Explore Chicago by Bike

Bikes in the park in Downtown Chicago (Photo: Welcomia/Shutterstock)

Be it the more than 200 miles of on-street bike lanes (make that 645 miles by 2020) or the ever-growing Divvy bike-sharing system (look for the light blue bikes on practically every block), it’s no wonder Chicago is continually recognized by Bicycling magazine as one of the most bike-friendly cities in the country. Whether you own or rent your ride, here are five ways to take in the Windy City on two wheels.

1. Lakefront Trail. Lincoln Park Zoo, Millennium Park, the Museum of Science and Industry — these are just a few of the dozens of landmarks you’ll whizz past along the 18.5-mile Lakefront trail. Lake Michigan serves as a calming blue backdrop. On the north end of the trail, stop for frozen vodka lemonades at Castaways at North Avenue Beach, or head south to Hyde Park, where a cold beer and a hearth-roasted porchetta sandwich are waiting for you at The Promontory restaurant.
2. Pilsen. After you take the Lakefront tour, hightail it to the Divvy stop at Racine and 18th Street in Pilsen. A leisurely ride up and down 18th Street takes you past galleries, taquerias (fuel up with tacos from Nuevo Leon) and colorful street murals. You can set up a bike tour or explore the eclectic Mexican neighborhood on your own.
3. Milwaukee Avenue. Want to see Chicago like a commuter? Then take a ride on Milwaukee Avenue, one of the city’s bike-friendly “spoke routes” with a mile-long stretch of buffered, protected bike lanes. Avoid riding at peak times, as the lanes are subject to crowding. But otherwise, this is a great way to breeze through neighborhoods like West Town, Wicker Park and Logan Square. Stop at one of the bike-friendly cafés along the way, like Ancien Cycles Lounge, where you can snack on chef Kristine Subido’s chicken adobo empanadas.
4. Bloomingdale Trail. Chicago’s even more beautiful from above, so be one of the first to ride along the elevated Bloomingdale Trail, a brand new public park project slated to open June 6. Built on a defunct railroad line 16 feet above street level and running through four northwest neighborhoods, the 2.7-mile trail will pass by six parks, an observatory and art installations.
5. Lincoln Avenue. Another street with a popular designated bike lane is Lincoln Avenue, and you can take it from historic Lincoln Park (grab a Divvy at the corner of Lincoln Avenue and North Clark Street) all the way up to quaint Lincoln Square, passing cafés, antique stores, bars and parks along the way. After you return your bike at the corner of Lincoln Avenue and North Leavitt Street, keep walking past Old Town School of Folk Music and the Merz Apothecary until you reach the Chicago Brauhaus for a celebratory wiener schnitzel.

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