Expressway information is grouped according to travel direction through the Chicago area from the Loop (downtown), or from the city limits if a route does not originate in the Loop. This provides a general sense of navigation, but it violates the laws of expressway numbering. For example, I-90/94 is designated as an east-west route, but in Chicago it’s actually a due south route. Chicagoans usually speak of heading south on the Dan Ryan, not “west”.
Trivia: What was the first expressway in Chicagoland? It was just 5 miles long, and when it opened November 1, 1950 it was called the Calumet Expressway and Tri-State Highway. The road stretched from 159th Street to the Indiana state line. It is now part of the Bishop Ford and Kingery expressways.
North and Northwest
Lake Shore Drive
South, Southeast, and Southwest