Run, walk, and toast your accomplishment with a pour of wine at this delightful 5k event.

• Fun
• Competitive
• Quirky

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

EasygoingRUN

Course · Flat · Walkers welcome

A delightfully quirky, donut-themed race for all ages and paces, offering a sweet reward at the finish line.

• 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

Join a community-focused 5K in Humboldt Park, celebrating Earth Day with movement, environmental action, and a shared commitment to sustainability.

• Fun
• Scenic
• Festive
• 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

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

• Fun
• Quirky
• For a Cause

A unique 6-hour trail endurance challenge: complete a 5K every hour, on the hour, or you're out. It's a true test of grit and pacing.

• Competitive
• Quirky

Celebrate Cinco de Mayo with a supportive, stress-free run focused on community, culture, and charity in Chicago/Evanston.

• Fun
• Festive
• For a Cause

Celebrate community and movement at this festive 5K run and 1-mile walk, honoring Logos Missions and CMM anniversaries.

• Competitive
• Festive

Honor, remember, and run for freedom this Memorial Day on scenic routes with a supportive community, contributing to a meaningful cause.

• Fun
• Scenic
• Festive
• 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

A 2-mile fun run through Brookfield Zoo Chicago, featuring dinosaur displays, iconic views, and free post-race admission to the zoo and rides.

• Fun
• Scenic
• Quirky

Run, dance, and celebrate at this 5K music festival under the lights, supporting Stand Up To Cancer.

• Fun
• Quirky
• Festive
• 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 vibrant 5K and 1-mile Color Fun Run supporting Johnsburg High School football, blending community spirit with healthy activity.

• Fun
• Festive
• For a Cause

Celebrate Juneteenth with a supportive, community-focused run that honors resilience and contributes to charity. All paces welcome for a meaningful experience.

• Fun
• Festive
• 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

Run, walk, or dash on the actual runways and taxiways of Chicago Executive Airport, supporting local aviation scholarships.

• Fun
• Competitive
• Quirky
• For a Cause

Run a flat 5K to honor first responders and support vital non-profit organizations dedicated to those in traumatic circumstances.

• Festive
• For a Cause

Run a flat 10K in Chicago's mild June weather, celebrating Pride and supporting local LGBTQ+ organizations through this dedicated charity event.

• Festive
• For a Cause

Kick off your Fourth of July with a festive 4-mile run through the beautiful streets of Elmhurst, a cherished holiday tradition for over two decades.

• Fun
• Scenic
• Festive

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

Celebrate freedom and community this July 4th with a supportive run in Chicago that gives back with every mile.

• Fun
• Festive
• For a Cause