Many of you may have driven the Chicago Skyway, with its half-mile long bridge, known as the “High Bridge.” Have you ever wondered why there is a giant bridge on the way to Indiana? Why not simply build a road?
The answer lies in a quirk city law and the political ingenuity of Mayor Richard J. Daley. In the late 1950s, when Daley decided he wanted a toll road to Indiana, the Chicago city charter did not allow for the funding or construction of a toll highway. Daley, undaunted, recognized the lack of and legal restriction to building a toll bridge. Additionally, no restriction existed regarding the length of the approach to that bridge. The result: The 7.8 mile long Chicago Skyway is technically a bridge with a six mile approach.