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Runners get blasted with rainbow cornstarch at the Color Run 5K through Grant Park on June 7, 2015.
Photograph: Lynn Millspaugh

The best fun runs in Chicago

Find your next 5K (and maybe your next Tinder profile pic) in Chicago’s best races

By Kris Vire
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Maybe you’re not up to marathon speed, but you can still enjoy a good race. Chicago’s calendar is filled with 5K and 10K runs and walks—some gimmicky (hello, Ditka Dash), many benefiting good causes and all a welcome respite from your gym. Lace up your running shoes, get in the starting lane and make up for a late night at the cocktail bar with these great fun runs.

Chicago fun runs

Cupid's Undie Run sends pantless participants through the streets of Wrigleyville.
Photograph: Kristan Lieb

Cupid’s Undie Run

Get chilly for a cause at this “mile(ish)” run through Wrigleyville in your underthings. Chicago is one of nearly 40 cities to host a Cupid’s Undie Run every February, raising money for the Children’s Tumor Foundation.

February. cupidsundierun.org

The John Hancock Center
Photograph: Martha Williams

Hustle Up the Hancock

Every year more than 4,000 brave souls participate in this stair-climbing challenge at the John Hancock Center. Competitive climbers can do the full run up 94 floors, or you can do a half-climb starting on the 42nd floor. Runners raise funds for the Respiratory Health Association.

February. hustleupthehancock.org.

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Runners clad in green trotted through Grant Park during the annual Shamrock Shuffle, March 29, 2015.
Photograph: Max Herman

Shamrock Shuffle

Celebrate St. Patrick’s Day (season) at this annual 8K downtown run (the race starts and finishes in Grant Park). Runners raise funds for a variety of charities and causes.

March. shamrockshuffle.com.

Photograph: Grace Allen

Walk & Roll Chicago

Run or walk (5K), skate (10K) or bike (15K) through the Museum Campus at this family-friendly spring event benefiting the American Cancer Society.

April. walkrollchicago.org.

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Wrigley Field
Photograph: CC/Flickr/Arturo Pardavila III

Race to Wrigley

See the sights in Lakeview and run through the Wrigley Field concourse before hitting the finish line at this spring 5K to raise funds for Cubs Charities.

April. race-cubs.com.

Montrose Harbor
Photograph: Alaina McDavid

Susan G. Komen Race for the Cure

This Mother’s Day 5K, a longtime fundraiser for breast cancer research, now starts and finishes at Montrose Harbor with a route running up and back down the lakeshore.

May. komenchicago.org.

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Soldier Field
Wikimedia Commons

Soldier Field 10 Mile

Like the stadium’s name, this Memorial Day weekend 10-miler honors our military, with benefits going to local and national veterans’ charities. The race ends on the football field itself for an unforgettable finish.

May. soldierfield10.com.

Runners get doused with powdered color at the Color Run 5K through Grant Park on June 8, 2014.
Photograph: Mark Wright

The Color Run

For those who want their race to feel like a rave, this annual 5K run through Grant Park will pelt you with rainbow-tinted cornstarch and now includes a “foam zone.” It’s guaranteed to generate your new dating profile pic.

June. thecolorrun.com.

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Photo: Monaghan Photography

PAWS Chicago 5K

Pets can bring their humans along for this Montrose Harbor 5K benefiting the no-kill animal shelter.

June. my.pawschicago.org/5K.

Lincoln Park Zoo
Lincoln Park Zoo

Run for the Zoo

For nearly 40 years, this 5K/10K has had runners weaving through the Lincoln Park Zoo grounds and the surrounding park to help keep the zoo free and open to the public. There’s also a “Safari Stampede” obstacle course option for kids 8 and under.

June. lpzoo.org/united-run-zoo.

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Photograph: Ron Reason

Proud to Run

This annual 5K/10K walk and run has been a Pride weekend tradition for 35 years. Registration fees are distributed to a different lineup of Chicago-area LGBTQ nonprofits every year.

June. proudtorun.org.

Rock 'n' Roll 1/2 Marathon | Chicago | 2011
Photograph: Mandy Dempsey

Rock ‘n’ Roll Half Marathon

Run 13.1 miles through downtown with musical support all along the course, with a celebratory concert greeting you at the finish line in Grant Park.

July. runrocknroll.com/chicago.

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Soldier Field
Wikimedia Commons

Rock the Night 5K

Not a morning person? Register for this summer evening run through downtown, finishing with a post-race party on Soldier Field’s Stadium Green.

August. rockthenight5k.com.

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Photograph: AFC

AIDS Run & Walk Chicago

This popular 5K/10K along the lakefront benefits the AIDS Foundation of Chicago.

Fall. events.aidschicago.org.

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Hot Chocolate 5K/15K

Hot Chocolate 15K

Is there a better finish-line motivator than chocolate? We’re gonna say no. This fall 15K in Grant Park (there’s also a 5K option) knows how to reward runners as the temperature starts to drop.

October. hotchocolate15k.com/chicago.

Ditka Dash: Thousands of runners put on a Ditka mustache and ran a 5k this weekend at Soldier Field.
Photograph: Max Herman

Ditka Dash

If you still need evidence that Da Coach of Da Bears when they last won Da Super Bowl has officially achieved Chicago sainthood, look no further than this Mike Ditka cosplay 5K, which started a few years back and has improbably enough become an annual football-season event, with runners sporting pasted-on mustaches, headbands and Bears sweater vests.

October, ditkadash.com.

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Turkey Day Run
Photograph: John Bedessem

Turkey Day Run

This Thanksgiving Day 5K and 8K in Lincoln Park, nearly 40 years strong, is one of several Chicago-area turkey trots that will make you feel better about stuffing yourself later in the day.

Thanksgiving Day. turkeyday-5k.com/races/chicago.

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Photograph: Angela Mejia

Ugly Sweater Run

Rustle up your tackiest holiday knitwear for this merry and highly-Instagrammable 5K trek through the South Loop, and burn off some of those Christmas cookies. At the finish line you’ll be handed a Kahlua cocktail to help warm you back up.

December. theuglysweaterrun.com.

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