Run or walk a 5K, earn a wine stopper medal, and enjoy a celebratory pour at Chicago's Wild Blossom Meadery & Winery.

• Fun
• Quirky

Sat, Apr 11, 2026, 8:00 AM CDT·5K·Chicago, IL

EasygoingRUN

Course · Flat · Walkers welcome

A deliciously fun, donut-themed run for all ages and paces, featuring distances from a Half Marathon to a Kids Dash.

• Fun
• Quirky

Run a scenic 5K with your dog (or without!) to support Chicagoland Lab Rescue, complete with unique dog-themed swag and treats.

• Fun
• Scenic
• Competitive
• Quirky

A supportive, coffee-themed run in Chicago/Evanston where every post-race mile you log helps charity.

• Fun
• Quirky
• For a Cause

Run a beautiful Chicago course and earn a sweet reward: fresh donuts at the finish line, all while supporting charity.

• Fun
• Scenic
• Quirky
• For a Cause

Join the 55th anniversary of Walk & Roll Chicago, an inclusive event on the Lakefront Path supporting the American Cancer Society.

• Fun
• Scenic
• Quirky
• For a Cause

Four beers, one mile, and a unique blend of fun and competition await on the track, with options for all.

• Fun
• Competitive
• Quirky

Unleash your inner superhero for a great cause at this inclusive, stress-free run, celebrating every mile with a charity donation.

• Fun
• Quirky
• For a Cause

A uniquely relaxed run where slow is celebrated, competition is optional, and every mile helps a cause.

• Fun
• Quirky
• For a Cause

Indulge your sweet tooth and your love for running at this deliciously fun, stress-free event with a charitable twist. All paces welcome.

• Fun
• Quirky
• For a Cause

Run, walk, or polka your way through Chicago's scenic lakefront in this vibrant, culture-rich 5K, part of the Lithuanian Folk Dance Festival.

• Inaugural
• Fun
• Scenic
• Quirky
• Festive

Celebrate 10 years of sweet strides at Chicago's Stan's Donut Race, featuring multiple distances, delicious treats, and support for Cal's Angels.

• Fun
• Competitive
• Quirky
• Festive

Indulge in a sweet finish at this supportive, community-focused run, where donuts await you after a beautiful course.

• Fun
• Quirky
• For a Cause

Run for the carbs and stay for the bagels at this relaxed, community-focused event that supports charity with every mile.

• Fun
• Quirky
• For a Cause

Slow is the new fast at this chill, supportive run where every pace is celebrated and good vibes lead the way.

• Fun
• Quirky
• For a Cause

Honor 9/11 heroes and support our service members and first responders in this unique 5K, featuring an optional GORUCK rucking challenge.

• Quirky
• For a Cause

Indulge your sweet tooth on National Chocolate Day with a fun, stress-free run that supports your goals and gives back to charity.

• Fun
• Quirky
• Festive
• For a Cause

Run for a cause on an active runway at Skydive Chicago, supporting cancer research and celebrating resilience in a truly unique 5K.

• Fun
• Quirky
• For a Cause

Run a beautiful course and earn your donuts at the finish line, all while supporting charity in a friendly, stress-free group setting.

• Fun
• Quirky
• For a Cause

Run for the carbs and stay for the bagels at this community-focused event, where every mile supports a good cause.

• Fun
• Quirky
• For a Cause

Run or walk through Chicago's historic Rosehill Cemetery, a unique fall 5K among monuments, mausoleums, and 'eternal spirits'.

• Fun
• Scenic
• Quirky
• Festive

Run a haunted half marathon or 5K in costume, enjoy scenic lakefront views, and celebrate with Halloween treats and a post-race party.

• Fun
• Scenic
• Competitive
• Quirky

Embrace the Halloween spirit with a fun, supportive run that gives back, offering 5K, 10K, and 13.1 distances.

• Fun
• Quirky
• Festive
• For a Cause

A supportive, stress-free run with a sweet PB&J theme, where every mile helps a charity. Perfect for personal goals and good vibes.

• Fun
• Quirky
• For a Cause