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Chicago, on Lake Michigan in Illinois, is known as the “Second City” and the “Windy City.” Famed for its bold architecture, it has a skyline punctuated by skyscrapers such as the iconic John Hancock Building and the 1,451-ft. Willis Tower (formerly the Sears Tower). The city is also renowned for its art and museums, including the Art Institute of Chicago. Chicagoans love sports, music, comedy, and food – not necessarily in that order.

Running tours in Chicago are a great way to see the major sites and to enjoy the lakefront trail. Lake Michigan is an outstanding backdrop for running in every season. The Lake Front trail is dotted with sights, too. There’s no better way to experience the city than on foot.

Sightrunning tours take you past the must-see spots in the city, like Millennium Park (Cloud Gate a/k/a“The Bean”), Grant Park past the Chicago Marathon finish line to Buckingham Fountain, up the Magnificent Mile past the John Hancock Building, on our fabulous River Walk and to Navy Pier.

Whether you’re in town for the first time or the twentieth, and whether you’re a seasoned runner or a novice, check out our running tours in Chicago and discover the city from the local perspective. Our guides will share their favorite running routes, city facts, and recommendations for the best places to eat and experience Chicago.