Chicago Biking Events

chicago bike events

Bike the Drive
What better way to start off the summer than by kicking the cars off Lake Shore Drive and biking along Chicago’s beautiful lakefront? Bike the Drive is a great event for everyone from children on training wheels to dedicated cyclists. This fundraising event benefits and is organized by the Active Transportation Alliance, which works to improve biking, walking, and transit in the Chicago area.

It all starts downtown at Columbus and Jackson — keep in mind that riders can only enter Lake Shore Drive at designated locations to ensure safety. Rider registration numbers and helmets are also required. The Drive opens to bicyclists at 5:30am. Rest-stops along the way manned by hundreds of volunteers provide water and assistance. Entry to the Drive closes at 9am, and by 9:15 bikers must begin to move off to the Lakefront trail.

At 10:30am car traffic resumes on Lake Shore Drive… but don’t worry; the fun doesn’t end there! From 8am-noon participants can enjoy a cheap all-you-can-eat pancake breakfast from Goose Island, music, and family activities.

The 2010 Bike the Drive will take place on May 30, and registration is already open for all you eager bikers! You can also save $5 if you sign up before February 28. For more information or to register for the ride, visit

L.A.T.E. Ride
L.A.T.E. Ride is an annual event that is hosted by and benefits Friends of the Parks, a non-profit parks advocacy group in Chicago. Every year since 1989 nearly 10,000 people join in on the ride, making it the city’s biggest charity bicycle ride.

On the evening of the Ride, participants meet at Buckingham Fountain starting at 11pm to pick up their Rider Goody Bag and information packet. If you haven’t registered yet, you can do so on arrival. Between 11pm and 2am bikers will be able to enjoy a live band at Buckingham Fountain, hang with friends, and even have the chance to win prizes for “Best Lit Bike” and “Best Decorated Helmet.”

At around 1:30am riders are released in intervals (to avoid crowding) depending on what group you’ve been placed in. Then comes the really fun part: participants embark on a 25-mile ride through the city of Chicago. Passing along the lakefront, through city streets, by Greek Town, and swerving between skyscrapers makes this ride one of the most interesting you’ll ever do in Chicago. Not to mention it’s in the middle of the night!

Cycling at your own pace (remember, it’s not a race!) you can plan to finish between 3:30am and 6am, at which point you’ll be treated to a well-deserved sunrise breakfast at Buckingham Fountain.

The 2010 L.A.T.E. Ride will happen on Saturday, July 10 – Sunday, July 11. Be sure to rest up the day before, and if 25 miles is more than you’ve ridden in a while, you may even want to do a bit of training in the weeks before. Keep in mind that helmets are always required. For more information or to register, check out

Bike to Work Week
You may have heard of National Bike to Work Day, but Chicago (as always) takes it one step further. Bike to Work Week is exactly what it sounds like — a week dedicated to encouraging Chicagoans to ditch the car, the L, or the bus for the week, and ride their bikes to work. Not only is it a wonderful thing to do for the environment, it’s a great way to get your daily exercise in! So pat yourself on the back and take a week off from the gym!

Another effort by the Active Transportation Alliance, Bike to Work Week consists of several events, all in an effort to encourage bike commuting. The central activity of the week challenges companies to compete with each other to see who can get the most employees to bike to work that week. Each business selects a team leader, who submits their results. And winners don’t just get bragging rights for being the greenest and healthiest business in the city — they also get some cool swag from program sponsors.

A good workout, saving the world, and free stuff… what more reason do you need? The event takes place in June. Stay tuned for more specific dates, or check out the event website here.

World Naked Bike Ride
Ride “as bare as you dare” through the streets of Chicago. World Naked Bike Ride asks you to take a stand in the boldest way possible. This worldwide event occurs simultaneously in 70 cities, with the intention of promoting both safer streets for bikers and a positive body image. Who can argue with those goals?

Though the event is certainly NOT for everyone, it is executed by a group of welcoming people who’s keyword is “responsibility.” The event slogan is “Celebrating the end of oil and the beauty of people.” If you’ve got a hippy side to you, believe in the cause, or just want to go for a liberating ride, then join in on this international phenomenon. The only rules? Be nice to everyone, and leave no trace.

The next Naked Bike Ride will go down on Saturday, June 12, 2010. Gathering beforehand from 6pm-9pm (including body painting! Awesome.) and the ride itself runs from 9pm-midnight. The location is not disclosed until a few days before the ride, and only to those who have registered on the event’s mailing list, so as to avoid creepsters showing up for the wrong reasons.

If this sounds like your jam, then go for it. Just be forewarned — you must be prepared to bike up to 20 miles… perhaps sans underwear. A little extra seat cushioning could do wonders. Just sayin’…

For more info on biking in the city, check out our article on that very topic.

Happy Biking!

Jackie Berkery

About Jackie Berkery

With a strong phobia of cubicles and those three little words (“nine to five”), I am thrilled to be working on UPchicago from the comforts of my own couch at three o’clock in the morning. I love to write. I love Chicago. Hello, dream job!

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