Outward Bound: The Best Places to Hike Near Chicago

As fall’s spectacular colors roll in, now’s the perfect time to lace up those hiking boots and explore the great outdoors.

If you’re like most of us, you are well and truly tired of staying at home. But, you also recognize that it’s just not safe to do all of your favorite urban activities. Enter hiking, the perfect safe and socially distant way to get out and get active during a gorgeous time of year. Here, we’re highlighting seven gorgeous hikes that are easily accessible from Chicago and the surrounding suburbs. Just make sure to always wear your mask around other happy hikers! 

The 606 Trail (aka the Bloomingdale Trail)

Length: 5.7-mile loop
Dogs: Yes, leashed
Difficulty: Easy
Location: Downtown, near Walsh Park

This loop is right in the city, so it might be more crowded than other, out-of-the-way spots. Make sure to keep your mask on if you can’t keep 6 feet of distance between you and other walkers. Technically, this is still in the city of Chicago, and it’s more of a walk than a hike. But hey, we don’t judge! This trail was built on an abandoned train line, so it gives you incredible city views as you wind your way around the 5.7-mile loop. It’s a great spot for both walkers and runners, and even features a rubberized running surface. There are a number of access points for the trail, and the fun city views and easy trail make it perfect for a family outing or just a quick walk.

Des Plaines River Trail

Length: 15.4 miles, point to point
Dogs: Yes, leashed
Difficulty: Easy
Location: Trailheads at Allison Woods Trail (Northfield) and Sunset Bridge Meadow Trail (River Grove)

This section of trail is actually part of the far larger Des Plaines River Trail (56.2 miles), but it’s the most easily accessible from the burbs and downtown—you can even take public transportation (either the bus or the Blue Line) to get to the trailheads. This gentle trail is very flat and wide, making it perfect for running or biking if plain old walking isn’t your thing. Enjoy the forest preserves and natural wetlands that surround the trail, and say “Aahhhh.”

Miguel Bandeira

Starved Rock Loop

Length: 5.1-mile loop
Dogs: Yes, leashed
Difficulty: Intermediate
Location: Deer Park

Starved Rock is no secret among the outdoorsy set in Chicago. This gorgeous little loop features rolling hills, a river, a waterfall, and gorgeous canyons and rock formations. This hike is a little bit more challenging (you’ll have to actually walk up a hill—a rarity in Illinois) and there are some rocky sections of the trail where you’ll need to walk carefully, especially in wet weather. Pro tip: Bring some binoculars—Starved Rock State Park is home to several bald eagle families.

Ryerson Conservation Park

Length: 6.5 miles
Dogs: Yes, leashed
Difficulty: Easy/Intermediate
Location: Riverwoods

This pretty little escape through Ryerson Woods feels light years removed from city life, and sections of the trail wind right alongside the banks of the Des Plaines River. You can forge your own route through 561 acres of land via a variety of winding options. Trails can get muddy and sloppy after wet weather, so leave your white sneakers at home.

Matthiessen State Park

Matthiessen State Park

Length: 5.8 miles
Dogs: Yes, leashed
Difficulty: Intermediate
Location: Utica

This is a little bit further afield, but it’s worth it the trek to see the variety of canyons, streams, and untouched forest area in this enormous state park. Don’t miss the gorgeous lookout points over the Vermillion River and waterfalls. The best part of the trail is arguably the sandstone canyon, which you can reach on your 5.8-mile hike (it’s a little hilly and can get muddy, but it’s not overly challenging). Feel free to cool off under the chilly cascades of water if you get overheated during your hike.

Hollows Conservation Area

Length: 3.6-mile loop
Dogs: Yes, leashed
Difficulty: Easy
Location: Cary

This is a pretty darn easy trail, but what really stands out about it is the opportunity for more than just hiking — those among us who enjoy kayaking and fishing will love Lake Atwood, which is stocked every year with bluegill, largemouth bass, and rainbow trout (you can also go ice fishing here in the winter months if that’s your jam). The trail itself is gently rolling and alternates between crushed limestone and a dirt track. Spend a pleasant day wending your way through open, grassy areas and into wetlands and forests.

Cortney Corlew

Indiana Dunes State Park

Length: Varied
Dogs: Yes, leashed
Difficulty: Intermediate/Challenging
Location: Chesterton, Indiana

You’ll need to cross the border into Indiana for this one, so ensure that there aren’t any new travel restrictions in place before you go. Try the West Beach 3-Loop, a 3.5-mile round trip that offers stunning views of the Chicago skyline as you traverse enormous sand dunes. Or, try one of the park’s other offerings, including the West Beach Trail, Ridge Hollow Loop, Cowles Bog Loop (the most difficult of the three), or the Ly-co-ki-we Trail. You can see everything from the skyline to the dunes to boggy wetlands and a wide variety of waterfowl and other wildlife.

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Jessica Suss is a native Chicagoan residing in Washington, D.C. She is currently getting her master’s degree in secondary English education at the University of Maryland. She enjoys petting other people’s dogs and is faithful to Lou Malnati’s alone. Jessica is also a supporter of MAZON and No Kid Hungry



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