In March 2004, the City of Chicago issued a request for qualifications (RFQ) for an operating agreement with a private operator to maintain, develop, operate and collect tolls on the Skyway for a period of at least 50 years. Ten teams responded to the RFQ in May 2004. The City created an evaluation committee made up of representatives from various City departments to review the submittals. The committee evaluated the teams' financial and technical qualifications based on several criteria, including expertise in toll road operations and maintenance, customer service and public safety. The bidding teams also had to demonstrate the capability to pay the purchase price for the Skyway and maintain the roadway to an acceptable standard.
In May 2004, the City of Chicago invited five qualified teams to submit proposals by October 2004. These five teams were asked to comment on the bid terms and to make first-round pricing offers. The bidders were then asked to provide detailed technical responses and final prices reflecting detailed operating standards established by the City's evaluation committee. The bidders were also given access to an internet-based data room that included information on the Skyway's financial history, and its historic engineering and traffic history. The City indicated that it would award the concession to the bidder offering the highest upfront lease payment; however, it did not publically announce a minimum asking price. Goldman Sachs and Loop Capital Markets served as financial advisers to the City on the privatization, while the law firms Mayer, Brown, Rowe & Maw LLP and Pugh, Jones & Johnson advised the City on the legal structuring of the deal.
The concession was awarded on October 28, 2004 to Skyway Concession Company, LLC, which consisted of Cintra, a Spanish toll road developer and operator, and Macquarie, an Australian investment bank and infrastructure developer. Skyway Concession Company bid $1.83 billion for the 99-year concession, 2.6 times higher than the next highest bidder. Skyway Concession Company would be responsible for all operating and maintenance costs throughout the 99-year concession period and a third-party engineer would conduct annual reviews to ensure that the concessionaire met the technical requirements of the agreement.
The agreement between Skyway Concession Company and the City of Chicago was the first long-term lease of an existing toll road in the United States. The bid was secured by a $55 million line of credit. Upon signing the lease, Cintra and Macquarie were obligated to make its payment to the City within 180 days. Two weeks after the award was announced, the Chicago City Council voted 45-0 in a special council meeting to approve the concession agreement.