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The best fun runs in Chicago

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

Photograph: Lynn Millspaugh

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

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

Hustle Up the Hancock

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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Shamrock Shuffle

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.

Walk & Roll Chicago

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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Race to Wrigley

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.

Susan G. Komen Race for the Cure

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 10 Mile

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.

The Color Run

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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PAWS Chicago 5K

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.

Run for the 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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Proud to Run

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 Half Marathon

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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Rock the Night 5K

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.

AIDS Run & Walk Chicago

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 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

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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Ugly Sweater Run

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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