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

Run or walk a scenic 5K through Eckert's Belleville Farm, then celebrate with wine and a medal that's also a wine stopper.

• Fun
• Scenic
• Competitive
• Quirky

Sat, Apr 18, 2026, 9:00 AM CDT·5K·Belleville, IL

EasygoingRUN

Course · Rolling · Timed race

Challenge yourself with a 5K, 10K, or the unique 'Double' race (9.31 miles total), complete with chip timing and post-race refreshments.

• Fun
• Competitive
• Quirky

Sat, May 23, 2026, 8:30 AM CDT·3.1 Miles, 3.11 Miles, 6.2 Miles, 9.31 Miles·Western Springs, IL

Steady EffortRUN

Course · Rolling · Timed race

Run or walk a 5K, then celebrate with a pour of award-winning wine at Cooper's Hawk Winery. A perfect blend of fitness and fun.

• Fun
• Quirky

Sun, May 24, 2026, 8:00 AM CDT·5K·New Lenox, IL

EasygoingRUN

Course · Flat · Timed race

Get ready to be doused in color at this untimed 5K, a joyful community event supporting Orient's 4th of July Celebration.

• Fun
• Quirky
• Festive
• For a Cause

Sat, May 30, 2026, 9:00 AM CDT·5K·Orient, IL

EasygoingRUN

Course · Flat · Family-oriented

Celebrate Global Running Day with Fleet Feet's community 5K, embracing summer vibes and supporting Girls on the Run.

• Fun
• Festive
• For a Cause

Wed, Jun 3, 2026, 6:00 PM CDT·1 Miles, 3.1 Miles·Bloomington, IL

EasygoingRUN

Course · Timed race

A festive, family-friendly Fourth of July run through Lakeland Park, offering a challenging 4-mile course and a 1-mile option.

• Fun
• Scenic
• Competitive
• Festive

Sat, Jul 4, 2026, 8:00 AM CDT·1 Miles, 4 Miles·Canton, IL

EasygoingRUN

Course · Family-oriented

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
• For a Cause

Sat, Jul 18, 2026, 7:00 AM CDT·0.5 Miles, 1 Miles, 3.1 Miles, 6.1 Miles, 6.2 Miles, 13.1 Miles, 26.2 Miles·Chicago, IL

EasygoingRUN

Course · Flat · Family-oriented

A charming, dog-themed 5k in Aurora, featuring scenic park views and special treats for both human and furry friends.

• Fun
• Scenic
• Quirky

Sat, Jul 18, 2026, 8:00 AM CDT·5K·Aurora, IL

EasygoingRUN

Course · Flat · Timed race

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

Sat, Sep 5, 2026, 8:00 AM CDT·1 Miles, 5K·South Barrington, IL

EasygoingRUN

Course · Rolling · Timed race

Run, walk, or bike to support family building. Enjoy a community day with post-race fun, all while raising vital funds for a meaningful cause.

• Fun
• Festive
• For a Cause

Sun, Sep 20, 2026, 8:30 AM CDT·5K·Glenview, IL

EasygoingRUN

Course · Flat · Family-oriented

Dash for a cause at the Northwest CASA Pumpkin Dash, a fun 5K/10K supporting survivors of sexual violence.

• Fun
• Festive
• For a Cause

Sun, Sep 27, 2026, 9:00 AM CDT·5K, 10K·Elk Grove Village, IL

EasygoingRUN

Course · Flat · Timed race

A Halloween-themed 5K run or walk through Busse Woods, capped off with a celebratory wine pour and unique finisher swag.

• Fun
• Competitive
• Quirky
• Festive

Sat, Oct 3, 2026, 3:00 PM CDT·5K·Elk Grove Village, IL

EasygoingRUN

Course · Flat · Timed race

Enjoy a chip-timed 5K on a scenic campus, complete with music, food trucks, and family-friendly activities for a vibrant community day.

• Fun
• Scenic
• Competitive
• Quirky
• Festive

Sun, Oct 25, 2026, 10:00 AM CDT·1 Miles, 3.1 Miles·University Park, IL

EasygoingRUN

Course · Flat · Family-oriented