10 Best Trail Runs Near Chicago

With gently rolling terrain, diverse habitats, a variety of wildlife, well-maintained trail systems and forests that provide an enjoyable year-round escape, the Chicago metro area is an ideal spot to lace up your shoes and strike out on a trail run. Several state and local parks are located within an hour to two from downtown, and the Indiana Dunes National Lakeshore is about an hour’s drive across the state line. To get started on your next trail run in the Chicago-metro area, check out these ten top runs as shared by the Trail Run Project community.

Prairie Creek Woods Trail

    • Location: Wilmington, IL in Midewin National Tallgrass Prairie, 56 miles southwest of Chicago
    • Length: 1.7-mile round-trip loop
    • Difficulty Rating: Easy
    • Best For: A beginner-friendly trail with the option to add on mileage
    • Dogs: Leashed

This loop is an excellent introduction to trail running on easy terrain at Midewin National Tallgrass Prairie. The 1.7-mile loop explores a forested oak savanna, and the shaded trail is enjoyable even in the humid summer months. You won’t encounter any roots or rocks on the gently undulating terrain, which alternates between mown grass and wood chips. In the spring, keep your eyes peeled for frogs hopping about between the blossoming wildflowers. On the west side, the trail loops around to an overlook of Buttonbush Pond. From here, the trail winds back to the trailhead through oak and hickory forests. If you would like to extend your run, continue on the Henslow Trail or Blodgett Marsh Trail to further explore the restored tallgrass prairie.

Coffee Creek Watershed Preserve Loop

    • Location: Chesterton, IN in Coffee Creek Watershed Preserve, 48 miles southeast of Chicago
    • Length: 3.2-mile round-trip loop
    • Difficulty Rating: Easy
    • Best For: A speedy outing on a smooth and well-maintained trail system
    • Dogs: Leashed

This loop explores the 157 acres of Coffee Creek Watershed Preserve, taking runners on a tour of prairies, wetlands, forests and the preserve’s namesake Coffee Creek. This creek is home to salmon and steelhead trout, making it a favorite spot for anglers. Birding enthusiasts can spot a variety of species as the preserve is close to the Lake Michigan Flyway migration route.

The trails at the preserve feature a mixture of crushed gravel, brick pavers and boardwalks. Overall, the smooth, flat trails allow for an easy-going run; likewise, more advanced runners can push the pace without worrying about navigating around roots and rocks. Additional amenities include restrooms and a drinking fountain located at the pavilion at the north end of the park. The park also hosts several 5K events throughout the year.

Sag Valley Main Trail

    • Location: Palos Park, IL in Sag Valley Trail System, 37 miles southwest of Chicago
    • Length: 8.5-mile round-trip loop
    • Difficulty Rating: Easy/intermediate
    • Best For: A heart-pumping workout on rolling hills  
    • Dogs: Leashed

The trails at Sag Valley are some of the most picturesque in the entire Chicago area. With more than 20 miles of unpaved trails, runners have many routes to choose from at this forested preserve. The main route is an 8.5-mile loop on a well-marked dirt path comprised of well-packed footing and a series of moderate climbs. The most noteworthy climb is around mile four, where you ascend a steep set of stairs up to Swallow Cliff, a hundred-foot-high bluff. These wide stairs provide a leg-burning climb that makes for a satisfying, strength-building workout. After reaching the top of the bluff, the trail continues on, crossing several bridges over small streams. The rest of the trail provides a rolling run with a total of 364 feet of ascent. Be sure to use caution at the street crossings along the run, and utilize the pedestrian underpass at Lagrange Road.

Lake Defiance Trail

    • Location: Lakemoor, IL in Moraine Hills State Park, 52 miles northwest of Chicago
    • Length: 3.9-mile round-trip loop
    • Difficulty Rating: Easy/intermediate
    • Best For: A flat and shaded trail around a scenic lake
    • Dogs: Leashed

The Lake Defiance Trail is the main loop at Moraine Hills State Park, encircling the trail’s namesake lake. Lake Defiance is one of the few glacial lakes in the state of Illinois that remains undeveloped. Formed when a portion of the main glacier broke away and melted, the lake has been preserved in its mostly natural state. To protect the fragile shoreline, fishing is only allowed from designated piers along the boardwalk.

The trail tread is mainly flat, crushed limestone with a few paved sections interspersed throughout. The lush woods and wetlands around the lake provide welcome shade in the summer months. More than 200 bird species can be seen in the park, including great blue herons and green herons. Depending on the time of day, you may spot other wildlife such as red foxes, coyotes, white-tailed deer, cottontails or raccoons. If you are looking to extend your run, the nearby Leatherleaf Bog Trail and Fox River Trail are equally enjoyable options. You can either create a multiloop run or plan a return visit to explore the other trails.

Glenwood Dunes Trail

    • Location: Beverly Shores, IN in the Indiana Dunes National Lakeshore, 50 miles southeast of Chicago
    • Length: 6.8-miles round-trip loop
    • Difficulty Rating: Easy/intermediate
    • Best For: A woodland tour of Indiana Dunes National Lakeshore
    • Dogs: No Dogs

The Glenwood Dunes trail system is one of the longest and most extensive systems in the Indiana Dunes National Lakeshore, allowing you to piece together a trail adventure as short as one mile and as long as 15 miles depending on your route. The 6.8-mile run along the Glenwood Dunes Trail explores the woodland areas located to the south of the main dunes. In the spring and summer, you will run through a vibrant green landscape, and in the autumn, you will enjoy a showy display of color. The singletrack trail consists of well-packed dirt with boardwalks and bridges over any rough terrain. The trails are completely wooded and never flat—but not too hilly—an ideal combination for maintaining efficient leg turnover and speed. After your run, you can head over to the nearby Lake Michigan beaches to enjoy a refreshing dip or cooldown stroll along the lake.

Waterfall Glen Main Trail

    • Location: Darien, IL in Waterfall Glen Forest Preserve, 34 miles southwest of Chicago
    • Length: 9.7-mile round-trip loop
    • Difficulty Rating: Intermediate
    • Best For: A longer run on a smooth trail with few obstacles
    • Dogs: Leashed

The Waterfall Glen Main Trail loops around Argonne National Laboratory through a diverse ecosystem that includes moraines, kettles, prairie, oak savanna and small pine groves. The varied and rolling terrain makes this an enjoyable run, and the main challenge you will face is the distance, as there are no options to shorten the 9.7-mile loop. Be sure to bring plenty of water in the summer. There are several restrooms with water fountains along the loop so you can refill your water bottle or hydration bladder along the way.

The crushed limestone path provides easy footing, allowing you to focus on the scenery while keeping up a steady clip. Highlights of the loop include the multitiered cascade of Rocky Glen Waterfall, a man-made waterfall constructed by the Civilian Conservation Corps in the 1930s and a quick stop to enjoy the view at Sawmill Creek Bluff Overlook.

Deer Grove Forest Loop

    • Location: Inverness, IL in Deer Grove Forest Preserve, 35 miles northwest of Chicago
    • Length: 9.6-mile round-trip loop
    • Difficulty Rating: Intermediate
    • Best For: An extended, cruising run on rolling terrain  
    • Dogs: Leashed

This run combines two loop trails—the Yellow Loop and the Brown Loop—for a longer run that lets you explore the best unpaved trails at Deer Grove Forest Preserve. On the run, which has a total of 274 feet of ascent, you will enjoy rolling hills through restored savannas, prairies and wetlands. Several bridges lead over small ravines. In the spring, you can spot temporary ponds, which are home to several species of native amphibians like chorus frogs and blue-spotted salamanders. Along the trail, wildflowers like Dutchman’s breeches, wood anemone and jewelweed bloom in the spring.

The packed dirt trails are well-manicured so you can easily maintain your pace without worrying about your footing. Water is available at the Deer Grove East Trailhead on the east side of the loop for a convenient refill about halfway through your run. If you are short on time or looking for less mileage, you can opt for the 5.7-mile Yellow Loop or create your own route from the extensive trail network at Deer Grove.

Palos West Side Tour

    • Location: Burr Ridge, IL in Palos Park, 22 miles southwest of Chicago
    • Length: 12.2-mile round-trip loop
    • Difficulty Rating: Intermediate
    • Best For: A shaded singletrack excursion
    • Dogs: Leashed

One of the more popular multiuse loops at Palos Park, the Palos West Side Tour follows a series of singletrack trails with a few sections of equestrian trails and a quick crossing of 95th Street. The well-traveled trails are easy-to-follow, but are generally uncrowded, allowing you to enjoy stretches of solitude through the forest. On your run, you may spot deer, chipmunks, squirrels and perhaps a coyote. Spring wildflowers and fall foliage make this a pleasant run throughout the year. Water is available at the Bullfrog Lake campground office if you need a refill. Palos Park also features a more extensive trail network, so if the full 12.2-mile loop is too long, you can easily customize the length of your run.

Cowles Bog Trail

    • Location: Porter, IN in the Indiana Dunes National Lakeshore, 47 miles southeast of Chicago
    • Length: 4.7-miles round-trip loop
    • Difficulty Rating: Intermediate
    • Best For: A classic run with stunning views of Lake Michigan
    • Dogs: Leashed

This memorable 4.7-mile run explores several distinct habitats with swamps, ponds, marshes, black oak savannas and the shores of Lake Michigan. In 1965, Cowles Bog was designated as a National Natural Landmark due to its native plant diversity including black oak, red maple and yellow birch trees. A stand of white pines and tamarack trees grow on a floating mat of peat moss in the bog, and the area is now one of the highlights of the Indiana Dunes National Lakeshore.

This isn’t an easy run due to nearly 200 feet of climbing and descending on the steep dunes near Lake Michigan. Make sure to bring plenty of water and sunscreen. Breathtaking views of Lake Michigan and a pleasant run along the shore are your rewards for navigating these strenuous, sandy summits. If you enjoy the challenge of running along the beach, you can extend your run along the shore in either direction before climbing back up the dunes on the Cowles Bog Trail to return to the trailhead.

Matthiessen State Park Loop

    • Location: Deer Park, IL in Matthiessen State Park, 96 miles southwest of Chicago
    • Length: 2.7-mile round-trip loop
    • Difficulty Rating: Intermediate
    • Best For: A rocky, rooty obstacle course that will help you hone your coordination
    • Dogs: Leashed

This loop makes a great outing for more experienced trail runners or advanced beginners. The trails at Matthiessen State Park are filled with rocky, rooty and technical terrain. With a few staircases and some steeper ups and downs, this loop will give you a workout and test your ability to navigate more technical terrain. You will need to watch your footing, and there are sections where you may need to slow down and concentrate on your route choice.

The loop winds through the park’s deep canyons and heads past several waterfalls. Depending on water levels, prepare to get your feet wet at the creek crossings! The unique terrain and beautiful setting of Matthiessen State Park make this a worthwhile run. Finish with plenty of pep? Head back out to tackle another loop or venture out to explore some of the other trails in the state park.

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