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Upcoming 5K Races Near Sleepy Hollow, IL

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PSRR Free 5K Run/Walk logo

PSRR Free 5K Run/Walk

Shorewood, IL

Saturday, August 1st, 2026

5K
View details for race PSRR Free 5K Run/Walk
Heatwave Half Marathon - Greater Chicago logo

Heatwave Half Marathon - Greater Chicago

Greater Chicago, IL

Sunday, August 2nd, 2026

1 Mile
5K
10K
View details for race Heatwave Half Marathon - Greater Chicago
Heatwave Half Marathon - Greater Chicago logo

Heatwave Half Marathon - Greater Chicago

Elk Grove Village, IL

Sunday, August 2nd, 2026

1 Mile
5K
10K
View details for race Heatwave Half Marathon - Greater Chicago
SSW Running Club Club Challenge 5k logo

SSW Running Club Club Challenge 5k

Tinley Park, IL

Wednesday, August 5th, 2026

5K
View details for race SSW Running Club Club Challenge 5k
Track Night Chicago logo

Track Night Chicago

Chicago, IL

Saturday, August 8th, 2026

1 Mile
5K
View details for race Track Night Chicago
RUN FOR C'VILLE logo

RUN FOR C'VILLE

Carpentersville, IL

Saturday, August 8th, 2026

View details for race RUN FOR C'VILLE
Back-to-School Family Fun 5K logo

Back-to-School Family Fun 5K

Wheeling, IL

Saturday, August 8th, 2026

5K
View details for race Back-to-School Family Fun 5K
The Butterfly Cold Brew Spirits Run logo

The Butterfly Cold Brew Spirits Run

Joliet, IL

Saturday, August 8th, 2026

5K
View details for race The Butterfly Cold Brew Spirits Run
Miles for Miracles Run logo

Miles for Miracles Run

Mount Prospect, IL

Sunday, August 9th, 2026

1 Mile
5K
View details for race Miles for Miracles Run
2026 Wolverine 5K logo

2026 Wolverine 5K

Waterford, WI

Sunday, August 9th, 2026

5K
View details for race 2026 Wolverine 5K
Highlander Assault Obstacle Race logo

Highlander Assault Obstacle Race

Mchenry, IL

Saturday, August 15th, 2026

5K
15K
Trail
View details for race Highlander Assault Obstacle Race
Highlander Assault Obstacle Race logo

Highlander Assault Obstacle Race

Pingree Grove, IL

Saturday, August 15th, 2026

5K
15K
Ultra
Trail
View details for race Highlander Assault Obstacle Race
Prostate Cancer Awareness 5K Walk/Run/Bike-Most Worshipful Prince Hall Grand Lodge of IL (one race four locations simulantaneously) logo

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

Chicago, IL

Saturday, August 15th, 2026

5K
View details for race Prostate Cancer Awareness 5K Walk/Run/Bike-Most Worshipful Prince Hall Grand Lodge of IL (one race four locations simulantaneously)
RAMP River Run – 3K, 5K, & 1/2 Marathon Run logo

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

Rockford, IL

Saturday, August 15th, 2026

Half
5K
View details for race RAMP River Run – 3K, 5K, & 1/2 Marathon Run
Flight to the Finish logo

Flight to the Finish

Zion, IL

Saturday, August 15th, 2026

5K
Fast
View details for race Flight to the Finish
Alpine Races 5k and 10 Mile logo

Alpine Races 5k and 10 Mile

Lake Zurich, IL

Sunday, August 16th, 2026

10 Miles
5K
1 Mile
View details for race Alpine Races 5k and 10 Mile
Parkie’s 5K logo

Parkie’s 5K

Bolingbrook, IL

Saturday, August 22nd, 2026

5K
Fast
View details for race Parkie’s 5K
Alana's Eternal Light 5K logo

Alana's Eternal Light 5K

Genoa, IL

Saturday, August 22nd, 2026

5K
View details for race Alana's Eternal Light 5K
SMG 5K Race & 1 Mile Run logo

SMG 5K Race & 1 Mile Run

Downers Grove, IL

Saturday, August 22nd, 2026

5K
1 Mile
View details for race SMG 5K Race & 1 Mile Run
Warrior Foundation 5k logo

Warrior Foundation 5k

Loves Park, IL

Saturday, August 29th, 2026

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

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

Matteson, IL

Saturday, August 29th, 2026

5K
1 Mile
Trail
View details for race Tails on the Trail 5K & 1-Mile Wag & Walk
Skokie's Backlot Dash 5K and 1/2 Mile Youth Color Run logo

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

Skokie, IL

Saturday, August 29th, 2026

5K
View details for race Skokie's Backlot Dash 5K and 1/2 Mile Youth Color Run
Summer Sizzler- Greater Chicago logo

Summer Sizzler- Greater Chicago

Aurora, IL

Sunday, August 30th, 2026

5K
10K
1 Mile
View details for race Summer Sizzler- Greater Chicago
Summer Sizzler- Greater Chicago logo

Summer Sizzler- Greater Chicago

Greater Chicago, IL

Sunday, August 30th, 2026

5K
10K
1 Mile
View details for race Summer Sizzler- Greater Chicago
Rise & Run for Recovery logo

Rise & Run for Recovery

Lake Villa, IL

Sunday, August 30th, 2026

5K
View details for race Rise & Run for Recovery
5K Fun Run and Family Walk logo

5K Fun Run and Family Walk

Glenview, IL

Tuesday, September 1st, 2026

5K
View details for race 5K Fun Run and Family Walk
Time and a Half Relay & 5K logo

Time and a Half Relay & 5K

Chicago, IL

Sunday, September 6th, 2026

5K
View details for race Time and a Half Relay & 5K
Sandwich Fair Shake Up Shuffle logo

Sandwich Fair Shake Up Shuffle

Sandwich, IL

Monday, September 7th, 2026

5K
1 Mile
View details for race Sandwich Fair Shake Up Shuffle
Lake Geneva Wine Run 5k logo

Lake Geneva Wine Run 5k

Lake Geneva, WI

Monday, September 7th, 2026

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

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

Elwood, IL

Friday, September 11th, 2026

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

Woodland ROAR Run

Gurnee, IL

Friday, September 11th, 2026

5K
1 Mile
View details for race Woodland ROAR Run
Tunnel to Towers Climb - Chicago, IL logo

Tunnel to Towers Climb - Chicago, IL

Chicago, IL

Saturday, September 12th, 2026

5K
View details for race Tunnel to Towers Climb - Chicago, IL
9/11 Heroes Run - Chicago, Illinois logo

9/11 Heroes Run - Chicago, Illinois

South Barrington, IL

Saturday, September 12th, 2026

5K
1 Mile
View details for race 9/11 Heroes Run - Chicago, Illinois
Thin Mint Sprint 2026 logo

Thin Mint Sprint 2026

Fox River Grove, IL

Saturday, September 12th, 2026

5K
1 Mile
View details for race Thin Mint Sprint 2026
Itasca Oktoberfast 5K logo

Itasca Oktoberfast 5K

Itasca, IL

Saturday, September 12th, 2026

5K
Fast
View details for race Itasca Oktoberfast 5K
Ana Banana 5k & Fun Run logo

Ana Banana 5k & Fun Run

Morton Grove, IL

Saturday, September 12th, 2026

5K
1 Mile
View details for race Ana Banana 5k & Fun Run
Ana Banana 5k & Fun Run logo

Ana Banana 5k & Fun Run

Skokie, IL

Saturday, September 12th, 2026

5K
1 Mile
View details for race Ana Banana 5k & Fun Run
4th Annual Run for the Parks! 5K Run, Walk or Roll logo

4th Annual Run for the Parks! 5K Run, Walk or Roll

Chicago, IL

Sunday, September 13th, 2026

5K
1 Mile
Trail
View details for race 4th Annual Run for the Parks! 5K Run, Walk or Roll
RUN FOR UKRAINE logo

RUN FOR UKRAINE

Wheeling, IL

Sunday, September 13th, 2026

View details for race RUN FOR UKRAINE
Gift of Hope Community Foundation 5K Run, Walk & Roll logo

Gift of Hope Community Foundation 5K Run, Walk ...

Glen Ellyn, IL

Sunday, September 13th, 2026

5K
1 Mile
View details for race Gift of Hope Community Foundation 5K Run, Walk & Roll
El Grito 5K Family Run/Walk logo

El Grito 5K Family Run/Walk

Chicago, IL

Sunday, September 13th, 2026

5K
View details for race El Grito 5K Family Run/Walk
Women for Tomorrow 5k logo

Women for Tomorrow 5k

Burlington, WI

Sunday, September 13th, 2026

5K
View details for race Women for Tomorrow 5k
Miles for Manufacturing 5k and 1 Mile Walk logo

Miles for Manufacturing 5k and 1 Mile Walk

Chicago, IL

Wednesday, September 16th, 2026

5K
1 Mile
View details for race Miles for Manufacturing 5k and 1 Mile Walk
Glow in the Garden 5k logo

Glow in the Garden 5k

Rockford, IL

Friday, September 18th, 2026

5K
View details for race Glow in the Garden 5k
Raising Sickle Cell Awareness 1 Mile At A Time! Annual 1K/5K Walk, Jog or Run for a Cure! logo

Raising Sickle Cell Awareness 1 Mile At A Time!...

Chicago, IL

Saturday, September 19th, 2026

5K
View details for race Raising Sickle Cell Awareness 1 Mile At A Time! Annual 1K/5K Walk, Jog or Run for a Cure!
Run Like a Diva logo

Run Like a Diva

Chicago , IL

Saturday, September 19th, 2026

5K
Half
View details for race Run Like a Diva
Race to Recycle logo

Race to Recycle

South Beloit, IL

Saturday, September 19th, 2026

5K
1 Mile
View details for race Race to Recycle
Divas Chicago Half Marathon & 5k logo

Divas Chicago Half Marathon & 5k

Chicago, IL

Saturday, September 19th, 2026

5K
Half
View details for race Divas Chicago Half Marathon & 5k
12th Annual Christmas Without Cancer 5k Run/Walk (In-Person OR Virtual Option) logo

12th Annual Christmas Without Cancer 5k Run/Wal...

Evergreen Park, IL

Saturday, September 19th, 2026

5K
View details for race 12th Annual Christmas Without Cancer 5k Run/Walk (In-Person OR Virtual Option)
Blue Bridges 5K logo

Blue Bridges 5K

Blue Island, IL

Saturday, September 19th, 2026

5K
View details for race Blue Bridges 5K
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