Great Rides - Chicago, IL

Wondering where to ride? We got you. Check out our curated collection of local road, family, and mountain bike routes. Here, you’ll find the best places to bike in Chicago, IL along with great cycling routes in Chicago and Dupage County. Browse these options for guidance on where to ride in Chicago, GPS files, and metrics on your ride, like distance and elevation.

Here are a few of our favorite Chicago, IL rides.

The Garden Dirt Jumps

Distance: 0 mi
3400 N Rockwell St, Chicago, IL 60618

Andres Bike Park

Distance: 0 mi
1304 Sacramento Dr, Carpentersville, IL 60110

Beulah Park

Distance: 4 mi
1800 Kedron Blvd, Zion, IL 60099

Raceway Woods

Distance: 4.5 mi
State Rte 31, Carpentersville, IL 60110

Saw Wee Kee Park

Distance: 7.1 mi
7050 Sundown Ln, Yorkville, IL 60560

Outback Trail at Imagination Glen

Distance: 9 mi
2275 McCool Rd, Portage, IN 46368

Palos Forest Preserve

Distance: 40 mi
9500 Willow Springs Rd, Willow Springs, IL 60480

Kettle Moraine State Forest

Distance: 50 mi
N9097 Co Rd H, Whitewater, WI 53190

Lakefront Trail to Indiana Out and Back

Distance: 51.3 mi
Elevation: +/- 720 ft
Chicago, IL

Wicker Park to Highland Park

Distance: 46.5 mi
Elevation: +/- 789 ft
Chicago, IL

Wicker Park to Des Plaines

Distance: 29.2 mi
Elevation: +/- 252 ft
Chicago, IL

Lakefront Trail

Distance: 18.3 mi
Elevation: +/- 372 ft
Chicago, IL

Drive-In Bike Ride

Distance: 19.4 mi
Elevation: +/- 253 ft
Chicago, IL

North Beginners Road Ride

Distance: 24.8 mi
Elevation: +/- 545 ft
Chicago, IL

Brewery Out and Back

Distance: 72.9 mi
Elevation: +/- 916 ft
Chicago, IL

Alsip to Joliet

Distance: 59.3 mi
Elevation: +/- 1335 ft
Alsip, IL

Suburban Brewery Tour

Distance: 38.4 mi
Elevation: +/- 1010 ft
Willow Springs, IL

Chicago - North Branch Trail

Distance: 31.2 mi
Elevation: +/- 652 ft
Chicago, IL

The 606 Bloomingdale Trail

Distance: 5.6 mi
Elevation: +/- 29 ft
Chicago, IL

Humboldt Park Loop

Distance: 2.1 mi
Elevation: +/- 49 ft
Chicago, IL

Skokie Valley Trail

Distance: 6.4 mi
Elevation: +/- 29 ft
Chicago, IL

Ice Cream Ride

Distance: 4.7 mi
Elevation: +/- 14 ft
Chicago, IL

Lincoln Park 4.5-Miler

Distance: 4.5 mi
Elevation: +/- 97 ft
Chicago, IL

Busse Woods Loop

Distance: 7.3 mi
Elevation: +/- 111 ft
Cook County, IL

Morton Arboretum

Distance: 4.6 mi
Elevation: +/- 239 ft
DuPage County, IL

Lake Arlington

Distance: 1.9 mi
Elevation: +/- 24 ft
Arlington Heights, IL

Batavia to St. Charles

Distance: 10.6 mi
Elevation: +/- 276 ft
Geneva, IL

Limestone Loop

Distance: 87.9 mi
Elevation: +/- 1577 ft
Chicago, IL

Waterfall Glen Gravel

Distance: 9.3 mi
Elevation: +/- 418 ft
DuPage County, IL

River Trail Gravel Ride

Distance: 107.7 mi
Elevation: +/- 2014 ft
River Grove, IL

Lincoln Square to Kenosha, WI

Distance: 102.2 mi
Elevation: +/- 1327 ft
Chicago, IL