Chicago Running Events

Labor Day Weekend Evening Lake Cruise on Saturday, August 30th

Anita Dee II Boarding at Dusable Harbor (See map and directions at bottom of page for exact location) 30 Aug 2025

Labor Day Weekend Evening Lake Cruise on Sunday, August 31st

Anita Dee II Boarding at Dusable Harbor (See map and directions at bottom of page for exact location) 31 Aug 2025

Bike the Drive 2025

Grant Park Butler Field 31 Aug 2025

Mentors Who Run x RunTooHard - Humboldt/606

Drink happy thoughts Humboldt 23 Aug 2025

Chicago New Years Eve Bar Crawl

Chicago 31 Dec 2025

‍Queer Connections: Men of Color + Allies @ the Dignity 5K

AIDS Garden Chicago 17 Aug 2025

Haunted Halloween Night Lake Cruise on Saturday, October 25th

Anita Dee II Boarding at Dusable Harbor (See map and directions at bottom of page for exact location) 25 Oct 2025

TW Training x Summer House Cookie Run

Summer House Santa Monica 24 Aug 2025

Headshot Marathon - August 30

Dodd Camera 30 Aug 2025

Race Day Ready: 2025 Nike Marathon Collection and Demo Run

Fleet Feet South Loop 25 Sep 2025

Wilde Cabaret Sings "80s Mix Tape"

Sidetrack The Video Bar 16 Aug 2025

Run to Pub Historical Run n Brew.. Great Chicago Fire

Hawkeye's Bar and Grill 21 Sep 2025

Robot Apocalypse: Journey to the End of Night

Zoo Admin Building By The Lions 20 Sep 2025

Santa Hustle Chicago 5K, 10K, Kids Dash

Soldier Field 6 Dec 2025

Alpha Phi Alpha 5K Walk

8236 S Western Ave 6 Sep 2025

Chicago Color Run By Color Craze

Chicago, Illinois 23 Aug 2025

5K for Foster Youth

Dvorak (Anton) Park 27 Sep 2025

Poland Diamond League Watch Party with Matt Centrowitz

Fleet Feet South Loop 16 Aug 2025

Ready to Run 20 Miler

Montrose Lakefront Track 21 Sep 2025

Haunted Halloween Night River Cruise on Saturday, November 1st

Anita Dee ONE Boarding at Dusable Harbor (See map and directions at bottom of page for exact location) 1 Nov 2025

Haunted Halloween Night Lake Cruise on Friday, October 31st

Anita Dee II Boarding at Dusable Harbor (See map and directions at bottom of page for exact location) 31 Oct 2025

9th Annual Run From Prostate Cancer 5K Walk/Run

South Side YMCA 31 Aug 2025

Haunted Halloween Night River Cruise on Friday, October 31st

Anita Dee ONE Boarding at Dusable Harbor (See map and directions at bottom of page for exact location) 31 Oct 2025

cincOH 4th edition Chicago Tango Marathon (in collaboration with La Maravilla)

Epiphany Center for the Arts 29 Aug 2025

Oasis 5K Fun Run

Quest Multisport 13 Sep 2025

SPRINTS Chicago Marathon Party Run - MOST FUN YOU'll HAVE BEFORE RACE DAY

PiniPico Coffee & Empanadas 11 Oct 2025

The Lazy Run 0.5k

Lottie's Pub 11 Oct 2025

The Booost 3K Run

6100 W Fullerton Ave 25 Oct 2025

Gospel Run Chicago

39th Street Beach 6 Sep 2025

Divas Run - Team Race Meetup

Soldier Field 13 Sep 2025

2025 IFPIES Patient & Clinician Education Conference

Simpson Querrey Biomedical Research Center 303 E. Superior Street Chicago, Illinois 60611 11 Oct 2025

Queer Literary Horror Series Fun Run with Author David Jay Collins

The Lost Hours 29 Oct 2025

Run Like a Diva 5K and Half Marathon

1410 Special Olympics Dr, Chicago, IL 60605-2902, United States 13 Sep 2025

20th Annual Race to Wrigley 5K Charity Run Presented by AbbVie

1060 W Addison St 21 Sep 2025

Schurz Schuffle 5K 2025

Carl Schurz High School 18 Oct 2025

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

Anita Dee II TEMPORARILY LOCATED at BURNHAM HARBOR (See directions below) 30 Dec 2025

Rise to Shine 10K/5K/1M Run & Walk

1310 S Wood St, Chicago, IL 60608, United States 19 Oct 2025

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 2025

SkyRise Chicago 2025

Willis Tower 2 Nov 2025

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

Anita Dee II TEMPORARILY LOCATED at BURNHAM HARBOR (See directions below) 31 Dec 2025

Triathalon

Schubas 30 Oct 2025

Chicago Marathon 2025

Chicago Grant Park 12 Oct 2025

BeAware Walk, Run or Bike Breast Cancer Awareness 5k

New Memorial Missionary Baptist Church 11 Oct 2025

moveMENt Olympics 3.0

Bolt Fitness Chicago 26 Jul 2025

Chicago Color Craze Run

Chicago 23 Aug 2025

One Day at a Time, Inc 5K

New Memorial MBC 11 Oct 2025

Arab Summer Cruise (Chicago)

Anita Dee Yacht Charters 6 Sep 2025

2025 I’m Your Huckleberry 1M 5K 10K 13.1 26.2 - Benefits First Star

Chicago 2 Aug 2025

MMC - 20 Miler - Public

57th Street Beach House 20 Sep 2025

5k Beer Run x Alarmist Brewing | 2025 Illinois Brewery Running Series

Alarmist Brewing & Taproom 27 Sep 2025

UPS for DownS RUNS CHICAGO 2025

Grant Park 12 Oct 2025

MMC - Marathon Route Experience 2025 - Public

Roosevelt & Columbus 5 Oct 2025

5k Beer Run x Begyle Brewing | 2025 Illinois Brewery Running Series

Begyle Brewing 7 Sep 2025

Madonna Mile

Resurrection College Prep High School 28 Sep 2025

Chicago Fall Classic Half Marathon & 10K

Montrose Harbor 18 Oct 2025

5k Beer Run x ERIS Brewery & Cider House | 2025 IL Brewery Running Series

ERIS Brewery and Cider House 17 Aug 2025

Back of the Yards 5K Turkey Run

Back of the Yards, Chicago, Illinois 9 Nov 2025

VOLUNTEERS NEEDED: HP5K on 9/13/2025

Harold Washington Playlot Park 13 Sep 2025

Run Club / Walk Club

Golden Hour Acupuncture 15 May 2025