The best walking trails for a scenic stroll in Chicago

One of Chicago’s most popular trails—and the site of a former rail line—the 606 spans 2.7 miles across the city’s West Side. Opening to the public in 2015 after a decade of construction, it’s the city’s first elevated park, connecting the Wicker Park, Bucktown, Logan Square and Humboldt Park neighborhoods. In addition to its leafy, two-lane trail, The 606 also offers visitors a chance to check out some temporary and permanent art exhibitions, as well as plenty of play opportunities for kiddos—like the climbing web at Julia de Burgos park.

There are few things in Chicago more enjoyable than spending a day by the lake, and the Chicago Park District’s Lakefront Trail makes it easy to do. The whole trail runs along Lake Michigan's shore for 18.5 miles, from Edgewater Beach down to 71st Street. If you’re not up for conquering the entire trail in one go, stop off at Navy Pier, the Museum Campus or one of the four parks that sit along the trail.

One of the lengthiest trails in Chicago, the North Branch Trail follows the North Branch of the Chicago River, the Skokie River and the Skokie Lagoons. The bicycle trail and walking path stretches across 22 miles of Cook County, starting at Gompers Park on the city’s North Side, and extending all the way up to the Chicago Botanic Garden in suburban Glencoe. The trail was first constructed in the 1940s and continues to grow as time goes on, with recent mileage being added through Gompers Park in 2016. 

Sure, any park is a great place to go for a walk, but Millennium Park—stationed in the heart of the Loop—isn’t just any park. Walkers can take advantage of the area’s dedicated walking paths, which sprawl across Millennium Park’s 24.5 acres. For an even longer stroll, include Grant Park's paths to boost the total route to a 3.5-mile loop.

This historic park boasts a 2.1-mile beach, Prairie-style boathouse and lagoon loop that showcases the city's beautiful foliage and views. Time your trip to Humboldt Park with the onset of fall to see the leaves shift to fiery colors and squeeze in some end-of-season bird watching. At roughly 40 minutes, this walking path is great for beginners or a post-coffee run saunter.

Smack dab in the middle of Chicago's action is one of the city's most scenic walking paths. While seasoned Chicagoans may only consider the Riverwalk to be a tourist trap hosting a steady stream of kayaking and festive boating, the 3.4-mile path has plenty to offer locals. Stroll along the water to enjoy a path lined with inspiring public art, including ART on THE MART and the Vietnam Veterans Memorial Fountain. 

Sure, Navy Pier is a bit of an unconventional choice for a walking trail, but at 3,300 feet long, Chicago’s most famous pier is nearly one kilometer going just one way. Walk to the end of the pier and back, and you’ve racked up over a mile's worth of steps. If you’re hungry from all of that walking, Navy Pier is, of course, loaded with restaurants and rest areas, including the 200-foot-tall Centennial Wheel, a Ferris wheel that offers unmatched panoramic views of the city and Lake Michigan.

At just over a half-mile, the Promontory Point Loop isn't a lengthy walk, but it's one of the most beautiful strolls the city has to offer. Promontory Point—located on the city’s South Side—serves as the southern boundary of Burnham Park, a 598-acre park that runs from Soldier Field down to 51st Street. The tree-lined paved trail—which is at its most beautiful in the fall—has been on the National Register of Historic Places since 2018 and is ideal for a low-key walk.

Chicago has a lofty—and admirable—goal to build one continuous path along the riverfront. They’re not there yet, but the 312 RiverRun brings the city one step closer to realizing its vision. The path is a biking and walking trail that runs for 2.9 miles, starting in Horner Park and ending at Belmont Avenue. The trail also includes the Riverview Bridge, a new addition to the city’s beloved collection of water-spanning bridges, which runs for nearly one-fifth of a mile.

One of the city's newest walking trails, the Big Marsh Walking Trail is a nearly one-mile trail on the city’s far South Side. The walking trail is part of the 300-acre Big Marsh Park in the city’s South Deering neighborhood. Not only is it an ideal walking trail, but the woodchip path also serves as a prime area for birdwatching.

The best way to get to learn about a neighborhood is through the soles of your feet. Thanks to the Wrigleyville Exploration Trail, that's easy to do on the North Side. The trail connects the Wrigleyville neighborhood with Indian Woods Preserve, starting at the corner of Addison and Clark Streets—directly in front of Wrigley Field—and ending at a nature preserve. There are no marked signposts for the trail while walking through Wrigleyville, so it’s important to know beforehand which streets to turn on. The trail can be an out-and-back trail—totaling 15.8 miles—or knock off half of the distance and just walk one way for a 7.9-mile jaunt.

Kick off the day's steps challenge with a two-mile stroll from the Dempster Purple Line station to the Skokie Northshore Sculpture Park. Continue that walk with a self-guided tour along a 2-mile paved loop trail that winds through the park. While not technically located in Chicago, the Skokie Northshore Sculpture Park offers a great opportunity to not only take a walk, but also appreciate some art, passing by works like “Reaper” by Jamie Barber, an alien-like sculpture made out of parts found in salvage yards.