Become a Member

Get access to more than 30 brands, premium video, exclusive content, events, mapping, and more.

Already have an account? Sign In

Become a Member

Get access to more than 30 brands, premium video, exclusive content, events, mapping, and more.

Already have an account? Sign In



A Runner’s Guide to Chicago

This midwestern metropolis has everything a runner needs.

Get access to everything we publish when you sign up for Outside+.

You might not think of the home of deep-dish pizza as a mecca for fitness. But Windy City runners know that a pie from Gino’s East is just another way to carbo-load!

With multiple running clubs, a variety of locally owned running specialty stores and hundreds of running paths, Chicago is a runner’s delight. “Of all the places I’ve lived, Chicago has one of the best running communities,“ says marathoner Whitney Johnson, who’s resided in the city for five years. “No matter what time of day, how many miles I’m running or what the weather is like outside, I can always find a training partner.”

Great routes, great stores, and a great running community—as Frank Sinatra says, “Chicago is my kind of town.”

Chi-Town’s Must-Runs

Lakefront Path
With the city’s stunning skyline on one side and the calming waves of Lake Michigan on the other, the 17-mile Lakefront path is popular with runners and cyclists. The northern half of the trail, which weaves past Navy Pier and the Bucking-ham Fountain, is notoriously crowded, but the path is wide enough for everyone. And hey, you might make a few new friends.

North Branch Trail
Need to get in touch with nature? Start at the corner of Caldwell and Devon, then head north. The scenery changes with every passing mile of the North Branch Trail—forest preserves, fields of deer, lagoons and the Chicago River—before ending 17 miles later at the Botanic Garden.

Bloomingdale Trail
Runners looking for a bird’s-eye view of Chicago should take to Bloomingdale, a former elevated rail line turned running path. The 3-mile loop winds through four vibrant Chicago neighborhoods—Wicker Park, Bucktown, Humboldt Park and Logan Square—allowing for unique views of historic boulevards, parks and art plazas. Bonus: There’s not a single stoplight on this path—a rarity in this city!

Grant Park
Pressed for time? See all of Chicago’s best in just 4 miles by looping through Grant Park. Known as “Chicago’s Front Yard,” the paths of the park offer surprises around every turn, from beautiful flower gardens to stellar public art displays. Go early in the morning, as large crowds tend to clutter the sidewalks after 10 a.m.

Good Company

CARA Group Runs
Nine thousand runners strong (and growing!), the Chicago Area Runner’s Association (CARA) hosts free group runs almost every night throughout the metropolitan area. With turnouts ranging from 10 runners to more than 200, you’ll always find a friendly face (or a pace bunny). Visit for information.

Hash House Harriers
This self-proclaimed “drinking club with a running problem” follows unique mile markers (think dots of flour and toilet paper arrows) from one watering hole to the next in search of miles—and more brewskis. To join in on the fun, bring eight dollars and a sense of adventure. The group’s schedule can be found at

Windy City
Run with the gusts…In Chicago, wind is a way of life. It regularly blows off the lake at 10 to 12 miles per hour. When running with such strong winds at your back, you can feel invincible—that is, until you turn around. Trying to maintain a specific pace in a headwind can frustrate even the most level-headed runner.

Research has shown a headwind can set a runner back up to 12 seconds per mile. In windy conditions, go by effort, not pace. If your normal tempo pace is 8 minutes per mile but you’re finding that impossible to sustain in a headwind, turn off your watch and run what feels like your tempo pace. You’ll still reap the benefits of your tempo workout without the exhaustion of fighting with Mother Nature.

Dig In

Treat yourself with a post-run brunch. In addition to an amazing assortment of house-made pastries (you cannot miss the ooey-gooey Honey Butter Cinnamon Roll), this popular eatery uses freshly pressed orange and blueberry juices in their perfectly bubbly mimosas. Try the breakfast sandwich with egg whites, roasted tomatoes and kale. If you’re feeling naughty, order a side of brown sugar bacon too.

Lou Malnati’s
You simply cannot come to Chicago without a deep-dish pizza experience. Though locals debate over which city pizzeria is the best, Lou Malnati’s is up there for sure. Serving up buttery deep-dish crust with all the fixin’s since 1971, the pizzeria has 37 locations around the city to ensure you get easy access to a good pie. Try “The Lou,” a deep-dish crust piled high with garlicky spinach, mushrooms and roma tomatoes.

Extra Credit

Treat your feet to a pedicure at this bright, funky nail salon in the Wicker Park neighborhood. The nail technicians are friendly, quick, and—yay!—completely familiar with the, ahem, unique beauty of runners’ feet.

Millennium Park Workouts
Down dog for free under the beautiful steel ribbons of Pritzker Pavilion in Chicago’s Millennium Park. Every Saturday morning during warmer months, no-cost yoga, Pilates, and tai chi classes are provided in the pavilion’s Great Lawn, accompanied by live music performed by local bands and groups.

Naperville Running Company
More than 5,500 square feet of running shoes and gear, a high-energy staff, one-on-one attention for every customer—oh, and a two-lane indoor track—make this the one-stop run shop! Does shoe shopping get any better than this? It’s no wonder this Chi-town gem regularly wins “Best Running Store in America” awards from Competitor every year.