Chicago Bike to Work Week: Bike Month, the Challenge and Key Dates

Chicago rides the national Bike to Work Week inside a longer local program. The week sets the date. The month and the Challenge supply the events.

The national week

May is National Bike Month, promoted by the League of American Bicyclists and established in 1956.¹ Its anchor is Bike to Work Week. In 2026 the week ran May 11-17, and Bike to Work Day fell on Friday, May 15.¹ National Ride A Bike Day came earlier, on May 3.¹

Chicago Bike Month

Active Transportation Alliance publishes the Chicago Bike Month calendar. Throughout May, the month provides an opportunity to showcase the many benefits of bicycling.² The suburbs join in. For National Bike to School Day on May 6, the calendar lists schools participating in Arlington Heights, Aurora, Elmhurst, Schaumburg and other suburbs.² Slow rolls run on set Fridays of the month: Cycle Brookfield’s social ride on the first, Ride Riverside on the second, and Streamwood Biking’s family rides on the third.²

The Bike Commuter Challenge

The Challenge is the part that asks something of you. It is a month-long competition in which Chicagoland organizations compete to earn the most points by riding.² It is free.² The 2026 Challenge ran Monday, May 11 through Sunday, June 7.³ Rides to and from work count, plus other work-related trips by bike.⁴

You do not need to be experienced.² Logging a single trip helps your team.⁴

How points work

Action	Points
Each mile ridden	14
Five consecutive trips, weekends allowed	104
First-time bike commuter	254
Attending an event	154
One CTA bus or train trip	154
One Metra Bike Car trip	304

The CTA and Metra bonuses count once each during the Challenge.⁴ Streak bonuses are unlimited.⁴ Active Trans sorts organizations into tiers by employee count and business type.⁴ Riders who log miles by 11:59 p.m. enter a twice-weekly prize drawing.⁴ A Returning Rider raffle draws its winner at random from the top 10 returning riders.⁴

2026 winners

In the 5,000-plus employee tiers, Northwestern University won education institutions with 7,898 points, Rush University System for Health won among nonprofits with 6,252, and Cook County Health won among public agencies with 4,790.³ The Metropolitan Water Reclamation District took the 500-to-2,499-employee public tier with 5,890.³ Working Bikes won the 5-to-24-employee bike-related business tier with 2,435 points.³ The Field Museum took the 100-to-499-employee nonprofit tier with 2,579.³ The Illinois Department of Transportation won the 25-to-99-employee public tier with 478.³

Events worth planning around

Active Trans ran pop-up Celebration Stations in 2026 at three locations, where riders could pick up swag and snacks on the afternoon commute and talk with staff and volunteers.²

• Field Museum, on the Lakefront Trail. Wednesday, May 13, 4:30 to 6:30 p.m.²
• The 606 at Damen Avenue. Wednesday, May 27, 4:30 to 6:30 p.m.²
• Polish Triangle. Tuesday, June 2, 7 to 9 a.m.²

The Ride of Silence on May 20 honors people recently injured or killed while biking or walking.² Chicago riders gathered at Queen’s Landing at 5:30 p.m. and left at 6 p.m.² Participants had to register.² Suburban rides were planned in Arlington Heights, Elgin, Elk Grove Village, Elmhurst, Evanston and Skokie.²

Event parking has a history here. In 2006 the Millennium Park bike station offered free valet bicycle parking during summer performances at Millennium Park and festivals at Grant Park.⁵

Resources for new riders

Active Trans points beginners to Chicago Family Biking, which lists family-oriented rides across Chicagoland, and to Ride Illinois, which offers an interactive bike safety quiz for adults, children, motorists and truck drivers.² It also asks riders to support nonprofit community bike shops.²

How to take part

Start with your workplace. Captains create a team for their organization during registration.⁴ Then read the Chicago bike commuting guide and check bike parking downtown before your first ride. Managers will find the business case in why employers should promote bike commuting. All guides sit in the commuting hub.