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

The massive steel infrastructure of the Chicago Skyway Toll Bridge (specifically the “High Bridge” at 95th Street and S. Baltimore Avenue) represents a monumental feat of mid-20th-century engineering, combining structural strength, durability, and commercial utility with a striking architectural aesthetic.

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.

Chicago Skyway, 95th Street & Baltimore Avenue, Chicago. July 2016. Author’s photograph. 4.05 mb DSC_0772 (1)

This intersection is located on the city’s Far South Side in the South Chicago neighborhood. The area is heavily industrial, sitting just west of the Calumet River and directly underneath the massive steel framing of the Chicago Skyway High Bridge. The actual boundary of the city limits sits further east and south toward the Illinois-Indiana state line.

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.

Chicago Skyway. 95th St. & Baltimore Ave. July 2016. Author’s photograph. 4.93mb DSC_0765 (1).

The 1958 steel truss undergirding serves a vital operational purpose—allowing massive industrial shipping to pass underneath into the Calumet River while carrying thousands of daily vehicles above—as it simultaneously serves as a compelling subject for architectural art.