Section

EEvents

Bike the Drive, night rides, free bike valet and the city's cycling calendar.

Riders filling DuSable Lake Shore Drive in Streeterville during Bike the Drive

Bike the Drive Chicago: Date, Route, Cost and Rules

Bike the Drive closes DuSable Lake Shore Drive to cars for a 30-mile ride. The next ride is September 5, 2027. Start times, route, prices and rules.

Aerial view of Grant Park with Lollapalooza stages set up around Buckingham Fountain

Bike Valet at Chicago Festivals: Lollapalooza and Bike the Drive

Free bike valet at Chicago festivals: where Lollapalooza's valet stood in 2026, what Bike the Drive offers, and where bikes are not allowed inside.

Cyclists stopped beside a paved path on a spring club ride

Chicago Bike Clubs and Group Rides: Where to Join In

Chicago bike clubs and open group rides by day, pace and start point: Chicago Cycling Club, Major Taylor Cycling Club, women's rides, social rides and more.

Stage at Daley Plaza under a Bike Chicago 2011 Bike to Work Rally banner

Chicago Bike Week and Bike Month: Dates, Rallies and Rides

Chicago Bike Week was a City program built around a Bike to Work Rally. Today's flagship is May's Bike Month. Dates, events and the Ride of Silence.

Critical Mass riders gathered with bicycles around the Picasso sculpture in Daley Plaza

Chicago Critical Mass: Time, Route, History and Rules of the Ride

Chicago Critical Mass meets in Daley Plaza on the last Friday of every month. Start time, how the route works, history since 1997 and the Southside ride.

Riders on DuSable Lake Shore Drive with the downtown skyline behind them

Chicago Cycling Events Calendar: Rides, Races and Bike Month

Chicago cycling events by season: Bike Month, Bike the Drive, Chicago Grit, cyclocross and monthly Critical Mass, with the next confirmed dates.

Cyclocross racers carrying bikes up a grassy slope past course tape

Chicago Cyclocross Cup: 2026 Schedule, Categories and Entry Rules

Chicago Cyclocross Cup 2026: race dates through the December 6 Montrose Beach finale, categories, licenses, registration deadlines, points and staging.

Runners on a closed Chicago street during the marathon

Chicago Marathon Road Closures for Cyclists: Where You Can Ride

How the Chicago Marathon closes streets and what cyclists can ride: the 2026 course schedule, open crossings, bike valets, and the ban on bikes on the course.

Fulton Market District arch sign over a brick street in Chicago

Intelligentsia Cup Chicago: Now Chicago Grit, With 2027 Dates

The Intelligentsia Cup criterium series is now Chicago Grit: 10 races in 10 days across Chicagoland. 2027 dates, the 2026 schedule and how to watch or race.

Buckingham Fountain in Grant Park lit at night

The LATE Ride Chicago: History of the Overnight Bike Ride (Ended 2016)

The L.A.T.E. Ride was Chicago's overnight 25-mile group bike ride from Buckingham Fountain. It ended after 2016. How it ran, and where to ride at night now.

Photo credits (10)

Flickr user Wildcat Dunny / Wikimedia Commons · CC BY 2.0 · source
TonyTheTiger / Wikimedia Commons · CC BY-SA 4.0 · source
Oak Park Cycle Club / Wikimedia Commons · CC BY-SA 2.0 · source
Chicago Bicycle Program / Wikimedia Commons · CC BY 2.0 · source
JeremyA / Wikimedia Commons · CC BY-SA 2.5 · source
Kenneth C. Zirkel / Wikimedia Commons · CC BY-SA 4.0 · source
Furmanj / Wikimedia Commons · CC BY-SA 3.0 · source
Benjamin Lipsman / Wikimedia Commons · CC BY 2.0 · source
Bex Walton / Wikimedia Commons · CC BY 2.0 · source
Amaury Laporte / Wikimedia Commons · CC BY 2.0 · source