Running Races in Chicago, IL

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 · Timed race

Ascend Chicago's Prudential Plaza in a unique stair climb event, a distinct vertical challenge in the city.

Sun, Apr 12, 2026, 8:00 AM CDT·1 Miles·Chicago, IL

EasygoingRUN

Course · Flat · Timed race

A community 5K in Chicago supporting the National Breast Cancer Foundation and Project Fire Buddies. Run, walk, or crawl for a cause.

• For a Cause

Sat, Apr 18, 2026, 10:00 AM CDT·5K·Chicago, IL

EasygoingRUN

Course · Flat · Timed race

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

Sun, Apr 19, 2026, 9:00 AM CDT·3.5 Miles·Chicago, IL

EasygoingRUN

Course · Flat · Timed race

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

Sat, Apr 25, 2026, 7:30 AM CDT·13.1 Miles·Chicago, IL

Steady EffortRUN

Course · Flat · Timed race

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

• Fun
• Quirky
• For a Cause

Sat, Apr 25, 2026, 7:30 AM CDT·13.1 Miles·Chicago, IL

Steady EffortRUN

Course · Flat · Timed race

Experience Chicago's favorite neighborhood 5K, a family-friendly event supporting local food security efforts in historic Ravenswood.

• Fun
• For a Cause

Sun, Apr 26, 2026, 8:00 AM CDT·3.1 Miles·Chicago, IL

EasygoingRUN

Course · Flat · Walkers welcome

A welcoming, local-themed event in Chicago offering multiple distances, great swag, and a fun atmosphere for the whole family.

• Fun

Sat, May 2, 2026, 7:00 AM CDT·13.1 Miles·Chicago, IL

Steady EffortRUN

Course · Flat · Walkers welcome

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

• Fun
• Festive
• For a Cause

Sat, May 2, 2026, 7:30 AM CDT·13.1 Miles·Chicago, IL

Steady EffortRUN

Course · Flat · Timed race

A supportive sunrise run with scenic views and a meaningful charity component, welcoming all paces in a stress-free setting.

• Fun
• Scenic
• For a Cause

Sat, May 2, 2026, 7:30 AM CDT·13.1 Miles·Chicago, IL

Steady EffortRUN

Course · Flat · Timed race

A meaningful 5K run/walk in Chicago honoring fallen police officers and supporting their families, embodying remembrance and community care.

• For a Cause

Sat, May 2, 2026, 8:00 AM CDT·3.1 Miles·Chicago, IL

EasygoingRUN

Course · Flat · Timed race

Join the Chicago Empower Walk & 5K Run to support the autism community and make a tangible difference, whether you walk or run.

• For a Cause

Sat, May 2, 2026, 10:15 AM CDT·5K·Chicago, IL

EasygoingRUN

Course · Flat · Timed race

Run or walk a scenic lakefront 5K in Chicago, supporting Bright Star Community Outreach's vital work in under-resourced communities.

• Scenic
• Competitive
• For a Cause

Sat, May 16, 2026, 9:00 AM CDT·5K·Chicago, IL

EasygoingRUN

Course · Flat · Timed race

Run a scenic 5k through Wolf Lake's conservation area, support a local community center, and cheer on first responders in their special challenge.

• Scenic
• Competitive
• For a Cause

Run with purpose to support mental health awareness in a welcoming, stress-free environment.

• For a Cause

Sat, May 23, 2026, 7:30 AM CDT·13.1 Miles·Chicago, IL

Steady EffortRUN

Course · Flat · Timed race

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

Sat, May 23, 2026, 7:30 AM CDT·13.1 Miles·Chicago, IL

Steady EffortRUN

Course · Flat · Timed race

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

Sat, May 30, 2026, 7:30 AM CDT·10K·Chicago, IL

EasygoingRUN

Course · Flat · Timed race

Run for a cause at Chicago's Race for Peace 5K, supporting youth anti-violence programs with competitive and non-competitive options.

• Competitive
• For a Cause

Sat, May 30, 2026, 8:30 AM CDT·5K·Chicago, IL

EasygoingRUN

Course · Flat · Timed race

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

• Fun
• Quirky
• Festive
• For a Cause

Sat, May 30, 2026, 8:30 PM CDT·5K·Chicago, IL

EasygoingRUN

Course · Flat · Timed race

Run a scenic 15K through Lincoln Park Zoo, enjoying Chicago's skyline and Lake Michigan views, all while supporting a beloved institution.

• Scenic
• For a Cause

Sun, May 31, 2026, 7:30 AM CDT·15K·Chicago, IL

EasygoingRUN

Course · Flat · Timed race

Run, walk, or sprint to support Chicago's grassroots efforts against gun violence. Every step and contribution directly empowers local community organizations.

• For a Cause

Thu, Jun 4, 2026, 6:00 PM CDT·8K·Chicago, IL

EasygoingRUN

Course · Flat · Timed race

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

• Fun
• Competitive
• Quirky

Fri, Jun 5, 2026, 6:00 PM CDT·1 Miles·Chicago, IL

EasygoingRUN

Course · Flat · Timed race

Unite for a cause that touches us all at the Run for Breast Cancer, a supportive and stress-free event in Chicago.

• Fun
• For a Cause

Sat, Jun 6, 2026, 7:30 AM CDT·13.1 Miles·Chicago, IL

Steady EffortRUN

Course · Flat · Timed race

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

Sat, Jun 6, 2026, 7:30 AM CDT·13.1 Miles·Chicago, IL

Steady EffortRUN

Course · Flat · Timed race