4.6
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3,273
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Hiking around Chicago offers diverse outdoor experiences, from urban lakefront paths to expansive forest preserves and restored prairies. The region features the vast freshwater shoreline of Lake Michigan, extensive woodlands, wetlands, and savannas. Further afield, glacial formations like river-sculpted canyons and seasonal waterfalls characterize state parks, providing varied terrain for exploration.
Last updated: April 26, 2026
5.0
(1)
28
hikers
2.95km
00:45
10m
10m
Lace up your shoes for an easy 1.8-mile (2.9 km) hike along the Northwestern Medicine Wellness Way Fitness Trail. This paved route offers continuous, sweeping views of Lake Michigan andβ¦
3.0
(1)
16
hikers
4.54km
01:08
0m
0m
Embark on an easy urban hike along the Bloomingdale Trail, a flat, paved path offering a unique elevated perspective of Chicago. This accessible route spans 2.8 miles (4.5 km) withβ¦

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3.0
(1)
13
hikers
4.03km
01:01
10m
10m
Step onto the Chicago Lakefront Trail for an easy urban hike that blends cityscapes with refreshing lake views. This 2.5 miles (4.0 km) route offers continuous vistas of Lake Michiganβ¦
7
hikers
5.32km
01:21
10m
20m
Embark on the Magnificent Mile and Navy Pier Walk, an easy urban hike that guides you through the heart of Chicago. This route covers 3.3 miles (5.3 km) with aβ¦
7
hikers
4.91km
01:15
10m
10m
The Catherine Chevalier Woods River Loop offers an easy hiking experience, winding through lush oak and hickory woodlands. You will enjoy picturesque views of the Des Plaines River as theβ¦
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Popular around Chicago
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Navy Pier is a popular tourist attraction in Chicago, located on the shore of Lake Michigan
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The view is truly spectacular. You'll see iconic skyscrapers like the Willis Tower, 875 N. Michigan Ave (formerly the John Hancock Center), and the elegant St. Regis Chicago, all forming an impressive panorama over Lake Michigan.
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In the movie The Blues Brothers, Chez Paul is a high-end restaurant where Jake and Elwood Blues go to find their former bandmate, Alan "Mr. Fabulous" Rubin. Rubin, a trumpet player for the band, has left the music world and is now the maitre d' at the snooty establishment. The exterior shots of Chez Paul in The Blues Brothers were filmed at the actual location of the restaurant, which was at 660 North Rush Street in Chicago's River North neighborhood. While the exterior was the real deal, the interior scenes of the restaurant were actually shot on a soundstage on the West Coast. This was a common practice for film productions, as the owner of Chez Paul reportedly said it was easier than "shipping the McCormick mansion to the West Coast." The restaurant, which was a well-known institution in Chicago, has since closed.
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This is one of the many forest preserves along the Des Plaines River Trail. There are picnic tables, bathrooms and parking for trail access here. You can enjoy some great views of the river from here as well.
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Chicago and its surrounding areas offer a wide variety of hiking opportunities, with over 200 routes documented on komoot. These range from urban lakefront paths to extensive forest preserves and state parks, catering to different preferences and skill levels.
The hiking terrain around Chicago is surprisingly diverse. You'll find scenic lakefront paths along Lake Michigan, extensive woodlands and prairies within the Forest Preserves of Cook County, and dramatic canyons with seasonal waterfalls in state parks like Starved Rock. Further afield, Indiana Dunes National Park offers unique sand dune ecosystems.
The trails in Chicago are highly rated by the komoot community, with an average score of 4.7 stars from over 90 reviews. Hikers frequently praise the scenic views of Lake Michigan and the city skyline, the peaceful escape offered by the forest preserves, and the diverse natural beauty found just a short drive from the urban core.
Yes, for trails featuring waterfalls, consider venturing to Waterfall Glen Forest Preserve, which boasts a scenic waterfall along its almost 9.5-mile loop trail. Further afield, Starved Rock State Park and Matthiessen State Park are renowned for their numerous seasonal waterfalls and dramatic canyons, offering a more rugged hiking experience.
Many trails around Chicago are suitable for families. The Forest Preserves of Cook County offer numerous easy paths through woodlands and prairies. For urban exploration, the Chicago Riverwalk trail is an easy 3.0-mile path showcasing city architecture, perfect for a leisurely family stroll. Indiana Dunes National Park also has trails suitable for various ages, including those exploring unique dune ecosystems.
Many forest preserves and parks around Chicago are dog-friendly, generally requiring dogs to be on a leash. The Forest Preserves of Cook County, for example, welcome leashed dogs on their trails. Always check specific park regulations before heading out, as rules can vary.
Yes, there are several excellent circular routes. The 9.5-mile loop trail at Waterfall Glen Forest Preserve is a popular choice, offering diverse scenery. Within the city, the Clark/Lake to Navy Pier loop via Lakefront Trail β Chicago is a 5.5-mile urban loop that takes you through parks and along the lakefront.
Many trails offer views of iconic Chicago landmarks and natural features. Along the Lakefront Trail, you can see attractions like Buckingham Fountain and Crown Fountain, Millennium Park. The Michigan & Wacker to Adler Planetarium via Lakefront Path β Chicago route offers panoramic views of Lake Michigan and the city skyline. For natural monuments, the Montrose Beach Dunes Natural Area is a unique highlight.
Yes, many urban trails are easily accessible via Chicago's public transport system. The Chicago Lakefront Trail and the Chicago Riverwalk trail are prime examples, with numerous access points near CTA train and bus stops. The Bloomingdale Trail (The 606) is also well-served by public transit.
For extensive natural areas, the Forest Preserves of Cook County are an excellent choice, offering nearly 70,000 acres of woodlands, prairies, and wetlands with hundreds of miles of trails. Notable preserves include Waterfall Glen, Palos Preserves, and Deer Grove. You can find more information on their official website: cookcountyil.gov.
Chicago offers many easy and beginner-friendly trails. The Chicago Riverwalk trail is an easy 3.0-mile urban path. Many sections of the Chicago Lakefront Trail are flat and paved, ideal for leisurely walks. Additionally, the Forest Preserves of Cook County have numerous well-maintained, relatively flat trails suitable for beginners.
Beyond the well-known spots, consider Midewin National Tallgrass Prairie, about an hour from downtown. This expansive preserve offers 34 miles of trails through restored prairie, where you can even spot bison. Illinois Beach State Park, the only remaining beach ridge shoreline in Illinois, provides unique coastal hiking along Lake Michigan with dunes and marshes.


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