Make the most of the city’s very best season by hopping on two wheels and exploring these bike routes in Chicago, which include a mix of short, urban paths and longer, lush trails. Whether you’re a seasoned cyclist or just looking for a leisurely ride, these routes offer something for everyone, from stunning skyline views to serene green stretches. There’s no better way to take in Chicago’s vibrant neighborhoods and natural landscapes.
Lakefront Trail
The iconic 18-mile stretch that runs east of Lake Shore Drive, from Ardmore Street on the city’s North Side to 71st Street on the South Side, offers stunning lake and skyline views and nary a stop sign or traffic light — which is the very reason it’s usually super congested. Most times, you need to come armed with lots of patience for cyclists at a variety of skill levels, plus stray runners, walkers and skaters who may occasionally float into the dedicated bike lanes. Our tip: head here super early in the morning to be rewarded with a serene ride and the bonus of a Lake Michigan sunrise.
The 606 Trail
Also known as the Bloomingdale Trail, commuters and recreational cyclists love this 2.7-mile, multi-use path converted from an unused stretch of elevated rail line. Connecting Wicker Park, Bucktown, Logan Square and Humboldt Park, there are parks, gardens, art installations and plenty of scenic views along the way.
Milwaukee Avenue and Leavitt Street access point
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This roughly 20-mile trail runs through the forest preserves along the North Branch of the Chicago River, starting at Gompers Park and extending into the northern suburbs, with a mix of urban areas and long, serene green stretches along the way. There’s a four-mile loop around the Skokie Lagoons and access on the north end to the Chicago Botanic Garden in Glencoe. Bicycle racks near the visitor center offer a welcome invitation to hop off your bike and stroll the lush 285 acres. This is a popular trail for weekend road warriors looking to tackle distance rides.
Burnham Greenway Trail System
Starting at Eggers Grove on the South Side of the city, this 11-mile trail runs through the South Side of Chicago and ends at Green Lake Woods in the suburb of Calumet City, passing through several parks and forest preserves. This trail is part of the larger Burnham Greenway, two portions of a former railroad corridor between Chicago and Lansing, IL, that there are plans to eventually connect.
Burnham Greenway Trail North entry point
Major Taylor Bike Trail
Named for Marshall “Major” Taylor, an African American cyclist who was a world champion in the late 19th and early 20th centuries, this 7.6-mile paved trail stretches from Dan Ryan Woods to the Whistler Woods Forest Preserve in the south suburb of Riverdale, including some segments on street bike lanes, as well as through forest preserves and parks. Running through West Pullman, Beverly and Morgan Park, the path ends in the Whistler Woods Forest Preserve, just across the Little Calumet River.
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