Best city walk trails in Chicago, Illinois

552 Reviews
Explore the most popular city walk trails near Chicago with hand-curated trail maps and driving directions as well as detailed reviews and photos from hikers, campers and nature lovers like you.
Map of city walk trails in Chicago, Illinois
Top trails (29)
#1 - Rainbow Beach Dunes Trail
Rainbow Beach Park
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Length: 0.5 mi • Est. 11 m
Located on the south side and with one of the best views of the city, Rainbow Beach Dunes is another natural gem. Similar to Montrose Beach Dunes, it has an amazing diversity of plant life. As you walk through the area, you will see new panne wetlands forming in response to the restoration efforts by volunteers.Show more
#2 - Chicago Riverwalk
Chicago, Illinois
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Length: 2.7 mi • Est. 1 h 4 m
A family and pet-friendly paved route with great displays of downtown Chicago and its architecture. Accessibility: The trail surface is paved and typically at least five feet wide. The estimated grade is flat (all 1% or less) so most wheelchair and stroller users will likely be able to navigate the trail.Show more
#3 - LaBagh Woods Nature Observation Loop
Chicago, Illinois
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Length: 5.7 mi • Est. 2 h 18 m
This area features an abundance of wildlife inside the city limits: deer, owls, coyotes, turtles, and squirrels. The trail is well maintained. The traffic noise somehow gets trapped before making its way to the woods from the interstate, which makes this particular "escape from the city" that much more appealing.Show more
#4 - Bloomingdale Trail
Chicago, Illinois
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Length: 5.5 mi • Est. 2 h 13 m
As of June 2020, the trail reopened from 6am to 7pm. Show more
#5 - Chicago Riverwalk to Grant Park
Grant Park
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Length: 4.8 mi • Est. 1 h 58 m
#6 - West Ridge Nature Preserve
West Ridge Nature Preserve
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Length: 1.0 mi • Est. 25 m
Who knew such a jewel, undeveloped for 100 years, existed close to the busy intersection of Peterson and Western Avenues. 20 acres of woods surround a 4-acre pond to watch hawks, herons and foxes as well as spotting the occasional wood duck or coyote. A decade ago plans were in the works to convert this wilderness into a retail area. In 2005, a congressional earmark funded the acquisition of this land from Rosehill Cemetery. The acquired land was transferred to the Chicago Park District in 2011. The park district's renovation has transformed this wilderness into the West Ridge Nature Preserve, an oasis of native flora and fauna. Accessibility: This trail is estimated to have a slope of 0-5% meaning it will be mostly gentle across the route. The trail surface is paved with asphalt and concrete for most of the route with some packed gravel and wooden boardwalk sections. Users have noted that some portions may have some over growth of the vegetation but trail goers should find this trail navigable. Show more
#7 - Humboldt Park Lagoon and Beach Loop
Humboldt Park
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Length: 2.1 mi • Est. 52 m
Located in the vibrant and proud Puerto Rican neighborhood of Humboldt Park, this loop has something for everyone. The park gained notoriety when an alligator dubbed Chance the Snapper found his way into the lagoon, but these days the park is gator free. Rent paddle boats, take the free audio tour here: https://www.chicagoparkdistrict.com/parks-facilities/humboldt-park-audio-tour to learn about local history, or take a walk around the peaceful lagoons. There are also areas for fishing, playgrounds for the little ones, and dogs on leash are welcome to join in the fun. Show more
#8 - Ping Tom Memorial Park Loop
Ping Tom Memorial Park
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Length: 1.0 mi • Est. 25 m
This urban trail is a paved loop around the Ping Tom Memorial Park with several facilities including a play ground. Accessibility: This asphalt and concrete trail is estimated to range from 4-12 feet wide. The slope is estimated to be mostly gentle and range from 0-5%.Show more
#9 - Chicago Outerbelt Route
Chicago, Illinois
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Length: 220.0 mi • Est. Multi-day
#10 - Steelworkers Park Trail
Steelworkers Park
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Length: 0.8 mi • Est. 20 m
Great for families. This park features a community rock climbing wall built on the historic ore wall of the Steelworks industry. Accessibility: This asphalt trail is estimated to typically be at least 6 feet wide. The slope is estimated to range from flat to gentle. There does not appear to be any designated wheelchair accessible car parking spots at the small turnaround parking area.Show more
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