City Cast

The Best Chicago Cycling Routes

Sidney Madden
Sidney Madden
Posted on May 23   |   Updated on June 5
Jacoby on a bike

City Cast Chicago podcast host Jacoby Cochran on King Drive. (Courtesy of Blair Charleston)

Are you participating in the Bike Commuter Challenge? It’s a monthlong competition hosted by the Active Transportation Alliance encouraging Chicagoans to bike to work. City Cast Chicago podcast host Jacoby Cochran cycles a couple of days a week and shared his favorite routes.

Best elevated trail: The 606, aka Bloomingdale Trail

On an old train line, the trail runs from Wicker Park to Humboldt Park. Have a day off? Bike the popular path when others are at work.

Best waterfront path: Lakefront Trail

The 18-mile paved path from South Shore to Edgewater is easy to hop on if you’re on the east side of the city.

Best connecting trail: Burnham Greenway Trail

The tree-lined paths are cool, quiet, and link to longer trails near Wolf Lake and Eggers Grove in Hegewisch.

Best trail following the music: North Branch Trail

Also seeing Ms. Lauryn Hill at Ravinia? Bike 20 miles from North Park to Highland Park — and stop at the Chicago Botanic Garden along the way.

Best nearby nature trail: Salt Creek Trail

From Brookfield Zoo to Busse Woods, the 27-mile trail has a lot of natural beauty to take in, including the Des Plaines River.

Best trail name: Major Taylor Trail

Marshall “Major” Taylor was a Black cycling star in the late 19th and early 20th centuries. His namesake trail from Gresham to Riverdale includes the Calumet River. (There’s a local cycling club named in his honor!)

As for your fav newsletter writer? Well, I’m living proof you can forget how to ride a bike. I'm checking out adult learn-to-ride classes now.

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