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Cycling Found In Illinois

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Cycling Found in Illinois 2026 - 2027

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 2026 - 2027. 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 2026 - 2027 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

2026 10th Annual Gold Star 500

Springfield, Illinois
Sat 30 May 26 - Sat 26 Sep 26
Free - $450.00
🚀Boosted

Rock River Madness 2026: Dixon, Illinois

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

GlenVegas Gambler

Glendale, Illinois
Sat 25 Apr 26
$28.42 - $44.46

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
$79.99

Pedalpalooza

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

Tour de Tunnel Bike Ride Hosted by Revive Vienna

Vienna, Illinois
Sat 23 May 26
$38.10

Illini Weekend Getaway powered by Bicycle Illinois

Urbana, Champaign
Sat 30 May 26 - Sun 31 May 26
Free

Everybody Rides 2026

St. Charles, Illinois
Sun 31 May 26
$11.60 - $43.40

56th Annual Swedish Days Ride

Sugar Grove, Illinois
Sun 14 Jun 26
$27.50

Ride Across Illinois (RAIL) North powered by Bicycle Illinois

Moline, Rock Island
Sun 21 Jun 26
Free

RAGBRAI Transportation: Chicago to the Start of RAGBRAI powered by Bicycle Illinois

Chicago, Cook
Sat 18 Jul 26
Free

KMC Sage City Classic

Monticello, Illinois
Sat 22 Aug 26
$54.00

Mud Sweat and Gears MTB Race

Hudson, Illinois
Sat 29 Aug 26
Free - $27.50

Tour de Stooges

Lebanon, Illinois
Sat 02 May 26
$38.10

2026 10th Annual Gold Star 500

Springfield, Illinois
Sat 30 May 26 - Sat 26 Sep 26
Free - $450.00

Freedom Bike Ride

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

2026 CAMBr Chicagoland Race Series Powered by SRAM

Carpentersville-Hoffman Estates-Willow Springs, Illinois
Sun 26 Jul 26
Free - $48.70

HMFA’s Tour de Heartland Fundraiser

Greenview, Illinois
Sat 12 Sep 26
$43.40 - $48.70
Showing 1-19 of 19 results

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