SKYLINE FUND
497, 1996-04-23
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<PAGE>
                       SKYLINE FUND-REGISTERED TRADEMARK-
                       311 SOUTH WACKER DRIVE, SUITE 4500
                            CHICAGO, ILLINOIS 60606
 
                      IN ILLINOIS--(312) 913-0900 COLLECT
                   OUTSIDE ILLINOIS--(800) 458-5222 TOLL FREE
 
                                                               September 1, 1995
 
    Skyline SPECIAL EQUITIES PORTFOLIO-REGISTERED TRADEMARK- and Skyline SPECIAL
EQUITIES  II-REGISTERED TRADEMARK-  seek maximum  capital appreciation primarily
through investment  in  common stocks  that  the Adviser  considers  undervalued
relative to earnings, book value, or potential earnings growth.
 
    SKYLINE SPECIAL EQUITIES PORTFOLIO emphasizes investments in small companies
whose  outstanding  shares have  an  aggregate market  value  of less  than $500
million.
 
    SKYLINE SPECIAL EQUITIES II emphasizes investments in small and medium-sized
companies whose  outstanding  shares have  an  aggregate market  value  of  $400
million to $2 billion.
 
                 SKYLINE SPECIAL EQUITIES PORTFOLIO IS CLOSED.
                            SEE "PURCHASING SHARES."
 
    Skyline  Special  Equities Portfolio  and  Skyline Special  Equities  II are
"no-load" funds. There  are no  sales or redemption  charges, and  there are  no
"12b-1"  plans. Skyline Special Equities  Portfolio and Skyline Special Equities
II are series of Skyline Fund.
 
    This Prospectus is a concise statement of information you should know before
investing. Please retain it for future reference.
 
    A Statement  of Additional  Information regarding  Skyline Special  Equities
Portfolio  and Skyline Special Equities II and dated the date of this Prospectus
has been filed with  the Securities and Exchange  Commission and (together  with
any  supplement  to it)  is incorporated  in this  Prospectus by  reference. The
Statement of Additional Information may be obtained without charge by calling or
writing the Fund at the telephone numbers or address shown above.
 
                            ------------------------
 
THESE SECURITIES HAVE NOT BEEN APPROVED OR DISAPPROVED BY THE SECURITIES AND
    EXCHANGE COMMISSION OR ANY STATE  SECURITIES COMMISSION, NOR HAS  THE
       SECURITIES  AND  EXCHANGE COMMISSION  OR ANY  STATE SECURITIES
           COMMISSION PASSED  UPON THE  ACCURACY OR  ADEQUACY  OF
               THIS  PROSPECTUS.  ANY REPRESENTATION  TO THE
                       CONTRARY IS A CRIMINAL OFFENSE.

<PAGE>
                               TABLE OF CONTENTS
<TABLE>
<CAPTION>
                                                    PAGE
                                                    -----
<S>                                              <C>
HIGHLIGHTS.....................................           2
EXPENSE INFORMATION............................           3
FINANCIAL HIGHLIGHTS...........................           4
INVESTMENT OBJECTIVE AND POLICIES..............           5
RISKS..........................................           6
INVESTMENT RESTRICTIONS........................           6
PURCHASING SHARES..............................           6
REDEEMING SHARES...............................           8
NET ASSET VALUE................................           9
SHAREHOLDER SERVICES...........................           9
  Shareholder Accounts.........................           9
  Retirement Plans.............................           9
  Exchange Privilege...........................           9
 
<CAPTION>
                                                    PAGE
                                                    -----
<S>                                              <C>
  Automatic Investment Plan....................          10
  Systematic Withdrawal Plan...................          11
  Dividend Purchase Plan.......................          11
DIVIDENDS AND DISTRIBUTIONS....................          11
TAXES..........................................          11
MANAGEMENT OF THE FUND.........................          12
  The Trustees.................................          12
  The Adviser..................................          12
  Portfolio Transactions.......................          13
  Performance..................................          14
THE FUND AND ITS SHARES........................          14
  Shares.......................................          14
  Voting Rights................................          15
  Shareholder Inquiries........................          15
</TABLE>
 
                                   HIGHLIGHTS
 
    SKYLINE  SPECIAL  EQUITIES PORTFOLIO  and  SKYLINE SPECIAL  EQUITIES  II are
series (each, a "Portfolio" and collectively, the "Portfolios") of Skyline  Fund
(the  "Fund").  Each  Portfolio is  a  "no-load"  fund. There  are  no  sales or
redemption charges.
 
<TABLE>
<S>                               <C>
INVESTMENT OBJECTIVE AND
  POLICIES......................  SKYLINE SPECIAL  EQUITIES  PORTFOLIO  and  SKYLINE  SPECIAL
                                  EQUITIES  II  seek maximum  capital  appreciation primarily
                                  through  investment  in  common  stocks  that  the  Adviser
                                  considers  undervalued relative to earnings, book value, or
                                  potential  earnings   growth.  SKYLINE   SPECIAL   EQUITIES
                                  PORTFOLIO  emphasizes investments in  small companies whose
                                  outstanding shares have an  aggregate market value of  less
                                  than  $500 million. SKYLINE  SPECIAL EQUITIES II emphasizes
                                  investments  in  small  and  medium-sized  companies  whose
                                  outstanding  shares have an aggregate  market value of $400
                                  million to  $2  billion. (See  "Investment  Objectives  and
                                  Policies.")
INVESTMENT RISKS................  Each  Portfolio is designed for long-term investors willing
                                  to accept  more investment  risk  and volatility  than  the
                                  stock market in general.
MINIMUM PURCHASE................  $1,000  for  initial  investments and  $100  for subsequent
                                  investments.
DIVIDENDS AND CAPITAL GAINS.....  Income dividends and capital gains, if any, are distributed
                                  at  least   annually.   Distributions   are   automatically
                                  reinvested  in additional shares at  net asset value unless
                                  payment  in  cash   is  requested.   (See  "Dividends   and
                                  Distributions.")
REDEMPTION PRICE................  Current  net asset  value, without  charge. (See "Redeeming
                                  Shares.")
</TABLE>
 
                                       2
<PAGE>
 
<TABLE>
<S>                               <C>
INVESTMENT ADVISER..............  Skyline  Asset   Management,   L.P.  (the   "Adviser")   is
                                  investment  adviser to  the Fund. The  Adviser manages more
                                  than $500 million in assets as of August 31, 1995.  William
                                  M.  Dutton and Kenneth S. Kailin are the portfolio managers
                                  of Skyline Special Equities  Portfolio and Skyline  Special
                                  Equities  II, respectively. Each of them leads a team which
                                  is responsible  for  the  day-to-day  management  of  their
                                  respective  portfolios. (See  "Management of  the Fund--The
                                  Adviser.")
EXPENSES OF THE FUND............  Each Portfolio pays the Adviser  a comprehensive fee at  an
                                  annual  rate declining from 1.50%  of its average daily net
                                  asset value. The Adviser pays  out of its fee the  ordinary
                                  costs  and expenses  of the Portfolio.  (See "Management of
                                  the Fund--The Adviser.")
DISTRIBUTOR.....................  Funds Distributor, Inc.
</TABLE>
 
         NOTE: SKYLINE SPECIAL EQUITIES PORTFOLIO IS CURRENTLY CLOSED.
                            SEE "PURCHASING SHARES."
 
                              EXPENSE INFORMATION
 
    The following table shows all fees paid by shareholders or assessed  against
assets of the Portfolios:
 
<TABLE>
<CAPTION>
                                                                                               SKYLINE
                                                                                               SPECIAL       SKYLINE
                                                                                              EQUITIES       SPECIAL
                                                                                              PORTFOLIO    EQUITIES II
                                                                                             -----------  -------------
<S>                                                                                          <C>          <C>
SHAREHOLDER TRANSACTION EXPENSES
  Maximum Sales Load Imposed on Purchases (as a percentage of offering price)..............        none          none
  Maximum Sales Load Imposed on Reinvested Dividends (as a percentage of offering price)...        none          none
  Deferred Sales Load......................................................................        none          none
  Redemption Fees (1)......................................................................        none          none
  Exchange Fees............................................................................        none          none
ANNUAL OPERATING EXPENSES (AS A PERCENTAGE OF AVERAGE NET ASSETS)
  Management Fees (including operating expenses)(2)........................................        1.49%         1.50%
  12b-1 Fees...............................................................................        none          none
  Other Expenses...........................................................................           0%          .01%
                                                                                                  -----         -----
  Total Operating Expenses.................................................................        1.49%         1.51%
</TABLE>
 
- ------------------------
(1) A shareholder requesting payment of redemption proceeds by wire must pay the
    cost of the wire transfer (currently $7.50). See "Redeeming Shares."
 
(2) Under  the  advisory  agreements,  the  Adviser  pays  all  of  the ordinary
    operating expenses of each  Portfolio, except the fees  and expenses of  the
    Fund's  non-interested  trustees  and  the  reimbursement  of organizational
    costs. See "Management of the Fund--The Adviser" in this prospectus for more
    information. Mesirow Asset Management, Inc.  ("MAMI") served as the  adviser
    to  the Portfolios from their inception  through August 31, 1995. During the
    fiscal year ended  December 31,  1994, the expenses  paid by  MAMI from  its
    management  fee  to  other  service providers  to  Skyline  Special Equities
    Portfolio and Skyline  Special Equities II  amounted to 0.11%  and 0.26%  of
    average net assets respectively.
 
    The  purpose of  the table  is to assist  the investor  in understanding the
various costs  and  expenses that  an  investor  in the  Portfolios  will  bear,
directly or indirectly.
 
                                       3

<PAGE>
EXAMPLE
 
    You  would pay the following expenses on a $1,000 investment assuming (1) 5%
annual return and (2) redemption at the end of each time period for each of  the
Portfolios:
 
<TABLE>
<CAPTION>
                                                                            SKYLINE
                                                                            SPECIAL       SKYLINE
                                                                           EQUITIES       SPECIAL
                                                                           PORTFOLIO    EQUITIES II
                                                                          -----------  -------------
<S>                                                                       <C>          <C>
1 year..................................................................   $      15     $      15
3 years.................................................................          47            48
5 years.................................................................          81            82
10 years................................................................         178           180
</TABLE>
 
    The  Example should  not be  considered a  representation of  past or future
expenses; the actual expense  of the Portfolios and  the annual rates of  return
may be greater or less than those shown. Although information such as that shown
in  the Example  is useful in  reviewing the  expenses of the  Portfolios and in
providing a basis for  comparison of these expenses  with the expenses of  other
mutual  funds, it should not be used for comparison with other investments using
different assumptions or time periods.
 
                              FINANCIAL HIGHLIGHTS
 
    The tables below reflect the results of the operations of each Portfolio  on
a  per-share basis for the periods indicated. The information presented has been
audited and reported  on by  the independent auditors  of the  Fund. The  tables
should  be read in conjunction with  the financial statements of Skyline Special
Equities Portfolio  and  Skyline Special  Equities  II, which  may  be  obtained
without  charge from the  Fund upon request.  In addition to  the highlights set
forth below,  further information  about the  performance of  the Portfolios  is
contained  in the  Portfolios' Annual  Reports and  the Statement  of Additional
Information, which may be obtained from the Fund free of charge.
 
                       SKYLINE SPECIAL EQUITIES PORTFOLIO
<TABLE>
<CAPTION>
                                                                     YEAR ENDED DECEMBER 31,
                                    -----------------------------------------------------------------------------------------
                                       1994         1993         1992         1991         1990         1989         1988
                                    -----------  -----------  -----------  -----------  -----------  -----------  -----------
<S>                                 <C>          <C>          <C>          <C>          <C>          <C>          <C>
Net asset value at beginning of
 period...........................   $    17.83   $    17.12   $    12.67   $    10.32   $    11.49   $    10.32   $     7.99
  INCOME FROM INVESTMENT
   OPERATIONS
  Net investment (loss) income....        (0.08)       (0.09)       (0.01)        0.01         0.10         0.13         0.05
  Net realized and unrealized
   (loss) gain on investments.....        (0.18)        3.94         5.37         4.74        (1.17)        2.33         2.33
                                    -----------  -----------  -----------  -----------  -----------  -----------  -----------
    Total from Investment
     Operations...................        (0.26)        3.85         5.36         4.75        (1.07)        2.46         2.38
                                    -----------  -----------  -----------  -----------  -----------  -----------  -----------
  LESS DISTRIBUTIONS
  Dividends from net investment
   income.........................      --           --           --             (0.01)       (0.10)       (0.13)       (0.05)
  Dividends from net realized
   gains on investments...........        (1.93)       (3.14)       (0.91)       (2.39)     --             (1.16)     --
                                    -----------  -----------  -----------  -----------  -----------  -----------  -----------
    Total Distributions...........        (1.93)       (3.14)       (0.91)       (2.40)       (0.10)       (1.29)       (0.05)
                                    -----------  -----------  -----------  -----------  -----------  -----------  -----------
Net asset value at end of
 period...........................  $     15.64   $    17.83   $    17.12   $    12.67   $    10.32   $    11.49   $    10.32
                                    -----------  -----------  -----------  -----------  -----------  -----------  -----------
                                    -----------  -----------  -----------  -----------  -----------  -----------  -----------
TOTAL RETURN (g)..................        (1.15%)      22.85%       42.45%       47.28%       (9.28%)      23.98%       29.79%
RATIOS/SUPPLEMENTAL DATA
Ratio of expenses to average net
 assets...........................         1.49%        1.48%        1.51%        1.55%        1.59%        1.60%        1.70%
Ratio of net investment (loss)
 income to average net assets.....        (0.49%)      (0.54%)      (0.19%)       0.09%        0.95%        1.30%        0.61%
Portfolio turnover rate...........           82%         104%          87%         104%          98%          90%          68%
Net assets, end of period (in
 thousands).......................     $202,771     $228,011     $172,385      $37,495      $22,154      $21,056      $11,498
 
<CAPTION>
                                       APRIL 23,
                                      1987(a) TO
                                      DECEMBER 31
                                         1987
                                    ---------------
<S>                                 <C>
Net asset value at beginning of
 period...........................    $  9.61
  INCOME FROM INVESTMENT
   OPERATIONS
  Net investment (loss) income....       0.01
  Net realized and unrealized
   (loss) gain on investments.....      (1.63)
                                       ------
    Total from Investment
     Operations...................      (1.62)
                                       ------
  LESS DISTRIBUTIONS
  Dividends from net investment
   income.........................      --
  Dividends from net realized
   gains on investments...........      --
                                       ------
    Total Distributions...........      --
                                       ------
Net asset value at end of
 period...........................  $    7.99
                                       ------
                                       ------
TOTAL RETURN (g)..................     (16.86%)(b)
RATIOS/SUPPLEMENTAL DATA
Ratio of expenses to average net
 assets...........................       1.60%(c)(d)
Ratio of net investment (loss)
 income to average net assets.....       0.20%(c)(d)
Portfolio turnover rate...........        173%(c)
Net assets, end of period (in
 thousands).......................   $  6,605
</TABLE>
 
                                       4
<PAGE>
                          SKYLINE SPECIAL EQUITIES II
 
<TABLE>
<CAPTION>
                                                                                    FEBRUARY 9,
                                                                 YEAR ENDED         1993(A) TO
                                                              DECEMBER 31, 1994  DECEMBER 31, 1993
                                                              -----------------  -----------------
<S>                                                           <C>                <C>
Net asset value at beginning of period......................      $   10.79          $   10.00
INCOME FROM INVESTMENT OPERATIONS
  Net investment income.....................................           0.02               0.01
  Net realized and unrealized (loss) gain on investments....          (0.19)              1.00
                                                              -----------------  -----------------
    Total from Investment Operations........................          (0.17)              1.01
                                                              -----------------  -----------------
LESS DISTRIBUTIONS
  Dividends from net investment income......................          (0.02)            --
  Dividends from net realized gains on investments..........          (0.46)             (0.22)
  Return of capital distribution............................         --    (e)          --    (e)
                                                              -----------------  -----------------
    Total Distributions.....................................          (0.48)              (.22)
                                                              -----------------  -----------------
Net asset value at end of period............................      $   10.14          $   10.79
                                                              -----------------  -----------------
                                                              -----------------  -----------------
TOTAL RETURN................................................          (1.52%)            10.08%(f)
RATIOS/SUPPLEMENTAL DATA
Ratio of expenses to average net assets.....................           1.51%              1.51%(c)
Ratio of net investment income (loss) to average net
 assets.....................................................           0.22%             (0.10)%(c)
Portfolio turnover rate.....................................             82%               111%(c)
Net assets, end of period (in thousands)....................  $      99,638      $      58,608
                                                              -----------------  -----------------
                                                              -----------------  -----------------
</TABLE>
 
- ------------------------------
Notes to financial highlights:
 
(a) Commencement of operations.
 
(b) For the period April 23, 1987 to December 31, 1987.
 
(c) Ratios have been determined on an annualized basis.
 
(d) During  the  period from  April  23, 1987  through  December 31,  1987  fees
    totaling  $10,159 were reimbursed to  the Skyline Special Equities Portfolio
    or waived by MAMI.  Absent the foregoing, the  ratio of expenses to  average
    net  assets would have been  1.88%, and the ratio  of net investment loss to
    average net assets would have been (.08%).
 
(e) Distributions were less than $.01 per share.
 
(f) For the period February 9, 1993 to December 31, 1993.
 
(g) Total return  for Skyline Special  Equities Portfolio does  not reflect  the
    effect of any sales charges which may have been previously charged.
 
                       INVESTMENT OBJECTIVE AND POLICIES
 
    SKYLINE   SPECIAL  EQUITIES  PORTFOLIO  and   SKYLINE  SPECIAL  EQUITIES  II
(together, the  "Portfolios") have  the same  general investment  objective  and
follow  the same investment strategy.  The Portfolios differ in  the size of the
companies  in  which   they  invest.  Each   Portfolio  seeks  maximum   capital
appreciation  primarily  through investment  in common  stocks that  the Adviser
considers undervalued relative  to earnings, book  value, or potential  earnings
growth.  Companies in which the Portfolios invest generally fall into one of the
following three categories:
 
        1.   A company  that the  Adviser believes  will achieve  above  average
    growth  in earnings, but that is selling at a price/earnings ratio below the
    average for the overall stock market.
 
        2.  A company that has experienced problems leading to a depressed stock
    price where the Adviser believes that there is a reasonable likelihood  that
    the company's operations will improve.

                                       5
<PAGE>
 
        3.   A company that does not fall into the above categories, but because
    of  special  circumstances  appears  undervalued  and  consequently   offers
    potential for appreciation.
 
    SKYLINE SPECIAL EQUITIES PORTFOLIO emphasizes investments in small companies
whose  outstanding  shares have  an  aggregate market  value  of less  than $500
million; SKYLINE  SPECIAL  EQUITIES  II  emphasizes  investments  in  small  and
medium-sized  companies whose outstanding shares  have an aggregate market value
of $400 million to $2 billion.
 
    Each Portfolio is ordinarily substantially fully invested, and under  normal
market conditions, at least 65% of the assets of each Portfolio will be invested
in  common stocks. In  management of cash receipts  or liquidity for anticipated
redemptions, each  Portfolio  may  invest without  limitation  in  high-quality,
fixed-income securities, or hold assets in cash or cash equivalents.
 
                                     RISKS
 
    Because  of the  concentration of  the Portfolios  in stocks  of smaller and
medium-sized companies, which  tend to  be more  volatile and  less liquid  than
stocks  of larger companies, the Portfolios  may involve an above average degree
of risk. Smaller and  medium-sized companies, as  compared to larger  companies,
may  have a shorter history  of operations, may not have  as great an ability to
raise additional capital, may have a  less diversified product line making  them
susceptible  to market pressure, and may have  a smaller public market for their
securities. However, an attempt is made  to minimize the risk through  portfolio
diversification  and  the  use of  a  stock selection  strategy  that emphasizes
undervalued common stocks, many of which already reflect a lower price.
 
    There can be no  assurance that a Portfolio's  investment objective will  be
achieved.  Each Portfolio's investment objective and  policies may be changed by
the Fund's board of trustees without shareholder approval. However,  shareholder
approval  is  required  for  changes  in  a  Portfolio's  fundamental investment
restrictions. Any change in the investment objective of a Portfolio might result
in that Portfolio  having an  investment objective  that is  different from  the
investment  objective a shareholder considered appropriate at the time of making
an investment.
 
                            INVESTMENT RESTRICTIONS
 
    The  Fund  has   adopted  for  each   Portfolio  the  following   investment
restrictions,  among others,  that may  be changed only  with the  approval of a
majority of the outstanding shares of the Portfolio as defined in the Investment
Company Act of 1940. A Portfolio may not: (1) invest more than 5% of its  assets
(valued  at the  time of  investment) in  the securities  of any  single issuer,
excluding government obligations; (2)  invest in a security  if, as a result  of
such investment, the Portfolio would hold more than 10% (measured at the time of
investment) of the outstanding voting securities of the issuer of such security;
or (3) invest more than 5% of its assets (measured at the time of investment) in
the  securities  of  an issuer  with  less  than three  years  operating history
(including predecessors). All of the investment restrictions for each  Portfolio
are stated in the Statement of Additional Information.
 
                               PURCHASING SHARES
 
    Shares  of the  Portfolios may be  purchased by completing  a share purchase
application and  forwarding  it,  together  with a  check  for  the  investment,
directly   to   the   Fund   c/o   Firstar   Trust   Company,   P.O.   Box  701,
 
                                       6
<PAGE>
Milwaukee, WI 53201 or to the Distributor or an authorized broker-dealer who  is
responsible  for promptly delivering  the application and  initial investment to
the Fund. The  transfer agent is  unable to  accept third party  checks both  on
initial and subsequent share purchases.
 
    ON  MARCH 22, 1993 THE  FUND STOPPED ALL FURTHER  SALES OF SHARES OF SKYLINE
SPECIAL EQUITIES PORTFOLIO  EXCEPT THAT  (i) RETIREMENT  PLANS (INCLUDING  ERISA
ACCOUNTS  AND IRAS)  THAT WERE  SHAREHOLDERS OF THE  PORTFOLIO ON  THAT DATE MAY
PURCHASE SHARES TO BE ADDED TO EXISTING ACCOUNTS AND (ii) THE BOARD OF  TRUSTEES
IN  ITS DISCRETION MAY ELECT TO PERMIT  CERTAIN PERSONS, SUCH AS TRUSTEES OF THE
FUND AND EMPLOYEES OF THE ADVISER AND RETIREMENT OR OTHER BENEFIT PLANS IN WHICH
SUCH PERSONS MAY PARTICIPATE,  TO PURCHASE SHARES TO  THE EXTENT DESCRIBED  FROM
TIME TO TIME IN THE STATEMENT OF ADDITIONAL INFORMATION. All shareholders of the
Skyline  Special  Equities  Portfolio  may continue  to  reinvest  dividends and
distributions on  all or  any shares  owned. IF  YOU HAVE  QUESTIONS ABOUT  YOUR
ELIGIBILITY  TO PURCHASE  SHARES OF  SKYLINE SPECIAL  EQUITIES PORTFOLIO, PLEASE
CALL THE FUND AT (800) 458-5222. Sales of shares of Skyline Special Equities  II
are not affected by this restriction.
 
    The  purchase price of shares  in each Portfolio is  the net asset value per
share next  computed  after  receipt  by the  Fund  (from  the  Distributor,  an
authorized  broker-dealer or directly from a  shareholder) of an order completed
in accordance with the instructions on the account application. Your order  must
be  received by the Fund before the close  of regular session trading on the New
York Stock Exchange ("NYSE") (currently 3:00 p.m., Chicago time) to receive  the
net  asset value calculated on that day.  (See "Net Asset Value.") All purchases
must be made in U.S.  dollars and checks must be  drawn on U.S. banks. Unless  a
shareholder  elects to  participate in  one of  the shareholder  plans requiring
written instructions  to  the  Fund described  under  the  caption  "Shareholder
Services,"   a  shareholder  may  also  purchase  shares  by  giving  telephonic
instructions to purchase shares (including the shareholder's name and amount  to
be  invested) to an authorized broker-dealer  and instructing the dealer to wire
transfer the funds for the shareholder's  account. Funds transferred by wire  in
this  manner will be considered to be invested  upon receipt of the order by the
Fund.  Funds  may  be  invested  in  this  manner  only  through  an  authorized
broker-dealer. Any questions regarding this method of investment may be answered
by  calling (312) 913-0900 or (800)  458-5222. The minimum initial investment to
open an account is $1,000 and subsequent investments must be at least $100.  The
minimum initial investment to open an account for a spousal IRA (established for
a nonworking spouse) is $250.
 
    You  may also purchase (or redeem) shares through investment dealers, banks,
or other institutions. However, these institutions may charge for their services
or place limitations on the extent to which you may use the services offered  by
the  Fund. There are no  charges or limitations imposed  by the Fund (other than
nominal charges  for  wire transfers,  returned  checks and  similar  items,  as
described  in this  prospectus) if shares  are purchased  (or redeemed) directly
from the Distributor.
 
    The Fund reserves the right to reject purchase orders under circumstances or
in  amounts  considered  disadvantageous  to  existing  shareholders.  The  Fund
believes  that frequent  purchases and redemptions  of Fund  shares by investors
utilizing market-timing strategies  adversely affects the  Portfolios. The  Fund
therefore  intends to  reject purchase orders  from investors  identified by the
Fund as market-timers.  Should an  order to purchase  shares of  a Portfolio  be
canceled  because a shareholder's check does  not clear, the shareholder will be
responsible for  any  resulting  loss  incurred  by  that  Portfolio.  A  charge
(currently $15) will be assessed for any returned check.
 
                                       7
<PAGE>
    Generally,  the Fund does not  issue share certificates representing shares,
although share  certificates in  full share  amounts will  be furnished  upon  a
shareholder's written request. Fractional shares, if any, will be carried on the
books of the Fund without issuance of certificates.
 
                                REDEEMING SHARES
 
    Shareholders  of each  Portfolio may  redeem their  shares at  the net asset
value next determined after the request is received by the Fund. Your redemption
request in proper form must be received by the Fund before the close of  regular
session  trading on the  New York Stock Exchange  ("NYSE") (currently 3:00 p.m.,
Chicago time) to receive the net asset  value calculated on that day. (See  "Net
Asset  Value.") To redeem shares, a written request must be received by the Fund
or telephone authorization in proper form must be received by the Fund or be  on
file  with the  Fund. A  written request  for redemption  must be  signed by all
persons in whose names the  shares are registered. Redemption requests  received
by  facsimile  transmission  or other  electronic  means will  not  be accepted.
Signatures must conform exactly to the account registration.
 
    A signature guarantee is required on  the written redemption request if  (i)
the  redemption  proceeds are  to be  sent to  a bank  or brokerage  account not
previously authorized by the shareholder in accordance with the instructions  on
the  account application, (ii) the proceeds of the requested redemption would be
more than $10,000, or (iii) THE ADDRESS OF RECORD HAS CHANGED WITHIN THE LAST 60
DAYS. The  guarantor  must be  a  bank, member  firm  of a  national  securities
exchange,  savings and loan association, credit union or other entity authorized
by state  law to  guarantee signatures.  A notary  public is  not an  acceptable
guarantor. Additional documentary evidence of authority is required in the event
redemption  is  requested  by  a  corporation,  partnership,  trust,  fiduciary,
executor, or  administrator.  CHECKS TO  THIRD  PARTIES  OTHER THAN  A  BANK  OR
BROKERAGE  ACCOUNT AS AUTHORIZED ABOVE ARE NOT PERMITTED. Redemption checks will
not be  forwarded if  the redeeming  shareholder moves.  The redemption  request
should also indicate the change of address and include a signature guarantee.
 
    Telephone  redemptions  can be  authorized  on the  account  application. If
telephone redemptions  are  so  authorized,  the Fund  will  honor  requests  by
telephone at (312) 913-0900 or (800) 458-5222. Reasonable procedures are used to
confirm  that instructions received by telephone are genuine, such as requesting
personal identification information that appears on the purchase application and
recording the conversation.  The shareholder  bears the  risk of  any loss  that
might result from a fraudulent instruction, although the Fund may bear such risk
if  reasonable procedures  were not  used. To  reduce the  risk of  a fraudulent
instruction,  proceeds  of  telephone  redemptions  may  be  sent  only  to  the
shareholder's  address of record or to a bank or brokerage account designated by
the shareholder, in writing, on the purchase application or in a letter with the
signature(s) guaranteed. The  Fund reserves  the right to  record all  telephone
redemption requests.
 
    The  redemption price per share is the net asset value next determined after
receipt of  the  redemption  request,  which  may  be  more  or  less  than  the
shareholder's  cost  depending  upon  the value  of  the  Portfolio's investment
securities at the time of redemption (See "Net Asset Value.") There is no charge
for a redemption, but an authorized dealer may charge a fee for this service.  A
redemption  order received from a dealer must be at least $250 unless the entire
account is being redeemed.
 
    Payment for  shares redeemed  is made  by check  or wire.  Payment by  check
normally  is mailed within seven days after receipt of the redemption request in
proper form.  If specified in the account application, the check will be payable
and sent to a designated financial institution. A wire will be sent only to  the
shareholder's  bank or  brokerage account as  shown on  the account application.
Wire requests generally are
 
                                       8
<PAGE>
paid the next business  day, after deduction  of the cost  of the wire  transfer
(currently  $7.50).  That charge  and  any similar  service  fee may  be changed
without prior notice to shareholders. Wires to third parties are not permitted.
 
    The Fund  may suspend  or postpone  the right  of redemption  at times  when
trading  on the New York Stock Exchange  is restricted or as otherwise permitted
by the Securities and Exchange Commission.  If a shareholder attempts to  redeem
shares  within 15  days after they  have been  purchased by check,  the Fund may
delay payment of the  redemption proceeds until it  can verify that payment  for
the purchase of the shares has been (or will be) received.
 
    The  Fund reserves the right to redeem  shares in any account with a balance
of less than $750 in share value in any Portfolio. Prior to any such redemption,
the Fund will give the shareholder thirty days' written notice during which time
the shareholder may increase his investment to avoid having his shares redeemed.
The $750 minimum balance will be waived if the account balance drops below  $750
due to market activity.
 
                                NET ASSET VALUE
 
    The  price per share for  a purchase order or  redemption request is the net
asset value next determined after receipt of the order.
 
    The net asset value  of a share  of each Portfolio is  determined as of  the
close of regular session trading on the NYSE (currently 3:00 p.m., Chicago time)
each  day the NYSE  is open for trading.  The net asset value  per share of each
Portfolio is determined  by dividing the  difference between the  values of  the
Portfolio's  assets and  liabilities by the  number of  shares outstanding. Each
security traded on a national stock exchange or on the Nasdaq National Market is
valued at the last sale price, or, if there have been no sales on the  valuation
day,  at the most recent bid price. Other securities traded over the counter are
valued at the last reported bid price. Other assets and securities are valued by
methods the board of trustees believes will determine a fair value.
 
                              SHAREHOLDER SERVICES
 
    SHAREHOLDER ACCOUNTS.  Each shareholder receives an annual account statement
showing transactions  in Portfolio  shares  and with  a balance  denominated  in
Portfolio  shares.  In addition,  confirmations  are sent  to  shareholders upon
purchase, redemption, dividend reinvestment, and change of shareholder  address.
For  a fee, a shareholder  may obtain a historical  transcript of his account by
requesting one in writing from Firstar Trust Company.
 
    RETIREMENT PLANS.   Investors may use  the Fund as  an investment for  their
Individual  Retirement  Accounts  ("IRAs"),  profit  sharing  or  pension plans,
Section 401(k) plans, Section 403(b)(7) plans in the case of employees of public
school systems and certain non-profit organizations, and certain other qualified
plans. A master IRA plan,  information regarding plan administration, fees,  and
other details are available from the Distributor and authorized broker-dealers.
 
    EXCHANGE  PRIVILEGE.   The Fund offers  an exchange  privilege among Skyline
Special Equities  II and  two  portfolio series  of Portico  Funds,  Inc.--Money
Market  Fund and  U.S. Government Money  Market Fund (the  "Portico Money Market
Funds"). Because  sales of  shares  of Skyline  Special Equities  Portfolio  are
restricted,  the exchange privilege generally may not be used to purchase shares
of Skyline Special  Equities Portfolio.  An investor exchanging  out of  Skyline
Special  Equities  Portfolio may  not later  exchange  back into  that Portfolio
unless exchanges were limited to a Portico Money Market Fund.
 
                                       9
<PAGE>
    All exchanges are based  on the respective net  asset values per share  next
calculated  after the receipt  of an exchange request.  Shares of either Portico
Money Market Fund or either Portfolio  to be acquired must have been  registered
for  sale in the  investor's state. To be  effective on that  date, a request to
exchange into or  out of a  Portico Money Market  Fund must be  received by  the
purchase  or redemption cutoff time  described from time to  time in the Portico
Money Market  Funds  prospectus,  a copy  of  which  can be  obtained  from  the
Distributor at (312) 913-0900 or (800) 458-5222
 
    The  exchange privilege is  not available for  shares for which certificates
have been issued or which  have been held for fewer  than 15 days. Exchanges  by
telephone are an automatic privilege unless the shareholder notifies the Fund on
the  account  application  that  his  authorization  has  been  withheld. Unless
authorization is withheld, the Fund will honor exchange requests by telephone at
(312) 913-0900 or  (800) 458-5222.  The Fund reserves  the right  to record  all
telephone  exchange  requests. Reasonable  procedures are  used to  confirm that
instructions received  by telephone  are genuine,  such as  requesting  personal
identification  information that appears  on your application  and recording the
conversation. You will bear the risk  of loss due to unauthorized or  fraudulent
instructions  regarding your  account, although the  Fund may bear  such risk if
reasonable procedures  were not  used.  To reduce  the  risk of  any  fraudulent
instruction,  the  registration  of the  account  into  which shares  are  to be
exchanged must  be identical  to the  registration of  the originating  account.
During  periods of  volatile economic and  market conditions,  a shareholder may
have difficulty  making a  redemption request  by telephone,  in which  case  an
exchange request would have to be made in writing.
 
    The  Fund reserves the right at any  time without prior notice to suspend or
terminate the use of the exchange privilege  by any person or class of  persons.
The  Fund believes  that use  of the  exchange privilege  by investors utilizing
market-timing strategies adversely affects  the Portfolios. THEREFORE, THE  FUND
GENERALLY  WILL NOT HONOR  REQUESTS FOR EXCHANGES  BY SHAREHOLDERS IDENTIFIED BY
THE FUND AS "MARKET-TIMERS." Moreover, the  Fund reserves the right at any  time
without  prior  notice  to suspend,  limit,  modify, or  terminate  the exchange
privilege in its entirety. Because such a step would be taken only if the  board
of  trustees believes it would  be in the best  interests of the Portfolios, the
Fund expects that it would provide shareholders with prior written notice of any
such action  unless it  appears  that the  resulting  delay in  the  suspension,
limitation,  modification,  or  termination  of  the  exchange  privilege  would
adversely affect the Portfolios. IF THE FUND WERE TO SUSPEND, LIMIT, MODIFY,  OR
TERMINATE  THE EXCHANGE PRIVILEGE,  A SHAREHOLDER EXPECTING  TO MAKE AN EXCHANGE
MIGHT FIND THAT  AN EXCHANGE COULD  NOT BE PROCESSED  OR THAT THERE  MIGHT BE  A
DELAY IN THE IMPLEMENTATION OF THE EXCHANGE.
 
    EXCHANGES  OF SHARES ARE TAXABLE EVENTS AND MAY RESULT IN A GAIN OR LOSS FOR
FEDERAL INCOME TAX PURPOSES. A prospectus for the Portico Money Market Funds may
be obtained from the  Distributor or any  authorized broker-dealer. An  investor
considering  an exchange should refer to  the relevant prospectus for additional
information.
 
    AUTOMATIC INVESTMENT PLAN.   The Fund  has a pre-authorized  check plan  for
shareholders  who  wish  to make  automatic  periodic investments  in  shares of
Skyline Special Equities II. A shareholder may establish an automatic investment
plan for Skyline Special Equities II by  opening an account with $1,000 or  more
and delivering to the Fund an automatic investment plan application along with a
voided check. The plan enables Firstar Trust Company, the Fund's transfer agent,
to  withdraw  funds  from a  shareholder's  bank  account or  NOW  account  on a
predetermined basis for  investment in  shares of the  Portfolio. The  automatic
investment  plan is not available for Skyline Special Equities Portfolio, except
that retirement plan accounts established before March 22, 1993, may continue to
use  the   automatic  investment   plan.  A   shareholder  may   terminate   his
 
                                       10
<PAGE>
participation  in the  plan at  any time  without penalty  by written  notice to
Firstar Trust Company at least  15 days prior to  the next investment date.  The
Fund may modify or terminate the plan at any time, or from time to time, without
notice to shareholders.
 
    SYSTEMATIC  WITHDRAWAL  PLAN.    A shareholder  may  request  that  the Fund
periodically redeem shares of a  Portfolio having a specified redemption  value.
Payment  is sent by  check to the record  holder(s) of the  account. In order to
initiate the Systematic Withdrawal Plan, the  account must have a share  balance
of  $5,000 or more and the periodic withdrawal  must be in an amount of not less
than $100. The Fund  may modify or terminate  the Systematic Withdrawal Plan  at
any time, or from time to time, without notice to shareholders.
 
    DIVIDEND  PURCHASE PLAN.  A shareholder may have dividends and distributions
paid by a Portfolio automatically invested in shares of one of the Portico Money
Market Funds in  which an account  has been opened  through the Fund's  exchange
privilege.  Similarly, dividends paid  on shares in a  Portico Money Market Fund
account opened through the exchange  privilege may be automatically invested  in
shares  of Special Equities II.  The account into which  the dividends are to be
invested must meet any applicable  minimum balance requirement, and the  account
registration must be identical to the registration of the account from which the
dividends  or distributions are  paid. The minimum  subsequent investment amount
will be waived. Before establishing this plan to make investments in the Portico
Money Market Funds, a shareholder should  obtain and read carefully the  Portico
Money  Market Funds prospectus, a  copy of which may  be obtained by calling the
Distributor at (312) 913-0900 or (800) 458-5222.
 
                          DIVIDENDS AND DISTRIBUTIONS
 
    Shareholders may receive two kinds of distributions from the Fund: dividends
and capital gains distributions. All  dividends and capital gains  distributions
are  paid in the form of additional  shares credited to an investor's account at
net asset value per  share (without a sales  charge) unless the shareholder  has
requested on the account application or in writing that distributions be made in
cash.  The Portfolios expect to declare  and pay net investment income dividends
and distributions of net realized short- and long-term capital gains, if any, at
least annually.
 
                                     TAXES
 
    Each Portfolio is  a separate entity  for federal income  tax purposes.  The
Fund  intends for each Portfolio to  qualify as a "regulated investment company"
under Subchapter M of the Internal Revenue Code. To qualify, each Portfolio must
meet certain income, distribution and diversification requirements. In any  year
in  which a Portfolio so  qualifies it generally will  not be subject to federal
income or excise tax  to the extent  that its taxable  income is distributed  to
shareholders.
 
    Dividends  paid by the  Portfolios from net  investment income together with
distributions of  net short-term  capital  gains generally  will be  taxable  as
ordinary  income,  generally in  the  year received.  Distributions  declared in
October through December, to shareholders of  record before January 1, and  paid
during  January of the following year, will be considered paid on December 31 in
the calendar year  declared. A portion  of any dividend  paid by each  Portfolio
from   its  net   investment  income   generally  will   be  eligible   for  the
dividends-received deduction for corporations, depending upon the percentage  of
the  distributing  Portfolio's  net income  derived  from  qualifying dividends.
Distributions of net capital  gains (the excess of  net long-term capital  gains
over  net short-term losses) which are  designated as capital gain distributions
are taxable to shareholders as long-term capital gains, regardless of how long a
shareholder has held  shares in  the Fund.  To the  extent a  Portfolio makes  a
distribution   in   excess  of   its  current   and  accumulated   earnings  and
 
                                       11
<PAGE>
profits, the distribution will be treated first as a tax-free return of capital,
reducing the tax basis in  a shareholder's shares, and  then, to the extent  the
distribution  exceeds such basis, as a taxable  gain on the sale of such shares.
Shareholders will be informed  annually of the amount  and nature of the  Fund's
income and distributions.
 
    Under  federal law, exchanges and redemptions of shares, including exchanges
of shares in one Portfolio for shares in another Portfolio or another fund  with
which the Fund has exchange privileges, are taxable events and, accordingly, may
result   in  capital  gain  or  loss  for  shareholders  participating  in  such
transactions. Shareholders electing to reinvest dividends or redemption proceeds
in new shares will nevertheless be treated as having received such distributions
for tax purposes.
 
    Any dividends or distributions have the effect of reducing the per share net
asset value  of the  shares by  the amount  of the  dividends or  distributions.
Although  a dividend or distribution paid  shortly after shares are purchased is
in effect a return of capital, these distributions are subject to taxes, even if
their effect is to reduce  the per share net  asset value below a  shareholder's
cost.  The Fund will  notify you annually as  to the tax  status of dividend and
capital gains distributions paid by the Fund.
 
    Dividend distributions,  capital gains  distributions and  capital gains  or
losses  from redemptions and exchanges may be  subject to state and local taxes.
In certain states, a  portion of the Fund's  income derived from certain  direct
U.S.  Government obligations may be exempt from  state and local taxes. The Fund
will indicate each  year the  portion of  the Fund's  income, if  any, which  is
derived from such obligations.
 
    The  Fund is required by  federal law to withhold,  currently at the rate of
31%, from  reportable  payments  (which  may  include  dividends,  capital  gain
distributions,  and proceeds from redemptions) paid to shareholders who have not
provided  a  social  security  or  taxpayer  identification  number,  have   not
represented  that they either are not currently subject to backup withholding or
are exempt from backup withholding, and have not certified that such information
is correct. Any amounts withheld will be credited against a shareholder's normal
federal income tax liability.
 
    The tax treatment  of non-resident alien  individuals, foreign  corporations
and  other  non-U.S.  shareholders may  differ  from that  described  above. All
shareholders should consult  their own advisors  concerning federal, state,  and
local  tax consequences of  an investment in the  Portfolios. This discussion is
included for general information only.
 
                             MANAGEMENT OF THE FUND
 
    THE TRUSTEES.   The board  of trustees  has overall  responsibility for  the
conduct  of the Fund's affairs. The trustees serve indefinite terms of unlimited
duration provided that  a majority of  trustees always has  been elected by  the
shareholders.  The trustees appoint their own successors, provided that at least
two-thirds of the  trustees, after such  appointment, have been  elected by  the
shareholders. Shareholders may remove a trustee, with or without cause, upon the
declaration in writing or vote of two-thirds of the Fund's outstanding shares. A
trustee  may be removed with or without  cause upon the written declaration of a
majority of the trustees.
 
    THE ADVISER.   The Fund's  investment adviser is  Skyline Asset  Management,
L.P.  The Adviser is  a Delaware limited  partnership formed in  1995 by Mesirow
Asset Management, Inc., which  was then adviser  to the Fund.  As of August  31,
1995, Mesirow Asset Management, Inc. transferred the general partner interest of
the  Adviser to Affiliated  Managers Group, Inc. ("AMG").  AMG is a Boston-based
private holding company that makes  equity investments in investment  management
firms  in which management personnel retain a significant interest in the future
of the business. Limited partnership interests in the
 
                                       12
<PAGE>
Adviser are held by corporations wholly owned by certain management personnel of
the Adviser, including the portfolio managers of each Portfolio. More than fifty
percent of the stock  of AMG is  controlled by TA  Associates, Inc., a  Delaware
corporation  founded in 1968  which directly or indirectly  has invested in more
than 200 enterprises prior to its investment in AMG.
 
    The Adviser manages the  investment and reinvestment of  the assets of  each
Portfolio. In addition the Adviser provides office space, facilities, equipment,
and  personnel for managing  the assets and  administering the Fund's day-to-day
operations, and provides shareholder and investor services.
 
    In return for the comprehensive fee  described below, the Adviser bears  all
ordinary  costs and expenses  attendant to operating  the Portfolios except fees
paid to non-interested trustees,  organizational and initial offering  expenses,
taxes,  interest  expense, portfolio  transaction  costs, and  any extraordinary
costs or expenses not  incurred in the course  of the Fund's ongoing  operation.
The   overall  expense  ratio  of  each  Portfolio  is  shown  in  the  "Expense
Information" table in this prospectus.
 
    For its  advisory,  management, and  administrative  services, and  for  the
assumption  of the Fund's  ordinary operating expenses,  each Portfolio pays the
Adviser a monthly comprehensive fee based  on its average daily net asset  value
at  the annual rate of 1.50%  of the first $200 million,  1.45% of the next $200
million, 1.40% of the next $200 million and 1.35% of average daily net assets in
excess of  $600 million.  Although the  Adviser believes  the fees  paid to  the
Adviser  are comparable to those  paid by other small  and mid-cap equity funds,
the fees are higher  than the average  fee paid by  all mutual funds  (including
money  market funds). Unlike most mutual funds, the Adviser rather than the Fund
pays out of  its fee the  Fund's ordinary operating  expenses. In addition,  the
Adviser  has agreed to limit each  Portfolio's expenses (including the Adviser's
fee but excluding extraordinary costs or  expenses not incurred in the  ordinary
course  of the Fund's operation) to 1.75% of the average daily net assets of the
Skyline Special Equities Portfolio and 2.0%  of the average daily net assets  of
Skyline  Special Equities  II. Expenses incurred  in excess of  these limits, if
any, will be reimbursed to the Portfolio by the Adviser.
 
    Each Portfolio  has  a  portfolio manager  who  works  with a  team  of  the
Adviser's  investment professionals  and analysts. William  M. Dutton, portfolio
manager for Skyline Special Equities Portfolio, and Kenneth S. Kailin, portfolio
manager for  Skyline Special  Equities II,  are responsible  for the  day-to-day
management of their respective portfolios. Mr. Dutton has been portfolio manager
of  Skyline Special Equities Portfolio since it began operations in 1987, and is
President and Chief Executive Officer of the Adviser and President of the  Fund.
In  addition, Mr. Dutton manages separately  managed accounts. Before August 31,
1995, Mr. Dutton was  executive vice president of  the Fund's former  investment
adviser.  Mr. Kailin has been the portfolio manager of Special Equities II since
it began operations in 1993, and  is Principal-Portfolio Manager of the  Adviser
and  an Executive Vice  President of the  Fund. In addition,  Mr. Kailin manages
separately managed accounts. Mr. Kailin was senior vice president of the  Fund's
former investment adviser from 1994 to August 31, 1995, vice president from 1992
to 1994, and an analyst prior thereto.
 
    PORTFOLIO TRANSACTIONS.  Decisions as to the purchase and sale of securities
for  a  Portfolio  and  the  execution  of  these  transactions,  including  the
negotiation  of   brokerage   commissions   on  such   transactions,   are   the
responsibility  of the Adviser.  In general, the Adviser  seeks to obtain prompt
and reliable execution  of purchase and  sale orders at  the most favorable  net
prices  or yields. In determining the best  net price and execution, the Adviser
may  take  into  account  a  broker's  or  dealer's  operational  and  financial
capabilities and the type of transaction involved.
 
    The Adviser may consider research services provided by the broker or dealer,
some  of which may be useful to the  Adviser in its other business functions. To
the extent such research services are taken into
 
                                       13
<PAGE>
account, the execution price paid may be higher, but only in reasonable relation
to the benefit  of such research  services as  determined in good  faith by  the
Adviser.  The Adviser is authorized to place portfolio transactions with brokers
or dealers participating in  the distribution of shares  of the Portfolios,  but
only  if the Adviser  reasonably believes that the  execution and commission are
comparable to those available from other qualified firms.
 
    The  historical  portfolio  turnover  rates  of  Skyline  Special   Equities
Portfolio  and  Skyline  Special  Equities  II  are  included  in  the Financial
Highlights.
 
    PERFORMANCE.  From time to time, in advertisements and sales literature, the
Fund may  present  information regarding  the  total return  on  a  hypothetical
investment  in  a Portfolio  for  various periods  of  performance and  may make
comparisons of such total return to  various stock indices (groups of  unmanaged
common  stocks), or to the  Consumer Price Index or  groups of comparable mutual
funds.
 
    Total return  for a  period is  the percentage  change in  value during  the
period  of an investment in a Portfolio's  shares, including the value of shares
acquired through reinvestment of all dividends and capital gains  distributions.
The  average annual total return for a given period may be calculated by finding
the average annual compounded  rate of return that  would equate a  hypothetical
$1,000  investment to the value of that investment that could be redeemed at the
end of  the period,  assuming  reinvestment of  all  distributions. All  of  the
calculations  described  above will  assume  the reinvestment  of  dividends and
distributions in additional shares  of the Portfolio. Income  taxes will not  be
taken into account.
 
    In  addition to the figures described above,  the Fund might use rankings or
ratings determined by Lipper Analytical  Services, Inc., an independent  service
that  monitors the performance of over 1,000 mutual funds, Morningstar, Inc., or
another service to compare the performance  of a Portfolio with the  performance
of  (i) other  funds of  similar size and  investment objective  or (ii) broader
groups of  funds.  The Fund  may  also  provide information  about,  or  compare
performance  of  a Portfolio  to,  the historical  returns  on various  types of
financial assets.
 
    Performance of a Portfolio will vary from time to time, and past results are
not indicative of likely future performance. Performance information supplied by
the Fund may  not provide  a basis of  comparison with  other investments  using
different reinvestment assumptions or time periods.
 
    Further  information about the  Portfolios' performance is  contained in the
Annual Reports of Special Equities Portfolio and Special Equities II, copies  of
which may be obtained without charge by calling the Fund at 1-800-458-5222.
 
                            THE FUND AND ITS SHARES
 
    The Fund was organized as a Massachusetts business trust on February 4, 1987
and  is an open-end, diversified management investment company. Special Equities
Portfolio began  operations  April  23,  1987, and  Special  Equities  II  began
operations  on February 9, 1993. In approving  the use of a combined prospectus,
the board of  trustees considered the  possibility that one  Portfolio might  be
liable  for misstatements in  the prospectus of  information regarding the other
Portfolio.
 
    SHARES.  Under the terms of the Agreement and Declaration of Trust, the Fund
may issue an unlimited number of shares of beneficial interest without par value
for each series of  shares authorized by the  trustees. There are currently  two
series authorized and outstanding. All shares issued will be fully paid and non-
 
                                       14
<PAGE>
assessable  and will have  no preemptive or  conversion rights. Each  share of a
series  is  entitled  to  participate  pro  rata  in  any  dividends  and  other
distributions declared by the Fund's board of trustees on shares of that series.
All  shares of a  series have equal rights  in the event  of liquidation of that
series.
 
    Under Massachusetts law,  the shareholders  of the Fund  may, under  certain
circumstances,  be held personally  liable for the  Fund's obligations. However,
the  Fund's  Agreement   and  Declaration  of   Trust  disclaims  liability   of
shareholders,   the  Fund's  trustees,  or  the  Fund's  officers  for  acts  or
obligations of  the  Fund  or a  Portfolio  and  requires that  notice  of  such
disclaimer  be given in each agreement,  obligation, or contract entered into or
executed by  the  Fund  or the  board  of  trustees. The  Fund's  Agreement  and
Declaration  of  Trust  provides for  indemnification  out  of the  assets  of a
Portfolio of all losses and expenses  of any shareholder held personally  liable
for the obligations of that Portfolio. Thus, the risk of a shareholder incurring
financial  loss  on account  of  shareholder liability  is  remote, since  it is
limited to circumstances  in which the  disclaimer is inoperative  and the  Fund
itself is unable to meet its obligations.
 
    VOTING  RIGHTS.    Each  share  has  one  vote  and  fractional  shares have
fractional votes.  A separate  vote of  the shareholders  of each  Portfolio  is
required for approval of the Fund's investment advisory agreement, any change in
a  Portfolio's fundamental investment policies and restrictions, and any matters
which affect  an  individual Portfolio.  Shareholders  of a  Portfolio  are  not
entitled to vote on any matter not affecting that Portfolio. All shareholders of
the Fund vote together in the election of trustees.
 
    SHAREHOLDER  INQUIRIES.  Inquiries should be  addressed to Skyline Fund, c/o
Skyline Asset Management, L.P., 311 South Wacker Drive, Chicago, Illinois 60606.
Telephone inquiries may be made at (800) 458-5222 or at (312) 913-0900.
 
                                       15

<PAGE>
SHAREHOLDER SERVICES:
    SKYLINE FUND
    311 South Wacker Drive, Suite 4500
    Chicago, IL 60606
    (800) 458-5222
    (312) 913-0900
 
INVESTMENT ADVISER:
    SKYLINE ASSET MANAGEMENT, L.P.
    311 South Wacker Drive
    Chicago, IL 60606
 
DISTRIBUTOR:
    FUNDS DISTRIBUTOR, INC.
    One Exchange Place, 10th Floor
    Boston, MA 02109
 
CUSTODIAN AND TRANSFER AGENT:
    FIRSTAR TRUST COMPANY
    P.O. Box 701
    Milwaukee, WI 53201
 
INDEPENDENT AUDITORS:
    ERNST & YOUNG LLP
    233 South Wacker Drive
    Chicago, IL 60606
 
LEGAL COUNSEL:
    BELL, BOYD & LLOYD
    Three First National Plaza, #3300
    Chicago, Illinois 60602
 
    NO  DEALER, SALESMAN OR  ANY OTHER PERSON IS  AUTHORIZED, IN CONNECTION WITH
THE OFFER CONTAINED IN THIS PROSPECTUS, TO ACT AS AGENT FOR SKYLINE FUND, NOR IS
ANY PERSON AUTHORIZED TO GIVE ANY INFORMATION OR TO MAKE ANY REPRESENTATIONS NOT
CONTAINED IN THIS PROSPECTUS OR IN SUPPLEMENTARY INFORMATION OR IN  SUPPLEMENTAL
SALES  MATERIAL AUTHORIZED BY  SKYLINE FUND, AND  NO PERSON IS  ENTITLED TO RELY
UPON ANY INFORMATION  OR REPRESENTATION  NOT CONTAINED HEREIN  OR THEREIN.  THIS
PROSPECTUS  DOES NOT  CONSTITUTE AN OFFERING  IN ANY JURISDICTION  IN WHICH SUCH
OFFERING MAY NOT LAWFULLY BE MADE.
 
    SKYLINE FUND,  THE  SKYLINE LOGO,  SKYLINE  SPECIAL EQUITIES  PORTFOLIO  AND
SKYLINE  SPECIAL EQUITIES II ARE REGISTERED SERVICE MARKS OF AFFILIATED MANAGERS
GROUP, INC.
 
        ---------------------------------------------------
       S K Y L I N E  F U N D-REGISTERED TRADEMARK-
 
       SKYLINE SPECIAL EQUITIES PORTFOLIO-REGISTERED TRADEMARK-
       SKYLINE SPECIAL EQUITIES II-REGISTERED TRADEMARK-
 
       ----------------------------------------------
        PROSPECTUS
 
        ---------------------------------------------------
        SEPTEMBER 1, 1995

<PAGE>

                     SKYLINE SPECIAL EQUITIES PORTFOLIO

      Skyline Special Equities Portfolio (the "Portfolio") will open to new 
investors effective May 1, 1996.

      Skyline Fund reserves the right to close the Portfolio to new 
investors if additional cash flow is deemed detrimental to management of the 
Portfolio.  However, if the Portfolio closes to new investors, the board 
intends to allow all persons owning shares of the Portfolio as of the date on 
which the Portfolio stops accepting new investments (the "Closing Date") to 
continue to add to their accounts.  In addition, the board currently expects 
that it would permit the following persons to continue to open new accounts 
after the Closing Date:

      -  persons owning shares of the Portfolio as of the Closing Date;

      -  clients of any financial advisor or planner who has $250,000 or more 
         of client assets invested in the Portfolio as of the Closing Date; 
         and

      -  clients of Mesirow Asset Management, Inc., Skyline Fund's former 
         investment adviser, and Mesirow Financial, Inc., Skyline Fund's 
         former distributor.



Supplement dated April 23, 1996 to the
Prospectus dated September 1, 1995 of Skyline Fund



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