Credit: Tomasz Zajda -
Credit: Tomasz Zajda –

Bike to Work Challenge
The annual Bike to Work event now spans two weeks, rewarding commuters for putting down the Ventra card or the car keys and picking up a helmet and U-lock. Prizes will be awarded; more information can be found at Through-Fri 6/29, kick-off rally (date to be rescheduled) Daley Plaza, 50 W. Washington, 312-346-3278, free. 

Chicago’s Mellowest Bike Tour Learn more about our bike map from its creator, John Greenfield—who guides cyclists through some of his preferred routes. Wed 6/27, 6 PM, Daley Plaza, 50 W. Washington, 312-560-3966, Active Transportation Alliance

Critical Mass At this monthly group ride, bikes of all shapes and sizes join forces and stop traffic via . . . critical mass. Camaraderie is encouraged; old-timey bikes are a given. Fri 6/29, 6-11 PM, Daley Plaza, 50 W. Washington, 312-346-3278,, free.


Dare2tri Tandem Bike Training Grab a buddy and hop on a bicycle built for two. Dare2tri, an organization that organizes outings for folks with physical disabilities, offers training on how to ride tandem, plus information about volunteering. Arrive promptly at 10 AM. Sat 6/30, 10 AM-noon, Wilson at Lake Shore Dr, free.

Illinois Beach State Park Bike Adventure Experience an overnight stay at the Illinois Beach State Park, located north of the city along Lake Michigan near Zion. Of course, you’ll arrive via bike, and along the way guides will point out the sights and scenery of northeast Illinois. Participants return by train, and there’s an option to spring for a hotel if sleeping in nature isn’t your thing. Campfire included. Sat 6/30, 7 AM-Sun 7/1, 6:11 PM, Buckingham Fountain, 500 S. Columbus, 312-555-1212, $80.

Louis Sullivan Architecture Tour This guided bike tour heads from the north side down to the Loop, with many stops along the way to admire Louis Sullivan’s work. RSVP is required; visit to sign up and learn the starting location. Sun 6/24, 9 AM-2 PM, location TBA, free.

Pothole Art Bike Tour Cruise around Edgewater scoping out potholes that have been decorated by artist Jim Bachor—described by the website the Chainlink as “stunning and sometimes snarky mosaic works.” The entry fee includes a sticker designed by Bachor. Sun 7/1, 9 AM-5 PM, Broadway and Thorndale, $25.

Tour de Fat Prepare your bike for a parade! The annual Tour de Fat offers beers, live music by Best Coast, and camaraderie among fellow bike enthusiasts. Beer proceeds benefit West Town Bikes. Sat 6/30, 10 AM-5 PM, ride begins at 11 AM, Humboldt Park, 1440 N. Sacramento, 312-742-7549,, $15.

Women and Trans Night BYO bike project to West Town Bikes Wednesday nights, when only women and trans individuals are allowed. Instructors are on hand to assist with everything from brake adjustments to larger-scale repairs. Attendees are encouraged to bring snacks and drinks. Wednesdays 7-10 PM, West Town Bikes, 2459 W. Division,, $10 an hour.