Chicago Holiday Events

Holiday events Happening Next in Chicago, IL

11th Annual Arts in the Dark Halloween Parade 2025

State Street 18 Oct 2025
HALLOWEEN

Diwali Celebration Party

Alhambra Palace Restaurant 24 Oct 2025
FESTIVALS USD 55 TO 82

Chicago Halloween Party Cruise | Pier Pressure® Black Pearl

Spirit of Chicago Yacht 31 Oct 2025
ENTERTAINMENT USD 30 TO 56

Nightmare on Chicago Street 2025

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

RAGS AND RICHES in Chicago

Subterranean 25 Oct 2025
ART

Daft Disko Halloween: Chicago @ Navy Pier

Bar Sol Navy Pier 31 Oct 2025
HALLOWEEN USD 21

Virtual Riot, Grabbitz, Leotrix in Chicago

Concord Music Hall 29 Nov 2025
CONCERTS

The Wintrust Magnificent Mile Lights Festival

The Magnificent Mile, Chicago 22 Nov 2025
FESTIVALS

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

Old Crow Smokehouse - Wrigleyville 6 Dec 2025
PARTIES

The Boos & Booze Chicago Halloween Bar Crawl | West Loop

Punch Bowl Social 25 Oct 2025
PARTIES USD 14 TO 37

The Boos & Booze Chicago Halloween Bar Crawl | Lake View

Neon Gardens 25 Oct 2025
PARTIES USD 14 TO 31

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

Old Crow Smokehouse - Wrigleyville 13 Dec 2025
PARTIES

Randolph Street Market’s November Holiday Show

Chicago Antique Market Randolph Street 15 Nov 2025
HOLIDAY

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

737 N Michigan Ave 13 Dec 2025
KIDS USD 67 TO 85

Mid-Autumn Festival 2025

Set in Stone Gathering Space 4 Oct 2025
FESTIVALS FREE

2025 Chicago Halloween Bar Crawl

Chicago 1 Nov 2025
PARTIES USD 9 TO 18

Soulful Sounds in Chicago

Wicker Park Lutheran Church 30 Oct 2025
COMEDY

Chicago Halloween Bar Crawl

Chicago 25 Oct 2025
PARTIES USD 15 TO 36

Wrigleyville Holiday Cavalcade!

The Newport Theater 24 Dec 2025
HOLIDAY USD 15 TO 215

Harvest Ball

Ballroom Dance Chicago 18 Oct 2025
WORKSHOPS USD 87

Mannheim Steamroller Christmas at Nederlander Theatre Chicago

Nederlander Theatre Chicago 20 Dec 2025
ART

Chicago St. Patrick's Day Bar Crawl

Chicago 14 Mar 2026
PARTIES USD 0 TO 36

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
FIREWORKS USD 113 TO 217

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

West Fulton Market 6 Dec 2025
FOOD-DRINKS FREE

AHEE in Chicago

Concord Music Hall 22 Nov 2025
CONCERTS

Galena Country Fair

Galena IL 11 Oct 2025

Chicago Day of The Dead Bar Crawl - Dia De Muertos

Chicago 1 Nov 2025
DAY-OF-THE-DEAD USD 15 TO 31

Vienna Boys Choir: Christmas in Vienna

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

Just Dance - GaGa Themed Party

Subterranean 17 Oct 2025
PARTIES

Adult Prom Scholarship Fundraiser

Purcell Hall 25 Oct 2025
NONPROFIT USD 55 TO 87

Tablao en Casa: Otoño Flamenco

The Ruth Page Center for the Arts 25 Oct 2025
MUSIC USD 10 TO 100

Holiday Soirée

Institute of Cultural Affairs 14 Nov 2025
HOLIDAY USD 0 TO 98

The Holiday in Concert at Auditorium Theatre Chicago

Auditorium Theatre Chicago 20 Dec 2025
ART

The Movement at The Outset

The Outset 8 Nov 2025

Gabby's Dollhouse Live!

The Chicago Theatre 15 Nov 2025
ART

Stardew Valley - Symphony of Seasons - Chicago

The Chicago Theatre 11 Oct 2025
ART

Boys Night Out

Bottom Lounge 31 Oct 2025
TRIPS-ADVENTURES

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

BottlesUp! 26 Oct 2025
DRAWING-PAINTING USD 54

Chicago Official Ugly Sweater Bar Crawl

PB&J: Pizza Beer and Jukebox 20 Dec 2025
UGLY-CHRISTMAS-SWEATER-DAY USD 0 TO 31

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

Old Crow Smokehouse - Wrigleyville 19 Dec 2025
PARTIES USD 78 TO 101

De Dia Los Muertos Halloween Rooftop Party

Selva 1 Nov 2025
HALLOWEEN USD 30 TO 108

Chicago SantaCon 2025

PB&J: Pizza Beer and Jukebox 20 Dec 2025
PARTIES USD 0 TO 31

WAKE IN FRIGHT - Music Box Of Horrors Screening!

Music Box Theatre 5 Oct 2025
FESTIVALS

Historic Pullman House Tour, October 11-12, 2025

Pullman Exhibit Hall 11 Oct 2025
MUSIC USD 24 TO 31

A Christmas Carol

Albert Ivar Goodman Theatre 14 Nov 2025
CHRISTMAS-CAROLS

Jay Bragg Presents: Christmas in New Vaudeville

UncommonGround - Lakeview 13 Dec 2025
ENTERTAINMENT USD 18 TO 23

The Boos & Booze Chicago Halloween Bar Crawl | Wicker Park

Chop Shop 25 Oct 2025
HALLOWEEN USD 14 TO 31

Chicago Santa Bar Crawl

PB&J: Pizza Beer and Jukebox 20 Dec 2025
PARTIES USD 0 TO 31

The Official Christmas Bar Crawl - Chicago

SPIN 20 Dec 2025
PARTIES USD 7 TO 35

Bird and Byron

Beat Kitchen 22 Nov 2025
CONTESTS

bar italia at Thalia Hall

Thalia Hall 14 Nov 2025
CONTESTS

Shannon Rovers 99th Annual Dinner Dance

Soldier Field, Special Olympics Drive, Chicago, IL, USA 18 Oct 2025
MUSIC USD 146 TO 1,763

Cozy Worlds Market

Uni Uni Boba 6 Dec 2025
ART FREE

Festival del Arte Popular

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

Home Alone in Concert

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

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

Lake View 14 Mar 2026
PARTIES USD 19 TO 60

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

West Loop 14 Mar 2026
PARTIES USD 19 TO 60

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

Wicker Park 14 Mar 2026
PARTIES USD 19 TO 60

Wings & Things: Honoring the Monarch Butterfly with RIP Repurposed

The Insect Asylum 1 Nov 2025
WORKSHOPS USD 23 TO 179

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

Lincoln Park 14 Mar 2026
PARTIES USD 14 TO 60

Jon McLaughlin and Friends: Home For The Holidays

Park West 5 Dec 2025
TRIPS-ADVENTURES

Merry Merry Chicago at Chicago Symphony Center

Chicago Symphony Center 19 Dec 2025
CONTESTS

Holiday House Party

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

Radiant Transitions - 1/2 Day Wellness Retreat

InTouch & Motion Therapy 4 Oct 2025
HEALTH-WELLNESS USD 212 TO 319

Hells Kitchen - Musical by Alicia Keys at Nederlander Theatre Chicago

Nederlander Theatre Chicago 14 Nov 2025
ART

Quadrille Ball

Ballroom Dance Chicago 15 Nov 2025
WORKSHOPS USD 87

Macabre Pullman Tour - Oct 26

Pullman Exhibit Hall 26 Oct 2025
HOLIDAY USD 0 TO 23

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

Old Crow Smokehouse - Wrigleyville 5 Dec 2025
PARTIES

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

Old Crow Smokehouse - Wrigleyville 12 Dec 2025
PARTIES USD 78 TO 101

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

Headquarters Beercade 14 Mar 2026
PARTIES USD 19 TO 60

Jinkx and DeLa Holiday Show at Chicago Theatre

Chicago Theatre 7 Dec 2025
ART

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

Old Crow Smokehouse - Wrigleyville 27 Dec 2025
PARTIES

A Live Presentation of 2001: A Space Odyssey

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

Wednesday at Riviera Theatre - IL

Riviera Theatre - IL 17 Nov 2025
ART

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

Old Crow Smokehouse - Wrigleyville 20 Dec 2025
PARTIES

Mannheim Steamroller Christmas

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

The Chicago Art Girls Holiday Pop-Up Shop

Alexander Graham Bell Elementary School 13 Dec 2025
POP-UPS

Chusoek Korean Thanksgiving Party

Welles Park Gazebo 5 Oct 2025
THANKSGIVING FREE

Lesbian Pre-Thanksgiving Potluck party

Andersonville, Chicago 23 Nov 2025
FOOD-DRINKS

Christmas with the Celts at Ramova Theatre

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

Chicago Halloween Bar Crawl 2025 | Saturday, November 1st

Joy District 1 Nov 2025
HALLOWEEN USD 18 TO 39

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

Headquarters Beercade 27 Dec 2025
PARTIES

Candlelight: The Best of Hans Zimmer

Stan Mansion 25 Sep 2025
CANDLELIGHT-CONCERTS

CJO at Winter's with Devon Sandridge

Winter's Jazz Club 19 Oct 2025
MUSIC

2025 Fuller Award Ceremony for Jackie Taylor

Black Ensemble Theater 20 Oct 2025
ART FREE

DOGE Holiday (DOHO) Bar Crawl 2025

The Whale Chicago 13 Dec 2025
PARTIES

Halloween Haunted Bike Night

Tarnish 28 Oct 2025
HALLOWEEN

John Denver Tribute: A Rocky Mountain Christmas

Broadway Playhouse at Water Tower Place 20 Dec 2025
FESTIVALS

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
ART USD 29

The Shops - Holiday Edition #1

Water Tower Place (Level 3 Next to JJill and White House Black Market) 13 Dec 2025
HOLIDAY USD 29 TO 290

Santa Hustle Chicago 5K, 10K, Kids Dash

Soldier Field 6 Dec 2025
KIDS

Cyanotype Holiday Cards

Lot'sa 7 Dec 2025
WORKSHOPS USD 71

DIA DE MUERTOS MARKET

2102 W Cermak Rd 25 Oct 2025
DAY-OF-THE-DEAD USD 23

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

Water Tower Place ( Level 3 at FASHIONBAR) 13 Dec 2025
ART USD 45 TO 695