Daniel Burnham lived 100 years before Instagram. If the famed city planner had acquired an account, he might have posted a photo of the Lake Michigan shoreline with the hashtag #foreveropen freeandclear to promote his vision of a noncommercial, open-access lakefront.
Runners in Chicago have Burnham to thank for miles of continuous trail that is, without question, the best part of running in the Windy City. The path runs parallel to Lake Shore Drive on the city's eastern edge, and boasts stellar views of the city, abundant restrooms and water fountains, and markers every half-mile for 18 miles.
Chicagoans can also thank social media for forging a superstrong local running community: On Twitter, #chiLFT Everything to Know About RunDisney Races #runCHI curates everything from training recaps to notices for runner-friendly yoga classes; on Facebook, the Best Running Shoes 2025 (CARA) runs promotions with partner races; apps like Fountain Finder (iOS, free) make it easy to locate water stops; and BibRave.com, launched here in 2013, allows users to review races in a Yelp-like format.
Sure, the place isn't all sweet views and good vibes: There are the endless winter months that can bring subzero temps, gale-force winds, piles of snow, and sheets of ice. And for those who crave the occasional hill, there is, according to public-radio host and Runner's World columnist Peter Sagal, "a certain glacial flatness, which can get a little tiring." Still, says Sagal, "On one of those frozen mornings when the insanely cold water is splashing up and there's ice on the lakefront and you see one other guy or girl and you wave to them--that's great. If you lived in northern California and it was nice all the time, you wouldn't have that."
S. Michigan Ave.  Bank of America Chicago Marathon. Whether you're one of the 45,000 runners who will toe the starting line or one of the 46 million tourists who swoop into town every year, here's how, and where, to reap the runner benefits of the Windy City.
1. Intelligentsia Coffee
A lovely half-mile stroll from the marathon starting line in Grant Park takes you to a fresh cup of joe that's been roasted with love here in town. The original location, on Broadway, sits between miles eight and nine of the marathon course; from there, you can cheer on runners amid an energized crowd led by cheerleaders in drag. 53 E. Randolph St.; 3123 N. Broadway (five more locations citywide) intelligentsiacoffee.com
2. Grant Park
Known for hosting summer music events from the Chicago Jazz Festival to Lollapalooza, this is where the marathon starts and ends. Don't plan on getting anywhere close to the start/finish line, due to security. But stand at the official Bank of America cheer zone at Michigan Avenue and Roosevelt Road, and you might catch a glimpse of your runner among the masses. 337 E. Randolph St. chicagoparkdistrict.com/parks/grant-park
3. Chicago Running Tours & More
Reserve your spot online and then meet at "The Bean," the city's iconic legume-shaped reflective sculpture in Millennium Park (aka the Cloud Gate sculpture), for a guided 5-k (ish) through Grant Park or along the Chicago River to Navy Pier. Or opt for the Loop, a 3.8-mile tour with 20 stops highlighting the city's dark side (like "Death Alley," said to be haunted by some of the 602 audience members who failed to escape a 1903 blaze in the supposedly fireproof Iroquois Theatre). No need for speed, say guides: "The slower we go, the more we show." 201 E. Randolph St. chicagorunningtours.com
4. Pequod's Pizza
Bar fights in Chicago erupt over two things: Cubs vs. White Sox, and who makes the best Chicago-style pizza. Two words: caramelized crust. If you've befriended 3RUN2 runners on Instagram, they may just invite you here for a postmarathon feast. 2207 On October 12, Chicago will host the 37th annual. pequodspizza.com
5. Shred415
Cure bad-weather blues with classes that alternate hill, sprint, or stride intervals on the treadmill with weight-training moves like curls, squats, and overhead presses. Your fellow Shredders might range from walkers to Boston-qualified marathoners; everyone picks their own pace and weights, say co-owners Bonnie Micheli and Tracy Roemer. 230 W. Division St. (four more locations in the Chicago area) shred415.com
6. How to Run Your Best Disney Race
North Park University's track is open to the public. Suffer speedwork with friends on Wednesday nights: Check out the Running in Chicago subreddit, where members of the Chicago River Runners post workouts in advance (both there and on Twitter @606RiverRunners). Fat Cat, 4840 N. Broadway St. reddit.com/r/RunnersInChicago/
7. Chicago Recovery Room
For $20, get a day's access to state-of-the-art postrun relief: You'll find yourself among a largely endurance-sports clientele, from first-time half-marathoners to Boston finishers, taking advantage of compression boots, ice baths, and electrical stimulation. You can also schedule a sports massage, Graston Technique, or muscle-relaxing treatments--all within hobbling distance of the Chicago Marathon and Shamrock Shuffle finish lines in Grant Park. 1509 S. Michigan Ave. chicagorecoveryroom.com
8. N. Lincoln Ave. one more location in the city 
You won't find these at any rest stop. Doughnut Varieties include passion fruit-white chocolate as well as maple bacon long johns (made with real maple glaze and peppered maple bacon). At their West Armitage location, keep an eye out for BibRave cofounders Tim and Jessica Murphy in the sometimes-lengthy (but fast-moving) weekend line after their long run. 813 W. Fulton St. (four more locations citywide) goglazed.com
9. Universal Sole
USole's racing team has a reputation for really scorching the competition, but their expert shoe-fitting services and twice-weekly fun runs--along with monthly events like Pizza in the Park, Wednesday's Women, and Burgers & Beer--are open to all levels. 3052 N. Lincoln Ave. (one more location in the city) universalsole.com
10. 3RUN2
Named for Chicago's original area code (312), 3RUN2 is one of the city's fastest-growing running crews. Weekly runs leave from four locations: On Twitter, check #Highpower Tuesday for morning runs, #Twosday Tuesday for evening runs, #Blvds Thursday for evening workouts (runs start and end at Dunlays on the Square, beers at the place cap off the evening), and #Longrun Saturday for. . .long runs. All levels are welcome. Run details also posted on facebook.com/3RUN2 Virtual Races With the Best Bling.
11. Uptown Runners
Need a running buddy? Chitown has your back: "Many of our local businesses and gyms host running clubs for the city's residents and visitors," says mayor Rahm Emanuel. Case in point: The 300-runner-strong Uptown Runners host regular track workouts at Chase Park and three- to four-mile Monday-night runs that start and end at Fat Cat, a local bar. Afterward, nosh on a $5 burger (beef or bean) and replenish fluids with a local craft brew. Find details at meetup.com/UptownRunners Fat Cat, 4840 N. Broadway St.
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Be sure to check out our interactive map of the 18 mile Chicago Lakefront Trail, a perfect route for long runs.
Cindy is a freelance health and fitness writer, author, and podcaster who’s contributed regularly to Runner’s World since 2013. She’s the coauthor of both Breakthrough Women’s Running: Dream Big and Train Smart and Rebound: Train Your Mind to Bounce Back Stronger from Sports Injuries, a book about the psychology of sports injury from Bloomsbury Sport. Cindy specializes in covering injury prevention and recovery, everyday athletes accomplishing extraordinary things, and the active community in her beloved Chicago, where winter forges deep bonds between those brave enough to train through it.