Best Bike Rides in Chicago: Trails Ranked by Type of Ride

Chicago is an urban biker’s town: greenways, converted rail trails and park paths run through the city, the Forest Preserves of Cook County and dozens of neighborhoods¹. No bike? Rent a Divvy¹. Here is where to ride, sorted by the kind of ride you want. The full list lives in Routes & Trails.

The ride to do first: Lakefront Trail

Start with the Lakefront Trail. It runs from Ardmore Avenue on the north to 71st Street on the south². The route passes Lincoln Park, Grant Park, Burnham Park and Jackson Park and connects most Chicago beaches⁷. Stops worth a break include Promontory Point, the Peggy Notebaert Nature Museum, the South Shore Cultural Center and Jackson Park¹. Since 2018 a separate 18-mile bike trail runs beside the 18.5-mile pedestrian trail². See the Lakefront Trail map and mileage guide for sections.

The short ride: The 606

The 606 is a 2.7-mile rail trail run by the Park District⁶. It sits above city streets, with four neighborhood parks connected at ground level⁴. It opened on June 6, 2015⁶. The trail is open daily from 6 a.m. to 11 p.m.⁴. Pair it with the Bucktown and Wicker Park ride.

The long ride: North Branch Trail

The North Branch Trail runs through deep woods and open fields and is one of Chicago’s premier paved bike trails¹. From Bunker Hill, a ride of 15+ miles on a paved, rolling route reaches the Chicago Botanic Garden³. The shorter Bunker Hill to Linne Woods route covers 8 miles on paved, mostly flat trail³.

Rides on the water

The 312 River Run connects Clark Park, California Park and Homer Park along nearly 2 miles of the Chicago River, from Belmont to Montrose⁵. Its Riverview Bridge is a winding 1,000-foot section that crosses the river⁵.

To the north, the North Shore Channel Trail is a paved path from River Park in Lincoln Square to downtown Evanston¹. It passes through the Skokie Northshore Sculpture Park, which has over 60 works of art¹. For the whole route, read Chicago to Evanston by bike.

Rides on the South Side

The Major Taylor Trail runs between Dan Ryan Woods and Whistler Woods near Calumet Park¹. It is named for Marshall “Major” Taylor, an African American racer and civil rights activist, and it passes murals honoring his life¹.

Forest preserve and day-trip rides

Ride	Length	Surface
Des Plaines River Trail	More than 56 miles, connecting a dozen forest preserves1	Forest preserve corridor1
Cal-Sag Trail	Nearly 14 miles one way1	Paved1
Waterfall Glen Gravel Loop	9.5 miles1	Crushed limestone, 10 feet wide1
Palos Trail System	More than 40 miles1	Unpaved single-track1

Off-road and bike parks

The Palos Trail System has more than 40 miles of unpaved single-track in the southwest suburbs¹. Closer in, Big Marsh Bike Park has six bike trails and other areas to appeal to all kinds of bicyclists¹.

On-street riding downtown

The Loop has several completely protected lanes separated from traffic, including those on Dearborn Avenue and on Washington and Randolph Streets⁵.