Feature image: July 2016. Chicago Skyway Toll Bridge, 95th St. & S. Baltimore Ave 4.03mb DSC_0774 (1). Author’s photograph.

This photograph of the Chicago Skyway Toll Bridge (also known as the “Skyway”) is at the exact point where it spans the Calumet River and Calumet Harbor, a major harbor for industrial ships. Built by the City of Chicago in 1958 this massive steel undergirding is part of the 7.8 miles long expressway toll road that connects Chicago’s Dan Ryan freeway on the South Side to the Indiana Toll Road. The main feature of the Skyway is this half-mile long steel truss bridge known as the “High Bridge” whose maximum vertical clearance allowing ships and objects to pass safely underneath is 125 feet or about 10-12 building stories. The Chicago Skyway truss is primarily made of rolled and built-up steel beams for incredible weight-bearing strength, durability and functionality.

The Skyway was operated and maintained by the City of Chicago until January 2005 when Skyway Concession Company, LLC assumed its operations under a 99-year operating lease. The lease agreement between Skyway and the City of Chicago was the first privatization of an existing toll road in the United States. In February 2016, Skyway was purchased by three Canadian Pension Funds (OMERS Infrastructure, CPP Investment Board, and Ontario Teachers’ Pension Plan) and in December 2022 global toll road operator Atlas Arteria Group based in Australia, acquired 66.67% stake in the Skyway with OTPP retaining the rest. see – The Skyway – Chicago Skyway – retrieved December 19, 2025. While exact current figures go up and down, best estimates put daily vehicular traffic on the Chicago Skyway, both cars and trucks, at between 40,000 and 50,000 per day. see – FHWA – Center for Innovative Finance Support – Value Capture – Case Studies: Hays County, Texas Transportation Reinvestment Zones – retrieved December 19, 2025.