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UPDATED JUL 14, 2020

You don’t have to dodge traffic to enjoy biking in Chicago. From the urban trails to off-the-beaten path routes, these are all the best places for a ride.




Running from the South Side all the way north to Rogers Park, it’s no surprise that this 18.5-mile trail is perhaps the most well-known and popular in Chicago. As its name implies, the trail outlines the eastern tip of the city, so you have nothing but clear views of Lake Michigan on one side and a reminder of just how beautiful the Chicago skyline truly is on the other. You’ll also pass wetlands, dunes, beaches, bird sanctuaries, museums, and harbors, so prepare to dismount that bike a few times because you’ll probably want to take a few pics.

The 606 is home to cyclists, runners, and walkers alike in the Humboldt Park, Wicker Park, Bucktown, and Logan Square neighborhoods. The 2.7 miles of elevated trail is a quick (and fit) way to get from east to west while passing several parks, neighborhood overlooks, and an observation deck. And for all you history buffs out there, look for signs describing the trail’s background story; it used to be an old railroad track built in the 1800s, right after the Great Chicago Fire.

Have you biked the downtown Riverwalk since it got a major makeover? If you haven't, you'll notice new bars, restaurants, fishing perches, marinas, and even a water theater, Chicago’s renovated 1.9-mile Riverwalk may be one of the city’s shorter bike paths, but you won’t miss out on any action here. The Riverwalk makes it easy to bike under bridges and through the heart of downtown where you’ll be up close and personal with the city’s diverse architecture and energetic crowds.

If you’re ever looking to bike to Evanston but are bummed that the Lakefront Trail doesn’t stretch quite that far north, fear not — the North Shore Channel Trail does. Starting in Chicago’s Lincoln Square and ending in northern Evanston, you’ll get to bike your way over asphalt, limestone, and dirt. Our favorite part of the trail is that it winds along both sides of the North Shore Channel and the northern tip of the Chicago River, so you’ll witness some wild (literally) nature views that make the mixed terrain totally worth it.

Make a day out of this one because not only is it 33.5 miles, but you’re going to want to stop and smell the roses — and millions of other flowers and plants, too. By that, we mean the 385-acre Chicago Botanic Garden, which will either be at the beginning or end of your journey depending on when you start. Plus, the all-asphalt path makes it easy to soar past the north branch of the Chicago River and Skokie Lagoons, a giant forest preserve, and multiple suburban golf courses. Do they make bike bags that fit golf clubs yet?

Okay, so we’ve been mentioning the Chicago River a lot, but there are actually other rivers in Cook County (shocking, we know), and you and your bike deserve a change of scenery. Luckily, the Des Plaines River has its own trail to make it easy to accomplish. The 56-mile trail runs northeast from Cook County, so you’ll ride across bridges, past wetlands, and next to nature preserves until you reach the Wisconsin border.

Explore one of the few forest preserves in Chicago without even having to get off your bike, thanks to the Major Taylor Trail. Named after the renowned African-American cyclist and civil rights activist Marshall Taylor, this seven-mile trail paves across 257 acres of the Dan Ryan Woods and through seven different neighborhoods on the South Side. You can also find shorter, unpaved trails in the more southern parts of the Dan Ryan Woods.

Do you ever daydream at work about escaping to an island filled with nature, great views, and outdoor-obsessed cyclists just like you? Well, if you work downtown, why not go on your lunch break? And even if you don’t work downtown, Northerly Island (which is actually a peninsula) isn’t hard to find — it’s just east of the Lakefront Path, and slightly south of the Museum Campus. The bike path is only one mile in length, but it loops around 91 acres, so you can turn your daydreams into a reality for as long as you want (or at least until your boss starts getting suspicious).

Bike alongside a Metra train on this 9-mile trail between Wilmette and Highland Park. There’s really no guessing as to where you’re headed on the Green Bay Trail, as each trailhead conveniently coincides with marked Metra stops. And bonus points if you happen to bike the trail during the Ravinia Festival — a string of outdoor concerts that take place in Ravinia Park from June through September, every year since 1905.

Thanks to its name, it’s no secret that you’ll witness many of Illinois’ restored prairie lands on this path (61 miles worth, to be exact). The trail extends from Chicago to the western suburbs, reaching across three different counties (Cook, DuPage, and Kane). Oh, and don’t be shocked if other cyclists aren’t the only people you encounter; horseback riders frequent it as well.

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