Chicago, once lauded by Bicycling Magazine as the best bike city in the U.S., truly lives up to its reputation. Over the past decade, biking in Chicago has exploded in popularity, transforming the urban landscape. Dedicated bike lanes, both shared and protected, are now commonplace, weaving through the city streets (notably on Dearborn Avenue and Washington and Randolph Streets in the Loop). For an authentic Chicago experience, nothing beats exploring the city on two wheels, especially with the network of urban trails like The 606 and the scenic Lakefront Trail designed specifically for cyclists.
Looking for the best bike routes and cycling events in Chicago? You’ve landed in the right spot. Jump on a Divvy bike, Chicago’s convenient bike-share system boasting over 580 stations and 5,800 bikes citywide, and start your two-wheeled adventure.
Experience Bike the Drive
Cyclists on Lake Shore Drive during Bike the Drive Chicago
Bike the Drive event in Chicago showcasing cyclists enjoying car-free Lake Shore Drive
Each year, Chicago’s iconic Lake Shore Drive transforms into a cyclist’s dream during Bike the Drive. This annual event, typically held at the end of May, closes this stunning lakefront thoroughfare to cars, inviting thousands of cyclists to pedal through a traffic-free paradise. Whether you opt for the full 30-mile route or choose shorter segments at designated checkpoints, Bike the Drive offers an unparalleled way to experience Chicago’s breathtaking lakefront.
Discover the Lakefront Trail
Chicago Lakefront Trail with cyclists and city skyline
Bicyclists enjoying a ride on the Chicago Lakefront Trail with the iconic downtown skyline in the background
Even outside of the Bike the Drive event, the Lakefront Trail provides an exceptional Bike Chicago experience. Stretching 18 miles from the city’s south side all the way north, this paved path offers stunning views of Lake Michigan to the east and the impressive Chicago skyline to the west. Cycling the Lakefront Trail is a fantastic way to immerse yourself in the vibrant spirit of Chicago, passing by harbors, world-class museums, a picturesque golf course, inviting beaches, diverse restaurants, captivating public art and sculptures, historic community hubs, theaters, and even a serene bird sanctuary. Recent improvements, including separate paths for pedestrians and cyclists, enhance safety and ease of use, making it even more enjoyable to embrace Chicago’s urban outdoors.
Explore The 606 Trail
The 606 elevated bike trail in Chicago
The 606 trail, an elevated park and bike path, offering a unique urban cycling experience in Chicago
For a unique bike chicago adventure, venture onto The 606. This innovative 2.7-mile elevated trail repurposed an unused elevated train line that once ran along Bloomingdale Avenue on Chicago’s West Side. Now, it’s a celebrated multi-use path for biking, jogging, and walking, seamlessly connecting the trendy neighborhoods of Wicker Park, Bucktown, Logan Square, and Humboldt Park. Beyond cycling, The 606 offers an observatory for city views, thought-provoking art installations, enriching educational programs, green spaces for relaxation, and various other amenities, making it a community focal point.
Join the Naked Bike Ride
Looking for a daring bike chicago experience? Every June, Chicago hosts its annual Naked Bike Ride. This clothing-optional, free event attracts hundreds of participants in varying degrees of undress and is part of a global movement held in cities worldwide. The ride aims to promote cycling as a sustainable mode of transport and celebrate positive body image. Check-in for Chicago’s Naked Bike Ride begins at 6 pm in the West Loop, with the ride typically taking place from 8 pm to 11 pm.
Cycle the Chicago Riverwalk
Chicago Riverwalk with cyclists and urban scenery
The Chicago Riverwalk, a vibrant pedestrian and cyclist path along the Chicago River in downtown Chicago
The award-winning Chicago Riverwalk offers a wealth of activities, from fishing and kayaking to river tours and riverside dining. Cycling is another fantastic way to experience the Riverwalk. A 1.25-mile path runs along the Main Branch of the Chicago River, and conveniently, a Divvy station is located nearby. Keep in mind that the Riverwalk is primarily a pedestrian zone, so enjoy a slow and leisurely bike chicago ride, taking in the captivating river views, the towering city skyline, and the bustling atmosphere that makes this area a vibrant destination to spend your time.
Explore North Side Bike Trails
For cyclists seeking a more nature-immersed bike chicago workout, explore the North Side Trails. The North Shore Channel Trail leads to the Skokie North Shore Sculpture Park, while the North Branch Trail offers a longer, more immersive experience. A recent extension has created a continuous trail from Foster Avenue all the way to the Botanic Gardens in suburban Glencoe. This gorgeous route winds through the Cook County Forest Preserves, providing opportunities to spot local wildlife like deer, raccoons, and birds of prey. Connect with the North Branch Trail Alliance for organized rides and events along this scenic trail throughout spring and summer.
Anticipate the 312 RIVER RUN
Exciting developments are on the horizon for bike chicago enthusiasts with the upcoming 312RiverRun trail. This project will link three parks – Clark Park, California Park, and Horner Park – with a unified path stretching nearly 2 miles along the Chicago River from Belmont to Montrose. A highlight will be the Riverview Bridge, a unique 1,000-foot winding section crossing the Chicago River, expected to be completed by the end of 2018. Subsequent phases, planned for 2019, will introduce a pedestrian and bike path from California Park to Horner Park, further expanding Chicago’s impressive network of bike-friendly trails.
