Chicago Holiday Events

Chicago Social and Language Exchange (Make New Friends) ✨

Timothy O'Toole's Pub Chicago 24 Apr 2026

Saturday, 31st of October, 2026: Annual Nocturna All Hallows’ Eve Ball w/ DJ Scary Lady Sarah + more

Metro Chicago 31 Oct 2026

Chicago Halloween Bar Crawl

Kaiser Tiger 24 Oct 2026

Chicago Halloween Party Cruise | Pier Pressure® Black Pearl

Spirit of Chicago Yacht 31 Oct 2026

CHICAGO ZOMBIE CRAWL - Halloween Bar Crawl - Wrigleyville Party Pass

Wrigleyville 30 Oct 2026

Chicago Halloween Bar Crawl 2026

PB&J: Pizza Beer and Jukebox 31 Oct 2026

Nimba's Hands on Jollof Cooking Class

3252 S Morgan St 24 Sep 2026

Future Travel World™ Chicago — International Travel & Experience Show

Marriott Marquis Chicago 26 Sep 2026

Book Launch: Children of the Wolf by Abby Geni

Women & Children First 16 Sep 2026

Chicago Official Thanksgiving Eve Bar Crawl 2026

Downtown Chicago 25 Nov 2026

Blue Man Group - A New Holiday Surprise at CIBC Theatre

CIBC Theatre 24 Nov 2026

Blue Man Group - A New Holiday Surprise

CIBC Theatre 12 Dec 2026

Jinkx and DeLa Holiday Show at Auditorium Theatre Chicago

Auditorium Theatre Chicago 6 Dec 2026

Chicago - Holiday Cocktail Tasting Festival - November 14

Hubbard Inn 14 Nov 2026

Soulful Sounds in Chicago

Athenaeum Center for Thought & Culture 11 Oct 2026

Merry, Merry Chicago!

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

R&B Fest Is Coming To Chicago!

Sound-Bar 14 Nov 2026

The Metropolitan Jazz Octet with Dee Alexander

3111 N Western Ave Chicago IL 60618 24 Oct 2026

St. Patrick's Day Lucky Charms River North Bar Crawl | Afternoon

Headquarters Beercade 13 Mar 2027

Broadway In Chicago - Blue Man Group "A New Holiday Surprise"

CIBC Theatre 25 Nov 2026

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

Headquarters Beercade 4 Dec 2026

Black Wednesday @ PARLAY RIVER NORTH

Parlay River North 25 Nov 2026

St. Patrick's Day Lucky Charms West Loop Bar Crawl

West Loop 13 Mar 2027

Black Wednesday @ PARLAY LINCOLN PARK

Parlay Lincoln Park 25 Nov 2026

R&B Fest - Chicago

Sound Bar 14 Nov 2026

St. Patrick's Day Lucky Charms Lincoln Park Bar Crawl

Lincoln Park 13 Mar 2027

Soulful Holiday Lights Trolley Celebrating Motown, R& B & House

230 W North Ave 28 Nov 2026

Chicago SantaCon Bar Crawl 2026

PB&J: Pizza Beer and Jukebox 19 Dec 2026

The Christmas Bar Crawl - Chicago

SPIN 19 Dec 2026

The Naughty List Bar Crawl - Chicago

Black Hole Bar 28 Nov 2026

ANFANG / BEYOND LEGACY / BELLEVUE HOLIDAY / LOVE CUTS

Cubby Bear 25 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

St. Patrick's Day Lucky Charms Wrigleyville Bar Crawl

Blue Bayou 13 Mar 2027

St. Patrick's Day Lucky Charms River North Bar Crawl | Morning

River North 13 Mar 2027

Chicago Wicker Park Naughty Santa Bar Crawl

DSTRKT and Wicker Park Venues 5 Dec 2026

May 5, 2026 * * GET- READY TO START "Free" Strength & Line Dance @ 10:30am!

6550 S Harvard Ave 22 Sep 2026

Renegade Chicago

Bridgeport Art Center 18 Dec 2026

Fa La La Fabulous Holiday Market - Chicago

3656 N Halsted St, Chicago, IL, United States, Illinois 60613 14 Nov 2026

The Chicago Art Girls Holiday Pop-Up Shop

Alexander Graham Bell Elementary School 12 Dec 2026

Holiday Winter Dash Beer Run | 2026 Illinois Brewery Running Series

Goose Island Taproom 6 Dec 2026

Cocktail Class at TRUCE: Holiday Cocktail Lab

TRUCE 1 Dec 2026

Hallmark Christmas Experience

The Loop 27 Nov 2026

A Holiday Cabaret with The Uptones

UncommonGround - Lakeview 5 Dec 2026

It's A Wonderful Life: A Live Radio Play at Paradiso at Athenaeum Theatre - IL

The Chicago Theatre 11 Dec 2026

Roo's Very Merry Pet Market

Fairlie 339 North Bell Chicago 13 Dec 2026

Make the Yuletide Gay at LVPC!

Lake View Presbyterian Church 18 Dec 2026

Late Nite Catechism: Christmas Bingo

Stars and Garters Theater 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

PROMCHELLA: The Art of Becoming — A Holiday Fashion Show

6330 S Stony Island Ave 7 Nov 2026

Get Lit: Santa's Book Fair

American Writers Museum 9 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

Candlelight House Tour 2026

11141 S Cottage Grove Ave 13 Dec 2026

Historic Pullman Model Train Experience-2026

HPF Pullman Exhibit Hall 26 Dec 2026

HERE: for the holidays

The Newport Theater 2 Nov 2026

Felt Decor- Friday, December 4th

Revolution Brewing - Brewery & Taproom 4 Dec 2026

NO SOMMS ALLOWED: Champagne L2

Rogers Park Social 12 Dec 2026

Holiday Swing Social: Class + Social Dancing

Ballroom Dance Chicago 19 Dec 2026

The Balzekas Museum Guild Holiday Craft Fair

Balzekas Museum Of Lithuanian Culture, South Pulaski Road, Chicago, IL, USA 21 Nov 2026

2026 Holiday Community Networking Event

Clarity Partners, LLC 10 Dec 2026

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

Chicago 14 Mar 2026

Read the Room Silent Book Club-November Meetup

Sonder Exchange 8 Nov 2026

Monthly Group Ukulele Lessons in Pilsen. FREE Ukulele Giveaway!

1637 W 18th St 11 Oct 2026

Winter DIY Facial Bar at SpaDerma!

SpaDerma Wicker Park 9 Dec 2026

Love Actually In Concert

Auditorium Theatre 12 Dec 2026

Wintrust Magnificent Mile Lights Festival®

The Magnificent Mile 21 Nov 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 16 Sep 2026

Fizzmas!

3868 N Lincoln Ave 2ND FLOOR, Chicago, IL, United States, Illinois 60613 14 Dec 2026

Dr. Seuss’ How the Grinch Stole Christmas! The Musical

James M. Nederlander Theatre 9 Dec 2026

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

Wrigleyville's Best Bars TBA 12 Dec 2026

11th Annual Kris-Miss Toy Drive

1449 W. Taylor St., Chicago, IL 4 Dec 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

Lesbian Pre-Thanksgiving Potluck party

Andersonville, Chicago 22 Nov 2026

Lesbian/Queer women Pre-Christmas Party

Andersonville, Chicago 20 Dec 2026

Workplace Diversity & Inclusion – Empower Teams in Chicago, IL

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