Now you can earn rewards when you take the shortest route to (and through) Chicago. Join Chicago Skyway’s loyalty program and enjoy perks just for taking Chicago’s Shortcut. The more you drive, the more you earn! Built by the City of Chicago in 1958, the Chicago Skyway Toll Bridge (also known as the “Skyway”) is a 7.8-mile-long toll road that connects the Indiana Toll Road to the Dan Ryan Expressway on Chicago's South Side. Our mission is simple - to provide the safest, fastest and most reliable link from the northwest Indiana border to the heart of Chicago. Since 2005, we have invested over 120 million dollars on improvements to the Skyway, including an expansive technology build-out to allow for electronic payment of tolls. Today, we are proud to say that almost 70% of our drivers choose to use the benefits of E-ZPass/I-PASS payment. We hope you enjoy your visit to our corner of the Midwest. Have a safe trip and thank you for choosing the Chicago Skyway!