The best walking trails for a scenic stroll in Chicago

One of Chicago’s most popular trails, the 606 spans 2.7 miles across the city’s west side. The path was a decade-long project, constructing the path on an abandoned rail line. Completed in 2015, 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 opportunities for kids to have fun like on 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 the shore for 18.5 miles, from Edgewater Beach down to 71st Street. If you’re not up for taking on 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 along the Skokie Lagoons. The bicycle trail and walking path spans for 22 miles across 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 with recent mileage being added through Gompers Park in 2016. 

Of course any park is a great place to go for a walk, but Millennium Park in the heart of the Loop isn’t just any park. Walkers can take advantage of the park’s dedicated walking paths, which span Millennium Park’s 24.5 acres. For an even longer walk, include Grant Park paths as well to boost the total to a 3.5 mile loop.

This historic park boasts a 2.1-mile beach and lagoon loop that shows all the beautiful foliage and views. Plan it perfectly during the fall to see the leaves change while squeezing in some birdwatching. At roughly 40 minutes, this walking path is great for beginners or a post-coffee run saunter.

Right in the middle of the city's action is one of the most scenic walking paths. While you may only see the Riverwalk as a touristy stream of kayaking and festive boating, the 3.4-mile-long path is lined with public art, including Art on the Mart and the Vietnam Veterans Memorial Fountain. 

One of the city's newest walking trails, the Big Marsh Walking Trail is a .8 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 trail also serves as a prime area to go birdwatching.

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 1 kilometer just going one way. Walk to the end of the pier and back, and you’ve racked up over a mile. If you’re hungry from all of that walking, Navy Pier is, of course, loaded with restaurants and areas to rest, including the 200-foot-tall Centennial Wheel, a Ferris wheel that offers panoramic views of the city and Lake Michigan.

It’s not a lengthy walk, at just .6 miles, but the Promontory Point Loop is one of the city’s most beautiful. Promontory Point, on the city’s South Side, is 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 an easy walk.

The city has a goal to have one continuous path along the riverfront. They’re not there yet, but the 312 RiverRun puts them one step closer. The path is a biking and walking trail that runs for 2.9 miles, starting in Horner Park and ending at Belmont Ave. 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.

The best way to see a neighborhood is to just take a stroll through it, and that’s easy to do on the North Side with the Wrigleyville Exploration Trail. The trail connects the Wrigleyville neighborhood with Indian Woods Preserve, starting at the corner of Addison and Clark, directly in front of Wrigley Field, and ending at the nature reserve. 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, totaling 7.9 miles.

It’s a two-mile walk to get from the Dempster Purple Line station to the Skokie Northshore Sculpture Park. Continue that walk on a self-guided tour through the park along a 2-mile paved loop trail. Although not technically 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.