Chicago Holiday Events

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

Headquarters Beercade 29 Nov 2025

The Wintrust Magnificent Mile Lights Festival

The Magnificent Mile, Chicago 22 Nov 2025

Ornament Painting at Café Con Leche

Cafe Con Leche 11 Dec 2025

🎄 The Elfed Up Christmas Crawl 🎅🏻

60610 20 Dec 2025

Chicago SantaCon 2025

PB&J: Pizza Beer and Jukebox 20 Dec 2025

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

Old Crow Smokehouse - Wrigleyville 6 Dec 2025

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

737 N Michigan Ave 13 Dec 2025

Randolph Street Market’s November Holiday Show

Chicago Antique Market Randolph Street 15 Nov 2025

Woodys & Ignite Glass: Ornament Show 2025

Ignite Glass Studios 15 Nov 2025

The Holiday in Concert at Auditorium Theatre Chicago

Auditorium Theatre Chicago 20 Dec 2025

4th Annual Austin Community Dinner & Gift Giveaway

4757 W Lake St 20 Dec 2025

Holiday Gift Party at Oliva Gallery

Oliva Gallery 19 Dec 2025

Merry Makers Christmas Market

5504 West Lawrence Avenue, Chicago, IL, USA 29 Nov 2025

24 Hour Play Festival and Food Drive

4001 N Ravenswood Ave 22 Nov 2025

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

West Lawn Branch, Chicago Public Library 13 Dec 2025

Holiday Banned Book Drive

Jamii Center for Arts and Media 22 Nov 2025

Twas The Week Before Christmas in Chicago

Irish American Heritage Center 5 Dec 2025

Chicago Official Ugly Sweater Bar Crawl

PB&J: Pizza Beer and Jukebox 20 Dec 2025

Gratitude Sound Bath

Wildlight Yoga 16 Nov 2025

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

Old Crow Smokehouse - Wrigleyville 27 Dec 2025

Holiday Gift Market

The Salt Shed 30 Nov 2025

Zen&B: A Reset Before The Holidays

422 1/2 E 87th St 21 Nov 2025

Breakfast With Santa 2025

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

Black Friday Weekend at The Bassment

The Bassment 28 Nov 2025

A Flamenco Christmas

Saint Mary of the Lake Catholic Church 5 Dec 2025

It's A Goblin Market Friendsgiving

Goblin Market Manga & Curiosities, North Lincoln Avenue, Chicago, IL, USA 30 Nov 2025

Holiday Tree Lighting at NEWCITY

NEWCITY 14 Nov 2025

Cozy Worlds Market

Uni Uni Boba 6 Dec 2025

Wrigleyville Holiday Cavalcade!

The Newport Theater 24 Dec 2025

A NIGHT OFF: ALL BLACK AFFAIR!

Time Out Market Chicago 26 Nov 2025

Connecting Dots Holiday Celebration

Surge Billiards 5 Dec 2025

Chicago Real Estate Holiday Party

Navigator Taproom 11 Dec 2025

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

West Fulton Market 6 Dec 2025

Lesbian Pre-Thanksgiving Potluck party

Andersonville, Chicago 23 Nov 2025

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

Colvin House 5 Dec 2025

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

230 N Clark St 14 Mar 2026

Keeping It Real Estate Meetup: Holiday Party!

Navigator Taproom 9 Dec 2025

Cozy & Bright: A Family Holiday Movie Night

657 W Fulton St 21 Nov 2025

Jingle + Mingle First Friday

Prism Spaces 5 Dec 2025

Lessons & Carols

1001 N Crosby St 5 Dec 2025

WINTER WALK ON WILSON

4618 N Broadway, Chicago, IL 60640-5012, United States 5 Dec 2025

Club Christmas Inn

Hubbard Inn 15 Nov 2025

Virtual Riot, Grabbitz, Leotrix in Chicago

Concord Music Hall 29 Nov 2025

Ugly Sweater Disco Bingo

Edison Park Inn 20 Dec 2025

Holiday Soirée

Institute of Cultural Affairs 14 Nov 2025

Vienna Boys Choir: Christmas in Vienna

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

Cranksgiving Chicago

Cosmic Bikes Inc. 22 Nov 2025

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

Old Crow Smokehouse - Wrigleyville 20 Dec 2025

2025 Lycée French Market

1929 W Wilson Ave, Chicago, IL, United States, Illinois 60640 15 Nov 2025

DKG Holiday Party!!

A and N Mortgage Services, Inc. 13 Dec 2025

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

Old Crow Smokehouse - Wrigleyville 12 Dec 2025

Transgenders For Romney: A Christmas Extravaganza!

The Lincoln Lodge 13 Dec 2025

CHRISTMAS MINI-GOLF

Awaken Chicago Church 5 Dec 2025

KATCH Holiday Party

HAIBAYÔ 6 Dec 2025

Candlelight House Walk - 2025

Pullman Exhibit Hall 14 Dec 2025

Breakfast with Santa

Warwick Allerton - Chicago 14 Dec 2025

ONE LAST SLAY: The Promontory Finale

The Promontory 24 Dec 2025

Photos With Santa at the Southport Holiday Stroll 2025

Sheil Park 5 Dec 2025

You Are Beautiful Community Holiday Party!

You Are Beautiful 12 Dec 2025

JAZZCRACKER

Nicholas Senn Theater 6 Dec 2025

Yngstr Exchange Kids' Clothing Swap

Monday Coffee Co. 16 Nov 2025

Concrete Rose 773 Christmas Prom Night Gala

Bellagio 223 13 Dec 2025

Gratitude Yoga at Rauner Family YMCA

Rauner Family YMCA 22 Nov 2025

12 Days of Christmas Dance Competition

2156 W Ogden Ave 13 Dec 2025

Candy Cane Lane

Hubbard Inn 21 Nov 2025

AHEE in Chicago

Concord Music Hall 22 Nov 2025

SMALL BUSINESS SATURDAY AT THE CENTER

The Center of Order and Experimentation 29 Nov 2025

SkyART Holiday Market

3450 W Lake St 6 Dec 2025

Cosmo Rotary Social at Mag Mile Holiday Lights Parade

Sweetwater Tavern & Grille (Michigan Plaza - Chicago) 22 Nov 2025

Queer Book Fair

Goblin Market Manga & Curiosities, North Lincoln Avenue, Chicago, IL, USA 5 Dec 2025

Fall to Table: Friendsgiving Edition

Trogo Kitchen and Market 5 Dec 2025

Holiday Express, to Chicago's Lighting of the Christmas Tree

Millennium Park 21 Nov 2025

CRF C.A.R.E.S. Annual Holiday Party

Mordecai 12 Dec 2025

Mindful Market

Wildlight Yoga 29 Nov 2025

Film Workers’ Holiday Market

Cine City Studios 2429 W 14th St, Chicago 22 Nov 2025

The Chicago Art Girls Holiday Pop-Up Shop

Alexander Graham Bell School 13 Dec 2025

Christmas Pajamas & Prosecco Party

Hubbard Inn 13 Dec 2025

Christmas in Chicago Concert

The Moody Church 13 Dec 2025

Holiday Paint & Sip @ La Michoacana

10533 S Ewing Ave 22 Nov 2025

KEWN Gift Wrapping and Networking Holiday Brunch

Community Alternatives Unlimited 6 Dec 2025

Demo & Dine: Holiday Desserts

Eataly Chicago 12 Dec 2025

Hands-On: Gnocchi al Burro e Tartufo (Holiday Edition)

Eataly Chicago 15 Nov 2025

SEASONAL BAKED GOODS! KOMBUCHA TASTING!

The Center of Order and Experimentation 16 Nov 2025

The Winter Affair

Hubbard Inn 6 Dec 2025

Cornelia Arts Building December Open Studios 2025

1800 W Cornelia Ave, Chicago, IL, United States, Illinois 60657 5 Dec 2025

Night 4 - Bells & Whispers

International Museum of Surgical Science 14 Dec 2025

Under the Misteltoe

Hubbard Inn 20 Dec 2025

Third Friday Open Studios November 21, 2025

Bridgeport Art Center Chicago 21 Nov 2025

The Real Housewives of North Pole

4335 N. Western Ave, Chicago, IL, United States, Illinois 60618 20 Nov 2025

Decompress Before the Holiday Stress!

LILY Therapy & Wellness, Inc. 19 Nov 2025

The Official Christmas Bar Crawl - Chicago

SPIN 20 Dec 2025

A Holiday Celebration of Art and Belonging - Membership Appreciation Party

Ukrainian Institute of Modern Art 6 Dec 2025

Gnocchi al Burro e Tartufo

Eataly Chicago 20 Dec 2025

PomSquad Fitness HOLIDAY CHEER 2025!

Visceral Dance Center 7 Dec 2025

Wine and Cheese: Holiday Edition

Eataly Chicago 22 Nov 2025

Don't Buy Trouble: Holiday Party

FACETS of Chicago 3 Dec 2025

Naughty & Nice Party

Hubbard Inn 12 Dec 2025

Krampusnacht! presented by the Illumi-Naughtie Occult Burlesque

The Newport Theater 5 Dec 2025

Randolph Street Market

1341 W Randolph St, Chicago, IL 60607-1523, United States 15 Nov 2025

Protection & Boundaries: Staying Grounded Through the Holidays”

Shine Bright in Life 13 Nov 2025