Best Trails Near Chicago IL
Filter Result
Select Activity

Best Trails Near Chicago IL

116
Trails
0 - 65 mi
Range
50
Road Biking
49
Walking
32
Other activities
Chicago has 116 trails in the vicinity, including 50 for road biking, 49 for walking and 32 for other activities. These trails range from 0 to 65.6 miles in length. The longest trail in Chicago is Fox River Trail a well-known trail measuring 65.6 miles in total length. The most popular trails are Chicago Lakeshore Path: South Hike, Jackson Park Loop and Chicago Boulevard Lakefront Ramble. Trails.com member Mary W. recently completed Grant Park - Chicago.
Best Trails in Chicago 116 Results
Activity
Select
Rating
Difficulty
Skill Level
Technical Difficulty
Physical Difficulty
Class
Length
Elevation Gain
Vehicles
Surface
Trail Type
Campsites
Additional Use
Accessibility
Features
Grade
Access
 PREMIUM MEMBER
The Chicago lakefront walk is saved for last because it is something a little different. ...
This ride brings you through some of the best parks just west of Lake Shore Drive. It ...
Enjoy stunning views of the downtown skyline as you hike along this strip of parkland ...
A bike tour in downtown Chicago? You must be crazy! A reasonable reaction if you've ever ...
East of Lake Shore Drive is the land of milk and honey. There's no better place for city ...
Bucktown might more appropriately be called X-town, due to all the Gen-X types that have ...
A gleaming 319-acre jewel on the downtown lakefront, Grant Park is rich in Chicago history ...
This may be the best downtown urban paddle in the country! By heading up the Chicago River ...
Kayaking along the Lake Michigan waterfront provides a unique view of the city skyline. ...
At the heart of Jackson Park is a wooded island containing a serene Japanese garden and ...
The main attractions in Hyde Park are the University of Chicago and the charming neighborhood ...
Dan Ryan Black Trail Loop is a hiking trail in Chicago, Illinois. It is within Dan Ryan ...
Paseo is a hiking and biking trail in Chicago, Illinois. It is 4.2 miles long and begins ...
West 84th Street Path is a hiking and biking trail in Chicago, Illinois. It is within ...
Major Taylor Bicycle Trail is a hiking and biking trail in Chicago, Illinois. It is within ...
If you’re like many cyclists, sometimes the momentum behind a bike ride is generated wholly ...
This ride reveals a south side of Chicago that is vast and persistently interesting. Visit ...
Enjoy a classic Chicago bike ride along the Lakefront Path as it winds past harbors, beaches, ...
What's more appropriate to say than "Route 66 Rocks"? The mother road, the main street ...
The Logan Square ride is a study in Chicago boulevards. There are few other places in ...
Uptown is what you'd call a vintage ride. It's one of the last great architectural neighborhoods ...
This is a ride for Chicago newcomers who need a quick tour of what's just on the edge ...
The Prairie District is one of the lesser-known Chicago sights. It's south of Grant Park ...
Load More

Find Chicago Trails by Activity

Other Trails in Nearby Cities