Chicago Holiday Events

Colombian Fest Chicago 2026

Humboldt Park 17 Jul 2026

Merry, Merry Chicago!

220 S Michigan Ave, Chicago, IL, United States, Illinois 60604 18 Dec 2026

Chicago Halloween Party Cruise | Pier Pressure® Black Pearl

Spirit of Chicago Yacht 31 Oct 2026

Chicago Labor Day Weekend All White Attire Party Cruise

Spirit of Chicago Yacht 6 Sep 2026

Randolph Street Market

1341 W Randolph St, Chicago, IL 60607-1523, United States 25 Jul 2026

Chicago Official Thanksgiving Eve Bar Crawl 2026

Downtown Chicago 25 Nov 2026

Chicago Halloween Bar Crawl

Kaiser Tiger 24 Oct 2026

Chicago Halloween Bar Crawl 2026

PB&J: Pizza Beer and Jukebox 31 Oct 2026

The Christmas Bar Crawl - Chicago

SPIN 19 Dec 2026

Chicago SantaCon Bar Crawl 2026

PB&J: Pizza Beer and Jukebox 19 Dec 2026

Chicago's BYOB Party Bus Holiday Lights Tour 'Tis The Season

Headquarters Beercade 4 Dec 2026

Daily Stoic Live | Onstage with Ryan Holiday

Gateway Theater at Copernicus Center 19 Aug 2026

Labor Day at ROOF on theWit | All White Attire | 9.7.26!

ROOF on theWit 7 Sep 2026

J Holiday - Nahum Thorton Grymes at City Winery - Chicago

City Winery - Chicago 14 Aug 2026

Chicago Christmas in July Bar Crawl 2026

PB&J: Pizza Beer and Jukebox 25 Jul 2026

She & Him

The Riviera Theatre 20 Sep 2026

Home Alone 2: Lost In New York - Live In Concert

50 E Ida B Wells Dr, Chicago, IL, United States, Illinois 60605 19 Dec 2026

Renegade Chicago

Bridgeport Art Center 18 Dec 2026

Chicago Social and Language Exchange (Make New Friends) ✨

Timothy O'Toole's Pub Chicago 24 Apr 2026

The Naughty List Bar Crawl - Chicago

Black Hole Bar 28 Nov 2026

Terrapin Flyer - Days Between - A Celebration of Life of Jerry Garcia at Martyrs' Night 5

3855 N Lincoln Ave, Chicago, IL, United States, Illinois 60613 9 Aug 2026

The Chicago Art Girls Holiday Pop-Up Shop

Alexander Graham Bell Elementary School 12 Dec 2026

Strings at Sunset: ATLYS at Scratch Goods

Scratch Goods 29 Jul 2026

GAY Soul Food (Chicago)

Definition Theatre 14 Aug 2026

Holiday Winter Dash Beer Run | 2026 Illinois Brewery Running Series

Goose Island Taproom 6 Dec 2026

The Shops - Holiday Edition #2 - Final 2026 Pop-up!

Water Tower Place (Level 3 Next to JJill and White House Black Market) 19 Dec 2026

REVOLUTIONARY: The Exhibition

Vjosa Cafe & Events 17 Jul 2026

Xmas In July Afternoon Acoustic Charity Concert

Olive Black Chicago 25 Jul 2026

Terrapin Flyer - Days Between - A Celebration of Life of Jerry Garcia at Martyrs' Night 3

3855 N Lincoln Ave, Chicago, IL, United States, Illinois 60613 6 Aug 2026

Late Nite Catechism: Christmas Bingo

Stars and Garters Theater 6 Dec 2026

The Shops - Holiday Edition #1

Water Tower Place (Level 3 Next to JJill and White House Black Market) 12 Dec 2026

FashionCamp: WINTER HOLIDAY EDITION 2026

FashionBar (Level 3) 12 Dec 2026

Roo's Very Merry Pet Market

Fairlie 339 North Bell Chicago 13 Dec 2026

Holiday Swing Social: Class + Social Dancing

Ballroom Dance Chicago 19 Dec 2026

Artecito Beetles @ OPEN

2214 S Sacramento Ave, Chicago, IL, United States, Illinois 60623 18 Jul 2026

Ugly Sweater Christmas Pop Up Shop

The West Side 19 Dec 2026

TBOX | Chicago's 30th Annual 12 Bars of Xmas/Santa Crawl | 12+ Wrigley Bars

Wrigleyville's Best Bars TBA 12 Dec 2026

S3 Greater Lawn: Growing Together: Community Based Mural w/ Holiday Gerry

4150 W 55th St 7 Jul 2026

Backstory with Larry Potash and Rankin/Bass' Rick Goldschmidt on WGN-TV

WGN-TV 22 Nov 2026

Chicago Retro Holiday Singers Auditions

Mayfair Presbyterian Church 12 Aug 2026

Terrapin Flyer - Days Between - A Celebration of Life of Jerry Garcia at Martyrs' Night 4

3855 N Lincoln Ave, Chicago, IL, United States, Illinois 60613 7 Aug 2026

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

Chicago 14 Mar 2026

Meet People Social Chicago Friday | Cultural International Party

Hopsmith Chicago 1 Nov 2024

How to Stop Renting Your Skills and Start Owning Your Income

Chicago: Moved to Virtual Session 14 Jan 2026

VIRGOS TAKE ANTIGUA 🇦🇬

The Loop 4 Sep 2026

Workplace Diversity & Inclusion – Empower Teams in Chicago, IL

For venue details reach us at: [email protected] 19 Nov 2025