The best running trails around Chicago
4.6
(149)
24,062
runners
381
runs
Jogging around Chicago offers a diverse experience, blending urban landscapes with extensive green spaces and the prominent Lake Michigan shoreline. The region features miles of flat, paved paths along the lake, unique elevated trails, and scenic routes through large city parks. The Chicago River also provides distinct urban waterscapes for running, complemented by numerous forest preserves in the wider area.
Best jogging routes around Chicago
- The most popular jogging route is Riverwalk East to Northerly Island via Lakefront Trail — Chicago, a 5.8 miles (9.4 km) trail that takes about 58 minutes to complete. This route offers views of the Chicago Riverwalk and Lake Michigan shoreline.
- Another top favourite among local runners is Calders Flamingo - Sculpture – View of La Salle Street Bridge loop from Van Buren Street, a difficult 24.7 miles (39.8 km) path. This extensive route explores downtown Chicago's architectural landmarks and river views.
- Local runners also love the Maggie Daley Park via Lakefront Trail — Chicago, a 11.0 miles (17.7 km) trail leading through urban parks and along the Lake Michigan shoreline, often completed in about 1 hour 49 minutes.
- Jogging around Chicago is defined by its expansive Lake Michigan shoreline, urban riverwalks, and numerous city parks. The network offers options for various ability levels, from easy urban loops to longer, more challenging runs.
- The routes in Chicago are highly rated by the komoot community with an average score of 4.6 stars from more than 100 reviews. More than 24,000 runners have used komoot to explore Chicago's varied terrain.
Last updated: April 24, 2026
4.7
(17)
1,300
runners
9.38km
00:58
20m
20m
Moderate run. Good fitness required. Mostly paved surfaces. Suitable for all skill levels.
4,501
runners
Hard run. Very good fitness required. Mostly paved surfaces. Suitable for all skill levels.
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4.7
(7)
570
runners
17.7km
01:49
30m
30m
Hard run. Very good fitness required. Mostly paved surfaces. Suitable for all skill levels.
5.0
(1)
262
runners
9.38km
00:58
0m
0m
Moderate run. Good fitness required. Mostly paved surfaces. Suitable for all skill levels.
247
runners
15.7km
01:37
20m
20m
Hard run. Very good fitness required. Mostly paved surfaces. Suitable for all skill levels.
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Tips from the Community
This bright red sculpture, made of steel and standing 16 meters tall, was unveiled in 1974 on Federal Plaza, directly in front of the Kluczynski Federal Building. It is a so-called stabile—an abstract, stationary sculpture—and a beautiful example of Calder's unique style.
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Windy but the best view of Chicago
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The Original Chicago Stock Exchange Arch is a historic architectural remnant located at the Art Institute of Chicago. It was salvaged from the Chicago Stock Exchange Building, designed by renowned architects Louis Sullivan and Dankmar Adler and completed in 1894. The building was an iconic example of the Chicago School of architecture but was controversially demolished in 1972. To preserve a piece of this architectural masterpiece, the arch from the main entrance was saved and later installed in the Art Institute’s south garden, designed by Dan Kiley. The arch is celebrated for its intricate ornamentation, showcasing Sullivan’s signature style of organic and geometric motifs. It stands as a monument to Chicago's architectural heritage and the city's commitment to preserving its historical treasures.
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Great positions are museum campus, navy pier , the ferry wheels, boats tours …
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Also suitable for the lame and worthwhile: you can almost drive ahead and even those who come on foot will be richly rewarded for their efforts!
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Park No. 572, also known as the West Bloomingdale Trailhead, invites you to explore its 15.60-acre expanse on Chicago's Northwest Side. As a vital component of the 606 project, this innovative elevated green space repurposes an old railroad embankment into a recreational trail and park system. Stretching between Ashland Ave and Ridgeway at Bloomingdale Ave, the trail offers a scenic path for walkers, runners, and bikers.
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Park No. 567 welcomes you to explore its vibrant and naturally enchanting surroundings. Admire a captivating mural that graces the park, inviting contemplation and appreciation. For an uninterrupted experience, consider an early visit. On a serene Sunday at 9 am, witness the park come alive with walkers, runners, and bikers, but don't let the mild congestion deter you. Take a pause, delve into the profound artistry of the mural, and carry its inspiration with you as you continue your journey through this enchanting urban oasis.
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Embark on an urban adventure along the Bloomingdale Trail, transformed from an old rail line into the vibrant masterpiece known as The 606. Spanning 2.7 miles, this multi-use recreational trail and park offer more than just a pathway – it's an alternative transportation corridor, a living work of art, and a lush green space for everyone to relish. Whether you're cycling, jogging, or hiking, The Bloomingdale Trail invites you to immerse yourself in a unique blend of urban rejuvenation and natural beauty, a testament to Chicago's commitment to innovative public spaces.
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Frequently Asked Questions
How many running routes are available in Chicago?
Chicago offers a wide variety of running routes, with over 380 options available on komoot. These range from easy urban loops to more challenging, longer runs, ensuring there's something for every runner.
Are there running routes for all skill levels in Chicago?
Yes, Chicago's running network caters to all abilities. You'll find over 50 easy routes perfect for beginners, more than 270 moderate options, and nearly 60 challenging trails for experienced runners.
What kind of landscapes can I expect on Chicago's jogging paths?
Jogging in Chicago offers a unique blend of urban landscapes, expansive park systems, and stunning natural features. You can run along the scenic Lake Michigan shoreline, explore the unique urban waterscapes of the Chicago Riverwalk, or venture into extensive forest preserves like Waterfall Glen and Busse Woods for a more natural environment.
Are there any family-friendly running trails in Chicago?
Many of Chicago's parks and trails are suitable for families. The flat, paved paths along the Lake Michigan shoreline, such as sections of the Lakefront Trail, are excellent choices. Additionally, parks like Grant Park and Lincoln Park offer wide-open spaces and accessible paths perfect for a family run.
Which running routes offer the best views of the city skyline?
For unparalleled city skyline views, the Lake Michigan shoreline routes are ideal. The Riverwalk East to Northerly Island via Lakefront Trail — Chicago route provides views of both the Chicago Riverwalk and the Lake Michigan shoreline, offering iconic cityscapes.
Are there any circular running routes in Chicago?
Yes, many routes in Chicago are designed as loops. For example, the Wilson to North Avenue Beach via Lakefront Trail loop — Chicago offers a substantial circular run along the lakefront, providing diverse scenery without retracing your steps.
What are some interesting landmarks or attractions I can see while jogging in Chicago?
Chicago's running routes often pass by significant landmarks. Along the Lakefront Trail, you can see cultural institutions like the Museum Campus and Soldier Field. In the city center, routes might take you past attractions such as Cloud Gate (The Bean), Buckingham Fountain, and the architectural marvels along the DuSable Bridge.
Are there any elevated running trails in Chicago?
Yes, Chicago features a unique elevated trail known as The Bloomingdale Trail (The 606) — Chicago. This 2.7-mile path provides a distinct urban jogging experience through several northwest neighborhoods, offering different vantage points and public art installations.
What do other runners enjoy most about jogging in Chicago?
The running routes in Chicago are highly rated by the komoot community, with an average score of 4.6 stars. Runners frequently praise the expansive Lake Michigan shoreline, the unique urban riverwalks, and the numerous city parks that offer diverse and scenic options for all abilities.
Are there any longer, more challenging running routes for experienced runners?
Absolutely. For those seeking a more extensive challenge, the Calders Flamingo - Sculpture – View of La Salle Street Bridge loop from Van Buren Street is a difficult 24.7-mile (39.8 km) path that explores downtown Chicago's architectural landmarks and river views.
Can I find running routes that combine urban parks with the lakefront?
Many routes seamlessly blend urban parks with the stunning lakefront. The Maggie Daley Park via Lakefront Trail — Chicago is a great example, leading through vibrant urban parks and along the beautiful Lake Michigan shoreline.
What are the best times of year for jogging in Chicago?
Spring, summer, and fall generally offer the most pleasant conditions for jogging in Chicago. The mild temperatures and vibrant scenery make these seasons ideal for exploring the city's diverse trails and lakefront paths. While winter jogging is possible, be prepared for colder temperatures and potential snow.
Most popular routes around Chicago
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