Chicago Running Events

2025 Chicago Skechers Hot Chocolate Run

301 S Columbus Dr, Chicago, IL 60604, United States 2 Nov 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

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

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

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

Chicago New Years Eve Bar Crawl

Chicago 31 Dec 2025

Dreams & Nightmares Halloween Party

228 W Chicago Ave 31 Oct 2025

Don't Buy Trouble: A Lawyer Pulls Back The Curtain On Closing

FACETS of Chicago 5 Nov 2025

Halloween Costume 5K Night Run

Portage Park 25 Oct 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

Juárez Athletics Workout with Orangetheory and Adidas Running

Benito Juarez Community Academy 26 Oct 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

The Booost 3K Run

6100 W Fullerton Ave 25 Oct 2025

1 Lung Marathon

The Lincoln Lodge 21 Oct 2025

Queer Literary Horror Series Fun Run with Author David Jay Collins

The Lost Hours 29 Oct 2025

Santa Hustle Chicago 5K, 10K, Kids Dash

Soldier Field 6 Dec 2025

Fright Night + Screams & Shots Weekend Pass – Chicago 2025

Joy District 31 Oct 2025

SkyRise Chicago 2025

Willis Tower 2 Nov 2025

Gilmore Girls Trivia Night

Cultivate by Forbidden Root 23 Oct 2025

Peloton Kids Foundation Chicago 5K!

Lincoln Park Conservatory (Free with Reservations) 24 Oct 2025

Book Club Run of Refugee High with Elly Fishman

Chi Tea 22 Nov 2025

Made in Chicago Fun Run/Walk with David Hammond and Monica Eng

Avalon Branch, Chicago Public Library 8 Nov 2025

Chicago City Builders Book Club: Nature's Metropolis, Part Two

Arup 4 Mar 2026

Triathalon

Schubas 30 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

Chi Town Half Marathon & 10K

Montrose Harbor 4 Apr 2026

Running Tour of The Salt Shed with Photographer Sandra Steinbrecher

The Salt Shed 16 Nov 2025

Bike, Walk, Run

1686 E Hayes Dr 26 Oct 2025

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

Chicago 2 Aug 2025

Pretty Girls Love Vibes & Music

Chalet 1 Mar 2025

Holiday Winter Dash Beer Run | 2025 Illinois Brewery Running Series

Goose Island Taproom 7 Dec 2025

Back of the Yards 5K Turkey Run

Back of the Yards, Chicago, Illinois 9 Nov 2025