Chicago's Best Bike Rides

By Chuck Sudo in Arts & Entertainment on Apr 17, 2013 4:10PM

With each passing year, Chicago is becoming more bicycle-friendly. Although some may say there's a long way to go, those of us who remember when there weren't designated bike lanes on the city's main arteries marvel at how far Chicago has come.

Bicyclists have had champions in Mayors Richard M. Daley (an avid cyclist) and Rahm Emanuel, who participates in triathlons. Emanuel pledged to add 100 miles of new bike lanes in his first term. With most of those lanes being protected or buffered lanes, Emanuel and Chicago Department of Transportation Commissioner Gabe Klein (an avid cyclist himself) are working to make bicycling safer in Chicago.

In addition to making cycling safer, there are numerous annual rides that put Chicago on display for people with pedal power, plenty of trail rides connecting us from the lakefront to the suburbs, and even off-road rides for those of us who are mountain biking enthusiasts. Here are some of our favorites. If there's a ride you feel we missed, leave it in the comments.

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Thousands of bicyclists take to Lake Shore Drive every Memorial Day weekend for the MB Financial Bank Bike the Drive. (Photo credit: iitichai)

The MB Financial Bank Bike the Drive has grown over the years to become one of the most popular organized rides in Chicago. In my opinion, it rivals New York's Five Boro Bike Tour for pure beauty. Every Memorial Day weekend Lake Shore Drive is shut down for hours to allow tens of thousands of bicyclists free rein of the roadway in 15- and 30-mile loops. I've participated in Bike the Drive multiple times and the novelty has not worn off yet. Depending on how the wind blows, you'll also get a nice workout pedaling against it.
The 2013 MB Financial Bank Bike the Drive takes place May 26.

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The L.A.T.E. Ride (Photo credit: shrosa814)
Now in its 25th year the L.A.T.E. (Long After Twilight Ends) Ride claims Chicago's streets for its own while the city sleeps (and drinks and pukes and hooks up). It's a mostly peaceful ride through downtown, the South Loop and Chinatown, the North side and the lakefront path, ending just as the sun rises in Grant Park. Forget last call — this is the way to go through the night and greet the sunrise.
The L.A.T.E. Ride takes place June 29-30. Register here.

Formerly known as the Boulevard Bike Tour, the Four Star Bike and Chow offers bicyclists a choice of four different rides ranging from 12 to 62 miles. What separates this ride from Bike the Drive and the L.A.T.E. Ride is cyclists share the roads with other traffic, meaning safety and adhering to the rules of the road is paramount. The ride is a great way to experience the north and northwest sides of the city, as well as highlights of the northern border suburbs.
This year's Four Star Bike and Chow takes place Aug. 25. Register here.

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Photo credit: Carlton Hollis
If you're hesitant to negotiate Chicago's streets by bike, consider any of the bike-friendly trails around the city and suburbs. The lakefront trail is a shared route with runners and pedestrians but provides a beautiful view of the lakefront and, if you're traveling south of Museum Campus, a fast connection to Hyde Park, McCormick Place and other points south of Madison Street. The Green Bay Road Trail connects Chicago to the north shore suburbs and is a wonderful workout combining paves and crushed gravel trails. The North Branch trail connects the far Northwest side of the city with the Chicago Botanic Garden via 25 miles of winding lanes through the Forest Preserve system. The Illinois Prairie Path, a 61-mile stretch of bike lanes intersecting Cook, Kane and DuPage counties, is the first successful rails-to-trails project in the country.

For mountain biking enthusiasts, there isn’t much selection but what is available is worth breaking out the fat tires. Kettle Moraine State Forest in southeastern Wisconsin is a short drive away and features 31.5 miles of off-road cycling ranging from novice for new off-roaders to technically challenging trails for cyclists pining for some breathtaking climbs and descents. Easily the best off-road biking closest to the city limits is located at the Palos Forest Preserves. (95th Street and Wolf Road, Willow Springs)

Fixed-gear cyclists are meant to be ridden on banked tracks, not city streets. The Chicago Velo Campus is the first velodrome in the city limits in decades and provides weekly track clinics and races, year-round training and track bike rentals.
The Chicago Velo Campus is located at 8615 S. Burley Ave.

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Time trials on the Chicago Velo Campus's track. (Photo credit: Edmund White)

Mayor Emanuel's pledge to add 100 miles of bike lanes — most of them protected or buffered — means your commute will become significantly easier to handle. The Kinzie Street protected bike lane has already shown dividends and other lanes on Milwaukee Avenue, Elston Avenue, 18th Street, Dearborn Street and 31st Street make connecting to downtown and the lakefront easier and safer. Plans are in place to connect the longer stretches of protected bike lanes.