Best Places to Run in Chicago

This 18-mile paved trail along the shore of Lake Michigan offers great views of the lake and the Chicago skyline, and passes a number of local parks and attractions. It’s popular with local runners, walkers and bicyclists as well as tourists, so if your trip is in the summer you may find it a bit crowded in the middle section near the museums. The southern end of the trail is generally less crowded, but if you get an early start at the north end, you can take a side trip through the Lincoln Park Zoo before it fills with visitors. Distance markers every half mile help you track your progress, and there are plenty of water fountains and restrooms along the way.

The Chicago Riverwalk is a flat 1.3-milepaved path along the south side of the Chicago River downtown. Set amid some of the city’s architectural gems, it features public lawn space, floating gardens, overlooks and a water plaza. It’s perfect for a quick out-and-back jog or you can connect to the Lakefront Trail for a longer outing.

Grant Park, between busy Michigan Avenue and the lakeshore, offers a scenic detour from the Lakefront Trail or an interesting route on its own. The park includes notable attractions including The Art Institute of Chicago; Buckingham Memorial Fountain; Millennium Park, home of the iconic Cloud Gate (aka The Bean) and Crown Fountain; and the Museum Campus. Depending on the paths you choose, you can take a short, tree-lined diversion from the Lakefront Trail or a 3- to 5-mile route around the park.

Take a break from the main tourist destination area along the lakefront and head to the Humboldt Park neighborhood, where you’ll find a beautiful 219-acre park of the same name. Explore the many well-maintained trails that wind through gardens and restored prairie, over bridges and past monuments and lagoons. A large hill offers a great view of the city skyline.

Just southeast of Grant Park is Northerly Island, a man-made peninsula that formerly was an airstrip. The southern part of the peninsula is now a nature preserve featuring landscaped wildlife habitats, a lagoon and fabulous views of the city skyline. The paved path through the nature preserve is about a mile long, making a nice addition to a Lakefront Trail or Grant Park run or a lovely short nature walk on its own. To create a natural environment for the animals that inhabit the preserve, there is no artificial lighting, so you’ll want to explore this path during daylight hours.

Not far from Humboldt Park is the Bloomingdale Trail, commonly known as the 606. You can take a run in the city minus the stoplights and traffic on this 2.7-mile elevated path that runs from Logan Square to Bucktown. Formerly an abandoned rail line, it’s now a tree-lined, landscaped park offering separate pedestrian and bike paths, city views and public art. Be warned: This path leads past some of the city’s best dining spots, and with 12 access points along the way, you’ll be tempted to hop off and explore nearby restaurants.