Chicago Holiday Events

11th Annual Arts in the Dark Halloween Parade 2025

State Street 18 Oct 2025

Diwali Celebration Party

Alhambra Palace Restaurant 24 Oct 2025

Chicago Halloween Party Cruise | Pier Pressure® Black Pearl

Spirit of Chicago Yacht 31 Oct 2025

Nightmare on Chicago Street 2025

E Chicago St, Elgin, IL 60120, United States 25 Oct 2025

RAGS AND RICHES in Chicago

Subterranean 25 Oct 2025

Daft Disko Halloween: Chicago @ Navy Pier

Bar Sol Navy Pier 31 Oct 2025

Virtual Riot, Grabbitz, Leotrix in Chicago

Concord Music Hall 29 Nov 2025

The Wintrust Magnificent Mile Lights Festival

The Magnificent Mile, Chicago 22 Nov 2025

Chicago's BYOB Party Bus Holiday Lights Tour | Navy Pier

Old Crow Smokehouse - Wrigleyville 6 Dec 2025

The Boos & Booze Chicago Halloween Bar Crawl | West Loop

Punch Bowl Social 25 Oct 2025

The Boos & Booze Chicago Halloween Bar Crawl | Lake View

Neon Gardens 25 Oct 2025

Chicago's BYOB Party Bus Holiday Lights Tour | Navy Pier

Old Crow Smokehouse - Wrigleyville 13 Dec 2025

Randolph Street Market’s November Holiday Show

Chicago Antique Market Randolph Street 15 Nov 2025

Breakfast with Santa Chicago Neiman Marcus Saturday, December 13, 8:30am

737 N Michigan Ave 13 Dec 2025

Mid-Autumn Festival 2025

Set in Stone Gathering Space 4 Oct 2025

2025 Chicago Halloween Bar Crawl

Chicago 1 Nov 2025

Soulful Sounds in Chicago

Wicker Park Lutheran Church 30 Oct 2025

Chicago Halloween Bar Crawl

Chicago 25 Oct 2025

Wrigleyville Holiday Cavalcade!

The Newport Theater 24 Dec 2025

Harvest Ball

Ballroom Dance Chicago 18 Oct 2025

Mannheim Steamroller Christmas at Nederlander Theatre Chicago

Nederlander Theatre Chicago 20 Dec 2025

Chicago St. Patrick's Day Bar Crawl

Chicago 14 Mar 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 2025

The 12 Cocktails of Christmas - Get on the Waitlist for Tickets

West Fulton Market 6 Dec 2025

Colvin Concerts: Kevin Wood's BeDazzled (Extended Holiday Extravaganza)

Colvin House 5 Dec 2025

AHEE in Chicago

Concord Music Hall 22 Nov 2025

Galena Country Fair

Galena IL 11 Oct 2025

Chicago Day of The Dead Bar Crawl - Dia De Muertos

Chicago 1 Nov 2025

Vienna Boys Choir: Christmas in Vienna

220 S Michigan Ave, Chicago, IL, United States, Illinois 60604 29 Nov 2025

Just Dance - GaGa Themed Party

Subterranean 17 Oct 2025

Adult Prom Scholarship Fundraiser

Purcell Hall 25 Oct 2025

Tablao en Casa: Otoño Flamenco

The Ruth Page Center for the Arts 25 Oct 2025

Holiday Soirée

Institute of Cultural Affairs 14 Nov 2025

The Holiday in Concert at Auditorium Theatre Chicago

Auditorium Theatre Chicago 20 Dec 2025

The Movement at The Outset

The Outset 8 Nov 2025

Gabby's Dollhouse Live!

The Chicago Theatre 15 Nov 2025

Stardew Valley - Symphony of Seasons - Chicago

The Chicago Theatre 11 Oct 2025

Boys Night Out

Bottom Lounge 31 Oct 2025

Paint Night: Honor Your Lost Pet This Día de los Muertos

BottlesUp! 26 Oct 2025

Chicago Official Ugly Sweater Bar Crawl

PB&J: Pizza Beer and Jukebox 20 Dec 2025

Chicago's BYOB Party Bus Holiday Lights Tour | Navy Pier

Old Crow Smokehouse - Wrigleyville 19 Dec 2025

De Dia Los Muertos Halloween Rooftop Party

Selva 1 Nov 2025

Chicago SantaCon 2025

PB&J: Pizza Beer and Jukebox 20 Dec 2025

WAKE IN FRIGHT - Music Box Of Horrors Screening!

Music Box Theatre 5 Oct 2025

Historic Pullman House Tour, October 11-12, 2025

Pullman Exhibit Hall 11 Oct 2025

A Christmas Carol

Albert Ivar Goodman Theatre 14 Nov 2025

Jay Bragg Presents: Christmas in New Vaudeville

UncommonGround - Lakeview 13 Dec 2025

The Boos & Booze Chicago Halloween Bar Crawl | Wicker Park

Chop Shop 25 Oct 2025

Chicago Santa Bar Crawl

PB&J: Pizza Beer and Jukebox 20 Dec 2025

The Official Christmas Bar Crawl - Chicago

SPIN 20 Dec 2025

Bird and Byron

Beat Kitchen 22 Nov 2025

bar italia at Thalia Hall

Thalia Hall 14 Nov 2025

Shannon Rovers 99th Annual Dinner Dance

Soldier Field, Special Olympics Drive, Chicago, IL, USA 18 Oct 2025

Cozy Worlds Market

Uni Uni Boba 6 Dec 2025

Festival del Arte Popular

1852 W 19th St, Chicago, IL, United States, Illinois 60608 10 Oct 2025

Home Alone in Concert

220 S Michigan Ave, Chicago, IL, United States, Illinois 60604 12 Dec 2025

St. Patrick's Day Lucky Charms Lake View Bar Crawl

Lake View 14 Mar 2026

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

West Loop 14 Mar 2026

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

Wicker Park 14 Mar 2026

Wings & Things: Honoring the Monarch Butterfly with RIP Repurposed

The Insect Asylum 1 Nov 2025

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

Lincoln Park 14 Mar 2026

Jon McLaughlin and Friends: Home For The Holidays

Park West 5 Dec 2025

HOH 2025: MACABRE, AVERNUS, BONES, TTCM, BRAINBLEED, DISROBE & CONDITION CRITICAL

Reggies 27 Dec 2025

Merry Merry Chicago at Chicago Symphony Center

Chicago Symphony Center 19 Dec 2025

Holiday House Party

1200 S. DuSable Lake Shore Drive, Chicago, IL, United States, Illinois 60605 6 Dec 2025

Radiant Transitions - 1/2 Day Wellness Retreat

InTouch & Motion Therapy 4 Oct 2025

Hells Kitchen - Musical by Alicia Keys at Nederlander Theatre Chicago

Nederlander Theatre Chicago 14 Nov 2025

Quadrille Ball

Ballroom Dance Chicago 15 Nov 2025

Macabre Pullman Tour - Oct 26

Pullman Exhibit Hall 26 Oct 2025

Chicago's BYOB Party Bus Holiday Lights Tour | Navy Pier

Old Crow Smokehouse - Wrigleyville 5 Dec 2025

Chicago's BYOB Party Bus Holiday Lights Tour | Navy Pier

Old Crow Smokehouse - Wrigleyville 12 Dec 2025

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

Headquarters Beercade 14 Mar 2026

Jinkx and DeLa Holiday Show at Chicago Theatre

Chicago Theatre 7 Dec 2025

Chicago's BYOB Party Bus Holiday Lights Tour | Navy Pier

Old Crow Smokehouse - Wrigleyville 27 Dec 2025

A Live Presentation of 2001: A Space Odyssey

220 S Michigan Ave, Chicago, IL, United States, Illinois 60604 9 Jan 2026

Wednesday at Riviera Theatre - IL

Riviera Theatre - IL 17 Nov 2025

Chicago's BYOB Party Bus Holiday Lights Tour | Navy Pier

Old Crow Smokehouse - Wrigleyville 20 Dec 2025

Mannheim Steamroller Christmas

Nederlander Theatre at Ford Center for the Performing Arts 19 Dec 2025

The Chicago Art Girls Holiday Pop-Up Shop

Alexander Graham Bell Elementary School 13 Dec 2025

Chusoek Korean Thanksgiving Party

Welles Park Gazebo 5 Oct 2025

Lesbian Pre-Thanksgiving Potluck party

Andersonville, Chicago 23 Nov 2025

Shoe Fest 2025 Holiday Jam - Martyrs' - Chicago, IL

Martyrs' 26 Dec 2025

Christmas with the Celts at Ramova Theatre

3520 S Halsted , Chicago, IL, United States, Illinois 60609 20 Nov 2025

Chicago Halloween Bar Crawl 2025 | Saturday, November 1st

Joy District 1 Nov 2025

TBOX 2025 - Festa's 29th Annual Original 12 Bars Of Xmas Holiday Bar Crawl

Wrigleyville Chicago 13 Dec 2025

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

Headquarters Beercade 27 Dec 2025

Candlelight: The Best of Hans Zimmer

Stan Mansion 25 Sep 2025

Friday, 31st of October, 2025: Annual Nocturna All Hallows' Eve Ball w/ DJ Scary Lady Sarah + more!

Metro Chicago 31 Oct 2025

CJO at Winter's with Devon Sandridge

Winter's Jazz Club 19 Oct 2025

2025 Fuller Award Ceremony for Jackie Taylor

Black Ensemble Theater 20 Oct 2025

DOGE Holiday (DOHO) Bar Crawl 2025

The Whale Chicago 13 Dec 2025

Halloween Haunted Bike Night

Tarnish 28 Oct 2025

John Denver Tribute: A Rocky Mountain Christmas

Broadway Playhouse at Water Tower Place 20 Dec 2025

Old Neighborhood Retro Teen Club Dance

St Jerome School 18 Oct 2025

Meghan Quinn in Chicago - Merry Christmas You Filthy Animal

The iO Theater 15 Oct 2025

The Shops - Holiday Edition #1

Water Tower Place (Level 3 Next to JJill and White House Black Market) 13 Dec 2025

Santa Hustle Chicago 5K, 10K, Kids Dash

Soldier Field 6 Dec 2025

Cyanotype Holiday Cards

Lot'sa 7 Dec 2025

DIA DE MUERTOS MARKET

2102 W Cermak Rd 25 Oct 2025

1st Annual Ball- The Pride Ball - Benefiting 'Life is Work!'

Water Tower Place ( Level 3 at FASHIONBAR) 13 Dec 2025