Chicago’s pedway has been built over many decades, starting as early as the late 19th century with a pedestrian bridge from the Louis Sullivan designed Carson Pirie Scott department store to a Loop Elevated rapid transit station. The majority of the pedway was developed since our second subway was built post World War II. Links in the pedway continue to be added in the Lakeshore East development area, on former rail yards, and site of the Aqua Tower and future Wanda Vista Tower. Stops on the tour include City Hall and other government center buildings, both Red and Blue Line subway stations that were the first link in the underground system, the Chicago Cultural Center with its Tiffany Dome, Block 37, the former Marshall Field, and Millennium Park and commuter rail station. We will explore the city’s changing attitude to pedway development over recent decades and renewed interest in celebrating the pedway from the various stakeholders.