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More cycling events nearby

  • 1130 Midway Plaisance, Chicago, Illinois, 60637, United States
    OpenStreetMap Google Maps
    Distance: 21.4 km from Brookfield
    Sat, Aug 08, 2026 at 8:30 AM

    We're back for another year once again as an official Illinois Cup race!

    Registration: Online entry closes at 11:59pm on Friday, August 7th. Day-of registration closes 20 minutes before each race. Riders are encouraged to enter more than one race — a second race is only $20.

    Licenses: This is a USAC sanctioned event (all USAC rules apply). All riders are required to have a USA Cycling license which can be purchased at USAC Licensing. One-day licenses will be available to for category 5 riders for $15 via online registration and on the day of the race. One-day licenses for experienced riders (all other categories) will can be purchased here for $35.

    Parking: If possible, riders are encouraged to ride to Hyde Park. Otherwise, Street parking will be available on 59th and 60th streets, adjacent to the course, as well as on the streets throughout Hyde Park. Additionally, the Metra Electric Line has a station less than a 10 minute walk from the start line.

    Sign-in & Bathrooms: Riders can pick up their bib number in Ida Noyes Hall. Bathrooms in Ida Noyes will also be open to riders throughout the day. Please do not wear your cleats inside the building.

    In place of an event website see OKCC instagram page for updates.

    Monsters Map 2026.png

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    Cycling via BikeReg
  • West Washington Street, Chicago, Illinois, 60602, United States
    OpenStreetMap Google Maps
    Distance: 19.3 km from Brookfield
    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

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    Cycling via RaceRoster
  • 5200 N. Lake Shore, Chicago, Illinois, 60660, United States
    OpenStreetMap Google Maps
    Distance: 23.8 km from Brookfield
    Aug 22 – 25, 2026 at 2:00 AM

    One of the world’s largest triathlons is also one of the world’s most accessible. From first-timers to seasoned veterans, kids to grandparents, nonbinary competitors to paratriathletes, the Chicago Triathlon has an experience for everyone on the shores of Lake Michigan.

    Event details and schedule

    Triathlon via Active.com
  • 227 Heritage Quarries Dr., Lemont, Illinois, 60439, United States
    OpenStreetMap Google Maps
    Distance: 16.8 km from Brookfield
    Sat, Nov 14, 2026 at 7:15 AM

    Race and Course Information

    The Forge Trail Run Festival will embrace the adventure and challenge of late-fall, mid-west trail running with 10K, 20K, 30K, and 60K events. The races will be run on single/double-track trails in The Forge and adjoining trails, within the woods and on some gravel around the historic Lemont Quarries and I&M Canal.

    The courses will start and finish within the Forge. The courses wind through the single and double track trails within the woods and some gravel trails around the historic Lemont Quarries and I&M Canal throughout the Forge and adjoining trails.

    The 10K will be one lap, the 20K (Half Marathon) will be two laps and the 30K will be a three lap course. Our newest offering - the 60K - will be six laps. Total mileage may not be precise, but will be close to the promoted distances. This is a trail race and we want the natural terrain and flow to guide the course and distance.

    The gravel trails are flat. The single-track sections have variable terrain and surfaces ranging from dirt, grass, rocks, mud, more rocks, roots, mulch, stumps, critters, etc. A few sections are technical with several short but steep inclines and downhills. The defining character and primary challenge of the course is the variable surface. There are not any significant elevation changes. We would rate this course as moderately challenging for experienced trail runners and more difficult for runners with less experience on trail.

    See full details
    6.2 Miles13.1 Miles18.6 Miles37.2 MilesGravelRunTrail via RunSignup
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