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9 cycling events in Chicago, Illinois

From big races to Saturday morning group runs—find cycling events and connect with the local endurance sports community.

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Chicago

9 events in Chicago
  • 200 E. Balbo Drive, Chicago, Illinois, 60605, United States
    OpenStreetMap Google Maps
    Sat, May 30, 2026 at 7:30 AM

    Walk & Roll Chicago unites the community behind the American Cancer Society's efforts to save lives from cancer. It is a one-of-a-kind event that offers participants of all ages and skill levels a 5K Walk, 5K Timed Run, 10K Skate, or 15K Bike along Chicago's Lakefront Path.

    2026 is the 55th anniversary of Walk & Roll Chicago! The date is Saturday, May 30, 2026 at Upper Hutchinson Field in Grant Park, Chicago.

    This is our new website platform for 2026!

    See full details
    5k10k15kCyclingRunWalk via RunSignup
  • Sat, Jun 13, 2026 at 12:00 PM

    Celebrate 2025 with a bicycling odyssey through Bronzeville. The annual Freedom Bicycle Ride offers a 18.65 KM route in Chicago. The virtual Freedom Bicycle Ride offers an 18.65 Mile challenge to be completed between June 14th through June 19th.

    The live route will travel through historic Bronzeville.

    Route can be viewed and downloaded at the links below

    Route: TBA

    Route will may be slightly different based on road conditions during that time but similar. Check back for updates.

    STARTING POINT & REGISTRATION INFORMATION

    Riders will start the ride in 2025 at the Timothy Community Center (4351 S. Drexel Blvd).

    REGISTRATION FEES ARE AS FOLLOWS:

    Individual: Free

    A group start takes place at 12 pm from the Timothy Community Center. Ride rain or shine. No refunds. The registration fee includes a route mapped through Ride With GPS, a water stop UNTIL 3pm. Riders are on their own for repairs. Parking is available near the start/finish!

    RIDER SUPPORT

    SAG support will not cover this route. They will have minimal tools to assist in minor bicycle repairs only. All riders should be prepared to make their own repairs. Riders will be on their own after that, or if they leave the route.

    SAFETY - Helmets are required. An adult must accompany all cyclists under the age of 16. Riders must obey all Illinois traffic laws.

    NOTICE - this is a RIDE not a RACE. Through this sign up platform "race" is automatically applied throughout the sections. This is not our doing, and we want everyone to know that this is a ride.

    See full details
    18.65kCyclingVirtual via RunSignup
  • Fri, Jun 19, 2026 at 7:30 AM

    Le Tour de Shore is 2-Day bicycle touring event from Millennium Park, Chicago, IL to the Indiana Dunes, (61 miles); and then, on day 2, to City Beach, New Buffalo, MI (45 miles). Explore dedicated lakefront and duneland bike paths, and scenic Harbor Country secondary roads. Proceeds to benefit Maywood Fine Arts, Maywood, IL, a not-for-profit organization providing programs in art, dance, drama, music, tumbling and voice to children in the Chicago area. The mission of Maywood Fine Arts Association is to provide a safe and nurturing environment in which children can develop skills and appreciation of the arts that will enable them to succeed academically and socially and obtain higher educational opportunities. Start Friday 6/19/2026 7:30am CT Millennium Park, 239 East Randolph St. Chicago, IL 60601 Finish Saturday 6/20/2026 3:00pm CT Oselka Park 601 E Indiana St, New Buffalo, MI 49117 THREE REGISTRATION CATEGORIES: 1. TWO DAY RIDE (Fri-Sat Jun 19-20) If you plan on staying overnight, Friday

    June 19th, at one of our participating hotels, inns, or at a private residence, then select the “TWO DAY RIDE” registration category. $150 early bird registration ($170 after 3/17/2026) Includes: > Cue Sheet > Route Maps > SAG stops every 20 miles or so with water, Gatorade, fruit, power snacks and restrooms. > Bike technicians at SAG stops – free tweaks, parts extra. > SAG support vehicles to assist with route emergencies. > Door-to-door gear check valet service to/from Chicago and participating hotel or inn, > Friday dinner is not included, but if you are staying at one of our participating hotels, a variety of restaurants are only a short walk from your hotel. 2. TWO DAY RIDE and CAMP (Fri-Sat Jun 19-20) If you would like to camp, Friday June 13th, at our group campsite at the Indiana Dunes State Park campground, then select the “TWO DAY RIDE and CAMP" registration category. $160 early bird registration ($180 after 3/17/2026) Includes: > All Ride Fee benefits plus
 > One tent camping

    spot Friday night at the Indiana Dunes State Park Nissaki Group campsites > Door-to-door gear check valet service to/from Chicago and the campground > Friday night dinner 6 pm - 8 pm, and Saturday morning breakfast 7 am - 8 am. 3. ONE DAY RIDE (Fri/Sat Jun 19/20) If you can only ride one day; either Friday Jun 19 Chicago to Indiana Dunes, or Saturday Jun 20 Indiana Dunes to New Buffalo, Michigan, then select the "ONE DAY RIDE" registration category. $100 early bird registration ($120 after 3/17/2026) Includes: > Friday 6/19, or Saturday 6/20 > All Ride Fee benefits plus... > Friday afternoon South Shore Train No. 30 is available back to Chicago. Leaves Dune Park 4:46pm CT. > Purchase rail tickets directly from South Shore Railroad. ...SATURDAY BUS RIDE BACK TO CHICAGO OPTION If you need a bus ride back to Chicago on Saturday June 20th from the end-of-ride BBQ celebration at Oselka Park 601 E Indiana St, New Buffalo, MI 49117, then select “Bus Ride Back to Chicago/Maywood, IL” during the

    registration process. Add $35 per After finishing Le Tour de Shore, relax and enjoy a comfortable coach bus ride back to Chicago or Forest Park, IL. ETD Oselka Park 601 E Indiana St, New Buffalo, MI 49117 Saturday 6/20/2026 3 pm CT. ETA Chicago and Maywood, 5 pm CT. We will packed your bike carefully, wrapped in a moving blanket, nested snuggly in a neat row inside a covered truck, which will follow your bus.

    See full details
    Cycling via BikeReg
  • Sun, Jun 21, 2026

    Have you ever dreamed of crossing Illinois on foot during a unique event? đŸ€© Don't miss the "Ride across Illinois Rail South" in Chicago! đŸƒâ€â™‚ïž

    Cycling via Finishers.com
  • 925 W Lake St, Chicago, IL 60607, Chicago, Illinois, 60607, United States
    OpenStreetMap Google Maps
    Sat, Jul 11, 2026 at 11:59 PM

    Please familiarize yourself with all rules and requirements for the event. Details can be found here https://www.midwestultracycling.com/mishigami

    Pairs Category:

    Each rider must have their own tracking device (Spot, InReach, etc). The same rules apply as solo riders, but they apply to the pair as a whole. No outside assistance is allowed for the pair. Sharing equipment, drafting, support, and resources between the two riders is fully permitted.

    Please reach out to [email protected] with any additional questions.

    Interested in supporting grassroots ultra racing? Email [email protected] for details on sponsorship packages.

    See full details
  • West Washington Street, Chicago, Illinois, 60602, United States
    OpenStreetMap Google Maps
    Sat, Aug 15, 2026 at 5:00 AM

    Tour Overview

    Starting from Cairo at Illinois' southernmost tip and ending in downtown Chicago, Bicycle Illinois is the only bicycle tour across the entire state of Illinois and one of the most challenging in the Midwest. You'll cycle for 6 days and cover at least 500 miles, an average of 85 miles per day, and century options are available every day as well.

    Whether you are a recreational cyclist looking for a sense of accomplishment or an athlete looking to challenge yourself and improve your cycling skills, Bicycle Illinois has something for you. You'll gain a new level of satisfaction and self confidence as you ride with new friends along the way!

    Included Services & Merchandise

    All the amenities you need are included at one low price. We've made it easy for you to focus on cycling and having fun!

    • Our experienced, caring, Professional Staff

    • The safest, most direct, fully paved Route which primarily follows back roads and bike paths

    • Pre-designated Rest Stops every 15 to 20 miles

    • Detailed Cue Sheets, Maps, and On-Road Signage

    • On Road SAG Vehicle Support

    • Inside and outside sleeping arrangements at our Nightly Lodging site including hot showers

    • All You Can Eat Food (including Breakfast, on road Snacks, and Sports Drinks)

    • Baggage Transportation between stopping towns

    • A T-Shirt and personalized Certificate of Completion

    Extra Services & Merchandise

    In addition, some very nice extras are also available as well!

    • Transportation to the Start for you, your bicycle, and your baggage before and after the tour

    • Hotels and free Hotel Baggage Delivery

    • Recommended Restaurants with nutritious dinners appropriate for cycling

    • Long-Term Parking in every nightly stopping town

    • Mechanical Support in town and on the road

    • Massage Therapy and daily Towel Service

    • Bicycle Illinois Jerseys, Water Bottles, Extra T-Shirts, Baseball Hats and Polo Shirts

    Tri-State Tour Chicago Century #2

    You can also continue your journey all the way to Wisconsin on the Tri-State Tour Chicago Century #2, which also includes a century option. You can cycle up to 7 centuries in a row - no other cycling event even comes close!

    Registration & Prices

    Check bicycleillinois.com for registration deadlines and additional price information. Partial day tours are also available.

    WE DO NOT ISSUE ANY REFUNDS AT ANY TIME FOR ANY REASON. If you do not participate and would like a refund, you MUST purchase an individual travel insurance plan, which will reimburse you according to the plan coverage. Many plans are very reasonably priced. As part of your online registration you will have the option to purchase an individual travel insurance plan offered through RegShield. This plan must be purchased as part of your initial online registration - it cannot be added later. If you do not purchase the RegShield plan you can still purchase another individual travel insurance plan. Click Here or visit https://www.travelexinsurance.com/index.aspx?location=27-019927-0199&go=bp to get the details and benefits of the plan offered through Travelex Insurance, get a quote, and purchase coverage.

    Additional Processing Fees Charged by RaceRoster

    Please visit bicycleillinois.com for more specific information about the additional processing fees charged by RaceRoster for online registration.

    Paper Registration

    Please visit bicycleillinois.com to download the paper registration forms if you do not wish to pay the additional processing fees charged by RaceRoster or wish to pay by check or money order. Unfortunately we cannot accept credit cards through paper registration.

    All information is subject to change. For more information about the event and the most current information please visit https://www.bicycleillinois.com/bicycleillinois/bicycleillinois.htm

    Copyright Bicycle Illinois

    See full details
    Cycling via RaceRoster
  • Sat, Nov 07, 2026 at 7:00 AM

    Public & Free

    Hear Ye Hear Ye By way of bipartisan act of Congress and signed by President Obama into federal law, National Bison Day will be henceforth observed the first Saturday of every November! To celebrate this momentous occasion of the newly-dubbed “National Mammal” join a glorious mixed road & light gravel ride to a bison herd / obstinacy at Midewin National Tallgrass Prairie.

    “Bison or Bust! The Tertiary Trek”

    This remix of our inaugural 2024 ride is on the preserve’s 30th anniversary, for which they domesticated their roughest gravel segment. Lunch orders will be delivered to the bison preserve’s welcome center. Rendezvous include Metric Coffee (All), Blackberry Market (A & B), Jitters Cafe (All), Midewin Welcome Center (All), and The Junction vintage shop (All) for the after party. Everyone returns same-day to LaSalle St. Station by a specially-reserved Metra car. Before Joliet, anyone starting with “A” group can switch to “B” by just waiting. Everyone can switch to any other group at Jitters in Joliet, as well as the Midewin Welcome Center. Join our Strava club for updates!

    “What are the ride rules?”

    • DO NOT PET THE FLUFFY COWS!
    1. All participants read, understand, and agree to the release / disclaimer / waiver at the bottom of the site before joining the ride

    2. Helmets required strapped onto your noggin’

    3. Bring a front and rear taillight as well as the tools, supplies, and know-how to change their own flats and address any mechanicals they may experience. From the 15th to 30th of October Comrade Cycles is offering free bike safety checks for our ride participants so get a checkup before the ride to cruise worry-free

    4. Observe best ride etiquette at all times: call out all slowing, stopping, speed bumps, holes, doors, cars, riders, runners, walkers, kids, turns, mechanicals, flats, gaps, and especially any pursuing buffaloes

    5. Keep your hands on your handlebars at all times, so flap your wings for rough roads instead of pointing. No riding without hands, we are too close together, roads are too unpredictable, and we have too far to go!

    6. Keep your eyes on the shoulders of the rider in front of you. They’ll call out and relay hazards as well as take the best line between them.

    7. That means if the rider ahead of you hits that minor road hole or whatever you do too, because it’s better than erratic unpredictable riding. No twitchy, racey, or unsafe group riding. There are plenty of other opportunities in other groups for that.

    8. No zooming in-between riders in peloton to make it three riders wide. Two wide? Stay that way. Single file? stay that way. It’s not a race, no need to jockey for position, and we will ask people to leave if they risk other riders’ safety

    9. Good vibes only! All with good vibes are welcome no matter their color shade, class, age, gender, sexual orientation, ethnicity, religion, profession, abilities, biking expertise, and strength.

    10. Good vibes only! That means no threatening or chauvinistic behavior of any kind is allowed be it racism, sexism, homophobia, classism, ethnic supremacism, or other forms of prejudice, threats, cruelty, or hatred nor are members of such ideologies permitted.

    11. No dangerous behavior is allowed and participants must follow all safety instructions of their ride leaders

    12. No unsolicited ‘coaching’ is allowed, especially any ‘helpful pushes’

    13. No triathlon aero handlebars are allowed they’re too unstable for the peloton

    14. No headphones

    15. Rides A and B require drop bars or something convincingly equivalent, like bullhorns. Point being that hybrid, flat, swoop, bull moose, albatross, wet noodle, whatever supercool other handlebars are only allowed for C group. This is just for safety in a peloton.

    16. No darting between riders. Is the peloton two riders wide? Keep it that way. Is it single-file? Keep it that way. Stay in your lane and ride with predictable behavior. This is not a race and anyone riding in ways that endanger others will be asked to find another ride.

    17. Join The ride Group appropriate for your abilities based on both practice and distance. Generally speaking, if you’ve been riding that distance in a week you’re ready to ride it in a day.

    18. Veteran brakeless fixed gear riders welcome but behind the peloton so pedal strikes don’t wipe others out.

    19. XXAndrew MichalskiXX or any other saboteurs

    “What group should I join?”

    For both Nachusa and Midewin routes the chillest group rolls at party pace, approximately 14mph, for around 40 miles. Both Midewin and Nachusa have a "B" group rolling for about 87 miles at 16-20mph once rolling. Both Midewin and Nachusa have an “A” group rolling at 18-24mph for about 130 miles. Whatever pace and distance you ride in a week you should able to do it in a day if you prepare well. Please practice riding in groups, calling out obstacles and "slowing" or "stopping" (see ride rules).

    No groups are true drop rides. However, on “A” group we have a lot of miles to cover before dusk so if you have a really bad mechanical more involved than a flat, we must ask that you either link up with the next group riding by (when possible) or catch up at the next rendezvous by taking a shorter break to depart with us again. Study the routes and tabs atop the Ride With GPS event page carefully to make your choice. Keep in mind the ride is planned to be very adjustable:

    • Midewin Routes
    • Until Joliet, you can downgrade from "A" group by just waiting for "B" group.

    • You can change to any group at Jitters cafe in Joliet, and at the Midewin visitor's center.

    • Midewin Routes

    o Until Joliet we ride decently close to the train lines for the Heritage Corridor Metra train, but please keep in mind it does not run on weekends, and National Bison Day is always on the first Saturday of November. If you find yourself bonking your ejection seat lies on the Lincoln Service train home from Summit or Joliet, Carl Sandberg or Illinois Zephyr train home from La Grange, or in a ride share to the nearest Rock Island line Metra station, a line which begins at Joliet Gateway Station.

    “What’s the timetable?”

    TBA

    “Do you have a waiver?”

    Riding in groups and on roadways is extremely dangerous. Serious bodily injury and death can occur even when you and those around you are exercising extraordinary care. You must ride at your own risk. Thank you for being careful! By joining any of our rides all cyclists hereby release ride organizers, agents, sponsors, advertisers, partners, volunteers, affiliates and all other persons and entities from all liability. (Thanks Breakfast Club ATX!)

    See full details

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