Chicago Cycling Events in 2025

Chicago is set to host exciting cycling events in 2025, offering riders of all skill levels the chance to enjoy scenic routes, races, and community rides.

Major Chicago Cycling Events in 2025

Chicago hosts some of the most exciting cycling events each year. However, dates are tentative and subject to change, so always confirm details with the official event organizers before participating.

Bike the Drive

Held in June, this event lets riders enjoy a car-free road along DuSable Lake Shore Drive. Cyclists of all ages can enjoy breathtaking views of Chicago, IL.

Tour de Fat Chicago

This fun-filled bike event combines a community ride with live entertainment, great food, and a costume contest. It helps support the Active Transportation Alliance and local cycling groups.

Chicago Grit

This challenging race pushes riders through off-road and gravel trails around Chicagoland. It’s perfect for cyclists who love adventure and want to test their endurance.

L.A.T.E. Ride

A unique nighttime ride through Chicago, this event takes cyclists on a scenic tour past famous landmarks. Expect great views and a lively atmosphere throughout the night.

Chicago Triathlon Bike Course

This bike leg, part of the Chicago Triathlon, offers a well-organized, competitive race along city streets. It attracts cyclists from around the world every year.

Other Notable Races and Rides

Chicago hosts many organized and charity rides throughout the month and year. Always click official sites for updates, date changes, and new events added to the cycling calendar.

Types of Cycling Events in Chicago, IL

Chicago hosts various cycling events, from competitive races to casual rides. Whether you prefer long-distance routes or social group rides, there’s something for every rider.

Organized Road Rides

These long-distance rides take cyclists through scenic roads with support stations and traffic control. Events like Bike the Drive offer a chance to enjoy a safe, organized ride.

Group Rides

Local bike shops, clubs, and social groups host casual rides for riders of all skill levels. These events help riders connect, improve their cycling skills, and enjoy exploring Chicago, IL.

Road Races

Competitive road races attract both amateur and elite cyclists. These fast-paced events occur on closed roads and often feature multiple distances and categories for different skill levels.

Mountain Biking Events

While Chicago is flat, mountain biking fans can find off-road events and gravel rides in nearby areas like the Palos Trail System, offering technical challenges and scenic views.

Cyclocross Races

These off-road races involve obstacles, mud, and fast-paced laps. Events like the Chicago Cyclocross Cup bring together competitive riders for exciting fall-season races.

Bike Tours and Festivals

Some events combine cycling with food, music, or sightseeing. The Tour de Fat and various brewery tours allow cyclists to explore the city while enjoying fun activities.

Safety Tips and Illinois Biking Laws

Proper planning is essential for a safe and enjoyable Chicago cycling event. Whether you’re joining a tour, race, or group ride, following safety guidelines and understanding Illinois bicycle laws helps ensure everyone’s safety.

• Before any ride, inspect your bike for issues. Check tire pressure, brakes, gears, and the chain to prevent mechanical failures. A well-maintained bicycle improves performance and reduces accident risks.
• Wearing a helmet is strongly recommended and required for some events. Illinois law (625 ILCS 5/11-1507) requires a front white light and rear red reflector for night riding. Carry a repair kit for minor fixes.
• Under the Illinois Bicycle Rules of the Road, cyclists have the same rights and responsibilities as motor vehicle drivers. Cyclists must ride in the same direction as traffic, use bike lanes where available, and obey all traffic laws.
• When riding in a group (625 ILCS 5/11-1505.1), communicate using hand and arm signals and call out hazards. Ride in a single lane subject to road width and maintain a steady speed.
• Most organized events require signing a waiver. The terms outline liability responsibilities in case of an accident, so read them carefully.
• Proper hydration and fueling are key for endurance events. Drink water regularly and consume energy-rich snacks during longer rides to maintain stamina.

What to Do if You’re Involved in an Accident During a Cycling Event

Accidents can happen, even during well-organized cycling events. Knowing what steps to take can help protect your health and legal rights.

• If you’re injured, move to a safe area and seek medical attention immediately. Even if injuries seem minor, some conditions, like concussions or internal damage, may not be immediately apparent.
• Notify event staff so they can document the incident. If the accident involves a motor vehicle or severe injuries, call the police to file a report.
• Get names and contact details from witnesses and anyone involved in the accident. If a motor vehicle was involved, collect the driver’s information, including insurance details.
• Take photos of the bike, injuries, road conditions, and any fixed or moving objects that contributed to the accident.
• If your injuries result in medical expenses or lost income, consulting an attorney may help. A Chicago bicycle accident attorney can guide you on your legal options and ensure you receive fair compensation.

Expert Legal Counsel if You’ve Been Injured During a Cycling Event!

If you were injured during a Chicago cycling event, Rosenfeld Injury Lawyers is here to help. Our experienced Chicago bicycle accident attorneys fight for injured riders, ensuring they receive compensation for medical expenses, lost wages, and pain and suffering.

We offer a free consultation and work on a contingency fee basis, meaning you pay nothing unless we win your case. Call us at (888) 424–5757 or fill out our contact form today to speak with a dedicated attorney about your legal options.

All content undergoes thorough legal review by experienced attorneys, including Jonathan Rosenfeld. With 25 years of experience in personal injury law and over 100 years of combined legal expertise within our team, we ensure that every article is legally accurate, compliant, and reflects current legal standards.