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CHICAGO'S BEST RUNNING ROUTES

11 PLACES

UPDATED JUL 2, 2020

In Chicago, running is in our DNA. And whether it was your first love or something you’re coming around to, there are miles of waterfront trails, urban paths, and lively neighborhoods to explore. We’ve run them all, and these are the best.

author

MAGGIE SCHAFER

FITT CHICAGO CONTRIBUTOR

This is pretty much why people exercise outdoors in Chicago. Nestled between Lake Shore Drive and Lake Michigan, this 18-mile trail is hands-down the best run in the city (and a lot of people know it). 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.

Though you'll hit a number of traffic lights along the way, this paved, car-less route makes for a fine morning jog. 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.

If you've been hesitant to sign up for the Chicagoland Spring Marathon, a run through Busse Woods will have you mashing the "register" button once you get back. The 7.7-mile, paved, multi-use trail is definitely up there in terms of beautiful runs, with bridges, ponds, and insane colors come autumn. A note for runners the early AM: if you hear a shrieking noise, don't panic — that just means you're near the elk pasture.

If the Lakefront is packed, try diverting to Northerly Island, just south of the Museum Campus; it's suprisingly quiet. Jutting out into Lake Michigan, this 91-acre man-made peninsula is stunning. The island’s restored native prairie almost seems strange against the skyline in the background, but we can’t deny that it’s magical.

Humboldt Park is a 207-acre park with well-maintained trails, restored prairies, lagoons, skyline views, field houses… the list goes on! And if you want to take your route into the namesake neighborhood, head north on the surrounding boulevards. Humboldt Blvd., Logan Blvd., and Kedzie Blvd. offer green spaces and dirt paths surrounded by stately turn-of-the-century homes. Only in Chicago: follow Augusta Blvd. out of the park to the corner of N Wolcott Ave., where the "Shit Fountain" statue reminds residents to pick up after their dog.

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 annual location of Lollapalooza, but don’t let that scare you away from this 319-acre park, home to Millennium Park, Buckingham Fountain, the Art Institute, the city’s Museum Campus, and public art. We're here for the delightful loop of pathways that can easily connect to the Riverwalk if you're looking to tack on the miles.

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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