Best Places to Run in Chicago

By AAA Travel Editor Laurie Sterbens | June 01, 2023

Whether you're a dedicated runner or just looking for ways to work off that extra slice of deep-dish pizza, there's no reason to spend precious Chicago vacation time on a boring hotel treadmill. This destination offers miles of scenic trails with views of the lakefront, downtown architecture, attractions, art and nature.

AAA/Laurie Sterbens

Chicago Lakefront Trail

5800 N. Sheridan Rd. to 7100 S. South Shore Dr.

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.

AAA/Frank Swanson

Chicago Riverwalk

Lake Shore Drive to Lake Street

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.

Wikimedia Commons/Diego Delso

Grant Park

337 E. Randolph St.

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.Read More

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Humboldt Park

1400 N. Humboldt Dr.

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.

Wikimedia Commons / CC BY/DwightSchruteDunderMifflin

Northerly Island

1521 S. Linn White Dr.

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.

AAA/Frank Swanson

The 606 (The Bloomingdale Trail)

1600-3700 W. Bloomingdale Ave.

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.