Join Chicago Critical Mass as thousands of bicyclists take over the downtown streets on a leisurely bike ride through Chicago.  The rides take place on the last friday of every month and are completely free and designed for all types of riders.  Chicago's Critical Mass bike rides start from Daley Plaza, Dearborn & Washington at 5:30 pm on the last Friday of each month, regardless of season or weather. Bobby's offers super discounts on Critical Mass Bike Rentals.

Bobby's Bike Hike offers overnight bike rentals, which includes a helmet and lock.

Join up to 9,000 bicyclists on Saturday night/Sunday morning July 11/12 for Chicago's only after-midnight ride through the city!  The 25-mile ride begins and ends in downtown Chicago at Buckingham Fountain.  Experience Chicago's magnificent lakefront bike path under the stars and moon.  Enjoy McDonald's breakfast as the sun rises over Lake Michigan.  Support Friends of the Parks' work to preserve, protect and improve all of Chicago's parks and forest preserves in Cook County. 

This is not a race, but a massive group ride through the City. Bobby's Bike Hike offers $25 overnight bike rentals, which includes a helmet, lock, and Bobby's super customer service.

Attention Chicago Area Hog Fans!  Explore downtown Chicago by bicycle with the Arkansas Chicago Alumni Club on Friday, July 17th.  Bobby’s Bike Hike – Chicago, owned by Arkansan Jeremy Lewno, has put together a tour of the Gold Coast, Chicago River, Millennium Park, Buckingham Fountain, Museum Campus and the gorgeous lakefront.  The tour is designed for all ages and fitness levels, and sure to be fun and informative for both long-time Chicagoans to recent transplants.

Price is $25, which includes a bicycle, helmet, and Bobby’s entertaining tour guides.  Tickets will be $30 day of  the event.  60% of proceeds will directly benefit the Chicago Arkansas Alumni Association.

Don’t miss out on the 21st Anniversary of Chicago Boulevard Lakefront Tour, benefiting the Active Transportation Alliance (formerly the Chicagoland Bicycling Federation). Choose from 15-, 35- or 62-mile routes through the City’s beautiful parks, grand boulevards and wonderful neighborhoods. Bobby's offers super specials on bike rentals, including maps and helmets so you won't miss the Chicago BLT Ride!

South Side Ramble For families and casual riders, this 15-mile route highlights the architecture and history of Chicago’s Hyde Park, Kenwood, Bronzeville and Chinatown neighborhoods. Ride starts between 8:30 and 9:30 a.m.

Boulevard Tour A tribute to Chicago’s famous architects and urban planners, this 35-mile journey winds through its extensive boulevard system and beautiful parks. This ride starts between 7:30 and 8:30 a.m.

Ultimate Neighborhood Ride Designed by the nonprofit Chicago Cycling Club, this 62-mile expedition includes the Boulevard Tour and an additional 27-mile loop through the city (route TBD). Start this tour between 7 and 7:30 a.m.

Includes bicycle, helmet, and lock! Sign up for actual event separately!