Skip to main content
Date:
Sat, Jun 13, 2026 at 12:00 PM – 3:00 PM
Location:
4351 S. Drexel
Chicago, Illinois
60653
United States
OpenStreetMap Google Maps
Links:
runsignup.com
Tags:
18.65k Cycling Virtual

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.

More cycling events nearby

  • 2026 Walk & Roll Chicago [runsignup.com]

    Sat, May 30, 2026 at 7:30 AM

    Description

    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 & 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!

    6.1 km from Chicago
    200 E. Balbo Drive, Chicago, Illinois, 60605, United States
    OpenStreetMap Google Maps

    5k 10k 15k Cycling Run Walk

  • Ride across Illinois Rail South [finishers.com]

    Sun, Jun 21, 2026

    Description

    Have you ever dreamed of crossing Illinois on foot during a unique event? 🤩 Don't miss the "Ride across Illinois Rail South" in Chicago! 🏃‍♂️

    6.8 km from Chicago
    Chicago, Illinois, United States
    OpenStreetMap Google Maps

    Cycling

  • Open Water Swim CHICAGO [runsignup.com]

    Tue, Jul 07, 2026 at 4:00 PM

    Description

    SUPPORTING THE COMMUNITY FOR 14 YEARS

    Open Water Swim CHICAGO was launched in 2012 to help new triathletes and novice swimmers experience open water swimming in a safe, non-intimidating environment....

    SUPPORTING THE COMMUNITY FOR 14 YEARS

    Open Water Swim CHICAGO was launched in 2012 to help new triathletes and novice swimmers experience open water swimming in a safe, non-intimidating environment. Since inception, more than 20,000 participants have directly enhanced their swim abilities from our clinics and special events!

    These community-focused sessions provide participants with expert coaching, gear check, wetsuit rental opportunities, life guard support and post-event socials with fellow participants and coaches.

    While we're best known for developing aspiring adults, OWS Chicago also serves experienced triathletes looking to refresh their skills and/or push themselves with fellow enthusiasts. Veterans often enroll in the Swim-On-Your-Own or the competitive Aquathlon options to stay focused on their performance goals.

    EVENT OPTIONS

    The Open Water Swim CHICAGO series features three ways to participate:

    1. Open Water Swim Clinics: Small group swim instruction for beginner, intermediate or advanced-level swimmers looking for open water tips and techniques.

    2. Swim-On-Your-Own: This option is for those participants who prefer to utilize the event services (gear check, wetsuit rental, etc) but swim independently.

    3. Competitive Aquathlon: Swimmers complete a 750m or 1500m swim followed by a 3.1 mile (5k) run along the lakefront.

    OUR COACHES

    The historic success of this entire swim operation revolves around support from our dedicated coaching community. Dozens of incredible local event professionals and coaches support each of our sessions. OWS Chicago is constantly incorporating new, qualified triathlon and swim-savvy coaches into the clinic curriculum. These sessions are a great way to give back to the sport, as well as meet potential new personal training clients. Please email us should you be interested in lending a hand.

    SERIES PARTICIPATION

    This may be a series, but the four sessions operate independently. Participants may enroll in one, two, three or all sessions -- relative to their goals and preference for learning in the small group environment. Participants should use these sessions to grow familiar with swimming in Lake Michigan, eventually gaining confidence to return with others and train on their own.

    EVENT LOCATION

    All OWS Chicago sessions are hosted at Ohio Street Beach located at 600 N. Lake Shore Drive in downtown Chicago. Parking can be tricky in the area, so we strongly recommend reserving a nearby garage using SpotHero.

    ENTRY DETAILS

    Registration rates open at a nominal $22 plus typical service fees for all swim clinic or swim-on-own sessions. Prices will increase to $30 within two weeks of each session. The Aquathlon fee is $30, rising to $40 within the same two week window (see schedule below):

    • Session #1 (May 27): Price increase (from $22 to $30, or $30 to $40 for Aquathlon) on Tuesday, May 13

    • Session #2 (June 24): Price increase (from $22 to $30, or $30 to $40 for Aquathlon) on Tuesday, June 10

    • Session #3 (July 22): Price increase (from $22 to $30, or $30 to $40 for Aquathlon) on Tuesday, July 8

    • Session #4 (Aug 19): Price Increase (from $22 to $30, or $30 to $40 for Aquathlon) on Tuesday, August 5

    Event capacity is limited to 150 participants per timeblock, many of which will sell-out in advance. Each Aquathlon will be limited to 75 participants. Participants must be 18 years or older by the event day. Participants must be able to tread water on their own, comfortably place their face under the surface, and maintain some level of forward propulsion to enroll.

    WETSUIT RENTALS

    Wetsuits are very common for open water swimming and triathlon. Not only do swim-specific wetsuits provide a bit of warmth against cold water temperatures (Lake Michigan water temperatures range between 55-75°F through the season), but they're constructed of neoprene -- providing an incredible amount of buoyancy to keep swimmers afloat and more hydrodynamic. It's estimated that 70% of athletes utilize a wetsuit for triathlon swimming.

    If you don't own a wetsuit, you're in good hands. Our friends from Urban Tri Gear provide a small inventory of demo wetsuits for use during the sessions (excluding the final event on August 19). A $25 rental fee applies, which can be used as credit towards purchase of a new wetsuit. Urban Tri Gear also offers 5-day wetsuit rentals ($55 sleeveless, $65 full-sleeve) as part of these sessions. The walk-up rental opportunity is great for last-minute needs, but we strongly recommend you contact them in advance to secure your rental suit that's guaranteed to fit you. They will coordinate all logistics.

    If you're able, we encourage you to try-out multiple wetsuits (long sleeve, sleeveless, swim skins, etc.) before you purchase one for yourself. It's a good idea to know what makes you most comfortable in the water, and to continually use the same wetsuit for the majority of your training and racing.

    REFUND POLICY

    These events have a strict no-refund and no-transfer policy, especially due to the limited capacity. If you are unable to attend for any reason, you are not eligible for reimbursement. Should the session be cancelled, management will do its best to offer a make-good relevant to the situation but refunds will not be issued. Thank you for understanding.

    MORE DETAILS

    Are you ready to learn more about Open Water Swim CHICAGO?

    Explore our three event options by clicking the links above.

    Click Here to learn more about the actual Event Day experience.

    View prior event photos and updates on our Facebook or Instagram pages.

    Click the "Register" button if you're ready to commit (opens to the public March 24).

    Send us an email with questions or other needs.

    We look forward to seeing you at Ohio Street Beach!

    • HOME -
    8.5 km from Chicago
    Chicago, Illinois, 60611, United States
    OpenStreetMap Google Maps

    Aquathlon Open Water Run Swim Triathlon Walk

  • 2026 Bicycle Illinois [bicycleillinois.com] [Register at raceroster.com]

    Sat, Aug 15, 2026 at 5:00 AM

    Description

    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...

    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

    7.4 km from Chicago
    West Washington Street, Chicago, Illinois, 60602, United States
    OpenStreetMap Google Maps

    Cycling Road

More cycling events nearby →
Like Wikipedia, anyone can contribute. Sign up to add your local events.