City Guide: Running in Chicago, Illinois

Looking for the top places to run, local running stores, group runs, and more? Here’s your guide to running in Chicago, Illinois.

(Feature photo by Iryna Olkhova/iStock.com)

Article last updated: November 7, 2025

Affiliate disclosure: Running Lifestyle may receive a small commission on travel bookings made through the links in this post. By using the links to book your travel experiences, you’ll support an independent media company that’s focused on creating great content for runners!

The Chicago City Guide is developed in partnership with Fleet Feet Chicago. Read more about Fleet Feet Chicago’s locations in the Running Stores section below!

Chicago is an ideal destination for combining interests in museums, cultural tours, sightseeing, good food, and, yes, running. Whether you’re in town for a family vacation or a work trip, be sure to schedule time for a few runs! There’s truly no better way to explore a city like this one than by foot.

The Lakefront Trail is the obvious choice for a run, which extends over 18 miles. If you’re looking for more exploration, check out Jackson Park on Chicago’s South Side or Lincoln Park on the north end (both connect to the Lakefront Trail), or head east to Humboldt Park and The 606 pedestrian trail.

If you’re looking for a destination race in Chicago, the city is host to several big ones, including the Shamrock Shuffle, Soldier Field 10, Mag Mile, and the Chicago Marathon. Downtown Chicago road races are flat and fast and attract great crowd support.

While in town, be sure to swing by a local Fleet Feet storefront for new gear and endurance nutrition to fuel you through the miles. And after your run, one word: donuts. There’s no shortage in Chicago, and you’ll find several recommendations below.

Bookmark this guide for your next trip to Chicago. Rather than researching where to go, you can spend more time on the trails and grabbing a post-run beer.

Planning your upcoming running vacations?
Find more destination running guides.

Running in Chicago, Illinois

Running in Chicago is just different — in the best way. Among top running routes, you’ve got miles and miles along the Lakefront Trail where you can enjoy views of Chicago’s skyline, beaches, and green spaces.

But honestly, the best part of running in Chicago is the running community. It’s super friendly, passionate, and always down to cheer you on. You’ll see runners training at all times of the year for local races, such as the Soldier Field 10 in the spring and the Bank of America Chicago Marathon in the fall.

When Is the Best Time to Visit Chicago, Illinois?

The best time to run in Chicago is March through October. March can be a little cold, depending on what Punxsutawney Phil sees over in Pennsylvania, but you can’t beat the pre-Shamrock Shuffle energy around Chicago.

June through August can get pretty warm. If you’re an early riser, you can join the thousands of runners on weekend mornings who are doing their long runs along the Lakefront Trail in preparation for their fall marathons.

September and October are the best months to run in Chicago. With September races, such as the Mag Mile and Lifetime Chicago Half, runners are getting in their last fitness checkpoint ahead of the Bank of America Chicago Marathon. In October, the marathon takes center stage.

Where to Stay in Chicago, Illinois

Running Lifestyle is pleased to be partnered with TravelRunner, your go-to source for running-friendly accommodations. Read recent hotel reviews from fellow runners and athletes, and book your perfect stay. Become a part of a community created by and for travel runners!

Use code GUIDE for 2.5% off your bookings on TravelRunner.com.

Where to Run in Chicago, Illinois

An aerial view of the Chicago Riverwalk sidewalk path on the left, the river on the right and tall downtown buildings in the background — Chicago Riverwalk (Photo by Alice Achterhof/Choose Chicago)

Chicago Riverwalk
While the Chicago Riverwalk is only about 1.25 miles long, it connects to the Lakefront Trail at the harbor. The west end of the Riverwalk is at West Wacker Drive and West Lake Street, and you’ll find access points at each major intersection on Wacker Drive heading east. Along the Riverwalk, admire Chicago’s architecture, watch the boat tours pass by, and scope out where you’d like to grab a bite to eat later in the day. Keep in mind that this is a popular tourist destination, so the path might be crowded during the day and on weekends.

A walking bridge leading into a park with lots of greenery and trees on a sunny day with a few white puffy clouds in the sky — Humboldt Park (Photo by James Andrews/iStock.com)

Humboldt Park
Humboldt Park is a gorgeous green space just off of The 606 (Bloomingdale Trail). Choose between running the 2.2-mile outer loop or meandering through the park along its paved paths, which pass by flower gardens, a lagoon, and a boathouse. Get in some extra miles by following North Humboldt Boulevard at the north end of the park for about one-third of a mile to hop on The 606 (more on The 606 below). Humboldt Park is located at 1440 North Humboldt Boulevard, Chicago, Illinois.

Jackson Park
Jackson Park offers several scenic running paths on Chicago’s South Side. The 1.9-mile Columbia Basin and Wooded Island Loop, for instance, meanders through tranquil wooded areas and around the Jackson Park Lagoon. If you need to get in a marathon training long run, hop on the Lakefront Trail and run north to Grant Park and back (about 9 miles one way). You’ll be treated to beautiful lakefront views and Chicago’s skyline vistas. Consider parking at the Hayes & Lake Shore Drive Lot to start your run.

An aerial view of downtown Chicago in the background, and in the foreground a park on the left and a sidewalk path adjacent to a lake on the right, on a sunny day — Lakefront Trail (Photo by jovannig/iStock.com)

Lakefront Trail
Chicago’s Lakefront Trail is a paved 18.5-mile route stretching from Ardmore Avenue in Edgewater (north end) to 71st Street in South Shore (south end). It’s an easy trail to access if you’re staying in downtown Chicago, and you’re sure to see plenty of other runners — this is a popular route for marathon training season! Along it, you’ll enjoy scenic views of Lake Michigan, the downtown skyline, and landmarks such as Montrose Beach, North Avenue Beach, and the Museum Campus. There are access points and restrooms available along the way. Find more information and a full trail map here.

A sidewalk path with bushes with green and red leaves on both sides, during the fall season, and a view of the Chicago city skyline in the background — Lincoln Park (Photo by @tequilagraphics/Choose Chicago)

Lincoln Park
There’s a lot to see in this expansive, lake-adjacent park, including the Lincoln Park Zoo, Lincoln Monument Gardens and statue located behind the Chicago History Museum, a lagoon, and great views of the downtown skyline. It’s easy to connect to the Lakefront Trail for additional mileage. This 5-mile loop takes you through the park and onto the Lakefront Trail for a visit to the North Avenue Beach Pier. If you have a car, you’ll find various metered street and surface parking lots throughout the park. On Wednesday and Saturday mornings (April through November), stop by Green City Market after your run.

North Shore Channel Trail
The North Shore Channel Trail is an 8.3-mile path stretching from Green Bay Road in Evanston to Francisco Avenue in Chicago. It offers a scenic route for runners alongside the North Shore Channel. While the southern section passes through urban areas with occasional street crossings, the northern portion provides a more tranquil experience, featuring sculptures and green spaces along the way. Consider starting from River Park (accessible by the Lawrence bus with metered street parking nearby).

A paved pedestrian path with a raling on the left side, street lights overhead, and trees with spring blooms on both sides, on a sunny day — The 606 (Photo by Antwon McMullen/iStock.com )

The 606
The 606, also known as the Bloomingdale Trail, is a 2.7-mile elevated pedestrian path running through Chicago’s Wicker Park, Bucktown, Logan Square, and Humboldt Park neighborhoods. Ideal for runners, the trail features a 10-foot-wide path with 2-foot-wide running tracks along both sides. You’ll enjoy scenic views and public art installations, plus there’s access to nearby parks and amenities along the route. Consider starting from Humboldt Park (details above) or the East Trailhead (accessible by the Ashland bus with metered street parking available). Find more trail information here.

As with any running route, take the necessary precautions for a safe run. Whenever possible, run with a buddy. Tell someone you know well where you’re going and when you expect to return, bring your cell phone and an ID, and remain aware of your surroundings.

Running Stores in Chicago, Illinois

The wall of a running store displaying running shirts, shorts, and tights, with a sign above that says "Running Changes Everything" — Fleet Feet Chicago (Photo by Christian Rasmussen)

Fleet Feet Old Town
Fleet Feet Old Town is one-third of a mile away from the Lakefront Trail. It’s the biggest Fleet Feet store in Chicago and has the largest inventory and selection of brands, especially in the carbon-plated shoe category. The Fleet Feet Racing Team, Fleet Feet Training x CES, Fleet Feet Boston Bound & Qualify, and Fleet Feet Racing Performance all train out of Old Town.
1706 North Wells Street, Chicago, Illinois; 312-587-3338

Fleet Feet South Loop
Another hub for Fleet Feet Training, Fleet Feet South Loop is the most accessible store by the Red, Orange, and Green Rail Lines. South Loop also has free parking with two-hour validation. It’s the hub for all Fleet Feet events during Chicago Marathon week.
150 West Roosevelt Road, Chicago, Illinois; 312-788-3338

Fleet Feet Lincoln Square
The second-oldest Fleet Feet store, Lincoln Square also houses Fleet Feet Training x CES. Nestled in the square of Ravenswood, this location has a strong contingency of Saturday morning run club runners.
4762 North Lincoln Avenue, Chicago, Illinois; 773-271-3338

Fleet Feet Lakeview
Small but mighty, Fleet Feet Lakeview sits in the vibrant Southport Corridor just a few blocks away from Wrigley Field.
3359 North Southport Avenue, Chicago, Illinois; 773-281-3338

Heartbreak Hill Running Company
Joining locations in Boston and Santa Monica, Heartbreak Hill Running Company stocks shoes for all types of runners, from the trail to the track. You’ll also find a selection of apparel, gear, and nutrition in this trendy space. In addition to retail, Heartbreak Hill provides training plans and a membership portal.
2148 North Halsted Street, Chicago, Illinois; 773-687-9034

Running Excels
Stop by this woman-owned running store in the Beverly neighborhood for a treadmill gait analysis, and choose from a lineup of the top running shoe brands. You’ll also find lululemon apparel here.
10328 South Western Avenue, Chicago, Illinois; 773-629-8587

Looking for more running stores outside of Chicago’s city limits? Here’s a list from the Chicago Area Runners Association. Plus, check out the Hoka, On, and New Balance storefronts, located in Chicago’s city center.

Run Clubs in Chicago, Illinois

We aim to keep this guide updated regularly, but things can change quickly! Before attending a run club on this list, call the associated store or check the group’s social media to confirm the date, time, and location.

Fleet Feet Lakewood Run Club
When: Mondays at 6 p.m.
Distance: 3 miles
Starting Point: Fleet Feet Lakeview at 3359 North Southport Avenue, Chicago, Illinois

Fleet Feet South Loop Run Club
When: Mondays and Wednesdays at 6 p.m. (women’s group on Wednesdays)
Distance: 3 miles
Starting Point: Fleet Feet South Loop at 150 Roosevelt Road, Chicago, Illinois

Fleet Feet Old Town Run Club
When: Mondays and Thursdays at 6 p.m.
Distance: 3 miles
Starting Point: Fleet Feet Old Town at 1706 North Wells Street, Chicago, Illinois

Fleet Feet Lincoln Square Run Club
When: Mondays at 6 p.m. and Saturdays at 8 a.m.
Distance: 3 miles
Starting Point: Fleet Feet Lincoln Square at 4762 North Lincoln Avenue, Chicago, Illinois

RunTooHard
When: Tuesdays at 6:30 a.m.
Distance: 5K
Starting Point: Frera Desserts at 1722 North Western Avenue, Chicago, Illinois

Lakeview Run Club
When: Tuesdays at 6:30 p.m.
Distance: 1.5-5 miles
Starting Point: Nettlehorst Elementary School at 3252 North Broadway, Chicago, Illinois

Cooldown Running
When: Wednesdays at 6:30 p.m.
Distance: 1-3 miles
Starting Point: Varies; check Instagram

Venados Running Club
When: Wednesdays at 7 p.m.
Distance: 3 and 5-mile options
Starting Point: Monochrome Brewery at 2102 South Carpenter Street, Chicago, Illinois

Gold Coast Run Club x Nameless Track Club
When: Fridays at 6:30 a.m.
Distance: Varies
Starting Point: Castaways at Lincoln Park; map here

Destination Races in Chicago, Illinois

F^3 Lake Half Marathon & 5K | January | Half Marathon, 5K
Bank of America Shamrock Shuffle | March | 8K
Lifetime Chicago Spring Half Marathon & 10K | May | Half Marathon, 10K
Soldier Field 10 | May | Chicago | 10 Miles, 10K
Bank of America Chicago 13.1 | June | Half Marathon
BTN Big 10K | July | 10K, 5K
Run Mag Mile | September | 10K, 5K
Lifetime Chicago Half Marathon & 5K | September | Half Marathon, 5K
Bank of America Chicago Marathon | October | Marathon
Abbott Chicago 5K | October | 5K

Learn more about each of these races in the Chicago Race Guide!

After a Run: Things to Do in Chicago

After a Run: Top Places to Eat in Chicago, Illinois

Beacon Doughnuts – This adorable donut counter is found in the alley off of Armitage. Made in small batches, rotating flavors may include caramel mocha, cinnamon coffee cake, and birthday cake sprinkle, among many others. Get there early — the shop closes for the day once donuts are sold out.
810 West Armitage, Chicago, Illinois; 773-698-2839

Beatrix Market — Swing by Beatrix Market and choose from grab-and-go pastries, salads, soups, sandwiches, pizzas, and hot dishes. Eat it there or take your meal to go. If you’re in town for a few days, you might want to bring a selection of foods back to your hotel for snacking.
Fulton Market: 834 West Fulton Market, Chicago, Illinois; 312-733-0370
The Loop: 155 North Wacker, Chicago, Illinois; 312-629-0025
DePaul Loop: 23 East Jackson Boulevard, Chicago, Illinois; 312-583-0598
Streeterville: 671 North St. Clair Street, Chicago, Illinois; 312-642-0001

BiXi Beer — Right on the edge of Logan Square, this Asian-fusion brewpub is a favorite meetup spot after weekend runs on The 606. Grab a cold beer or hit the brunch menu for bao buns and breakfast fried rice. Closed Wednesdays; open for brunch on the weekends.
2515 North Milwaukee Avenue, Chicago, Illinois; 773-904-7368

A person's hand sprinkling chocolate shavings on top of an iced latte in a plastic cup with a bag of coffee next to it, both on a table with a window to the outside in the background — Chicago French Press (Photo by Roosevelt Collection)

Chicago French Press — Just down the street from Fleet Feet’s South Loop location, this Black female-owned coffee shop is perfect for post-run caffeine and pastries to tide you over before you get in a full meal. Consider buying a bag of beans to take home — 5% of proceeds go toward nonprofits supporting women and children.
South Loop: 1021 South Delano Court, Chicago, Illinois; 312-957-1601
West Loop: University of Illinois at Chicago, 601 South Morgan, Chicago, Illinois
Hyde Park: 970 East 58th Street, Chicago, Illinois

Doughnut Vault — Find classic, old-fashioned donuts here, plus fun-flavored daily specials. Order at the window after a run on the Riverwalk.
401 North Franklin Street, Chicago, Illinois; 312-285-2830

Do-Rite Donuts & Chicken — Whether you’re craving a morning donut, breakfast sandwich, or a fresh-to-order fried chicken sandwich, Do-Rite has you covered. Three gluten-free donut flavors and three vegan donut flavors are available daily!
Willis Tower: 233 South Wacker Drive, Chicago, Illinois
Wrigleyville: 1027 West Addison, Chicago, Illinois
West Loop: 181 North Morgan Street, Chicago, Illinois
Streeterville: 233 East Erie Street, Chicago, Illinois

Firecakes — Small-batch donuts baked fresh daily, using a secret family recipe. Find a rotating lineup of flavors, plus a gluten-friendly and vegan chocolate donut. A great stop after a run at Lincoln Park or along the Riverwalk.
Lincoln Park: 2453 North Clark Street, Chicago, Illinois; 773-666-5277
River North: 68 West Hubbard Street, Chicago, Illinois; 312-329-6500

A glass case inside a bakery filled with donuts and pastries — Geraldine’s (Photo courtesy of Geraldine’s)

Geraldine’s — Fleet Feet Lincoln Square’s Saturday morning runners call themselves the “breakfast club,” mostly because they end up at Geraldine’s afterward for breakfast quiche and potatoes. In addition to breakfast served all day, you’ll find made-from-scratch pastries, coffee, and tea.
4743 North Lincoln Avenue, Chicago, Illinois; 312-684-0587

Groundswell Coffee Roasters — A cozy neighborhood coffee shop near Lincoln Park and the Lakefront Trail, Groundswell offers fresh pastries, good coffee, and breakfast burritos and sandwiches. You’ll also find plenty of plant-based options. It’s quiet and perfect for a solo cool-down or post-run journaling.
Ravenswood (near the Lakefront Trail): 4839 North Damen Avenue, Chicago, Illinois; 773-754-7590
West Loop: 1168 West Madison Street, Chicago, Illinois; 312-763-2165

Hero Coffee and Bagel Bar — Stop by this Latin-owned coffee and bagel shop after a run along the Lakefront Trail. Creative drinks, such as the hot rosemary chai and teddy graham latte, join traditional coffee and tea beverages. Bagel sandwiches include cream cheese and lox, and sausage and cheese.
Lakeview: 2950 North Sheridan, Chicago, Illinois; 773-661-1254
Printer’s Row: 439 South Dearborn Street, Chicago, Illinois; 312-631-3269
Jackson (patio only): 22 East Jackson Street, Chicago, Illinois; 312-285-2434

Little Goat Diner — Two doors down from Fleet Feet’s Lakeview location, this diner is a part of the restaurant network by award-winning Chef Stephanie Izard. With brunch, lunch, and dinner options featuring globally inspired fare, it’s a perfect spot to refuel.
3325 North Southport Avenue, Chicago, Illinois; 773-819-7673

Long Room Chicago — Traditionally a bar, the Long Room brings in food trucks for brunch and dinner throughout the week (check the schedule here). Choose from a drink menu of caffeinated and alcoholic beverages, and spend some time in the outdoor garden space. (No kids allowed after 5 p.m.)
1612 West Irving Park Road, Chicago, Illinois; 773-665-4500

Midwest Coast Brewing Company — The brewery’s owners brought their love of beer from the coast of California to the Midwest. Relax post-run with a seasonal pint or one of the core taps: West Coast IPA, German pilsner, English pale ale, or American brown ale. The spacious taproom features plenty of patio space, and it’s dog-friendly!
2137 West Walnut Street, Chicago, Illinois; 312-361-1176

Nookies on Wells — Just a few doors down from Fleet Feet’s Old Town location, Nookies is a great spot for brunch on the weekends after a long run. Open since 1973, you’ll find everything from French toast and crêpes to Mediterranean and Spanish breakfast skillets. If your run takes you later into the day, stop by for a sandwich, wrap, or burger.
1746 North Wells Street, Chicago, Illinois; 312-337-2454

Small Cheval — Fuel up at this trendy spot known for burgers, fried chicken, ice cream, and (boozy-optional) milkshakes. Relax in the alleyway patio in Old Town, at a picnic table on the large outdoor patio at Fulton Market, or inside a Chicago Cubs-inspired space in Wrigleyville, among other locations.
Old Town: 1345 North Wells Street, Chicago, Illinois; 312-837-3860
Fulton Market: 1352 West Lake Street, Chicago, Illinois; 312-248-8439
Wrigleyville: 1119 West Waveland Avenue, Chicago, Illinois; 312-374-1877

Stan’s Donuts & Coffee — While Stan’s is best known for its fresh-baked donuts, you’ll also find a vegetarian breakfast burrito, keto egg sandwich, and plenty of coffee here. This popular shop has dozens of locations around Chicago. Among them:
South Loop: 26 East Roosevelt Road, Chicago, Illinois; 312-834-0700
Uptown: 4601 North Broadway, Chicago, Illinois; 312-465-5020

More travel plans? Check out our other City Guides.

MORE ON RUNNING IN CHICAGO AND ILLINOIS

Erica Agran on Running 60+ Marathons and Chicago Running Tours

Running Podcast Co-host Karen Lesiewicz Shares About Nameless Track Club

Where to Run, Running Stores, Races, and more in Naperville, Illinois

Naperville’s Coach Paul Vandersteen Shares One Big Lesson for Runners

10 Destination Races in Chicago, Illinois