The Chicago Skyway is the only toll highway in Illinois that is not operated by the Illinois Toll Highway Authority. It is operated and maintained by the Streets and Sanitation Department of the City of Chicago.
Opened to traffic in 1958, the Chicago Skyway is a 7.8-mile toll bridge connecting the Dan Ryan Expressway (I-94) around Chicago to the Indiana Toll Road in Indiana; it is a shortcut between the City of Chicago and the State of Indiana. Automobiles currently pay a $2 toll for one-way use. A McDonald’s restaurant is available to motorists at the Skyway rest stop approximately at the road mid-point.
The Chicago Skyway does not carry any highway designation. Originally, it was designed as a portion of Interstate 90, but the City of Chicago discovered the Chicago Skyway never received this official interstate designation. Thus, all the I-90 signs along the skyway have a “TO” sign placed over them instead of any official designation.
In 2002, before construction-related delays forced motorists to seek alternative routes, the Skyway attracted a record 18.7 million motorists and took in $43 million in annual revenues–double the $21.5 million in toll revenues in 1993. A $250 million rebuilding of the road began in 2001 with main road work due to end in fall 2004.
According to the Chicago Tribune, in 2003, the Skyway served 17.4 million vehicles and generated $39.7 million in toll revenues.
— Chicago Department of Transportation