Upcoming Races Near Sleepy Hollow, IL

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Christmas in July Half Marathon and 5K (Chicago...

Elk Grove Village, IL

Saturday, July 18th, 2026

Half

View details for race Christmas in July Half Marathon and 5K (Chicago area)

Chicago Chinatown 5K Run

Chicago, IL

Saturday, July 18th, 2026

View details for race Chicago Chinatown 5K Run

Run for the Dogs 5k - Aurora

Aurora, IL

Saturday, July 18th, 2026

View details for race Run for the Dogs 5k - Aurora

Stan's Donut Race

Chicago, IL

Saturday, July 18th, 2026

10K

1 Mile

View details for race Stan's Donut Race

Rhythm of the Heart 5k Race & Walk

Loves Park, IL

Saturday, July 25th, 2026

View details for race Rhythm of the Heart 5k Race & Walk

The Huntley Historical Society - Sew Hop'd Be...

Huntley, IL

Saturday, July 25th, 2026

1 Mile

View details for race The Huntley Historical Society - Sew Hop'd Beer Mile

Fulton Market Loop Da Loop 5k

Chicago, IL

Sunday, July 26th, 2026

View details for race Fulton Market Loop Da Loop 5k

PSRR Free 5K Run/Walk

Shorewood, IL

Saturday, August 1st, 2026

View details for race PSRR Free 5K Run/Walk

Dim Sum & Then Some: The Uptown 5K/10K & Kids Dash

Chicago, IL

Saturday, August 1st, 2026

10K

View details for race Dim Sum & Then Some: The Uptown 5K/10K & Kids Dash

Heatwave Half Marathon - Greater Chicago

Elk Grove Village, IL

Sunday, August 2nd, 2026

1 Mile

10K

View details for race Heatwave Half Marathon - Greater Chicago

Heatwave Half Marathon - Greater Chicago

Greater Chicago, IL

Sunday, August 2nd, 2026

1 Mile

10K

View details for race Heatwave Half Marathon - Greater Chicago

SSW Running Club Club Challenge 5k

Tinley Park, IL

Wednesday, August 5th, 2026

View details for race SSW Running Club Club Challenge 5k

Twilight Fun Run

Palatine, IL

Friday, August 7th, 2026

View details for race Twilight Fun Run

Back-to-School Family Fun 5K

Wheeling, IL

Saturday, August 8th, 2026

View details for race Back-to-School Family Fun 5K

The Butterfly Cold Brew Spirits Run

Joliet, IL

Saturday, August 8th, 2026

View details for race The Butterfly Cold Brew Spirits Run

Ben's Memorial Mile

Downers Grove, IL

Saturday, August 8th, 2026

1 Mile

Fast

View details for race Ben's Memorial Mile

RUN FOR C'VILLE

Carpentersville, IL

Saturday, August 8th, 2026

View details for race RUN FOR C'VILLE

Track Night Chicago

Chicago, IL

Saturday, August 8th, 2026

1 Mile

View details for race Track Night Chicago

Miles for Miracles Run

Mount Prospect, IL

Sunday, August 9th, 2026

1 Mile

View details for race Miles for Miracles Run

Wisconsin Women's Triathlon

Pleasant Prairie, WI

Sunday, August 9th, 2026

View details for race Wisconsin Women's Triathlon

2026 Wolverine 5K

Waterford, WI

Sunday, August 9th, 2026

View details for race 2026 Wolverine 5K

Highlander Assault Obstacle Race

Mchenry, IL

Saturday, August 15th, 2026

15K

Trail

View details for race Highlander Assault Obstacle Race

Prostate Cancer Awareness 5K Walk/Run/Bike-Most...

Chicago, IL

Saturday, August 15th, 2026

View details for race Prostate Cancer Awareness 5K Walk/Run/Bike-Most Worshipful Prince Hall Grand Lodge of IL (one race four locations simulantaneously)

Highlander Assault Obstacle Race

Pingree Grove, IL

Saturday, August 15th, 2026

15K

Ultra

Trail

View details for race Highlander Assault Obstacle Race

RAMP River Run – 3K, 5K, & 1/2 Marathon Run

Rockford, IL

Saturday, August 15th, 2026

Half

View details for race RAMP River Run – 3K, 5K, & 1/2 Marathon Run

Flight to the Finish

Zion, IL

Saturday, August 15th, 2026

Fast

View details for race Flight to the Finish

Coon Creek Classic

Hampshire, IL

Sunday, August 16th, 2026

10K

1 Mile

View details for race Coon Creek Classic

Alpine Races 5k and 10 Mile

Lake Zurich, IL

Sunday, August 16th, 2026

10 Miles

1 Mile

View details for race Alpine Races 5k and 10 Mile

Parkie’s 5K

Bolingbrook, IL

Saturday, August 22nd, 2026

Fast

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Alana's Eternal Light 5K

Genoa, IL

Saturday, August 22nd, 2026

View details for race Alana's Eternal Light 5K

SMG 5K Race & 1 Mile Run

Downers Grove, IL

Saturday, August 22nd, 2026

1 Mile

View details for race SMG 5K Race & 1 Mile Run

Tails on the Trail 5K & 1-Mile Wag & Walk

Matteson, IL

Saturday, August 29th, 2026

1 Mile

Trail

View details for race Tails on the Trail 5K & 1-Mile Wag & Walk

Warrior Foundation 5k

Loves Park, IL

Saturday, August 29th, 2026

View details for race Warrior Foundation 5k

Skokie's Backlot Dash 5K and 1/2 Mile Youth Col...

Skokie, IL

Saturday, August 29th, 2026

View details for race Skokie's Backlot Dash 5K and 1/2 Mile Youth Color Run

Chicago Route 66 - 6.6K- Stop 1

Chicago, IL

Saturday, August 29th, 2026

View details for race Chicago Route 66 - 6.6K- Stop 1

Will County Brew Run 5k

Shorewood, IL

Saturday, August 29th, 2026

View details for race Will County Brew Run 5k

Summer Sizzler- Greater Chicago

Greater Chicago, IL

Sunday, August 30th, 2026

10K

1 Mile

View details for race Summer Sizzler- Greater Chicago

Rise & Run for Recovery

Lake Villa, IL

Sunday, August 30th, 2026

View details for race Rise & Run for Recovery

Valliant PT Cross Country Challenge 6k

Evanston, IL

Sunday, August 30th, 2026

View details for race Valliant PT Cross Country Challenge 6k

Summer Sizzler- Greater Chicago

Aurora, IL

Sunday, August 30th, 2026

10K

1 Mile

View details for race Summer Sizzler- Greater Chicago

5K Fun Run and Family Walk

Glenview, IL

Tuesday, September 1st, 2026

View details for race 5K Fun Run and Family Walk

Naperville Trails Half Marathon & 10K

Wheaton, IL

Saturday, September 5th, 2026

Half

10K

View details for race Naperville Trails Half Marathon & 10K

Time and a Half Relay & 5K

Chicago, IL

Sunday, September 6th, 2026

View details for race Time and a Half Relay & 5K

Geneva Lake Distilling Wine Run 5k

Lake Geneva, WI

Monday, September 7th, 2026

View details for race Geneva Lake Distilling Wine Run 5k

Sandwich Fair Shake Up Shuffle

Sandwich, IL

Monday, September 7th, 2026

1 Mile

View details for race Sandwich Fair Shake Up Shuffle

Woodland ROAR Run

Gurnee, IL

Friday, September 11th, 2026

1 Mile

View details for race Woodland ROAR Run

Elwood Community Days 5k Run & Walk 2026, In Me...

Elwood, IL

Friday, September 11th, 2026

View details for race Elwood Community Days 5k Run & Walk 2026, In Memory Of Our Fallen Heroes

Hobo Trail Runs 10k-25k-50k

Rockford, IL

Friday, September 11th, 2026

Ultra

10K

Trail

View details for race Hobo Trail Runs 10k-25k-50k

Thin Mint Sprint 2026

Fox River Grove, IL

Saturday, September 12th, 2026

1 Mile

View details for race Thin Mint Sprint 2026

Itasca Oktoberfast 5K

Itasca, IL

Saturday, September 12th, 2026

Fast

View details for race Itasca Oktoberfast 5K

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