253 Upcoming Races Near Pleasant Prairie, WI

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

The Milwaukee Beer Run 5k & .05k

Glendale, WI

Sunday, October 4th, 2026

Trail

View details for race The Milwaukee Beer Run 5k & .05k

We Love Teachers 5K - Chicago

Elk Grove Village, IL

Saturday, October 10th, 2026

View details for race We Love Teachers 5K - Chicago

Care4 Breast Cancer Hybrid 5K

Woodstock, IL

Saturday, October 10th, 2026

View details for race Care4 Breast Cancer Hybrid 5K

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El Trote De Las Calacas

Elgin, IL

Saturday, October 10th, 2026

View details for race El Trote De Las Calacas

12th Annual Harvest Hustle 5K

Niles, IL

Saturday, October 10th, 2026

View details for race 12th Annual Harvest Hustle 5K

2026 Bank of America Chicago Marathon

Chicago, IL

Sunday, October 11th, 2026

Marathon

Fast

View details for race 2026 Bank of America Chicago Marathon

National Sweetest Day

Nashotah, WI

Saturday, October 17th, 2026

Half

10K

Trail

View details for race National Sweetest Day

Chicago Fall Classic Half Marathon, 10K & 5K

Chicago, IL

Saturday, October 17th, 2026

Half

10K

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

Rosehill Cemetery 'Crypt' 5K Run/Walk

Chicago, IL

Saturday, October 17th, 2026

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

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

Spooky Sprint - Milwaukee

Milwaukee, WI

Saturday, October 17th, 2026

1 Mile

10K

View details for race Spooky Sprint - Milwaukee

Tombstone Trot

Waukesha, WI

Sunday, October 18th, 2026

View details for race Tombstone Trot

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

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

Mchenry, IL

Friday, October 23rd, 2026

Trail

View details for race Haunted Highlander Assault Trail Run

Haunted Highlander Assault Trail Run

Pingree Grove, IL

Friday, October 23rd, 2026

Trail

View details for race Haunted Highlander Assault Trail Run

Halloween Hustle

Palatine, IL

Saturday, October 24th, 2026

View details for race Halloween Hustle

Badger High School 5K GLOW Run/Walk

Lake Geneva, WI

Saturday, October 24th, 2026

View details for race Badger High School 5K GLOW Run/Walk

Hot Cider Hustle - Shorewood Half Marathon & 5K

Milwaukee, WI

Saturday, October 24th, 2026

Half

View details for race Hot Cider Hustle - Shorewood Half Marathon & 5K

Lake Bluff PTO Pumpkin Chase

Lake Bluff, IL

Saturday, October 24th, 2026

1 Mile

View details for race Lake Bluff PTO Pumpkin Chase

Dia de los Muertos Run/Walk

Milwaukee, WI

Saturday, October 24th, 2026

1 Mile

View details for race Dia de los Muertos Run/Walk

Scary in the Prairie 5k

Pleasant Prairie, WI

Saturday, October 24th, 2026

View details for race Scary in the Prairie 5k

Howl-o-ween 5k - Schaumburg

Rolling Meadows, IL

Saturday, October 24th, 2026

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

Haunted Halloween Half Marathon & 5km

Chicago, IL

Sunday, October 25th, 2026

Half

Trail

View details for race Haunted Halloween Half Marathon & 5km

Howl-o-ween 5k - Dan Ryan Woods

Chicago, IL

Sunday, October 25th, 2026

View details for race Howl-o-ween 5k - Dan Ryan Woods

Spooky Sprint - Greater Chicago

Greater Chicago, IL

Sunday, October 25th, 2026

1 Mile

10K

View details for race Spooky Sprint - Greater Chicago

Riverside Foundation Halloween Hustle 5K Walk o...

Lincolnshire, IL

Sunday, October 25th, 2026

View details for race Riverside Foundation Halloween Hustle 5K Walk or Run

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

Wheaton, IL

Sunday, October 25th, 2026

View details for race Hot Cider Hustle - Wheaton 8 Mile Run & 5K Run/Walk

Day of the Dead Family 5K Run/Walk

Wheeling, IL

Sunday, October 25th, 2026

View details for race Day of the Dead Family 5K Run/Walk

Lakefront Discovery Run

Milwaukee, WI

Saturday, October 31st, 2026

15K

View details for race Lakefront Discovery Run

Among the Trees

Dousman, WI

Saturday, October 31st, 2026

Ultra

Trail

View details for race Among the Trees

St. Francis Xavier Falcon 5K Run/Walk

La Grange Park, IL

Saturday, November 7th, 2026

View details for race St. Francis Xavier Falcon 5K Run/Walk

Vets Day 5K & 10K

Milwaukee, WI

Saturday, November 7th, 2026

10K

View details for race Vets Day 5K & 10K

Fast Track Cross Country Open

Schaumburg, IL

Sunday, November 8th, 2026

Trail

View details for race Fast Track Cross Country Open

Abominable Trail Race

Lake Geneva, WI

Saturday, November 14th, 2026

10K

15K

Trail

View details for race Abominable Trail Race

2026 Jingle Bell Run - Western Suburbs, IL

Wheaton, IL

Saturday, November 14th, 2026

1 Mile

View details for race 2026 Jingle Bell Run - Western Suburbs, IL

Brookfield Zoo Chicago Reindeer Run

Brookfield, IL

Saturday, November 14th, 2026

View details for race Brookfield Zoo Chicago Reindeer Run

Grayslake Central Turkey Trot

Grayslake, IL

Sunday, November 15th, 2026

View details for race Grayslake Central Turkey Trot

Run with the Turkeys 5K

Pleasant Prairie, WI

Saturday, November 21st, 2026

View details for race Run with the Turkeys 5K

Turkey Trails - Milwaukee

Milwaukee, WI

Saturday, November 21st, 2026

1 Mile

10K

View details for race Turkey Trails - Milwaukee

Elf Run

Hales Corner, WI

Sunday, November 22nd, 2026

10K

View details for race Elf Run

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

Lincolnwood, IL

Sunday, November 22nd, 2026

10K

Fast

View details for race Lincolnwood Turkey Trot: 5K, 10K, Walk, Dash

Indoor Turkey Triathlon

Pleasant Prairie, WI

Sunday, November 22nd, 2026

View details for race Indoor Turkey Triathlon

The Great Turkey Chase: Wolfpack 5K

Crystal Lake, IL

Sunday, November 22nd, 2026

View details for race The Great Turkey Chase: Wolfpack 5K

St. Charles Turkey Trot 5K

St. Charles, IL

Thursday, November 26th, 2026

View details for race St. Charles Turkey Trot 5K

Burlington Turkey Trot 5k Run/Walk

Burlington, WI

Thursday, November 26th, 2026

View details for race Burlington Turkey Trot 5k Run/Walk

Winnetka Turkey Trot 2025

Winnetka, IL

Thursday, November 26th, 2026

Trail

Fast

View details for race Winnetka Turkey Trot 2025

Milwaukee Turkey Trot 5K & 8K

Milwaukee, WI

Thursday, November 26th, 2026

View details for race Milwaukee Turkey Trot 5K & 8K

Palatine Park District Turkey Trot

Palatine, IL

Thursday, November 26th, 2026

View details for race Palatine Park District Turkey Trot

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