The History of the Chicago Skyway

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The history of the Chicago Skyway began in 1928, when the City Council of Chicago—motivated by the desire to strengthen connections between the city and the country’s Midwestern industrial base—requested a study for an elevated roadway to be constructed above the Pennsylvania Rail Road’s right of way. Although this proposal did not ultimately come to fruition, the planning set the stage on which the road would be built adjacent to this railroad. Concurrently, the Chicago Plan Commission had begun researching a southern extension of Lake Shore Drive beyond Jackson Park as a means to connect the city with Indiana. This study resulted in two possibilities for extending the roadway. The first possibility was to extend Lake Shore Drive along Stony Island Avenue to the Pennsylvania Railroad Right of way where it would proceed in the same manner as proposed in the 1928 plan; the second possibility was to simply extend the roadway along lake fill to Rainbow Beach Park, where it would then merge onto South Commercial Avenue which would carry it to Indiana Avenue.
A subsequent study in 1939 championed the Stony Island Avenue plan; however, the project was ultimately shelved because Lake Shore Drive does not permit commercial traffic, and because the roadway fell under the jurisdiction of the Parks Department which lacked a mechanism to finance infrastructure investment. Due to these constraints, the City decided to drop its roadway connection plan in 1945.
The project was revitalized

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