Best Walking Trails in Chicago

When you want to get outside, enjoy some fresh air, and explore Chicago, you can check out one of the city’s many walking trails. Whether you want to take a leisurely stroll along the water or join the hustle and bustle of the city, there’s a walking trail that’s right for you. Review this guide to learn about seven of the best walking trails in Chicago.

Lakefront Trail

The Chicago Lakefront Trail

Chicago Lakefront Trail, Chicago, Illinois by kenlund Licensed With CC BY-SA 2.0

The Lakefront Trail is one of the city’s most popular trails. The 18-mile paved trail features stunning views of Lake Michigan, providing the perfect scenery for your next walk or hike. You can walk past many of the city’s lakefront neighborhoods, including Uptown, Lakeview, and Lincoln Park. The trail also connects to various city parks and beaches.

Many people use the trail during the day, including commuters, runners, and bikers, though there’s plenty of room for walkers. The trail extends from Ardmore Avenue in the north to 71st Street in the south. It’s dog-friendly and wheelchair accessible. You can use the trail year-round, though it’s best enjoyed in the warmer months of May through October.

Location: 2529 E. South Shore Drive (south trailhead)

Hours: Open 24 hours

Chicago Riverwalk

Take urban hiking to the next level on the 1.25-mile Chicago Riverwalk. This popular trail is divided into four districts: the Confluence, Arcade, Civic, and Esplanade. Along the trail, you’ll view the city’s modern architecture amid the backdrop of the beautiful Chicago River. There are also many restaurants along the trail, so you can make a quick stop to refuel or end your walk with a gourmet meal.

Walkers and runners primarily use the trail. Dogs are allowed if they’re kept on a leash at all times. It’s wheelchair accessible, with ramps on State, Clark, and Franklin streets. The Chicago Riverwalk is open all year long.

Location: 306–370 W. Wacker Drive

Hours: 6 a.m. to 11 p.m. daily

Lincoln Park Trail

Enjoy a scenic walk through Lincoln Park, the largest public park in the city. The 5-mile Lincoln Park Trail takes you past many of the city’s top attractions, such as the Lincoln Park Zoo and the Chicago History Museum. Along the trail, you’ll also enjoy Victorian architecture, sweeping city views, and lush outdoor spaces, including the vibrant outdoor gardens of the Lincoln Park Conservatory.

The Lincoln Park Trail can be used for walking, running, or biking. Dogs are allowed on the trail. It’s wheelchair accessible, with designated spaces in a parking lot off North Clark Street near the southwest end of the trail. There are also plenty of benches to sit on and rest while you enjoy your walk.

Location: 500–5700 N. Lake Shore Drive

Hours: 6 a.m. to 11 p.m. daily

Bloomingdale Trail

An abandoned rail line on Chicago’s Northwest Side is now the Bloomingdale Trail, a 2.7-mile recreational trail. It’s the centerpiece of The 606, an alternative transportation corridor connecting four neighborhood parks, an observatory, and art installations. Along the path, you can enjoy wide-open green spaces interspersed with city views. There’s even a dog park along the trail if you want to bring your furry friend.

The Bloomingdale Trail is 10 feet wide, with 2-foot running tracks along both sides. All users are welcome to use the trail. It’s also the ideal spot for a picnic, with plenty of benches and tables located along the trail.

Location: 1805 N. Ridgeway Ave. (west trailhead)

Hours: 6 a.m. to 11 p.m. daily

Wrigleyville Exploration Trail

Sports lovers will enjoy the Wrigleyville Exploration Trail, which begins at the iconic Wrigley Field, home of the Chicago Cubs. The nearly 16-mile trail extends north to the Indian Woods Preserve. While you walk on this trail, you’ll enjoy plenty of scenic views and vibrant green spaces. Parts of the trail offer ideal locations for bird watching, so bring your binoculars and take some walking breaks to enjoy the scenery.

Walkers, runners, and bikers can use this trail. Portions of the trail are paved, while other parts run along the sidewalk. It’s dog-friendly and wheelchair accessible. There are designated accessible spaces in a parking lot off West Addison Street at the southeast end of the trail.

Location: 3556 N. Clark St.

Hours: Open 24 hours

Humboldt Park Beach Loop

When you want to escape the activity of the city, take a walk along the Humboldt Park Beach Loop. This 2.1-mile trail, located at Humboldt Park, offers views of several lagoons, historic buildings, and vibrant wildflowers. Enjoy peace and tranquility as you watch a variety of wildlife, including ducks, geese, and other birds. When you’re finished with your walk, you can even cool off with a quick dip in the natural swimming pond.

People use the trail for walking, hiking, running, and fishing. The trail is almost entirely paved and has accessible beach walks. Dogs are welcome on the trail if they’re leashed. It’s also a family-friendly trail, with playgrounds along the walking path and access to the beach area.

Location: 1400 N. Humboldt Drive

Hours: 6 a.m. to 11 p.m. daily

312 RiverRun

The 312 RiverRun, which fully opened last year with the completion of a pedestrian bridge, runs along the Chicago River. It extends nearly 2 miles and connects four neighborhoods to three city parks. You can walk the entire trail without having to cross a single street. While walking along the trail, you’ll also have access to various other park amenities, including baseball and softball fields, playgrounds, tennis courts, an indoor ice skating rink, and an outdoor pool.

Walkers, runners, and bikers can enjoy the fully paved path. Dogs are allowed if they’re on leashes. The trail is wheelchair friendly, with accessible spaces in a parking lot off West Belle Plaine Avenue at the trail’s north end.

Location: Access the trail from Clark, California, or Horner parks

Hours: 6 a.m. to 11 p.m. daily

Now that you know all about some of the best walking trails in Chicago, where do you plan to take your next walk? If you’re a local, did we miss one of your favorite trails? Send us a message and let us know. We’re always excited about finding new trails so we can get some exercise while exploring this wonderful city.