Upcoming 5K Races Near Sleepy Hollow, IL

Organize a race? Get it in front of thousands of runners.

Add it free Feature it

Run Like A Diva

Chicago, IL

Saturday, September 19th, 2026

Half

View details for race Run Like A Diva

Heritage Fest 10k

West Dundee, IL

Saturday, September 19th, 2026

10K

1 Mile

View details for race Heritage Fest 10k

Blue Bridges 5K

Blue Island, IL

Saturday, September 19th, 2026

View details for race Blue Bridges 5K

Better Than Yesterday 5K

Aurora, IL

Sunday, September 20th, 2026

View details for race Better Than Yesterday 5K

2026 D54 Education Foundation Run to Read

Schaumburg, IL

Sunday, September 20th, 2026

1 Mile

View details for race 2026 D54 Education Foundation Run to Read

Headless Horseman Hussle

Sleepy Hollow, IL

Sunday, September 20th, 2026

View details for race Headless Horseman Hussle

5K Fun Run/Walk

Glenview, IL

Sunday, September 20th, 2026

View details for race 5K Fun Run/Walk

Spartan Sprint 5K & Family Fun Run

Elgin, IL

Sunday, September 20th, 2026

View details for race Spartan Sprint 5K & Family Fun Run

Lawndale 5K

Chicago, IL

Saturday, September 26th, 2026

View details for race Lawndale 5K

Stone Bridge Half Marathon and 5k

Roscoe, IL

Saturday, September 26th, 2026

Half

Trail

Fast

View details for race Stone Bridge Half Marathon and 5k

Race to Cure Sarcoma Chicago

Chicago, IL

Saturday, September 26th, 2026

View details for race Race to Cure Sarcoma Chicago

1st Annual APRCC Coqui 5K Run/Walk

Aurora, IL

Saturday, September 26th, 2026

View details for race 1st Annual APRCC Coqui 5K Run/Walk

Bloomingdale Trail 5K

Chicago, IL

Saturday, September 26th, 2026

Trail

View details for race Bloomingdale Trail 5K

St. Jude Walk-Chicago

Brookfield, IL

Saturday, September 26th, 2026

View details for race St. Jude Walk-Chicago

Lake County Suicide Prevention Task Force 14th ...

Grayslake, IL

Saturday, September 26th, 2026

View details for race Lake County Suicide Prevention Task Force 14th Annual 5K Walk/Run for Awareness and Suicide Prevention

Golden Harvest Half Marathon & 5k/10k - Greater...

Greater Chicago, IL

Sunday, September 27th, 2026

1 Mile

10K

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

2026 Chi-Care 5K Run/Walk

Chicago, IL

Sunday, September 27th, 2026

View details for race 2026 Chi-Care 5K Run/Walk

F3 Naperville 5K Run & Walk

Warrenville, IL

Sunday, September 27th, 2026

View details for race F3 Naperville 5K Run & Walk

Plainfield Harvest Run 5k/10k & Kids Miler

Plainfield, IL

Sunday, September 27th, 2026

1 Mile

10K

View details for race Plainfield Harvest Run 5k/10k & Kids Miler

DeKalb Corn Classic

DeKalb, IL

Sunday, September 27th, 2026

10K

View details for race DeKalb Corn Classic

Lester Fun Run 2025

Downers Grove, IL

Sunday, September 27th, 2026

1 Mile

View details for race Lester Fun Run 2025

Northwest CASA Pumpkin Dash 5k / 10k

Elk Grove Village, IL

Sunday, September 27th, 2026

10K

View details for race Northwest CASA Pumpkin Dash 5k / 10k

Long Grove's Oktoberfest Half Marathon, 10K & 5K

Long Grove, IL

Saturday, October 3rd, 2026

Half

10K

View details for race Long Grove's Oktoberfest Half Marathon, 10K & 5K

Sweet Ride | Bike • Run • Walk

Willow Springs, IL

Saturday, October 3rd, 2026

Trail

View details for race Sweet Ride | Bike • Run • Walk

Haunted Wine Run 5k at Busse Woods

Elk Grove Village, IL

Saturday, October 3rd, 2026

Fast

View details for race Haunted Wine Run 5k at Busse Woods

Diplo's Run Club Chicago

Chicago, IL

Saturday, October 3rd, 2026

Code:FTR10

View details for race Diplo's Run Club Chicago

Hops for Hope 5K & BrewFest Presented by 93 Oct...

St. Charles, IL

Saturday, October 3rd, 2026

View details for race Hops for Hope 5K & BrewFest Presented by 93 Octane Brewery 2026

Boo Island - 5K Charity Run/Walk

Blue Island, IL

Saturday, October 3rd, 2026

Trail

View details for race Boo Island - 5K Charity Run/Walk

Angels Against Abuse 5K Walk/Run

Romeoville, IL

Saturday, October 3rd, 2026

View details for race Angels Against Abuse 5K Walk/Run

3rd Annual Downers Grove, IL Ostomy 5k

Downers Grove, IL

Saturday, October 3rd, 2026

View details for race 3rd Annual Downers Grove, IL Ostomy 5k

Cheesy Pretzel 5K and 1 Mile Walk

Bolingbrook, IL

Sunday, October 4th, 2026

1 Mile

View details for race Cheesy Pretzel 5K and 1 Mile Walk

JJC Foundation 5K Run/Walk

Joliet, IL

Sunday, October 4th, 2026

1 Mile

View details for race JJC Foundation 5K Run/Walk

Chicago - HFTC 5k

Chicago, IL

Sunday, October 4th, 2026

View details for race Chicago - HFTC 5k

2026 Lemons of Love Pink Lemonade 5K Run/Walk

Mount Prospect, IL

Sunday, October 4th, 2026

View details for race 2026 Lemons of Love Pink Lemonade 5K Run/Walk

13th Annual Head for the Cure 5K - Chicago

Chicago, IL

Sunday, October 4th, 2026

View details for race 13th Annual Head for the Cure 5K - Chicago

Fire Zone 5k

Lockport, IL

Sunday, October 4th, 2026

Trail

View details for race Fire Zone 5k

Care4 Breast Cancer Hybrid 5K

Woodstock, IL

Saturday, October 10th, 2026

View details for race Care4 Breast Cancer Hybrid 5K

12th Annual Harvest Hustle 5K

Niles, IL

Saturday, October 10th, 2026

View details for race 12th Annual Harvest Hustle 5K

El Trote De Las Calacas

Elgin, IL

Saturday, October 10th, 2026

View details for race El Trote De Las Calacas

Nik's 7K Home Run & 1.5 Mile Walk at MercyHealt...

Loves Park, IL

Saturday, October 10th, 2026

1 Mile

View details for race Nik's 7K Home Run & 1.5 Mile Walk at MercyHealth Sportscore Two (Indoor Sports Center)

JAIMIE COX MEMORIAL RUN

Roscoe, IL

Saturday, October 17th, 2026

Trail

View details for race JAIMIE COX MEMORIAL RUN

Cantigny 5K Run/Walk 2026 - Benefiting The Midw...

Wheaton, IL

Saturday, October 17th, 2026

1 Mile

View details for race Cantigny 5K Run/Walk 2026 - Benefiting The Midwest Shelter for Homeless Veterans

Chicago Fall Classic Half Marathon, 10K & Hot C...

Chicago, IL

Saturday, October 17th, 2026

Half

10K

View details for race Chicago Fall Classic Half Marathon, 10K & Hot Cider Hustle 5K

Rosehill Cemetery 'Crypt' 5K Run/Walk

Chicago, IL

Saturday, October 17th, 2026

View details for race Rosehill Cemetery 'Crypt' 5K Run/Walk

23rd Annual This Run's For Jack 2026

Glen Ellyn, IL

Sunday, October 18th, 2026

View details for race 23rd Annual This Run's For Jack 2026

Bolingbrook Howl-O-Ween 5K

Bolingbrook, IL

Sunday, October 18th, 2026

View details for race Bolingbrook Howl-O-Ween 5K

Richardson Farm Fall 5K & 10K with Family 1 Mil...

Spring Grove, IL

Sunday, October 18th, 2026

10K

1 Mile

Fast

View details for race Richardson Farm Fall 5K & 10K with Family 1 Mile Adventure Run

Haunted Highlander Assault Trail Run

Pingree Grove, IL

Friday, October 23rd, 2026

Trail

View details for race Haunted Highlander Assault Trail Run

Haunted Highlander Assault Trail Run

Mchenry, IL

Friday, October 23rd, 2026

Trail

View details for race Haunted Highlander Assault Trail Run

Howl-o-ween 5k - Schaumburg

Rolling Meadows, IL

Saturday, October 24th, 2026

View details for race Howl-o-ween 5k - Schaumburg

Prev 1 24 5 Next

Explore more in Sleepy Hollow, IL

Jump straight to races by distance, month, or type.

Distance

5K 10K Half Marathon Marathon

Month

June July August

Race type

Trail Boston Qualifiers Fast Courses

Run clubs

Run clubs in Sleepy Hollow

Nearby

Elgin Hoffman Estates Palatine McHenry Elk Grove Village Arlington Heights All Illinois races