Chicago, Illinois
Looking for the best hiking in Chicago? We've got you covered with the top trails, trips, hiking, backpacking, camping and more around Chicago. The detailed guides, photos, and reviews are all submitted by the Outbound community.
Top Hiking Spots in and near Chicago
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Chesterton, Indiana
Hike the 3 Dune Challenge
5.01.5 mi / 552 ft gainStart at the Indiana Dunes State Park Nature Center (the first exit off the roundabout in the park after the toll), after receiving your park map, and follow the 3 dune challenge. This challenge, looping trails 8 and 4, involves climbing to the top of Mt. Jackson (176 feet), Mt. Holden (184 feet)...Read more -
Cary, Illinois
The Hollows Trail
3.77 mi / 220 ft gainThe Hollows Trail is a loop trail that takes you by a lake located near Cary, Illinois.Read more -
Wilmington, Illinois
Hike the Twin Oaks and Bunker Field Trail
4.2 mi / 85 ft gainThe trail is open for use year-round, and is great for snowshoeing in winter months. This trail allows dogs, but please keep your dog on a leash throughout the duration to avoid disturbing the wonderful bison. Be weary of ticks - bring bug spray for you and your dog.Read more -
Lake Villa, Illinois
Hike Hastings Lake LCFP
5.02.37 mi / 88 ft gainPark in the lot off of Butler Lane (see map) to access the trail. This trail is open year round, is dog-friendly, and offers a variety of activities. In the winter, bring your snow gear!Read more
