Chicago Holiday Events

Waves Of Bollywood All White Glam Night

900 S Wells St 13 Sep 2025

10cc in Chicago

Park West 5 Sep 2025

11th Annual Arts in the Dark Halloween Parade 2025

State Street 18 Oct 2025

AVLI NIGHTS IN MYKONOS - WHITE ATTIRE PARTY

Avli on The Park (Chicago) 6 Sep 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

The Office E.N.T & ClubMeet4More Presents Carnival Night Cabin Party

Chicago, IL 5 Sep 2025

Diwali Celebration Party

Alhambra Palace Restaurant 24 Oct 2025

Daft Disko Halloween: Chicago @ Navy Pier

Bar Sol Navy Pier 31 Oct 2025

My Momma’s Era

Greenwood Oasis 27 Sep 2025

AHEE in Chicago

Concord Music Hall 22 Nov 2025

The Boos & Booze Chicago Halloween Bar Crawl | Lake View

Neon Gardens 25 Oct 2025

Mannheim Steamroller Christmas at Nederlander Theatre Chicago

Nederlander Theatre Chicago 20 Dec 2025

The Story So Far, Neck Deep, Origami Angel, Pain of Truth in Chicago

The Salt Shed Outdoors (Fairgrounds) 11 Sep 2025

Stardew Valley - Symphony of Seasons - Chicago

The Chicago Theatre 11 Oct 2025

Randolph Street Market’s November Holiday Show

Chicago Antique Market Randolph Street 15 Nov 2025

Children's Storytime: HILWA'S GIFTS by Safa Suleiman

Women & Children First 13 Sep 2025

Virtual Riot, Grabbitz, Leotrix in Chicago

Concord Music Hall 29 Nov 2025

Chicago Halloween Bar Crawl

Chicago 25 Oct 2025

Homecoming House Party: For the Culture

1200 S. DuSable Lake Shore Drive, Chicago, IL, United States, Illinois 60605 12 Sep 2025

Chicago Day of The Dead Bar Crawl - Dia De Muertos

Chicago 1 Nov 2025

The Boos & Booze Chicago Halloween Bar Crawl | West Loop

Punch Bowl Social 25 Oct 2025

Rituals of Remembering: Living Altars

4910 W Quincy St 20 Sep 2025

The Cinderella Escape in Chicago

Chicago 20 Sep 2025

The Boos & Booze Chicago Halloween Bar Crawl | Wicker Park

Chop Shop 25 Oct 2025

40+ Christians Mixer: Pairing Party

Prāzbar 6 Sep 2025

Pole Night - Latinx Heritage

Provocateur 19 Sep 2025

Dan Pelosi "Let's Party" at Everybody's Coffee

Everybody's Coffee (Wilson Abbey) 5 Sep 2025

The Holiday in Concert at Auditorium Theatre Chicago

Auditorium Theatre Chicago 20 Dec 2025

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

Old Crow Smokehouse - Wrigleyville 13 Dec 2025

Christian Singles Meet & Greet in Chicago!

Pinstripes 5 Sep 2025

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

Old Crow Smokehouse - Wrigleyville 27 Dec 2025

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

Old Crow Smokehouse - Wrigleyville 20 Dec 2025

Jinkx and DeLa Holiday Show at Chicago Theatre

Chicago Theatre 7 Dec 2025

Vienna Boys Choir: Christmas in Vienna

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

Carnivale's 20th Anniversary Party!

702 W Fulton Market, Chicago, IL, United States, Illinois 60661 10 Sep 2025

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

Old Crow Smokehouse - Wrigleyville 5 Dec 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

2025 Chicago Halloween Bar Crawl

Chicago 1 Nov 2025

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

Old Crow Smokehouse - Wrigleyville 12 Dec 2025

Chicago SantaCon 2025

PB&J: Pizza Beer and Jukebox 20 Dec 2025

SUMMER VIBES 2 - Yacht Party

Anita Dee Yacht Charters 7 Sep 2025

Just Dance!: Lady Gaga Nite [Chicago]

Subterranean 18 Oct 2025

Golden Hour featuring Jackson Jay Kidder

Epiphany Center for the Arts 4 Sep 2025

Chicago Santa Bar Crawl

PB&J: Pizza Beer and Jukebox 20 Dec 2025

Tipsy Rodeo

Morgan MFG 6 Sep 2025

IN CULINARY CONVERSATION WITH CHEF MATTHEW SKOLARUS

Boelter Foodservice Design, Equipment & Supply 24 Sep 2025

Gabby's Dollhouse Live!

The Chicago Theatre 15 Nov 2025

Boys Night Out

Bottom Lounge 31 Oct 2025

Christmas Wonderland Mini Photoshoots | Chicago, IL

Chicago, IL 27 Sep 2025

Fizz Band Night ft The Joshua Jern Orchestra!

3868 N Lincoln Ave 2ND FLOOR, Chicago, IL, United States, Illinois 60613 8 Sep 2025

The Boos & Booze Chicago Halloween Bar Crawl | River North

Headquarters Beercade 25 Oct 2025

A Christmas Carol

Albert Ivar Goodman Theatre 14 Nov 2025

2025 Fuller Award Ceremony for Jackie Taylor

Black Ensemble Theater 20 Oct 2025

Old Neighborhood Retro Teen Club Dance

St Jerome School 18 Oct 2025

Martha Mae Studio Sale | Art Supplies + Oil Paint

1727 W Grand Ave 13 Sep 2025

Santa Hustle Chicago 5K, 10K, Kids Dash

Soldier Field 6 Dec 2025

The Official Christmas Bar Crawl - Chicago

SPIN 20 Dec 2025

A Live Presentation of 2001: A Space Odyssey

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

Shannon Rovers 99th Annual Dinner Dance

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

Harvest Ball

Ballroom Dance Chicago 18 Oct 2025

Adult Prom Scholarship Fundraiser

Purcell Hall 25 Oct 2025

Home Alone in Concert

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

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

Old Crow Smokehouse - Wrigleyville 6 Dec 2025

Wings & Things: Honoring the Monarch Butterfly with RIP Repurposed

The Insect Asylum 1 Nov 2025

Galena Country Fair

Galena IL 11 Oct 2025

Alumni Gathering | Chicago Cubs

Wrigley Field 27 Sep 2025

Hells Kitchen - Musical by Alicia Keys at Nederlander Theatre Chicago

Nederlander Theatre Chicago 14 Nov 2025

Wednesday at Riviera Theatre - IL

Riviera Theatre - IL 17 Nov 2025

Weird Al Animal Mask Circle Pit

Douglass Park 19 Sep 2025

Sox Crawl - A Pregame Crawl Inside the Stadium - Game Ticket, Tweed Hat & Hockey Jersey Included!

Rate Field 20 Sep 2025

Historic Pullman House Tour, October 11-12, 2025

Pullman Exhibit Hall 11 Oct 2025

6th ANNUAL ROCK THE YACHT “ALL BLACK AFFAIR”

Anita Dee Yacht Charters 28 Sep 2025

The Chicago Art Girls Holiday Pop-Up Shop

Alexander Graham Bell Elementary School 13 Dec 2025

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

Headquarters Beercade 27 Dec 2025

Mannheim Steamroller Christmas

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

RUBII

Sleeping Village 7 Nov 2025

Carnivale’s 20th Anniversary Celebration

Carnivale Chicago 10 Sep 2025

bar italia at Thalia Hall

Thalia Hall 14 Nov 2025

Quadrille Ball

Ballroom Dance Chicago 15 Nov 2025

Hispanic Heritage with Jewel-Osco - Irving Park Rd, Chicago

Jewel-Osco 20 Sep 2025

The Shops - Holiday Edition #1

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

Chicago Labor History Tour: Haymarket / Packingtown 8:30 a.m.-12:15 p.m.

2301 S Prairie Ave 19 Sep 2025

Wrigleyville Holiday Cavalcade!

The Newport Theater 24 Dec 2025

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

BottlesUp! 26 Oct 2025

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

Wrigleyville Chicago 13 Dec 2025

Chicago Artopia Presents: Chris White, A Charlie Brown Christmas Trio

West Lawn Branch, Chicago Public Library 13 Dec 2025

The Movement at The Outset

The Outset 8 Nov 2025

DOGE Holiday (DOHO) Bar Crawl 2025

The Whale Chicago 13 Dec 2025

Christmas with the Celts at Ramova Theatre

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

Chicago Labor History Tour: Pullman/ Steel Makers 1:00 p.m.-5:00 p.m.

2301 S Prairie Ave 19 Sep 2025

SAVE THE DATE: CJO at Winter's with Devon Sandridge

Winter's Jazz Club 19 Oct 2025

Candlelight: The Best of Hans Zimmer

Stan Mansion 18 Sep 2025

John Denver Tribute: A Rocky Mountain Christmas

Broadway Playhouse at Water Tower Place 20 Dec 2025

WINTER WONDERLAND POP UP!

Kings Klothing Boutique 27 Dec 2025

Brandenburg Concertos

205 E Randolph St, Chicago, IL, United States, Illinois 60601 4 Dec 2025

Packers Opening Weekend Tailgate Party at Ranalli's in Lincoln Park

Ranalli's Pizza Bar - Lincoln Park, Chicago 7 Sep 2025

Moorish Science Temple of America 98th Annual National Convention

Charles A. Hayes Family Investment Center 15 Sep 2025