Road Biking Trails Near Chicago, IL
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Road Biking Trails Near Chicago, IL

37
Road-Biking
0 - 65 mi
Range
Chicago has 37 road-biking trails. These trails range from 0 to 65.6 miles in length. The most popular trails are Chicago Boulevard Lakefront Ramble, Lakefront North and Lakefront South. Trails.com member RE M. recently completed Waterfall Glen Trail. See all Chicago trails.
Best Trails in Chicago 37 Results
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 PREMIUM MEMBER
While following this winding trail through the diverse and sometimes rugged landscape ...
This ride brings you through some of the best parks just west of Lake Shore Drive. It ...
East of Lake Shore Drive is the land of milk and honey. There's no better place for city ...
Bucktown might more appropriately be called X-town, due to all the Gen-X types that have ...
A bike tour in downtown Chicago? You must be crazy! A reasonable reaction if you've ever ...
The Illinois Prairie Path, one of the first rail trails in the nation, runs along the ...
If you like riparian landscapes, you’ll love the Des Plaines River Trail as it winds alongside ...
The main attractions in Hyde Park are the University of Chicago and the charming neighborhood ...
As you circle the far western edge of Joliet on this ride, you’ll get an inkling of the ...
In 1848 the Illinois and Michigan Canal provided the final shipping link between the East ...
This route is jammed with scenic vistas and fascinating local history. While tracing the ...
This ride takes you through a scenic setting that straddles the Illinois-Indiana state ...
The first part of this ride follows the North Branch Trail, one of the great bike pathways ...
Enjoy a classic Chicago bike ride along the Lakefront Path as it winds past harbors, beaches, ...
This ride opens with a short stint on a heavily wooded section of the Major Taylor Trail, ...
The list of things to see and do along Chicago’s Lakefront Path will make your head spin: ...
Paseo is a hiking and biking trail in Chicago, Illinois. It is 4.2 miles long and begins ...
West 84th Street Path is a hiking and biking trail in Chicago, Illinois. It is within ...
Major Taylor Bicycle Trail is a hiking and biking trail in Chicago, Illinois. It is within ...
This ride reveals a south side of Chicago that is vast and persistently interesting. Visit ...
Enjoy a classic Chicago bike ride along the Lakefront Path as it winds past harbors, beaches, ...
What's more appropriate to say than "Route 66 Rocks"? The mother road, the main street ...
The Logan Square ride is a study in Chicago boulevards. There are few other places in ...
Uptown is what you'd call a vintage ride. It's one of the last great architectural neighborhoods ...
This is a ride for Chicago newcomers who need a quick tour of what's just on the edge ...
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