Join us as we explore one of Chicago’s most storied stretches of highway—the legendary Chicago Skyway along Interstate 90. This 15-mile journey takes us from the Indiana border straight into the heart of Chicago, giving a front-row seat to the urban energy and iconic sights that make this corridor so unique.
Our drive begins at the Indiana-Illinois state line, immediately embarking onto the Chicago Skyway. This elevated toll road, first opened in 1958, was originally conceived to bring traffic efficiently from Indiana and the steel towns of the south directly into Chicago. Today, it remains an essential route for commuters, travelers, and truckers crossing the Midwest. Right away, you’ll notice the towering Skyway Bridge, which spans the Calumet River and offers panoramic views of Chicago’s industrial south side—look to your left and right, and you’ll spot working freight yards, historic smokestacks, and the massive Lake Calumet.
As we head northwest, the Skyway slices through neighborhoods like South Deering and East Side, each with its own character and story. If you’re in no rush, consider a quick detour to visit the fascinating Pullman National Historical Park, just a few miles west off the highway, where you can step into Chicago’s railroad past and admire the unique architecture of this planned industrial community.
Our journey continues as we approach the major interchange with Interstate 94, also known locally as the Bishop Ford Freeway to the south and the Dan Ryan Expressway as we head north. Here, I-90 and I-94 merge, forming one of Chicago’s busiest and most vital arteries. If you’re keeping an eye out, you’ll catch glimpses of the towering skyline in the distance—an unmistakable sign that you’re nearing downtown.
Traveling north on the Dan Ryan Expressway, we pass through the South Loop, Bronzeville, and Bridgeport neighborhoods—places rich in history, culture, and Chicago soul. To your west is Guaranteed Rate Field, home of the Chicago White Sox, and to your east, you might catch sight of IIT’s modernist campus and the monumental buildings of historic Bronzeville. Even in the thick of city traffic, this stretch pulses with urban life, street art, and the endless motion of “The City That Works.”
As we approach the heart of the city, the skyline comes fully into view—towering glass, steel, and stone marking Chicago’s famous Loop. Our drive ends at the crucial interchange with Interstate 290 (the Eisenhower Expressway), right on the edge of downtown. From here, you’re only moments away from some of Chicago’s biggest attractions: Millennium Park, the Art Institute, Grant Park, and the bustling riverfront.
Things to See & Do Along the Route:
Calumet River & Lake Calumet: Impressive industrial vistas, unique to Chicago’s south side.
Pullman National Historical Park: Step into the past and learn about labor history and Chicago’s role in the railroad industry.
Bridgeport & Bronzeville: Check out local eateries, vibrant murals, and historic landmarks.
Downtown Chicago: Just off the route—don’t miss Millennium Park, the Chicago Riverwalk, or a stroll down Michigan Avenue.
🗺️ Route Map
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