Running in Chicago

While most visitors stick to the Lakefront Trail's northern stretch near Lincoln Park, the south side offers its own landmarks. Promontory Point in Hyde Park is a limestone edged peninsula jutting into Lake Michigan near 55th Street, a quieter place to pause mid run with skyline views back toward downtown, and it sits along the lakefront path near the University of Chicago campus.

Continuing south, the trail passes Jackson Park, site of the 1893 World's Columbian Exposition, where runners can loop past the Wooded Island and the Garden of the Phoenix, a Japanese style garden that has been restored multiple times since the fair. This stretch of the lakefront sees far less foot traffic than the Loop or Lincoln Park sections, making it a good option for runners who want the same paved, flat surface without the crowds.

For a change of scenery away from the lake, the Major Taylor Trail is a paved rail trail on Chicago's far south side, built along a former railroad corridor and named for pioneering Black cyclist Marshall "Major" Taylor. The trail runs for several miles between the Dan Ryan Woods area near 87th Street and the city's southern edge, giving south side runners a car free, tree lined route through neighborhoods rarely mentioned in typical Chicago running guides.

Because it follows an old rail bed, the grade stays gentle and consistent the entire way, and the trail connects onward toward the south suburbs for runners who want to extend their mileage. It is a useful option for anyone based away from downtown or the North Side who wants Lakefront Trail style paved running without the drive north.