Facing major budgetary issues, the City of Chicago looked to "monetize" (derive money from) its infrastructure assets. In October 2003, Mayor Richard M. Daley announced his desire to lease the Skyway under a long-term concession agreement during his annual budget address. Mayor Daley stated that "running a toll road is not a core function of city government" and believed that transferring the burden of the Skyway's debt and operating costs to a private owner would be a "great result for the taxpayers of the City."
At that time, the Skyway had 130 employees and was not organized as an independent transportation or taxing authority. The decision to privatize the road was not particularly sensitive for the Mayor or the City Council, as most of the Skyway's users were commuters from Indiana, not Chicago residents. The Skyway provided no major financial benefit to the City, as its tolls were set to cover costs and not to generate additional revenue. The Skyway only added to the City's total debt burden with its $465 million in outstanding bonds.
The City believed that the Skyway was an attractive asset to investors as it was a critical link for interstate traffic that had no direct competitive route and had seen strong growth in toll revenues over the past 20 years, averaging roughly eight percent per year. In addition, the Skyway had an established customer base and would not need major rehabilitation work in the near term. While the State of Illinois did not have legislation enabling public-private partnerships at the time, the City of Chicago was able to advance its plans to lease the Skyway, because it was owned by and located entirely within the city.