The Bucket List: 7 Bike Routes to Explore Chicago

Whether you’re an avid cyclist or just renting two wheels for the day, Chicago is a great city to explore by bike (weather permitting, of course). There are hundreds of miles of on-street bike lanes and off-street trails that provide access to some of Chicago’s best attractions. Here we share seven routes perfect for exploring Chicago on wheels. You can hop on the Lakefront Trail and take in postcard-worthy skyline views along 18-miles of lakefront or head over to Northerly Island to relax in nature before catching a concert at the outdoor amphitheater. There’s also the recently opened “rail-to-trail” project on The 606 that’s begging to be explored. Pick your route and get rolling.

1. The 606 (Bloomingdale Trail)

The 606 is a brand-spanking-new park in the form of a pathway for bikers—walkers and runners are also welcome. The 2.7-mile trail opened in 2015 after more than 10 years of planning. Converted from an old train line running through the city, a ride on The 606 takes you from Humboldt Park to Bucktown while providing ample views of nature, architecture, art and plenty of fellow bikers along the way.
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2. Chicago Lakefront Trail

Lake Michigan is one of city’s greatest assets and there are few better ways to enjoy it than on the Chicago Lakefront Trail (LFT). It’s easy to turn biking the trail into an all day activity. It runs 18 miles along the lakefront and passes multiple parks, beaches and attractions. Stop for a swim at North Avenue Beach or pop into Lincoln Park Zoo. The Shedd Aquarium or Adler Planetarium make a great places to stretch your legs when you ride by Museum Campus. When you get hungry for lunch, aim to stop and enjoy a picnic near Buckingham Fountain in Grant Park. Restrooms, water fountains and concessions can also be found along the way.

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3. Sheridan Road

Where the Lakefront Trail ends, Sheridan Road picks up. Take this route through the city’s northern lakeside neighborhoods and continue on through as many North Shore suburbs as your legs can handle. If Lake Michigan at your side isn’t a clear enough indicator that you’re heading in the right direction, keep your eyes peeled for the green Lake Michigan Cycling Tour signs. There’s no shortage of sights along the way.

Start in Edgewater with a swim at Kathy Osterman Beach (Hollywood Beach) and head north toward Loyola University. Take a slight detour and weave your way through the main campus before heading north out of the city. Northwestern University’s picturesque campus and the historic Grosse Point Lighthouse both make great stops in Evanston. If you have it in you, continue north to Willmette to see the stunning Bahá’í House of Worship designed by Jean-Baptiste Louis Bourgeois. Finally in Highland Park, the stunning outdoor amphitheater at Ravina Festival (open all summer long) makes for a great ending point where you can enjoy a live performance and a wine and cheese picnic under the stars before schlepping your bike back to the city via a Metra train.

4. Divvy

Divvy your way through Chicago using the city’s bike share program. Sign up for a 24-hour pass and you can check out a bike from any of the designated stations in 30-minute increments. With thousands of bright blue cruisers, it’s an easy way to enjoy short tours either around or to and from neighborhoods across the city. If you need some inspiration, start with a tour of Wicker Park and Ukrainian Village before popping into Big Star for tacos and tequila. Alternatively, Choose Chicago recommends a quick riverfront tour starting in the Theater District and ending at Daley Plaza.

5. Northerly Island

Don’t let the name fool you, Northerly Island is actually a 91-acre peninsula and getting both to and around it by bike is easy. Access the island via the Lakefront Trail/Solidarity Drive at Museum Campus and hop on the outer trail that loops the northern end of the peninsula. Don’t hesitate to take a detour using any of the paths that cut away toward the middle. The former site of the Meigs Field airport, today Northerly Island is home to nature trails, prairie, an outdoor amphitheater, art, as well as some of the best skyline views in the city.

6. Cook County Forest Preserve

If you’re really seeking an escape from the city, Cook County Forest Preserve has more than 300 miles of combined trails, both paved and unpaved, near the city. Be sure to bring plenty of water and consider packing a snack. Your ride will likely take you through heavily forested areas and some distance from busy roads and modern conveniences. The north branch trial system starts in the city at Caldwell and Devon avenues and will take you on a 20-mile tour through northwest Cook County. This route brings you by the Chicago Botanic Garden in Glencoe, a great stopping point to stretch your legs while taking in this 385-acre garden.

7. Bike and Brewery Tour

Bike and Brewery is a four-hour booze cruise from the tour company Bike and Roll. The ride will take you through neighborhoods like Pilsen and Chinatown and makes stops at a variety of restaurants along the way where you’ll learn about (and taste) parts of Chicago’s beer history. The best part may be that the ride ends with a tour of Lagunitas Brewing Company.

Paste Travel’s Bucket List columnist Lauren Kilberg is a Chicago-based freelance writer. Her travels have found her camping near the Pakistani border of India and conquering volcanoes in the Philippines.