Chicago Running Events

New Year's Eve Sunset Cocktail Cruise on Thursday, December 31st

Anita Dee II TEMPORARILY LOCATED at BURNHAM HARBOR (See directions below) 31 Dec 2026

Out of the Darkness Chicagoland Walk

Montrose Harbor 3 Oct 2026

2026 Chicago Skechers Hot Chocolate Run

301 S Columbus Dr, Chicago, IL 60604, United States 1 Nov 2026

Divas Chicago Half Marathon and 5K

Soldier Field 19 Sep 2026

All Inclusive New Year's Eve 2026 Fireworks Cruise aboard Anita Dee II

Anita Dee II TEMPORARILY LOCATED at BURNHAM HARBOR (See directions below) 31 Dec 2026

Afterwork Sunset or Fireworks Social Cruises on Lake Michigan

Anita Dee II Boarding at Dusable Harbor (See map and directions at bottom of page for exact location) 25 May 2026

Eve of the Eve Lake Cocktail Cruise on Wednesday, December 30th

Anita Dee II TEMPORARILY LOCATED at BURNHAM HARBOR (See directions below) 30 Dec 2026

Labor Day Weekend Fireworks Lake Cruise on Saturday, September 5th

Anita Dee II Boarding at Dusable Harbor (See map and directions at bottom of page for exact location) 5 Sep 2026

R&B LOVERS CRUISE

Anita Dee Yacht Charters 11 Sep 2026

Sunset Society (Underground Picnic)

CHICAGO LAKEFRONT TBA 15 Aug 2026

Ditka Dash

1410 Special Olympics Dr, Chicago, IL, United States, Illinois 60605 3 Oct 2026

AFRO FUSION ALL WHITE YACHT CRUISE

Anita Dee Yacht Charters 23 Aug 2026

Groove Qruise Yacht Party

111 N Jean Baptiste Pointe du Sable Lake Shore Dr 9 Aug 2026

Labor Day Weekend Evening Lake Cruise on Sunday, September 6th

Anita Dee II Boarding at Dusable Harbor (See map and directions at bottom of page for exact location) 6 Sep 2026

Chicago Triathlon

Monroe Harbor 22 Aug 2026

NIGERIAN INDEPENDENCE DAY YACHT CRUISE

Anita Dee Yacht Charters 27 Sep 2026

Chi Town Turkey Trot 5K & 10K

Dusable Harbor 26 Nov 2026

Chicago Fall Classic Half Marathon, 10K & 5K

Montrose Harbor 17 Oct 2026

The Charisma Cruise

Dusable Harbor 22 Aug 2026

cincOH 5th edition :: Chicago Tango Marathon

Epiphany Center for the Arts 28 Aug 2026

Get Your Rear in Gear - Chicago: 5K Run/Walk for Colon Cancer

W Montrose Harbor Dr, Chicago, IL, United States 15 Aug 2026

Bloomingdale Trail Run 2026

1600-3000 W Bloomingdale, Chicago, IL, United States, Illinois 60647 26 Sep 2026

Ready to Run 20 Miler

Montrose Beach 20 Sep 2026

UPS for DownS RUNS CHICAGO 2026

Grant Park 11 Oct 2026

Chicago Glow Run

Chicago, Illinois 15 Aug 2026

5k Fun Run x Begyle Brewing | 2026 IL Brewery Running Series

Begyle Brewing 13 Sep 2026

Chicago Marathon

Grant Park 11 Oct 2026

5k Fun Run x Alarmist Brewing | 2026 IL Brewery Running Series

Alarmist Brewing & Taproom 26 Sep 2026

5k Fun Run x ERIS Brewery & Cider House | 2026 IL Brewery Running Series

ERIS Brewery and Cider House 16 Aug 2026

5k Fun Run x Illuminated Brew Works | 2026 IL Brewery Running Series

Illuminated Brew Works 8 Aug 2026

5k Fun Run x Lake Effect Brewing Company | 2026 IL Brewery Running Series

Lake Effect Brewing Company 30 Aug 2026

5k Fun Run x Spiteful Brewing | 2026 IL Brewery Running Series

Spiteful Brewing Tap Room 25 Oct 2026

Queens In The City 5k Run

Washington Park 6 Sep 2026

Holiday Winter Dash Beer Run | 2026 Illinois Brewery Running Series

Goose Island Taproom 6 Dec 2026

Friends with Benefits

The Playground Theater 12 Sep 2026

Kenya Marathon Dinner 2026 Edition

Hilton Chicago 9 Oct 2026

Gilmore Girls Trivia Night

Cultivate by Forbidden Root 20 Aug 2026

13th Annual Head for the Cure 5K - Chicago

Lincoln Park 4 Oct 2026

Swim Across America - Chicago Open Water Swim

400 N Lake Shore Dr, Chicago, IL 60611-4308, United States 8 Aug 2026

Chicago Sunrise Wish Run | Free Community Run

601 W Montrose Ave, Chicago, IL 60613-5381, United States 16 Aug 2026

5k Fun Run x Printer's Row Brewing | 2026 IL Brewery Running Series

Printer's Row Brewing 17 Oct 2026

Trash People x PBR GO PLOGGING

Palmer Square Park - MEET AT THE HAND 30 Aug 2026

Thirza's Sprint Club

Wilson Turf Field 11 Jul 2026

First Friday Run Club

Orangetheory Fitness 1 May 2026

Lavender Virtual Race 1M 5K 10K 13.1 26.2 | Language of Flowers Collection

Chicago 27 Jun 2026

2nd Annual Breast Cancer Awareness Walk

Canaryville, Chicago, Illinois 4 Oct 2026

DEKA MILE Roadshow Hosted by Connected Fitness - Chicago, IL

Connected Fitness 6 Sep 2026

Seductive Sunday: A Rooftop RnB Experience

The Wild Hare & Singing Armadillo Frog Sanctuary 20 Sep 2026

Bee Happy Race 2026 | Fun Virtual 5K, 10K, Half Marathon

Chicago 16 May 2026

Zeus Virtual Race 2026 | Gods & Warriors Virtual Running Series

Chicago 13 Jun 2026

Cat Day Virtual Race 1M 5K 10K 13.1 26.2

Chicago 9 Aug 2026

TW Training x Summer House Cookie Run

Summer House Santa Monica 9 Aug 2026

One Day at a Time, Inc Annual Breast Cancer Awareness 5k

St.Luke Missionary Baptist Church 10 Oct 2026

Chicago Sunrise Wish Run | Free Community Run

601 W Montrose Ave 16 Aug 2026

Day of the Dog Virtual Race 1M 5K 10K 13.1 26.2

Chicago 22 Aug 2026

Move + Reading Night at Wild Mile

Wild Mile Chicago 18 Aug 2026

RUNFRIDAYS RUN SIGN UP

Lakefront Trail - Fullerton - 2400 N 14 Aug 2026

2026 Full Armor of God 1M, 5K, 10K, 13.1, 26.2

Chicago 7 Feb 2026

Race Through Hawaii Virtual Race | 5K, 10K, Marathon | Run Anywhere

Chicago 16 May 2026

UAC Cacao Ceremony

Chicago Marriott Downtown Magnificent Mile 8 Sep 2026

2026 New Year Challenge -Year of the Horse 2.026 Mile 20.26 Mile 202.6 MILE

Chicago 15 Feb 2026

Race Through Alaska 1M 5K 10K 13.1 26.2 Virtual Race

Chicago 18 Apr 2026

2026 First Responders 1M 5K 10K 13.1 26.2

Chicago 28 Mar 2026

I'm Your Huckleberry 1M 5K 10K 13.1 26.2

Chicago 28 Feb 2026

Race Through Colorado Virtual Race | 5K, 10K, Half Marathon | Run Anywhere

Chicago 9 May 2026

Race Through Georgia Virtual Race | 5K, 10K, Half Marathon & More | Run

Chicago 2 May 2026

Teacher Appreciation Virtual Race 2026 | Teach Love Inspire

Chicago 23 May 2026

Face Your Giants Virtual Race 2026 | Christian Virtual Run

Chicago 6 Jun 2026

Just One More Mile Virtual Race 2026 | Global Running Day Virtual

Chicago 3 Jun 2026

Purple Heart Day Virtual Race 2026 | 1M 5K 10K 13.1 26.2

Chicago 1 Aug 2026

Peony Virtual Race | 1M 5K 10K 13.1 26.2 | Language of Flowers Collection

Chicago 30 May 2026

2026 Be Brave 1M 5K 10K 13.1 26.2

Chicago 7 Mar 2026

Grand Opening Celebration of Read & Run Chicago’s Little Free Library

3018 W 54th St 13 Aug 2026

Yeti Frostbite Miles Virtual Race| Cryptid Quest Series 1M 5K 10K 13.1 26.2

Chicago 11 Jul 2026

The Chi-Town Showdown Scavenger Hunt

Cloud Gate 12 Jun 2023

Grief on the Move: Run Club

Alexander Hamilton Monument 28 Jun 2026

2026 Taco Sloth 1M, 5K, 10K, 13.1, 26.2

Chicago 22 Feb 2026

Consider the Wildflowers 1M 5K 10K 13.1 26.2

Chicago 1 Mar 2026

2026 Day of the Dead 1M 5K 10K 13.1 26.2

Chicago 14 Mar 2026

Race Through Alabama 1M 5K 10K 13.1 26.2 Virtual Race

Chicago 11 Apr 2026

Race Through Arizona 1M 5K 10K 13.1 26.2 Virtual Race

Chicago 25 Apr 2026

Soiree Saturdays

Chalet 1 Mar 2025

Dobbeck Run Club

Clarence F. Buckingham Memorial Fountain 23 Apr 2026

DoNskI ENT PRESENTS STAR POWER SATURDAYS THE HOTTEST DANCE PARTY IN CHICAGO

THE BAR 10 DOORS 14 Feb 2026

2026 Race to Read 1M 5K 10K 13.1 26.2

Chicago 6 Mar 2026

We Lost Our Cents 1 Mile Virtual Race 2026 | Finisher Medal & Charity Run

Chicago 11 Apr 2026

2026 Full Moon Challenge 12K and 12M

Chicago 7 Feb 2026

Unhinged and Feral 1M 5K 10K 13.1 26.2 - Now Only $18!

Chicago 3 Oct 2026