The best bike trails in Chicago for a long ride

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.

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 Niles, 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.

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.

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!

2.7 miles

While it may be one of the most urban and shortest bike trails in the area, the Bloomingdale Trail (known as "The 606" by locals) does give unbeatable views from the city's old Chicago & Pacific Railroad tracks. Packed with entry points, public art and green space, The 606 is probably the best trail for a casual bike ride. Spanning from Ashland Avenue in Bucktown to Ridgeway Avenue in Humboldt Park, the trail passes by some of the city's best restaurants, offering plenty of opportunities to refuel and recharge.

26 miles

Following the Calumet River past the Sag Quarries, the Cal-Sag Trail allows cyclists to travel between Lemont, IL and Calumet City, IL (near the Indiana border). The path passes by the Whistler Woods Forest Preserve, where you can 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.

44 miles 

Running north to south from Oswego to Algonquin and hugging the Fox River, the Fox River Trail is over 40 miles of mostly flat paved and unpaved rail-to-trail path. Passing through numerous western suburbs, you can cycle the path all at once or break in pieces with time for short detours. Hitting up the many breweries along the way—Two Brothers Roundhouse is a must see—makes a perfect boozy day trip, and if you’re seeking a different kind of adventure, there’s plenty of history and historic districts to keep it educational, too.

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.

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 between 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 County Line Road that will take you to the Chicago Botanic Garden.

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 Lincolnwood 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.

11.5 miles

The Burnham Greenway Trail System covers over 11 miles of paved path connecting Eggers Grove with the Thorn Creek Trail System on Chicago’s far South Side, just minutes from the Indiana border. You’ll pass by William W. Powers State Recreation Area, the only state park within the city limits, where you can fish and relax near Wolf Lake. Be warned—with different management entities along the way, it can feel disjointed, and the street crossings and residential areas make this trail more apt for leisure than serious training.

87 miles

When the I&M Canal (Illinois and Michigan Canal) was completed in 1848, it finally connected the Great Lakes with the Mississippi River and among other lasting impacts, solidified Chicago as a major trading hub, and later, great metropolis. Today, though this canal is no longer in use, you can clock some major miles following 87 miles of waterway from Willow Springs to LaSalle along mostly paved and some crushed gravel paths. Refuel along the way at breweries, stop by museums or enjoy short jaunts into the many green spaces.

13 miles 

Elk Grove’s Busse Woods may be minutes from O’Hare, but you’ll feel worlds away. The flat, foliage-thick trails in the 3,558-acre preserve bring you alongside pre-European trees like oaks, elm, maple, ash and more, as well as birdwatching and even elk sightings. A combination of flatwoods, upland forest and marsh, the 7.3-mile red paved loop offers sightings of these unique landscapes. After your ride, stick around for fishing or boating at the reservoir.

21.9 miles

Nature lovers, take notice. With a combined 21.9 miles of paved and unpaved trails, cyclists and mountain bikers have many opportunities to spot grebes, ducks, state-endangered blackbirds, herons and more in the 1,800 acres of Paul Douglas Preserve in Hoffman Estates. Leisure road bike riders should stick to the 6.5-mile red outer loop while mountain bikers can opt for several other single-track trails of 1-4.5 miles traversing grasslands, hills and wetland viewing.

16.4 miles

West of the city, there are 16.4 miles of paved and unpaved trails along the Salt Creek Trail System from Western Springs to Lyon. Crossing through Brookfield, Forest View, La Grange Park, Riverside and more, you’ll cross lush forest preserves, off-the-beaten path hiking trails and canoe launches. For a family-friendly day trip, take the 7.1-mile paved red trail from Brookfield to Western Springs and back, ending your outing with a visit to Brookfield Zoo.

22 miles

This early indigenous trail was once an old railway route that connected Chicago Heights and Joliet. The 22-mile route gives striking views of classic Illinoisian prairie grass, monstrous oak trees and sugar maples. Stop through quaint and historic towns like Frankfurt, where a local farmer's market convenes every Sunday during the summer. Bird-watching cyclists rejoice: The trail passes through Old Plank Road Prairie Nature Reserves, home to over 170 different bird species.