Chicago Cycling Events Calendar: Rides, Races and Bike Month

Chicago does not run on one cycling calendar. A nonprofit owns the spring, a race promoter owns July, a lakefront closure owns Labor Day weekend, and a leaderless monthly ride owns every last Friday. This page puts them in one order and states what each organizer has published.

The year at a glance

Event	Date	What it is
Chicago Bike Month	All of May; 2026 challenge May 11 to June 75	Month of commuter events from Active Trans
Ride of Silence	Third Wednesday in May10	Slow memorial ride
Chicago Grit	July 23 to August 1, 20271	10 days of criteriums
Bike the Drive	Sunday, September 5, 20272	30-mile car-free loop
Chicago Cyclocross Cup	Season finale December 6, 20264	Amateur cyclocross series
Critical Mass	Last Friday of each month3	Social ride from Daley Plaza

Spring: Chicago Bike Month and the Ride of Silence

Active Transportation Alliance frames May as Chicago Bike Month, a month to show the benefits of bicycling and push more people to try it⁵. Its anchor is the Bike Commuter Challenge, a free competition in which Chicagoland organizations earn points by riding⁵. The 2026 Challenge ran May 11 to June 7, and no riding experience was required⁵.

The month also puts pop-up Celebration Stations on commuter routes. In 2026 they stood on the Lakefront Trail at the Field Museum on May 13, on The 606 at Damen Avenue on May 27, and at the Polish Triangle on June 2⁵. Suburban groups add their own slow rolls through the summer, from monthly Friday rides to family outings⁵. Ride Illinois ran its Grand Illinois Bike Tour in Metro East from June 7 to 12, 2026⁵.

The Ride of Silence is the solemn entry. Riders pedal slowly and silently to honor people injured or killed while biking or walking^5,10. In Chicago it falls on the third Wednesday in May and has honored fallen riders since 2005¹⁰. The 2026 ride gathered at Queen’s Landing at 5:30 p.m. and left at 6 p.m.⁵. Attendance is free, and organizers ask riders to register¹⁰.

Chicago once had a City-run Bike Week as well. The City and its Department of Cultural Affairs and Special Events announced Chicago Bike Week for June 10 to 14, 2013, closing with a Bike to Work Rally on Daley Plaza¹¹. The Chicago Bike Week page covers it, and May’s Bike Month is the program to plan around today.

Summer: Chicago Grit

Chicago Grit is a 10-day criterium series that rides through 10 communities and ends in Fulton Market¹. The 2027 edition runs July 23 to August 1, 2027¹. The 2027 flyer appears after registration opens, typically in mid-April¹. The series raced under the Intelligentsia Cup name before its rebrand, and the Intelligentsia Cup page tracks that history.

Pros at Chicago Grit routinely average over 30 mph¹.

Late summer: Bike the Drive

Bike the Drive closes DuSable Lake Shore Drive to cars. The next ride is Sunday, September 5, 2027². The loop is 30 miles, riders may turn around at any rest stop, and starts run from 6:30 a.m. to 10:30 a.m.⁷. Active Trans recommends starting by 8 a.m.⁷. The ride runs rain or shine with no refunds². The full Bike the Drive guide has prices, entry points and the rules.

Festival days compete for the same downtown space. Lollapalooza filled Grant Park from July 30 to August 2, 2026¹². The festival bike valet guide explains where bikes can and cannot go.

Fall and winter: cyclocross

The Chicago Cyclocross Cup’s 2026 schedule lists ten races, and Big Marsh on September 20 was cancelled⁴. Races are held on Sundays, rain, snow or shine, unless noted⁴. The remaining series dates:

Date	Race
October 25	ABD Sycamore Speedway4
November 1	Campton Cross, a Halloween race4
November 7 and 8	Groundhog Psi-clocross; November 8 is the Illinois State Championships4
November 22	Quarry Cross at The Forge4
December 6	Montrose Beach4

An awards party follows in January 2027 on a date still to be set⁴. Dates and venues can change at the last minute, so check the series schedule before you load the car⁴. The Chicago Cyclocross Cup guide covers entry, categories and staging.

Every month: Critical Mass

Chicago Critical Mass starts in Daley Plaza at 6 p.m. on the last Friday of every month³. It has run since 1997, year-round and in all weather: hundreds ride in summer and often a handful in winter³. The route is usually posted on Facebook by the morning of the ride³. Read the Chicago Critical Mass guide before your first one.

The Southside Critical Mass meets on the first Friday of the month at 5:45 p.m. at Nichols Park, 55th and Kimbark, and rolls at about 6:15¹³. It does not ride from December through March¹³.

Events that no longer run

The LATE Ride, a night ride from Buckingham Fountain that benefited Friends of the Parks, held its final edition in 2016⁸. Organizers announced in December 2016 that it would not return in 2017⁸. The LATE Ride history has the details.

Where to find more

Ride Illinois keeps an Illinois Bicycle Calendar of organized and charity rides, races, advocacy events and community slow rolls⁶. Organizers can submit events through an online form⁶. For weekly rides, Half Acre Cycling maintains a list of open group rides for each day of the week, with start points and pace⁹. Its standing rules apply almost everywhere: helmets required, lights for evening rides, and a flat kit in your bag⁹. The group rides and clubs guide picks out the clubs behind them.

For wheels on event day, see the rental pages linked from each guide and the events hub.