60601
Trustee

-----------------------------------------------------------------------------------
Steven M. Golden L.L.C.                   360 N. Michigan Avenue, 19/th/ Floor
                                          Chicago, Illinois 60601

-----------------------------------------------------------------------------------
Hugh R. Lamle                             c/o M.D. Sass Investor Services, Inc.
                                          1185 Avenue of the Americas
                                          New York, NY 10036-2699

-----------------------------------------------------------------------------------
HLBL Family Partners LP                   c/o M.D. Sass Investor Services, Inc.
                                          1185 Avenue of the Americas
                                          New York, NY 10036-2699

-----------------------------------------------------------------------------------
Richard H. Rogel Revocable Living Trust   416 Shooting Star
dated 3/21/90                             P.O. Box 1659
                                          Avon, CO 81620

-----------------------------------------------------------------------------------
Richard Rogel - Charitable Remainder      416 Shooting Star
Trust                                     P.O. Box 1659
                                          Avon, CO 81620

-----------------------------------------------------------------------------------
</TABLE>

<PAGE>

                                  SCHEDULE III

                                  2001 Holders

<TABLE>
<CAPTION>
-----------------------------------------------------------------------------------
Investor Name                             Investor Address
-----------------------------------------------------------------------------------
<S>                                       <C>
Hugh R. Lamle                             c/o M.D. Sass Investor Services, Inc.
                                          1185 Avenue of the Americas
                                          New York, NY 10036-2699

-----------------------------------------------------------------------------------
HLBL Family Partners LP                   c/o M.D. Sass Investor Services, Inc.
                                          1185 Avenue of the Americas
                                          New York, NY 10036-2699

-----------------------------------------------------------------------------------
Richard H. Rogel Revocable Living Trust   416 Shooting Star
dated 3/21/90                             P.O. Box 1659
                                          Avon, CO 81620

-----------------------------------------------------------------------------------
Richard Rogel - Charitable Remainder      416 Shooting Star
Trust                                     P.O. Box 1659
                                          Avon, CO 81620

-----------------------------------------------------------------------------------
Ronald G. Zack, M.D.                      18211 W. Twelve Mile Road
                                          Lathrup Village, MI 48076

-----------------------------------------------------------------------------------
</TABLE>