A Local's Guide for Where to Run in Chicago
- October 11, 2024
In Chicago, you never run alone. A robust, diverse running community keeps the city flush with activity, from its picturesque parks and neighborhood routes to its miles of paved waterfront paths. You’ll see run clubs and solo striders, elite athletes and first-time racers, dawn patrollers and run-to-coffee regulars.
We know this because we spent a week with the Windrunners, a local run team powered by Nike that’s working to break down barriers for the next generation of female runners, fostering community one mile at a time. As Chicago’s first all-female, sub-elite racing team, they know a tip or two about how to best run their city. Here are their seven must-see spots.
1
Lakefront Trail
This impressive path hugs the shore of Lake Michigan for 18.5 miles, making it a top choice for long runs, sightseeing and, if you’re lucky, a tailwind heading back toward downtown.
“I love to tackle long runs on the Lakefront Trail, starting somewhere close to downtown and going south, however far you need. The way back downtown usually has the wind at your back and city views reeling you in.”
Robyn LaLonde, Windrunners Head Coach
After checking out this famous footpath, Windrunners athlete Amanda Zubricki recommends indulging in another Chicago staple: the city’s famous deep-dish pizza.
“After a long run or race, I love to treat myself to some pizza,” she says. “As we all know, Chicago has the best pizza in the United States. You’ll hear a lot of passionate debates over who has the best deep dish, but I can settle that easily: it’s Pequod’s Pizza.”
2
Pilsen
This bustling neighborhood on Chicago’s Lower West Side is steeped in Latino culture, recognized for its public art and lauded among Windrunners as a top running destination.
Alejandra Ruales, who lives in the neighborhood, still finds herself running a 5K route she created last year as part of a fundraiser she organized to collect winter clothing for migrants arriving in the city. "The route is meant to be savored," she says. "It can be a recovery run for both beginners and seasoned runners alike, inviting everyone to immerse themselves in the captivating artistry of Pilsen.”
“In the mornings, you can smell the fresh bread being made at the panaderias, see tamaleros starting to set up their stations and coffee being brewed at my favorite coffee shops."
Alejandra Ruales, Windrunners
Ruales favors her local Mandala Café for a post-run pitstop. “I usually order their cafe de olla latte and a pandebono [type of Colombian bread] as a post-workout treat,” she says. “Both are to die for!”
3
Oz Park
Channel your inner whimsy while lapping this city park, named for the late L. Frank Baum, a onetime Chicago resident who wrote the famed children’s book, “The Wonderful Wizard of Oz.”
“For short runs, I love running around Oz Park,” Zubricki says. “See if you can find all of the Wizard of Oz statues throughout, from Dorthy and Toto to the Cowardly Lion. The park also features a large hill if you need that training.”
One of the Windrunners’ favorite running shops, Heartbreak Hill Running Company, sits a block away from Oz Park, and is a go-to gear spot for Zubricki. "Heartbreak is great because they offer free community runs, such as speed runs on Thursday and long runs on Saturday, that are open to the public," she says. "During the summer, they also have a water station on the lakefront path where you can snag a drink, electrolytes and Swedish fish!" Inside the Heartbreak store, Zubricki also recommends trying Nike Form to get a running profile with the Nike Sport Research Lab. “You run on a treadmill for two minutes and after analyzing your form, they send you personalized Nike Training Club exercises and footwear suggestions.”
No matter what kind of runner you are, the Windrunners say there's a running culture for you in Chicago.
4
The 606
For a scenic 5K or tempo workout, you can’t beat The 606, an old rail line transformed into an elevated, 2.7-mile path featuring gentle turns and elevation changes, along with distance markers every tenth of a mile. A bonus: You'll find a water fountain and public restroom along the path. (“A runner’s dream!” as one Windrunner put it.)
With an out-and-back approaching 6 miles, multiple Windrunners also use The 606 for 10K workouts. “The miles seriously fly by on this beautiful path,” Zubricki says.
Take home a taste of Chicago by stopping by a Dark Matter Coffee location for a bag of local beans or grounds, Zubricki suggests. “My favorite spot for coffee before a run is in my apartment, as sleep is a very important source of recovery,” she says. “I try to give myself all the extra time to sleep before going out for a run, so I make my pre-run coffee at home with Dark Matter Coffee beans.”
5
Lincoln Park
The city’s largest park is best seen on foot, with miles of trails introducing runners to spectacular views, sculptures, green spaces and… zebras? The Windrunners recommend timing your outing to the Lincoln Park Zoo’s operating hours, allowing you to pass through the zoo and score a peek of its resident striped equines. Just make sure to study your route ahead of time to avoid navigational hiccups.
“Lincoln Park is a great place for a 10K route,” Ruales says. “You can truly find it all and get lost around its paths, see beautiful city views and trails and even get some great views of the zebras at the zoo.”
While Chicago is a top-tier running destination, it’s also an amazing city to explore on two wheels. Channel some cycling inspiration from a Windrunner favorite: Heritage Bikes & Coffee, where Susannah McCloskey goes for pre- and post-run joe. “They have tasty food and lattes, and it’s a more intimate space, so it’s great for a smaller group," she says.
6
North Avenue and Montrose Piers
While Navy Pier demands inclusion in any Chicago first-timer’s itinerary, runners intent on soaking in the city’s lakefront should look to the iconic pier’s less-touristy brethren. The Windrunners recommend the North Avenue and Montrose piers, which allow you to savor sprawling Lake Michigan panoramas as you set your pace — either speeding up, with the water as inspiration, or slowing down to soak in the scenery.
“My favorite spots to run are along the water, which makes me feel centered and calm, and piers are my absolute favorite because you have water on both sides, complete with city views."
Robyn LaLonde, Windrunners Head Coach
From the North Avenue pier, head due west to Corey’s NYC Bagel Deli, which, despite its name, even local LaLonde says is the best bagel in town, touting it as “fast, carb-packed and forever friendly.”
7
Jackson Park
Chicago is comprised of unique, diverse neighborhoods, and to get the full vibe, venture outside of the city’s central core. This South Side gem, the site of World's Columbian Exposition, more commonly known as the Chicago World's Fair, has miles of historic streets and trails to explore.
“This is my favorite park to run in: It’s huge and historically dense. My favorite parts are the hidden trails along the lake and the inner island, complete with the Japanese Garden, which makes for the world’s most amazing recovery interval.”
Robyn LaLonde, Windrunners Head Coach
Cool down with a visit to Sip of Hope Coffee’s Hyde Park Café, where all proceeds support mental health education. “Drink delicious coffee and try tasty pastries while supporting an amazing cause,” Zubricki says. Win-win.
Photos by Kelcey McKinney and Ashley Armitage.