Upcoming 5K Races Near Sleepy Hollow, IL

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Halloween Hustle

Palatine, IL

Saturday, October 24th, 2026

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Lake Bluff PTO Pumpkin Chase

Lake Bluff, IL

Saturday, October 24th, 2026

1 Mile

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The Fall Color 5K

Lisle, IL

Saturday, October 24th, 2026

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Batavia United Way Bat Race 5K & 10K

Batavia, IL

Saturday, October 24th, 2026

10K

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Badger High School 5K GLOW Run/Walk

Lake Geneva, WI

Saturday, October 24th, 2026

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Forte 5K Run/Walk

Channahon, IL

Saturday, October 24th, 2026

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Scary in the Prairie 5k

Pleasant Prairie, WI

Saturday, October 24th, 2026

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Hot Cider Hustle - Wheaton 8 Mile Run & 5K Run/...

Wheaton, IL

Sunday, October 25th, 2026

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Haunted Halloween Half Marathon & 5km

Chicago, IL

Sunday, October 25th, 2026

Half

Trail

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Howl-o-ween 5k - Dan Ryan Woods

Chicago, IL

Sunday, October 25th, 2026

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Spooky Sprint - Greater Chicago

Greater Chicago, IL

Sunday, October 25th, 2026

1 Mile

10K

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Haunted Oak 5K

Homer Glen, IL

Sunday, October 25th, 2026

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Fraidycat 5k,8k & Meow Mile

Oswego, IL

Sunday, October 25th, 2026

1 Mile

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Spooky Sprint - Greater Chicago

Shorewood, IL

Sunday, October 25th, 2026

1 Mile

10K

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Day of the Dead Family 5K Run/Walk

Wheeling, IL

Sunday, October 25th, 2026

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St. Francis Xavier Falcon 5K Run/Walk

La Grange Park, IL

Saturday, November 7th, 2026

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2026 Jingle Bell Run - Western Suburbs, IL

Wheaton, IL

Saturday, November 14th, 2026

1 Mile

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Abominable Trail Race

Lake Geneva, WI

Saturday, November 14th, 2026

10K

15K

Trail

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Grayslake Central Turkey Trot

Grayslake, IL

Sunday, November 15th, 2026

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Lisle Turkey Trot Tune-Up 5K

Lisle, IL

Sunday, November 15th, 2026

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Run with the Turkeys 5K

Pleasant Prairie, WI

Saturday, November 21st, 2026

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Tom-A-Hawk Turkey Trot 5k

Aurora, IL

Saturday, November 21st, 2026

Fast

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The Great Turkey Chase: Wolfpack 5K

Crystal Lake, IL

Sunday, November 22nd, 2026

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Lincolnwood Turkey Trot: 5K, 10K, Walk, Dash

Lincolnwood, IL

Sunday, November 22nd, 2026

10K

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5k Turkey Trot Family Tradition 2026

Elmwood Park, IL

Thursday, November 26th, 2026

1 Mile

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McHenry Kiwanis Club's Turkey Trot 5K

McHenry, IL

Thursday, November 26th, 2026

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Chi Town Turkey Trot 5K & 10K

Chicago, IL

Thursday, November 26th, 2026

10K

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Long Grove Turkey Trot 5K & 8K

Long Grove, IL

Thursday, November 26th, 2026

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St. Charles Turkey Trot 5K

St. Charles, IL

Thursday, November 26th, 2026

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Grove Express 5K

Downers Grove, IL

Thursday, November 26th, 2026

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Winnetka Turkey Trot 2026

Winnetka, IL

Thursday, November 26th, 2026

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Turkey Trails - Greater Chicago

Greater Chicago, IL

Saturday, November 28th, 2026

1 Mile

10K

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Schaumburg Turkey Trot Half Marathon & 5K

Elk Grove Village, IL

Saturday, November 28th, 2026

Half

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Turkey Trails - Greater Chicago

Shorewood, IL

Saturday, November 28th, 2026

1 Mile

10K

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Rotary Santa Run Walk & Reindeer Dash

Arlington Heights, IL

Saturday, December 5th, 2026

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Reindeer Run 5K 2026

Wheaton, IL

Saturday, December 5th, 2026

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Santa Hustle Chicago

Chicago, IL

Saturday, December 5th, 2026

10K

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Santa's Run through the Lights 5K Run/Walk

Geneva, IL

Saturday, December 5th, 2026

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The Village of Norridge 5K Reindeer Run and Kid...

Norridge, IL

Saturday, December 5th, 2026

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Lemont Frigid 5K

Lemont, IL

Sunday, December 6th, 2026

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Candy Cane Course- Greater Chicago

Elk Grove Village, IL

Saturday, December 12th, 2026

1 Mile

10K

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Candy Cane Course- Greater Chicago

Greater Chicago, IL

Saturday, December 12th, 2026

1 Mile

10K

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2026 Jingle Bell Run - Chicago, IL

Chicago, IL

Saturday, December 12th, 2026

1 Mile

View details for race 2026 Jingle Bell Run - Chicago, IL

Park Ridge Santa Stroll 5k - Stroll Mile - Jing...

Park Ridge, IL

Saturday, December 12th, 2026

1 Mile

View details for race Park Ridge Santa Stroll 5k - Stroll Mile - Jingle Jog

Catch the Elf 5k & 10k

Markham, IL

Saturday, December 19th, 2026

10K

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Cheers to New Year's 5k Run/Walk

Itasca, IL

Friday, January 1st, 2027

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18th Annual F^3 Lake Half Marathon & 5k

Chicago, IL

Saturday, January 30th, 2027

Half

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Abominable Snow Race

Lake Geneva, WI

Saturday, January 30th, 2027

10K

Trail

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Manhattan Irish Fest Parade 5k

Manhattan, IL

Saturday, March 6th, 2027

Fast

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Welcome to the 11th Annual SOB Run

Yorkville, IL

Saturday, March 13th, 2027

View details for race Welcome to the 11th Annual SOB Run

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