Stunning Trails For Hiking Near Chicago This Fall

While we all crave a spa day occasionally, nothing is as relaxing as exploring and hiking near Chicago, but there is no one-size-fits-all spot. Some people gravitate more toward a strenuous path surrounded by waterfalls, while others enjoy a quick trip with birdwatching in between.

Every season offers new and different ways to enjoy nature, with spring splashing with the newly melted snow, summer peaking with an abundance of colors, fall trees bursting with warm red and golden hues, and winter bringing a clean slate of snow to remind us the year as come to a close. No matter the time of year, if you’re going to take a road trip from Chicago, these are the best spots to head to for hiking near Chicago this Fall.

1. LaBagh Woods

Situated at the southern start of the famous North Branch Trail, LaBagh Woods is known for its thriving and diverse natural areas, including wooded landscapes, wetlands, savannas, and sedge meadows. It’s a perfect place for hiking near Chicago, and if you need a rest afterward, the site also offers picnic groves and large open fields.

📍Location: Lincolnwood, Illinois

🚗 Distance from Chicago: 11 miles

🏕 Hike Distance: 5.7 miles

2. Devil’s Lake State Park

Devil’s Lake State Park offers majestic views from 500-foot bluffs overlooking a 360-acre lake. Along the Ice Age Natural Scenic Trail, visitors have nearly 30 miles of hiking trails to take advantage of. After getting in a workout, you can head to the lakeshore picnic areas and swimming beaches for a laid-back evening.

📍Location: Sauk County, Wisconsin

🚗 Distance from Chicago: 192 miles

🏕 Hike Distance: 29 miles

3. Matthiessen State Park

Visitors will be delighted by the canyons, streams, prairies, and forests at Matthiessen State Park. Located in LaSalle County, Matthiessen is a paradise for recreational enthusiasts. One of our favorite spots for hiking near Chicago, you’ll find beautiful rock formations in addition to unusual and abundant vegetation and wildlife.

📍Location: LaSalle County, Illinois

🚗 Distance from Chicago: 84 miles

🏕 Hike Distance: 13 miles

4. Waterfall Glen Forest Preserve

For those who love chasing frothy waterfalls near Chicago, Waterfall Glen is the quintessential place to scout them. Hikers, bicyclists, horseback riders, and cross-country skiers alike can enjoy Waterfall Glen’s scenic areas of limestone and turf-covered routes spanning almost 11 miles.

📍Location: Daren, Illinois

🚗 Distance from Chicago: 23.3 miles

🏕 Hike Distance: 9.7 miles

5. Indiana Dunes National Park

Chesterton, Indiana, is ranked on our list of small charming towns near Chicago you must visit at least once. The town hosts Indiana Dunes National Park, which boasts various trails if you’re in the mood for a strenuous hike or leisurely bike ride, all flooding from the beautiful beaches of Lake Michigan nearby.

📍Location: Chesterton, Indiana

🚗 Distance from Chicago: 46 miles

🏕 Hike Distance: 3.4 miles

6. Kankakee River State Park

The park’s trail system stretches for miles along both sides of the Kankakee River. Hiking, biking, and cross-country ski trails are on the river’s north side, while horse and snowmobile trails are on the south. A 3-mile route along Rock Creek lets hikers enjoy the beauty of limestone canyons and a luscious streaming waterfall.

📍Location: Bourbonnais, Illinois

🚗 Distance from Chicago: 60 miles

🏕 Hike Distance: 3 miles

7. Big Foot Beach State Park

Located on the shores of Lake Geneva, Big Foot Beach State Park offers five miles of hiking trails, a family campground, a swimming beach, and picnic and playground areas. During the crisp, cool winter, people passionate about snowshoeing and cross-country skiing can head there for the popular winter activities.

📍Location: Lake Geneva, Wisconsin

🚗 Distance from Chicago: 83.7 miles

🏕 Hike Distance: 5 miles

8. Starved Rock State Park

Starved Rock State Park is a little journey outside of Chicago, but still just a one-tank trip under 100 miles away. Added to the National Register of Historic Places in 1998, Starved Rock is an incredible spectacle offering over 13 miles of hiking trails, numerous cascading waterfalls, and 18 different canyons.

Exploring the magnificent bluffs and canyons is the park’s primary attraction; however, there is an abundance of well-marked trails throughout.

📍Location: Oglesby, Illinois

🚗 Distance from Chicago:93 miles

🏕 Hike Distance: 13 miles

9. Fort Sheridan

Fort Sheridan has three main paved trails: the Hutchinson Trail, Lake Overlook Trail, and Parade Grounds Trail. Hutchinson Trail is a 1-mile trail from Sheridan Road along Hutchinson Ravine to Lake Michigan. The .2-mile Lake Overlook Trail runs from the Gilgare Lane parking lot along the top of the bluff to the pond and lake overlook. The .75-mile Parade Grounds Trail runs from the Gilgare Lane parking lot to the Parade Grounds.

There’s also an extra trail for birdwatching; the 1.7-mile Birding Trial Loop brings visitors over Janes Ravines, past the Army cemetery, and through woodlands and savanna for leisurely sightseeing.

📍Location: Lake Forest, Illinois

🚗 Distance from Chicago: 25 miles

🏕 Hike Distance: 3.65 miles

10. Chicago Outerbelt

While all the places we mentioned for hiking near Chicago are miles away, Chicago Outerbelt is right around the corner, and one of the things you have to do in Chicago at least once. The trail connects some of Chicago’s most notable nature surroundings, extending from Downtown’s Buckingham Fountain to the south suburbs, the Des Plaines River Trail, Lake County, and the Chicago lakefront.

📍Location: Greater Metropolitan Chicago

🚗 Distance from Chicago: Varies

🏕 Hike Distance: 210 miles

11. Witches Gulch

Hiking near Chicago? Before heading to this trail, you should know the Witches Gulch is only accessible by the Upper Dells boat tour. The sandstone in this area formed millions of years ago, and at a certain point, you can reach out and touch the narrow canyon on the hike. The walk itself is a 2-mile loop through a hardwood forest.

📍Location: Wisconsin Dells

🚗 Distance from Chicago: 200 miles

🏕 Hike Distance: 2 miles

12. Midewin National Tallgrass Prairie

Established in 1996, the Midewin National Tallgrass Prairie is the first national tallgrass prairie in the country. If you’re looking to hike near Chicago, there are over 20,000 acres of farm and industrial land, making it a striking landscape and the complex ecology of the prairie.

📍Location: Will County, Illinois