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Biker on trail
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9 Chicago bike trails for a long ride

Craving an extended afternoon of pedaling? Cruise through these scenic Chicago bike trails in and around the city.

Zach Long
Written by
Zach Long
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Getting on your bike and going for an extended ride can be a great way to unwind, but cruising through the streets (and traffic) of Chicago isn't usually very relaxing. Thankfully, you'll find amazing bike trails in and around Chicago that allow you to go for a long ride without having to dodge cars. You'll find routes that run north, west, south and along the lakefront, allowing you to take in amazing skyline views, stop for a drink at Chicago breweries or snag a slice at Burt's Place, which offers some of the best pizza in Chicago. We've tracked down the mileage of each trail and the sights you can expect to encounter along the way—now it's up to you to get in the saddle and explore these scenic Chicago bike trails.

Best Chicago bikes trails for a long ride

  • Attractions
  • Parks and gardens
  • North Park

15.9 miles (plus 4-mile loop)

Beginning in Gompers Park and stretching all the way north to the Skokie Lagoons, the North Branch Trail runs for nearly 16 miles, following the path of the North Branch of the Chicago River. The paved portion of the trail is perfect for biking, roller blading, running or walking, taking you through forests in Nile, Skokie, Morton Grove and Winnetka. The trail ends with a four-mile loop around the Skokie Lagoons, which can also be used to get to the nearby Chicago Botanic Garden.

  • Things to do
  • South Shore

18.5 miles

Stretching from Hollywood Avenue on the North Side to 71st Street to the south, the Lakefront Trail is a great way to experience one of Chicago's crown jewels: Lake Michigan. It also serves as a reminder for residents of why our city, edged by sparkling blue water, is a pretty nice place to live. Whether you walk, run, blade or bike, be alert and cautious: Some cyclists fly down the path as if competing in the Tour de France, while other pedestrians saunter along, oblivious to the flow of traffic. We recommend the scenic, less-crowded south shore portion of the trail, which boasts some phenomenal skyline views.

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  • Attractions
  • Sightseeing
  • Ashburn

7.6 miles

Named after African-American cyclist Marshall “Major” Taylor, who set world records and broke racial barriers in competitions in the late 1800s, this path winds through forest preserves, parks and neighborhoods on Chicago's Far South Side. Beginning in the Dan Ryan Woods at 81st Street, the Major Taylor Trail goes south to 95th Street, at which point it follows on-street bike lanes until resuming an off-street route at 105th Street. Running through West Pullman, Beverly and Morgan Park, the path ends in the Whistler Woods Forest Preserve, just across the Little Calumet River.

  • Attractions
  • Sightseeing
  • Suburbs

56 miles

Ready for a ride to the Wisconsin border? The Des Plaines River Trail follows its namesake waterway all the way from Elmwood Park to the small community of Russell, Illinois—just south of the Wisconsin state line. It's a 56-mile trek that winds through a variety of forests and parks, including the Gurnee Woods Forest Preserve, Adler Memorial Park and the Ryerson Conservation Area. Don't forget to pack a few extra water bottles!

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13 miles

Following the Calumet River past the Sag Quarries, the Cal-Sag Trail will eventually allow cyclists to travel between Lemont, IL and Calumet City, IL (near the Indiana border). For now, this mostly-paved trail gets you as far as Freedom Park in Alsip, IL—the remaining 13 miles of the trail are still under construction. When the eastern section is completed, the Cal-Sag Trail will pass by the Whistler Woods Forest Preserve, where you'll be able to connect to the Major Taylor Trail. Parking is available at Sag Quarries, but if you don't feel like driving, you can take the Metra Heritage Corridor to Lemont and find your way to the Cal-Sag Trail.

  • Attractions
  • Sightseeing
  • Lincoln Square

7 miles

Following the North Branch of the Chicago River, this paved trail begins in River Park and heads due north to Evanston, depositing you at Green Bay Road. Along the way, you'll cross the recently completed Lincoln Village Pedestrian Bridge, breeze through Legion Park, gaze at the chain restaurants surrounding Lincolnwood Town Center and take in the public art on display in the Skokie Northshore Sculpture Park. If you bike to the end of the trail, you could continue north to the Bahá'í House of Worship in Wilmette or catch a ride home from the Central Street Metra or Noyes Purple Line stations.

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  • Attractions
  • Sightseeing
  • Suburbs

27–30 miles

The first rails-to-trails project in the United States, the Illinois Prairie Path is a network of trails that runs through many of Chicago's west suburbs. The crushed limestone path begins in Maywood (just west of Forest Park where the CTA Blue Line ends) and runs 16 miles to Wheaton, where it branches off into trails that will take you to Elgin, Aurora, Batavia and Geneva. True to its name, the various routes pass through some sections of restored prairie wildlife as well as several parks.

8.9 miles

Connecting Wilmette and Highland Park, the Green Bay Trail is a great way to explore the North Shore—especially if you've already made the trip to the nearby Bahá'í House of Worship. The trail begins in front of Wilmette's Village Hall, following the Metra's Union Pacific / North Line. Most of the trail is paved, with the exception of a portion netween Glencoe and Highland park that is covered in crushed stone. Along the route, you'll pass Ravinia Park (home of the Ravinia Festival), various country clubs and a trail at Country Line Road that will take you to the Chicago Botanic Garden.

 

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  • Attractions
  • Sightseeing
  • North Park

6 miles

If you're looking for a direct route to Skokie from the Far North Side, you can't beat the Valley Line Trail (a.k.a. the Skokie Valley Trail), a paved path that runs through Sauganash and Lincoln Wood on its way to the Northern suburb. If you're coming from Chicago, you can hop on the trail just to the east of Bryn Mawr and Kostner avenues, continuing north past greenspaces like Sauganash Park and the Emily Oaks Nature Center. The trail appears to end just past the Skokie-Dempster Yellow Line station, but there's an extension farther north at Golf Road and Laramie Avenue, taking you under I-94 to Old Orchard Road.

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