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  • Le Tour de Shore 2026 [letourdeshore.com] [Register at bikereg.com]

    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.

    2.4 km from Chicago
    239 E Randolph St, Chicago, Illinois, 60601, United States
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    Cycling

  • Ride across Illinois Rail South [finishers.com]

    Sun, Jun 21, 2026

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

    1.9 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

    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 -
    2.5 km from Chicago
    Chicago, Illinois, 60611, United States
    OpenStreetMap Google Maps

    Aquathlon Open Water Run Swim Triathlon Walk

  • Fulton Market Grand Prix Community Bike Ride [chicago-grit.com] [Register at bikereg.com]

    Sun, Jul 26, 2026 at 11:59 PM

    271 m from Chicago
    1000 W Fulton Market, Chicago, Illinois, 60607, United States
    OpenStreetMap Google Maps

    Cycling

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

    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

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

    Cycling

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