The Ultimate Guide to Chicago Races This Fall 2019

If cooler temps put you in the mood to leave your air-conditioned gym and lace up your running shoes, now’s the perfect time to do it. And nothing helps keep up the motivation to run like a race on the horizon. From pumpkin runs to half marathons, we’ve found a whole crop of upcoming Chicago-area races that are fun, unique, and support a good cause. (And don’t forget to cheer on the participants of the Chicago Marathon on Oct. 13.) So, get in your outdoor running before the first polar vortex hits and sign up for a few of these fall races that give back. If you’re new to running or just a bit rusty, be sure to check out our guide to training for a 5K before you get started!

Sept. 21

Run for Rosé 5K

Together We Tri presents this run/walk with a post-race wine tasting.

Type: 5K, 1-mile walk, kids dash

Location: Gallery Park, Glenview

Benefits: JDRF

Oct. 5 

AIDS Run & Walk Chicago

This popular race at Soldier Field is always a great time, plus it raises awareness for AIDS research and treatment.

Type: 5K, 10K

Location: Soldier Field

Benefits: AIDS Foundation of Chicago


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Oct. 6 

Brain Up 5K

Help fund brain cancer research during this 5K in Maggie Daley Park.

Type: 5K

Location: Maggie Daley Park

Benefits: Brain Up

Bucktown 5K

A neighborhood favorite, this race supports spouses and dependents of fallen law enforcement officers, firefighters, and paramedics, and includes lots of goodies and fun along the course.

Type: 5K

Location: Burr Elementary School

Benefits: 100 Club of Chicago

Stride Against Violence

Run along the lake at Montrose Harbor to raise funds during Domestic Violence Awareness Month.

Type: 5K

Location: Montrose Harbor

Benefits: Apna Ghar


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RBC Race for the Kids

Round up the family for some exercise and fun to support children’s health.

Type: 5K

Location: University of Chicago Campus — Hyde Park

Benefits: University of Chicago Medicine Comer

Oct. 12

Rosehill Cemetery Crypt

We triple-dog-dare you to run this spooky race through Chicago’s largest cemetery.

Type: 5K

Location: Rosehill Cemetery

Benefits: American Diabetes Foundation

Oct. 19

Pumpkins in the Park

This run is all about the costumes and spooky fun to support the Chicago Park District’s programming.

Type: 5K

Location: Lincoln Park South Fieldhouse

Benefits: Chicago Park District’s Night out in the Parks


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Wine Run

Finally, you can combine your love of running and wine, while raising funds for animals.

Type: 5K

Location: Dan Ryan Woods

Benefits: Fetching Tails Foundation

Country Sole

Enjoy country music, a southern breakfast, and beer while supporting the Fetching Tails Foundation.

Type: Half Marathon, 10K, 5K

Location: Montrose Beach

Benefits: Fetching Tails Foundation

Oct. 20 

Frank Lloyd Wright Races

This unique race takes you past eight historic Frank Lloyd Wright homes and raises money for Oak Park’s Scholarship Fund.

Type: 10K, 5K

Location: Oak Park River Forest High School

Benefits: Oak Park District Scholarship Fund


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Oct. 26

Halloween Hustle

A spooky race that encourages costumes and ends in a festive party in Palatine, while supporting the empowerment and education of fathers looking for assistance.

Type: 5K

Location: Downtown Palatine

Benefits: Fathers Helping Fathers

Oct. 27

Beer Run Spiteful Brewing

Run or walk for local brews and two good causes, including the Chicago Park District.

Type: “5K-ish”

Location: Spiteful Brewing

Benefits: Chicago Parks Foundation and Chicago Run

Nov. 2

Hot Cider Hustle

Caramel apples and hot cider await you at the finish line, all for a good cause.

Type: 8K

Location: Chicago Lakefront

Benefits: Best Buddies


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Allstate Hot Chocolate

Epic goodie bags and lots (we mean lots!) of chocolate are included in this popular race that helps grant wishes to children.

Type: 15K/5K

Location: Grant Park

Benefits: Make-A-Wish 

Nov. 28

Edison Park Turkey Trot

Support two charities before you dive into that Thanksgiving dinner.

Type: 5K

Location: Edison Park

Benefits: Illinois Spina Bifida Association and Huntington’s Disease Society of America Illinois Chapter

Turkey Trot Chicago

Help those less fortunate by running to raise funds for the Greater Chicago Food Depository.

Type: 5K/8K

Location: Lincoln Park

Benefits: Greater Chicago Food Depository


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Long Grove Turkey Trot

Apple cider doughnuts, a fleece hoodie, hot cider, and beer are all perks of this run through historic Long Grove.

Type: 5K/8K

Location: Long Grove

Benefits: Northern Illinois Food Bank

Evanston Flying Turkey

Race along the beautiful lakefront course while benefiting two local charities.

Type: 5K

Location: Evanston

Benefits: Evanston Vineyard Food Pantry and Foundation 65

Nov. 30

Grant Park Turkey Trot

Run off that Thanksgiving meal during this race in Grant Park that supports healthy play environments in schools.

Type: 5K/10K

Location: Grant Park

Benefits: Playworks Illinois

Dec. 7

Santa Hustle

Grab your Santa hat and kick off the holiday season with this festive run at Soldier Field.

Type: 5K

Location: Soldier Field

Benefits: Bear Necessities Pediatric Cancer Foundation


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Dec. 14

Jingle Bell Run

A festive fun-run where 100 percent of your registration fee goes toward the Arthritis Foundation.

Type: 5K/1-mile walk

Location: Chicago History Museum

Benefits: Arthritis Foundation

Macaire Douglas lives in Chicago with her husband and two sons. She proudly supports Share Our Spare, a local nonprofit that collects goods for children in need.




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