UPDATED FEB 14, 2020

Sure, most of us have a go-to running spot, but it’s never a bad idea to change things up once in a while. Whether you prefer hitting the pavement for a sweat session in the city or kicking a run through a park, Chicago has plenty of routes to meet your needs.




Nestled between Lake Shore Dr. and Lake Michigan, this 18-mile trail is the kind of route you’d call “a gem.” Going from the South Shore neighborhood to Lakeview, it takes runners past harbors, beaches, parks, and cultural landmarks like the Shedd Aquarium and Navy Pier. Oh, and you’ll have a view of the skyline for a good part of your run.

Follow the river! Beginning at the junction of Foster and Lawrence and extending towards Evanston, this trail runs along the North Shore Channel and the North Branch of the Chicago River. Surrounded by greenery, it seems infinitely further away from downtown than it actually is.

Jutting out into Lake Michigan, this 91-acre man-made peninsula is stunning. And running around here is surprisingly quiet, considering it is located just south of the Museum Campus. The island’s restored native prairie almost seems strange against the skyline in the background, but we can’t deny that it’s magical.

Located in the hipper-by-the-minute neighborhood of the same name, Humboldt Park is a 207-acre park with well-maintained trails, restored prairies, lagoons, skyline views, field houses… the list goes on! If you want to take your route out of the park, head north on the surrounding boulevards. Humboldt Boulevard, Logan Boulevard, and Kedzie Boulevard offer green spaces and dirt paths surrounded by stately turn-of-the-century homes.

Going through popular West Side neighborhoods, this 2.7-mile trail was built on the tracks of an unused elevated line. Because of this, it’s just high enough above ground to afford stunning views of the city. Enjoy the 606's six ground level parks, art installations, event plaza, and more as you run.

Ever been on a Chicago architecture tour? Floating down the river, you get spectacular views of our city’s favorite buildings. But you can get all these views on your run, too. The Chicago Riverwalk runs under Wacker Dr. through the downtown stretch of the Chicago River. The only trick is trying to avoid joining all the people enjoying happy hour on the outdoor patios until after you finish your run!

It may be a top tourist attraction and the location of Lollapalooza, but don’t let that scare you away from this 319-acre park. Having been around since the foundation of Chicago, Grant Park is home to Millennium Park, Buckingham Fountain, the Art Institute, the city’s Museum Campus, public art, and harbors. Oh, and running trails. Lots of them.

Like Grant Park, Lincoln Park has a lot going on. There’s the Lincoln Park Zoo, the Peggy Notebaert Nature Museum, the Chicago History Museum, the Alfred Caldwell Lily Pool, and the North Pond Nature Sanctuary. These attractions only add to our favorite parts of the park: running paths, natural scenery, and skyline views. So if you feel the need to stop for a mid-run selfie at one of the picturesque spots along the way, we won’t judge.

If you want to get out of the city, head southwest to the Palos Preserves for 15,000 acres of high-quality natural areas. Approximately 40 miles of unpaved trails give runners plenty of route options, and you might even come across something you won’t usually find in the Chicago area: hills!

While not necessarily a running trail, this diagonal avenue is the best way to get a taste of multiple Chi-town neighborhoods in just one run. Beginning in West Town, it takes you through Wicker Park, Bucktown, Logan Square, and Avondale’s “Polish Village.” As its name suggests, the avenue keeps going all the way to Milwaukee.

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