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Chicago isn’t all about deep-dish pizza and architecture tours—it’s also a great destination for hikers. In fact, you don’t have to go very far to discover some pretty epic trails just outside America’s Second City. From towering sand dunes and cascading waterfalls to limestone canyons and fields full of bison, here are the hikes you shouldn’t miss.
Starved Rock and Sandstone Point Overlook Trail
Where: LaSalle County, Illinois
Length: 4.3 miles loop
Time: 2.5 hours
Difficulty: Moderate
What to Expect: It’s hard to pick a single trail in Starved Rock State Park when each is more beautiful than the last, and eight lead to impressive waterfalls in age-old canyons. Consider tackling Starved Rock and Sandstone Point Overlook Trail on your first visit for its outstanding view of the Illinois River from the park’s namesake, a 125-foot butte.
Pets Permitted: Dogs are welcome, but must be on a leash.
Cowles Bog Trail
Where: Porter County, Indiana
Length: 4.3 miles loop
Time: 2 hours
Difficulty: Moderate
What to Expect: A highlight of Indiana Dunes National Park, this route is just one of 14 trails in the newly designated federal landmark. Featuring marshes, ponds, swamps, beaches and black oak savannas, it’s also one of the most ecologically diverse preserves in the nation. Look out for unusual features like oaks growing right out of the sand and rare birds.
Pets Permitted: Dogs are welcome, but must be on a leash.
Waterfall Glen Trail
Where: DuPage County, Illinois
Length: 9.3 miles loop
Time: 3.5 hours
Difficulty: Easy
What to Expect: Set in the nearly 2,500-acre Waterfall Glen Forest Preserve, this comprehensive trail circles around the entire park’s hilly terrain. Hike through prairies, savannas, and oak maple woodlands, pausing to admire a cascading waterfall and a vista overlooking the Des Plaines River.
Permitted: Dogs are welcome, but must be on a leash.
Henslow Trail
Where: Will County, Illinois
Length: 10.4 miles out-and-back
Time: 4 hours
Difficulty: Easy
What to Expect: In 2015, Bison were reintroduced to the Midewin National Tallgrass Prairie, a 18,500-acre preserve and the first federal tallgrass prairie in the country. Hike through the animals’ habitat (the bison themselves are fenced off) and experience the prairie that once covered much of the Midwest before it was destroyed. Bring your binoculars and keep your eyes open for black-necked stilts, Henslow’s sparrows, and the rare black-billed cuckoo, too.
Pets Permitted: Dogs are welcome, but must be on a leash.
Rock Creek Trail
Where: Kankakee and Will Counties, Illinois
Length: 3.2 miles loop
Time: 1.5 hours
Difficulty: Easy
What to Expect: Follow alongside this wet trail’s namesake creek and discover wooded bluffs and limestone canyons on your way to a waterfall. A tributary of Kankakee River, it’s rated as one of the purest streams in the state, so don’t hesitate to take a dip.
Pets Permitted: Dogs are welcome, but must be on a leash.
Lake Defiance Trail
Where: McHenry County, Illinois
Length: 3.8 miles loop
Time: 1.5 hours
Difficulty: Easy
What to Expect: Winding around 48-acre Lake Defiance, one of the few glacial lakes in Illinois that remains largely undeveloped, this trail in Moraine Hills State Park immerses hikers in the region’s woodlands and wetlands. Of special note are the many boulders that were deposited by the glacier that retreated thousands of years ago.
Pets Permitted: Dogs are welcome, but must be on a leash.
Dells Canyon and Bluff Trail
Where: LaSalle County, Illinois
Length: 2 miles loop
Time: 1 hour
Difficulty: Moderate
What to Expect: The uninitiated hiker might miss out on this gorgeous trail in Matthiessen State Park, situated right next to its more famous neighbor Starved Rock State Park. Come here for a similarly scenic—and much less crowded—experience. Highlights include lady slipper orchids, a waterfall, and sandstone formations as you follow the route’s guiding creek.
Pets Permitted: Dogs are welcome, but must be on a leash.
Palos Yellow Trail Loop
Where: Cook County, Illinois
Length: 9.9 miles loop
Time: 4 hours
Difficulty: Moderate
What to Expect: If you want an epic hike without leaving the metro area, this should do the trick. Set in the biggest forest in Chicago’s Cook County, this trail’s gravel loop will guide you through the upland forests, flowering fields, and ravines of Cap Sauers Holding Nature Preserve. If you’re lucky, you might even catch a glimpse of a bald eagle.
Pets Permitted: Dogs are welcome, but must be on a leash.
North Branch Trail System
Where: Cook County, Illinois
Length: 20.5 miles point-to-point
Time: Varies
Difficulty: Easy
What to Expect: Looking for something even more convenient? The city’s North Branch Trail System winds from Caldwell and Devon Avenues to the Chicago Botanic Garden in Glencoe. Pick a section that twists through forest preserves and the Skokie Lagoons or stop in Morton Grove for deep dish pizza at Pequod’s.
Pets Permitted: Dogs are welcome, but must be on a leash.
Ice Age National Scenic Trail
Where: Wisconsin
Length: 1,200 miles point-to-point
Time: Varies
Difficulty: Moderate
What to Expect: And now for something completely different: a massive, prehistoric trail in Wisconsin. Harkening back to a time some 15,000 years ago when an ice sheet covered much of North America, this route traces ancient sedimentary formations such as kames (sand mounds) and eskers (long, winding ridges) and provides fascinating insight into glacial history.
Pets Permitted: Dogs are welcome in some areas.
Grand Mere Beach Nature Trail
Where: Berrien County, Michigan
Length: 3.6 miles loop
Time: 1.5 hours
Difficulty: Moderate
What to Expect: A walk on the beach might not be the first thing that comes to mind when you think of Chicago, but that’s exactly what you’ll find at Grand Mere State Park in nearby Michigan. Best known for its magnificent sand dunes on Lake Michigan’s eastern shore harbors, hikers come here to loop through the sand and woods before taking a dip in the crystal waters. For a bigger challenge, consider climbing up Baldtop, a 760-foot dune.
Pets Permitted: Dogs are welcome, but must be on a leash.
Des Plaines River Trail
Where: Lake and Cook Counties, Illinois
Length: 56.2 miles point-to-point
Time: Varies
Difficulty: Moderate
What to Expect: Following along the Des Plaines River, this long multi-use trail snakes through 12 forest preserves, as well as a diverse selection of meadows, lakes, wetlands, and woodlands. Hikers can take their pick from a selection of short strolls, adventurous treks, and everything in between.
Pets Permitted: Dogs are welcome, but must be on a leash.
Pond and Oak Ridge Trail
Where: Ogle County, Illinois
Length: 4.3 miles loop
Time: 2 hours
Difficulty: Moderate
What to Expect: Named for a sandstone bluff along the Rock River, Castle Rock State Park offers several short trails with epic views of its ravines and rolling topography. Take this particular path into the dense woodlands out to a scenic pond and overlook.
Pets Permitted: Dogs are welcome, but must be on a leash.
Chicago Outerbelt Route
Where: Cook County, Illinois
Length: 210 miles loop
Time: Varies
Difficulty: Moderate
What to Expect: The ultimate way to check many of Chicago’s natural highlights and popular attractions: by foot on the Outerbelt Route, which merged existing forest and park land surrounding the metro area in 2018. Choose to explore the mega-trail segment by segment, or reserve a spot at one of its many campsites to keep the adventure going.
Pets Permitted: Dogs are welcome, but must be on a leash.
Deer Grove Yellow Loop Trail
Where: Cook County, Illinois
Length: 5.7 miles loop
Time: 2.5 hours
Difficulty: Moderate
What to Expect: The Chicago area’s first forest preserve, Deer Grove boasts some of the healthiest natural land in the state just outside the city. Hike through 2,000 acres of diverse ecosystems, such as wooded ravines, wetlands, upland forests, and prairie, and of course say hi to the friendly resident deer.
Pets Permitted: Dogs are welcome, but must be on a leash.
