Biking in Chicago: How to explore the city on two wheels

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MB Bike the Drive | MB Bike the Drive website

Summertime in Chicago is the perfect time to get up and get active, and what better way to do that than by taking a ride in the city named the most bike-friendly in the United States by Bicycling magazine in 2016.

We’ve got you covered with some suggestions for enjoying outdoor cycling fun, from the most popular to the lesser known, whether you’re an avid rider or newcomer just looking to explore the city on two wheels.

Want to try something beyond the lakefront trail?

The Cal-Sag and Des Plaines River trails offer bikers paved and unpaved options, views of prairies, forests and more.

One of the Chicago area’s newest trails, the Cal-Sag western section opened in 2015 and currently runs 13 miles from Route 83 and Archer Avenue in Willow Springs to Cicero Avenue in Alsip. The paved trail includes scenic views with connections to the Palos Forest Preserve, and the Centennial and I&M Canal trails. 

The Des Plaines River Trail is unpaved crushed stone and most ideal for mountain biking and walking. Extending nearly 52 miles from North Avenue in River Forest to just south of the Wisconsin border, bikers can enjoy forests, prairies, fishing and playgrounds.

Another suburban site is the Illinois Prairie Path, running from Maywood west to the Fox River. The 61-mile trail includes lakes and meadows and splits in Wheaton into the Elgin and Aurora branches, with additional spurs to Geneva and Batavia.

Want to stay in the city?

On May 27 the famous MB Bike the Drive event will give bikers of all skill levels the chance to soak in Chicago’s skyline while cycling nearly five hours along Lake Shore Drive. Free drinks and snacks will be offered at rest stops, and a post-race festival in Grant Park will include a pancake breakfast, electric bike tests, free giveaways, activities for children and live music. Participants are also welcome to join the 30-Mile Challenge during Bike the Drive. All you have to do is make sure to get a 30-Mile Challenge bib during packet pickup before hitting the trail and track your mileage via a smartphone app. All proceeds benefit the Active Transportation Alliance and its mission of improving biking, walking and transit in Chicago.

Cyclists can also partake in the 27th annual Chicago Bike Week June 21-29. The event’s highlight is a two-week-long Bike Commuter Challenge where employers throughout the city earn points by gathering the greatest number of employees to ride a bike to work during the week.

Among the city’s more popular bike destinations is the 606 Bloomingdale Trail on the Northwest Side. The 2.7-mile paved trail tends to be heavily congested with bikers, runners, strollers and dog-walkers. The 606 features five entry and exit spots with Divvy bike stations, including a spot near the middle at Milwaukee and Wabansia Avenues.

Experienced and beginner bikers alike can check out the North Branch Trail, which runs between Gompers Park near Foster and Kostner avenues north to the Chicago Botanic Gardens in Glencoe.

From Gompers Park, a series of streets and trails take riders east to the North Shore Channel Trail that runs north to Evanston. On the north end, a trail along Lake-Cook Road connects the North Branch Trail to the Green Bay Road Trail, From there you can go north all the way to Wisconsin, connecting to the Robert McClory Bike

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