NEW ISSUE—BOOK-ENTRY ONLY RATINGS: See “RATINGS” herein In the opinion of Mayer Brown LLP, Chicago, Illinois and Pugh, Jones, Johnson & Quandt, P.C., Chicago, Illinois, Co-Bond Counsel, under existing law, and assuming compliance by the City with certain covenants, interest on the 2010B Bonds (i) is excluded from the gross income of the owners thereof for federal income tax purposes and (ii) is not a specific item of tax preference for purposes of the federal alternative minimum tax imposed on individuals and corporations, nor is it included in adjusted current earnings when calculating corporate alternative minimum taxable income. Interest on the 2010C Bonds and the 2010D Bonds is not excluded from the gross income of the owners thereof for federal income tax purposes. Interest on the Bonds is not exempt from present State of Illinois income taxes. See “TAX MATTERS” herein for a more complete discussion and APPENDIX E for the form of opinions to be delivered by Co-Bond Counsel. $246,540,000 CITY OF CHICAGO Chicago Midway Airport Second Lien Revenue Bonds $84,000,000 $63,470,000 $82,610,000 $16,460,000 Series 2010B Series 2010C Series 2010D-1 Series 2010D-2 (Non-AMT) (Taxable) (Taxable) (Taxable) Dated: Date of Delivery Due: As shown on the inside cover pages The City of Chicago, Chicago Midway Airport Second Lien Revenue Bonds, Series 2010B (Non-AMT) (the “2010B Bonds”), the City of Chicago, Chicago Midway Airport Second Lien Revenue Bonds, Series 2010C (Taxable) (the “2010C Bonds”), the City of Chicago, Chicago Midway Airport Second Lien Revenue Bonds, Series 2010D-1 (Taxable) (the “2010D-1 Bonds”), and the City of Chicago, Chicago Midway Airport Second Lien Revenue Bonds, Series 2010D-2 (Taxable) (the “2010D-2 Bonds” together with the 2010D-1 Bonds, the “2010D Bonds” and the 2010D Bonds together with the 2010B Bonds and the 2010C Bonds, the “Bonds”), are fully registered bonds issued in the name of Cede & Co., as registered owner and nominee of The Depository Trust Company, New York, New York (“DTC”). DTC is securities depository for the Bonds. Purchases of the Bonds will be made in book- entry form and purchasers will not receive certificates representing their interests in the Bonds purchased. Principal of and interest on the Bonds is payable by The Bank of New York Mellon Trust Company, N.A., Chicago, Illinois, as trustee (the “Second Lien Trustee”), to DTC, which in turn will remit such principal and interest payments to its participants for subsequent disbursement to the beneficial owners of the Bonds. As long as Cede & Co. is the registered owner as nominee of DTC, payments on the Bonds will be made to such registered owner, and disbursal of such payments to beneficial owners will be the responsibility of DTC and its participants. The Bonds are limited obligations of the City of Chicago (the “City”) payable solely from and secured by a pledge of Second Lien Revenues (as defined herein) derived from the operation of the Chicago Midway International Airport (“Midway”) and certain other moneys. The Bonds are payable from the Second Lien Revenues on a parity basis with certain currently outstanding City of Chicago, Chicago Midway Airport Second Lien Revenue Bonds described herein, and any other Second Lien Obligations (as herein defined) that may be outstanding from time to time under the Second Lien Indenture, all as more fully described herein. Certain additional customer facility charges are pledged to the 2010C Bonds as described under “SECURITY FOR THE BONDS – Description of Revenues” and “ESTIMATED FUNDING SOURCES FOR 2010-2016 CIP – Customer Facility Charges.” The Bonds and the obligations to pay principal of and interest thereon are not general obligations of the City and do not constitute an indebtedness or loan of credit of the City, the State of Illinois (the “State”) or any political subdivision thereof within the meaning of any constitutional or statutory limitation of the State. Neither the faith and credit nor the taxing power of the City, the State or any political subdivision thereof is pledged to the payment of the principal of or interest on the Bonds. Interest on the 2010B Bonds and the 2010D Bonds (the “2010 Term Rate Mode Bonds”) is payable on January 1 and July 1 of each year, commencing January 1, 2011 and on their respective mandatory tender dates. Interest on the 2010C Bonds is payable on January 1 and July 1 of each year, commencing January 1, 2011. The 2010 Term Rate Mode Bonds are not subject to redemption during their respective initial fixed-term Rate Periods. The 2010C Bonds are subject to extraordinary, optional and mandatory redemption prior to maturity. The 2010 Term Rate Mode Bonds are subject to mandatory tender by the Owners thereof for purchase by the City on the dates set forth on the inside cover pages at a purchase price equal to the principal amount thereof plus accrued interest thereon. The 2010 Term Rate Mode Bonds not purchased on such dates will be subject to mandatory redemption on such dates at a price equal to the principal amount thereof plus accrued interest thereon. There will be no credit or liquidity facility in place to pay the purchase price of the 2010 Term Rate Mode Bonds upon the mandatory tender thereof or to pay the principal thereof and interest thereon upon the mandatory redemption thereof. See “CERTAIN INVESTMENT CONSIDERATIONS RELATING TO THE AIRLINES, THE AIRLINE INDUSTRY AND MIDWAY – Airport Market Access.” Payment of the principal portion of the purchase price of the 2010 Term Rate Mode Bonds is not secured by a pledge or lien on Second Lien Revenues, but rather is payable solely from remarketing proceeds, if any. Payment of the principal of and interest on the 2010 Term Rate Mode Bonds upon the mandatory redemption thereof, is secured by a pledge of and lien on the Second Lien Revenues. Any failure of the City to pay the 2010 Term Rate Mode Bonds upon the mandatory redemption thereof will constitute an event of default under the Second Lien Indenture. At the direction of the City, and upon compliance with conditions set forth in the Second Lien Indenture, the 2010 Term Rate Mode Bonds may be converted to bear interest at the Daily Rate, Weekly Rate, Flexible Rate, the Adjustable Long Rate or a Fixed Rate as set forth herein. This Official Statement generally describes the 2010 Term Rate Mode Bonds only while bearing interest at their respective initial Term Rates. This Official Statement does not describe the terms of any subsequent Rate Periods or periods or any other Interest Modes other than the respective initial Term Rate Mode for the 2010 Term Rate Mode Bonds, which terms would be set forth in a separate offering document with respect thereto. For maturities, principal amounts, interest rates, prices or yields, initial Rate Periods (for the 2010 Term Rate Mode Bonds) and CUSIP numbers, see inside cover pages. The Bonds are offered when, as and if issued by the City and accepted by the Underwriters, subject to the approval of their validity by Mayer Brown LLP, Chicago, Illinois, and Pugh, Jones, Johnson & Quandt, P.C., Chicago, Illinois, and certain other conditions. Certain legal matters will be passed on for the City by its Corporation Counsel, for the Underwriters by their co-counsel, Miller, Canfield, Paddock and Stone, P.L.C., Chicago, Illinois, and Charity & Associates, P.C., Chicago, Illinois. It is expected that delivery of the Bonds in book-entry form will be made through the facilities of DTC on or about October 26, 2010. J.P. Morgan Ramirez & Co., Inc. Backstrom McCarley Berry & Co., LLC Estrada Hinojosa & Company, Inc. Wells Fargo Bank, National Association October 15, 2010 MATURITIES, AMOUNTS, INTEREST RATES, PRICES OR YIELDS AND CUSIP NUMBERS $246,540,000 CITY OF CHICAGO CHICAGO MIDWAY AIRPORT SECOND LIEN REVENUE BONDS $84,000,000 CHICAGO MIDWAY AIRPORT SECOND LIEN REVENUE BONDS, SERIES 2010B (NON-AMT) MATURITY INTEREST INITIAL END OF INITIAL RATE MANDATORY (1) (JANUARY 1) PRINCIPAL AMOUNT RATE YIELD PERIOD TENDER DATE CUSIP* 2034 $84,000,000 5.000% 2.430% December 31, 2014 January 1, 2015 167562 LF2 $63,470,000 CHICAGO MIDWAY AIRPORT SECOND LIEN REVENUE BONDS, SERIES 2010C (TAXABLE) MATURITY PRINCIPAL INTEREST (JANUARY 1) AMOUNT RATE YIELD CUSIP* 2016 $1,085,000 3.782% 3.782% 167562 LG0 2017 1,125,000 4.082% 4.082% 167562 LH8 2018 1,170,000 4.709% 4.709% 167562 LJ4 2019 1,225,000 4.859% 4.859% 167562 LK1 2020 1,285,000 5.009% 5.009% 167562 LL9 2021 1,350,000 5.259% 5.259% 167562 LM7 2022 1,420,000 5.509% 5.509% 167562 LN5 2023 1,500,000 5.709% 5.709% 167562 LP0 2024 1,585,000 5.859% 5.859% 167562 LQ8 2025 1,680,000 6.009% 6.009% 167562 LR6 $10,250,000 7.068% Term Bonds due January 1, 2030 Price: 100.00% CUSIP*: 167562 LS4 $14,435,000 7.118% Term Bonds due January 1, 2035 Price: 100.00% CUSIP*: 167562 LT2 $25,360,000 7.168% Term Bonds due January 1, 2041 Price: 100.00% CUSIP*: 167562 LU9 (1) The 2010B Bonds will be subject to mandatory tender by the Owners thereof for purchase by the City on such dates. If for any reason the City is unable to pay the Purchase Price for the 2010B Bonds on the mandatory tender date, the 2010B Bonds will be subject to mandatory redemption on such dates by the City at a redemption price equal to the principal amount thereof plus accrued interest thereon.