The Chicago Skyway Bridge is a 7.8-mile toll road built in 1958 to connect the Dan Ryan Expressway to the Indiana Tollway. For almost 50 years, it has been operated and maintained by the City of Chicago Department of Streets and Sanitation and the Skyway is the only toll highway in Illinois that is not operated by the Illinois Toll Highway Authority.

In 2002, before construction-related delays forced motorists to seek alternative routes, the Chicago Skyway attracted a record 18.7 million motorists whose tolls amounted to $43 million dollars in revenue–twice the $21.5 million in tolls collected in 1993. In 2003, during the final phase of reconstruction, the Chicago Skyway served 17.4 million motorists who paid $39.7 million dollars in toll revenue.

A $250 million dollar road reconstruction project that began in 2001 came to an end in the November 2004 and January 2005 will begin a new era for the Chicago Skyway. In a transaction that gave the City of Chicago a $1.83 billion dollar cash infusion, the Skyway Concession Company, LLC* (SCC) will assume operations on the Skyway on a 99-year operating lease. SCC will be responsible for all operating and maintenance costs of the Skyway but has the right to all toll and concession revenue. This agreement between SCC and the City of Chicago is the first privatization of an existing toll road anywhere in the United States.