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Cycling Found In Illinois

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Cycling Found in Illinois 2025 - 2026

Illinois is a brilliant place to take on a Gran Fondo. Find the perfect event for you with our comprehensive listings of bike races in Illinois 2025 - 2026. Whatever terrain you’re after you can find it in the Prairie State. Try out an urban event in Chicago or head out to rolling hills to experience some of the best cycling that Illinois has to offer. The term Gran Fondo is taken from Italian and roughly translates to ‘big ride’. With some events up to 300 miles long the name is pretty apt. Although don’t be put off most events have much shorter routes on offer too. Whether you’re a newcomer to riding and taking on your longest ride yet, or an experienced cyclist wanting to push yourself in a large group, a Gran Fondo will have the perfect challenge for you. Check out our exhaustive 2025 - 2026 Illinois Gran Fondos calendar list below, and use our month, distance and terrain filters to find your next challenge.

Race Calendar: Cycling Found In Illinois

🚀Boosted

Freedom Bike Ride

Chicago, Illinois
Sat 13 Jun 26 - Fri 19 Jun 26
Free
🚀Boosted

2026 Walk & Roll Chicago

Chicago, Illinois
Sat 06 Jun 26
Free - $38.10
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ORC Stair Climb

Evanston, Illinois
Sat 21 Feb 26
$27.50

The Dirty South Roubaix 2026

Alto Pass, Illinois
Sat 07 Mar 26
$87.25 - $92.60

Rock River Madness 2026: Dixon, Illinois

Dixon, Illinois
Sat 02 May 26
$32.80 - $48.70

Seeds & Stones Roubaix

Waterman, Illinois
Sat 02 May 26
$49.99

2026 Walk & Roll Chicago

Chicago, Illinois
Sat 06 Jun 26
Free - $38.10

Pedalpalooza

Crystal Lake, Illinois
Sat 16 May 26 - Sun 17 May 26
$16.90 - $27.50

Freedom Bike Ride

Chicago, Illinois
Sat 13 Jun 26 - Fri 19 Jun 26
Free

HMFA’s Tour de Heartland Fundraiser

Greenview, Illinois
Sat 12 Sep 26
$43.40 - $48.70
Showing 1-8 of 8 results

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