Upcoming 5K Races Near Sleepy Hollow, IL

Name: Race To the Flag
Start: 2026-05-24
End: 2026-05-24
Location: Westmont

Gigi Fit 5k

Roscoe, IL

Saturday, April 25th, 2026

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Coach's Corner Spirits Run

Belvidere, IL

Saturday, April 25th, 2026

View details for race Coach's Corner Spirits Run

Arny Johnson 5k - 10 mile

Loves Park, IL

Saturday, April 25th, 2026

10 Miles

Trail

View details for race Arny Johnson 5k - 10 mile

Good Life Race

Oak Park, IL

Sunday, April 26th, 2026

1 Mile

Fast

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Ravenswood Run presented by Fleet Feet x Altra

Chicago, IL

Sunday, April 26th, 2026

View details for race Ravenswood Run presented by Fleet Feet x Altra

Anderson Humane's Walk4Animals & 5K Run

Batavia, IL

Sunday, April 26th, 2026

1 Mile

View details for race Anderson Humane's Walk4Animals & 5K Run

Avoca School District 37 Family Fun Run/Walk *P...

Wilmette, IL

Sunday, April 26th, 2026

View details for race Avoca School District 37 Family Fun Run/Walk *Please note date change*

Woods Creek Feet Meet

Crystal Lake, IL

Sunday, April 26th, 2026

1 Mile

View details for race Woods Creek Feet Meet

Plainfield Twisters 5k Fundraiser and Charity run

Plainfield, IL

Sunday, April 26th, 2026

View details for race Plainfield Twisters 5k Fundraiser and Charity run

EmpoweRun / Walk 5K

Libertyville, IL

Saturday, May 2nd, 2026

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Miles for Smiles 5K

Mchenry, IL

Saturday, May 2nd, 2026

View details for race Miles for Smiles 5K

Byron Rocks 5k & 10k - Run it. Walk it. Ruck it.

Byron, IL

Saturday, May 2nd, 2026

10K

View details for race Byron Rocks 5k & 10k - Run it. Walk it. Ruck it.

HOH5K Run/Walk/Roll benefitting the D28 Homer O...

Northbrook, IL

Saturday, May 2nd, 2026

View details for race HOH5K Run/Walk/Roll benefitting the D28 Homer O. Harvey Scholarship Fund

Insight Y.O.B Walk-A-Thon 2026

Berkeley, IL

Saturday, May 2nd, 2026

View details for race Insight Y.O.B Walk-A-Thon 2026

The Universal Sole Spring Trail Challenge

Willow Springs, IL

Saturday, May 2nd, 2026

Trail

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Chicago Police Memorial Foundation Run to Remember

Chicago, IL

Saturday, May 2nd, 2026

View details for race Chicago Police Memorial Foundation Run to Remember

Hometown Half Marathon & 5k/10k - Greater Chicago

Chicago, IL

Saturday, May 2nd, 2026

1 Mile

10K

View details for race Hometown Half Marathon & 5k/10k - Greater Chicago

Fight Hunger 10K, 5K + 1 Mile Fun Run

Wheaton, IL

Saturday, May 2nd, 2026

10K

1 Mile

View details for race Fight Hunger 10K, 5K + 1 Mile Fun Run

Chicago Empower Walk & 5K Run

Chicago, IL

Saturday, May 2nd, 2026

View details for race Chicago Empower Walk & 5K Run

Hanover Township Sprint 2 Spring 5k

Elgin, IL

Saturday, May 2nd, 2026

View details for race Hanover Township Sprint 2 Spring 5k

Jacobs Farm Charity Fun Run

Streamwood, IL

Saturday, May 2nd, 2026

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Run for BEER - Solemn Oath Brewery

Chicago, IL

Sunday, May 3rd, 2026

View details for race Run for BEER - Solemn Oath Brewery

Tailwagger Trot

Lisle, IL

Sunday, May 3rd, 2026

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Miles for the Military 5k

Lombard, IL

Saturday, May 9th, 2026

1 Mile

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Ribbons of Hope 5k

New Lenox, IL

Saturday, May 9th, 2026

1 Mile

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La Carrera de las Madres 2026

Chicago, IL

Saturday, May 9th, 2026

View details for race La Carrera de las Madres 2026

Ribbons of Hope 5k

Mokena, IL

Saturday, May 9th, 2026

1 Mile

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Mama's Run 2026

Zion, IL

Saturday, May 9th, 2026

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Pink 5k Oak Brook Park District

Oak Brook, IL

Saturday, May 9th, 2026

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Quarryman Challenge

Lemont, IL

Saturday, May 9th, 2026

10 Miles

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Stars & Spikes: Totally Rad 5k

Lombard, IL

Saturday, May 9th, 2026

1 Mile

View details for race Stars & Spikes: Totally Rad 5k

Barrington Mother's Day 5K Run/Walk

Barrington, IL

Sunday, May 10th, 2026

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Family Service Association 5k

Elgin, IL

Saturday, May 16th, 2026

Trail

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Wildflower Run

Bristol, WI

Saturday, May 16th, 2026

Trail

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Annual Super Hero Shuffle 5k/10k Run/walk

Lake Geneva, WI

Saturday, May 16th, 2026

10K

1 Mile

Trail

View details for race Annual Super Hero Shuffle 5k/10k Run/walk

Wolf Lake 5k

Chicago, IL

Saturday, May 16th, 2026

View details for race Wolf Lake 5k

2026 Harlem Huskie Hustle 5K Walk/Run & 1 Mile ...

Machesney Park, IL

Saturday, May 16th, 2026

1 Mile

View details for race 2026 Harlem Huskie Hustle 5K Walk/Run & 1 Mile Walk/Run and Kids Fun Run

BeACTIVE

Joliet, IL

Saturday, May 16th, 2026

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Bright Star Community Outreach 5K Run/Walk - Ho...

Chicago, IL

Saturday, May 16th, 2026

View details for race Bright Star Community Outreach 5K Run/Walk - Hope in Action

Run for D103 5K Run/Walk

Lincolnshire, IL

Saturday, May 16th, 2026

View details for race Run for D103 5K Run/Walk

Wheel Run for Meals

Beloit, WI

Saturday, May 16th, 2026

10K

Fast

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2026 LOGOS MISSIONS RUN FOR LOVE

Glenview, IL

Saturday, May 16th, 2026

View details for race 2026 LOGOS MISSIONS RUN FOR LOVE

Darien Dash

Darien, IL

Sunday, May 17th, 2026

10K

1 Mile

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5k for Hopeful Beginnings

Palatine, IL

Sunday, May 17th, 2026

View details for race 5k for Hopeful Beginnings

Kenilworth Memorial Day 5k

Kenilworth, IL

Sunday, May 17th, 2026

View details for race Kenilworth Memorial Day 5k

2026 Willard 5k Fun Run

River Forest, IL

Sunday, May 17th, 2026

View details for race 2026 Willard 5k Fun Run

Dash for the Dogs 13th Annual 5K Run/Walk

Barrington, IL

Sunday, May 17th, 2026

1 Mile

View details for race Dash for the Dogs 13th Annual 5K Run/Walk

Western Springs Tower Trot

Western Springs, IL

Saturday, May 23rd, 2026

10K

Ultra

View details for race Western Springs Tower Trot

Frontline OCR

Byron, IL

Saturday, May 23rd, 2026

10K

1 Mile

View details for race Frontline OCR

Race To the Flag

Westmont, IL

Sunday, May 24th, 2026

View details for race Race To the Flag

Explore more in Sleepy Hollow, IL

Distances:

5K 10K Half Marathon Marathon

Months:

April May June

Tags:

Trail Boston Qualifiers Fast Courses

State:

All Illinois races

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