Chicago Holiday Events

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

Headquarters Beercade 29 Nov 2025

Ornament Painting at Café Con Leche

Cafe Con Leche 11 Dec 2025

🎄 The Elfed Up Christmas Crawl 🎅🏻

60610 20 Dec 2025

Howliday Wag N' Shop Dog-Friendly Market Fundraiser

4011 N Ravenswood Ave, Chicago, IL 60613-2409, United States 6 Dec 2025

Chicago's Byob Party Bus Holiday Lights Tour 'Tis The Season | Navy Pier

Santa's Workshop at Old Crow Smokehouse 6 Dec 2025

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

737 N Michigan Ave 13 Dec 2025

Chicago SantaCon 2025

PB&J: Pizza Beer and Jukebox 20 Dec 2025

The Official Christmas Bar Crawl - Chicago

SPIN 20 Dec 2025

Händel's Messiah | Saturday 12/13 | Chicago

Holy Name Cathedral, Chicago 13 Dec 2025

The Holiday in Concert at Auditorium Theatre Chicago

Auditorium Theatre Chicago 20 Dec 2025

Cozy Worlds Market

Uni Uni Boba 6 Dec 2025

Christmas in Chicago Concert

The Moody Church 13 Dec 2025

Suicide Prevention and Mental Wellness Event

641 W 63rd St 4 Dec 2025

Holiday Gift Party at Oliva Gallery

Oliva Gallery 19 Dec 2025

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

Old Crow Smokehouse - Wrigleyville 27 Dec 2025

Naughty or Nice Speed Dating

6947 S South Chicago Ave 13 Dec 2025

St. Al’s Christmas Ball

1429 W Wellington Ave, Chicago, IL 13 Dec 2025

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

West Lawn Branch, Chicago Public Library 13 Dec 2025

Chicago Official Ugly Sweater Bar Crawl

PB&J: Pizza Beer and Jukebox 20 Dec 2025

FREE! Meet Santa, take family photos!

4254 N Milwaukee Ave 7 Dec 2025

Twas The Week Before Christmas in Chicago

Irish American Heritage Center 5 Dec 2025

Breakfast with Santa

Warwick Allerton - Chicago 14 Dec 2025

Krampus Market

Old Irving Brewing Co. 7 Dec 2025

Wrigleyville Holiday Cavalcade!

The Newport Theater 24 Dec 2025

4th Annual Austin Community Dinner & Gift Giveaway

4757 W Lake St 20 Dec 2025

Chicago St. Patrick's Day Bar Crawl

Chicago 14 Mar 2026

FREE Recovery Community - Chicago - Christmas Party

3338 N Broadway, Chicago, IL 60657-3520, United States 13 Dec 2025

THE GIFT OF GIVING HOLIDAY GALA

The Metropolitan 4 Dec 2025

Cocktails x Crafts: Winter Wreath Workshop

Fora 4 Dec 2025

Breakfast With Santa 2025

The Salvation Army Ray and Joan Kroc Corps Community Center Chicago 6 Dec 2025

Winterland Tree Lighting Ceremony

3637 N Clark St, Chicago, IL, Chicago, IL, United States, Illinois 60613 5 Dec 2025

Celebrating Motown Soulful Music Holiday Lights Trolley BYOB

230 W North Ave 6 Dec 2025

Holiday Dance Party! with the "In Full Swing" Jazz Orchestra

Chicago Union Station 10 Dec 2025

Connecting Dots Holiday Celebration

Surge Billiards 5 Dec 2025

DKV Trio *Night Two*

Elastic Arts 27 Dec 2025

National Coquito Festival 2025

2726 W Roscoe St, Chicago, IL 60618-5910, United States 13 Dec 2025

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

West Fulton Market 6 Dec 2025

John Vincent Holiday Show

Rizzo's Bar & Inn 21 Dec 2025

Vjosa Holiday Market

Vjosa Cafe & Events 13 Dec 2025

Keeping It Real Estate Meetup: Holiday Party!

Navigator Taproom 9 Dec 2025

The Chicago Cookie Market

Christmas Club Pop-Up Bar 14 Dec 2025

Home Alone - 7 Course Holiday Immersive Movie & Dinner Experience

The Drake 12 Dec 2025

DKV Trio *Night One*

Elastic Arts 26 Dec 2025

Renegade Chicago

Morgan Manufacturing 20 Dec 2025

NEW YEAR'S EVE EVENT & FIREWORK VIEWING ON NAVY PIER

Sable at Navy Pier Chicago, Curio Collection by Hilton 31 Dec 2025

TRANSVENGENCE VOL. 10: Holiday Edition

Podlasie Club 7 Dec 2025

Hands-On Pasta: Tagliolini Burro e Caviale

Eataly Chicago 7 Dec 2025

DKG Holiday Party!!

A and N Mortgage Services, Inc. 13 Dec 2025

Candlelight House Walk - 2025

Pullman Exhibit Hall 14 Dec 2025

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

Old Crow Smokehouse - Wrigleyville 12 Dec 2025

End of Year Holiday Bash!

The Pleasure Chest 19 Dec 2025

ALPFA SA Holiday Bash

Centre Court Productions 19 Dec 2025

NSN Chicago Holiday Soirée - Champagne Celebrations

The Metropolitan 6 Dec 2025

Jay Bragg Presents: Christmas in New Vaudeville

UncommonGround - Lakeview 13 Dec 2025

Shopping Extravaganza and Holiday Treat Stroll

Lakeview East Chamber of Commerce 6 Dec 2025

Boogie Wonderland at Howl at the Moon Chicago

Howl at the Moon Chicago 19 Dec 2025

Chicago Real Estate Holiday Party

Navigator Taproom 11 Dec 2025

Cocktails x Crafts: Winter Wreath Workshop

Fora 18 Dec 2025

December Book Exchange

Three Avenues Bookshop 14 Dec 2025

Graduate Council Presents: Holiday Cocoa & Crafts

UChicagoGRAD 4th Floor Lounge 5 Dec 2025

Fall to Table: Friendsgiving Edition

Trogo Kitchen and Market 5 Dec 2025

Shop Jarvis Square

R Public House 6 Dec 2025

Holiday Themed Paint N Sip

Morgan Park United Methodist Church 6 Dec 2025

Chicago Santa Bar Crawl

PB&J: Pizza Beer and Jukebox 20 Dec 2025

Gingerbread House Pottery Class

1142 W 18th St 5 Dec 2025

A Flamenco Christmas

Saint Mary of the Lake Catholic Church 5 Dec 2025

Holiday Sip & Shop II at Hopsmith

Hopsmith Chicago 6 Dec 2025

ONE LAST SLAY: The Promontory Finale

The Promontory 24 Dec 2025

Copilot Holiday Toy Swap

Copilot Dog Training 6 Dec 2025

Artist Holiday Soirée

Roosevelt Collections Shops ( 150 West Bldg) 6 Dec 2025

Chicago AF Holiday Party

Cafe Deko 12 Dec 2025

Ugly Sweater Disco Bingo

Edison Park Inn 20 Dec 2025

Lakeside Pride Sax Ensemble's Holiday Concert at Dorothy!

Dorothy 11 Dec 2025

Christmas Pajamas & Prosecco Party

Hubbard Inn 13 Dec 2025

ROCK AND ROLL STYLE STANDUP SHOW

The Lincoln Lodge 20 Dec 2025

UIMA Winter Makers Market

Ukrainian Institute of Modern Art 13 Dec 2025

Paint & Sip: Season’s Bright Ornament

Lux Accents Studios 12 Dec 2025

Holiday House Party

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

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

230 N Clark St 14 Mar 2026

Golden Hour featuring Jackson Jay Kidder

Epiphany Center for the Arts 4 Dec 2025

Where Is The Cool?

Byline Bank Aragon Ballroom 19 Dec 2025

Paint & Sip: Candy Cane Cheers

Lux Accents Studios 19 Dec 2025

Galapagos4 Holiday Reunion Party: Qwel Robust & Offwhyte

Reggie's Rock Club 12 Dec 2025

HOLIDAY POLAROIDS WITH MARTHA (THE DOG)!

The Center of Order and Experimentation 13 Dec 2025

Maybe It’s A Holiday Party!

Lucky Horseshoe Lounge 12 Dec 2025

Free: Bollywood Groove Winter Celebration!

Chicago Cultural Center 13 Dec 2025

Holiday Shop x lululemon Fulton Market

lululemon Fulton Market 11 Dec 2025

"ALL THE FEELS" (R&B • Trap Soul • Slow Jams)

Row 24 Chicago 26 Dec 2025

ICE Watch and Rapid Response Appreciation Holiday Party

Haymarket House 11 Dec 2025

Latin Street Christmas Social 📍 Athenaeum Center

Athenaeum Center for Thought & Culture 7 Dec 2025

Bess & Marley's Holiday Spectacular

4001 N Ravenswood Ave Unit 303-B 6 Dec 2025

A Brothers Sinatra HOLIDAY SPECIAL at Schubas

Schubas Tavern 7 Dec 2025

NABA Chicago Annual Holiday Party

Flight Club Chicago 11 Dec 2025

Sip + Shop at the L1 Retail Store

L1 Retail Store 4 Dec 2025

Sat, 6 December: Scary Lady Sarah's Krampus/Xmas Party- All Alt Holiday Music + Gift Exchange

DMen Tap 6 Dec 2025

Under the Misteltoe

Hubbard Inn 20 Dec 2025

In-person class: Christmas Cookie Decorating (Chicago)

Gateway To Learning 19 Dec 2025

Santa's Secret Soiree

Hubbard Inn 19 Dec 2025

Holiday Gift Sale

4945 S Dorchester Ave 6 Dec 2025

The Pippins at Winter Walk on Wilson

Uptown Chamber of Commerce 5 Dec 2025