Chicago Holiday Events

Winter WonderFest 2025 - Navy Pier

Navy Pier 5 Dec 2025

Joffrey Ballet - The Nutcracker at Lyric Opera House

Lyric Opera House 5 Dec 2025

Cirque Du Soleil Twas The Night Before at Chicago Theatre

Chicago Theatre 11 Dec 2025

ONE LAST SLAY: The Promontory Finale

The Promontory 24 Dec 2025

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

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

Cirque Du Soleil - Twas The Night Before

The Chicago Theatre 23 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

A Live Presentation of 2001: A Space Odyssey

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

Holiday Pop-Up Bar Crawl To Christkindlmarket In Wrigleyville Wonderland

Wrigleyville Wonderland 28 Nov 2025

Black Blazers and Dresses NYE Affair

Park Tavern 31 Dec 2025

New Year's Eve Chicago at Homeslice

Homeslice 31 Dec 2025

New Year’s Eve: A Celebration at Terrace 16

Terrace 16 31 Dec 2025

Authors on Tap: Margot Douaihy and Gillian Flynn

Exile in Bookville 16 Jan 2026

New Year's Eve Chicago at LG's

LG's Irish Bar & Kitchen 31 Dec 2025

WONDERLAND 'NYE 2026 (Tier 1)

BASSLINE|| 2239 - CHICAGO 31 Dec 2025

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

Reggies 27 Dec 2025

BYOB Party Bus Holiday Lights Tour

Headquarters Beercade 27 Dec 2025

Second City Chicago - Rudolph Runs Wild at Second City Chicago - Mainstage

Second City Chicago - Mainstage 6 Dec 2025

BYOB Party Bus Holiday Lights Tour

Old Crow Smokehouse 27 Dec 2025

New Year's Eve Chicago at Galeria

Galeria Chicago 31 Dec 2025

NYAvlí at Avlí On The Park

Avli on The Park 31 Dec 2025

Noche Buena Wrigleyville | Chicago's First and Only Latin Christmas Bar

Moe's Cantina - Wrigleyville 28 Nov 2025

The Chosen Few Djs Holiday Party.

Bourbon on Division 26 Dec 2025

Winter Break Camps

Griffin Museum of Science and Industry 29 Dec 2025

Old Crow's Anti-Valentine's Day Party

Old Crow Smokehouse 14 Feb 2026

CHICAGO BOLLYWOOD CHRISTMAS PARTY @LORE NIGHTCLUB

Lore Chicago 24 Dec 2025

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

Headquarters Beercade 29 Nov 2025

Sleigh All Night

Hubbard Inn 26 Dec 2025

New Year's Eve Chicago at Americano

Americano, Lincoln Park 31 Dec 2025

AirOtic Naughty Noël

Experience 868 4 Dec 2025

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

Row 24 Chicago 26 Dec 2025

Butch Please: Let's Get Ugly

Jackhammer 27 Dec 2025

No Cover Food & Wine Lover's New Year's Eve at Volo

Volo Restaurant Wine Bar 31 Dec 2025

Christmas Day Masses

1351 W Evergreen Ave, Chicago, IL, United States, Illinois 60642 25 Dec 2025

A Very Vintage Christmas — The Brando’s Holiday Popup (Loop Location)

Brando's Speakeasy 9 Dec 2025

New Year’s Eve Dinner at Boleo

Boleo 31 Dec 2025

New Year's Eve Dinner at Boleo

Kimpton Gray Hotel 31 Dec 2025

2025 Wrap Party

Hubbard Inn 27 Dec 2025

Gnocchi al Burro e Tartufo

Eataly Chicago 30 Dec 2025

Balkan Winter Wonderland 2025 | PRYSM

PRYSM Chicago 24 Dec 2025

Christmas Eve - Feast Of The Seven Fishes

620 N State St, Chicago, IL, United States, Illinois 60654 24 Dec 2025

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

Martyrs' 26 Dec 2025

TBOYSKR1PCLUB presents BEEFCAKES & BEARS & BOYS! OH MY!

The Newport Theater 23 Dec 2025

The Biggest Party of the Year at Row 24

Row 24 Chicago 24 Jan 2026

Wrigleyville Holiday Cavalcade!

The Newport Theater 24 Dec 2025

NEW YEARS DAY HANGOVER BRUNCH

Bellagio 223 1 Jan 2026

Wine and Cheese: Perfect Holiday Picks

Eataly Chicago 23 Dec 2025

Holiday Fun with Fondue

Eataly Chicago 23 Dec 2025

DKV Trio *Night One*

Elastic Arts 26 Dec 2025

DKV Trio *Night Two*

Elastic Arts 27 Dec 2025

12/23 Photos with Santa at JoJo’s Winter Wonderland!

23 West Hubbard Street, Chicago, IL, United States, Illinois 60654 23 Dec 2025

SBK Salsa Tuesdays @ Renaissance Bronzeville (Christmas Celebration)

The Renaissance Bronzeville 23 Dec 2025

Eve of the Eve SBK Salsa Tuesdays @ Renaissance Bronzeville

The Renaissance Bronzeville 30 Dec 2025

Christmas Scavenger Hunt in Chicago: Help Santa save the Holiday!

Chicago Fire Relic 12 Dec 2025

Historic Pullman Model Train Experience

HPF Pullman Exhibit Hall 27 Dec 2025

Christmas Day! Mini Snow Globe & Candle Making Workshop

3414 W Foster Ave 24 Dec 2025

A Very Vintage Christmas — The Brando’s Holiday Popup (Lincoln Park)

Brando's Lincoln Park 10 Dec 2025

2025 Bronzeville Kwanzaa Celebration & Vendor Fair

4131 S State St, Chicago, IL 60609-2942, United States 27 Dec 2025

New Year’s Celebration at The Crab Pad!

The Crab Pad 31 Dec 2025

The Capricorn Bash at Room 43

Room43 26 Dec 2025

FREE Photos with Santa + FREE Holiday Cookies

3217 W 47th Pl 23 Dec 2025

Gingerbread House Workshop

The Shops at North Bridge 19 Dec 2025

Pilsen Industry Toy Drive

1726 S Racine Ave 23 Dec 2025

Free Drag Bingo at Graystone Tavern's 8 Crazy Nights

The Graystone Tavern 23 Dec 2025

Holiday - Play

Albert Ivar Goodman Theatre 30 Jan 2026

Winter Breads Baking Class

Bettie's Chicago 27 Dec 2025

Chicago - HoHo Holiday Classic

Fifth Third Arena 26 Dec 2025

OneOne Club Happy Hour

Chef Art Smith’s Reunion, Navy Pier, East Grand Avenue, Chicago, IL, USA 26 Dec 2025

Wine Tasting at The Christmas Inn

Hubbard Inn 23 Dec 2025

Dance Camp

Ballroom Dance Chicago 27 Dec 2025

The Ice Age: Preserving Beauty & Fertility

The One Spa Chicago 14 Jan 2026

Christmas Dinner at FireLake Grill House & Cocktail Bar

221 North Columbus Drive, Chicago, IL, United States, Illinois 60601 22 Dec 2025

A Caribbean Christmas Carol adapted and directed by Jacqueline Wade

Zhou B Art Center, 4th Floor Women of Color Theatre 7 Dec 2025

Holiday Affair 2025: A Pink and Green Celebration

Hyatt Regency Chicago 27 Dec 2025

Chicago St. Patrick's Day Bar Crawl

Chicago 14 Mar 2026

Holiday Tournament Series | Coed 4's Tournament at St. Andrew Gym in Chicago ⛄

St. Andrew's School Gymnasium 6 Jan 2026

DIY Ugly Sweater + Candle Making Workshop

3414 W Foster Ave 6 Dec 2025

Mariano's Presents: Crafting Cocktails Cali Style with 19 Crimes! 🍷 (Select Stores)

Select Mariano's 27 Dec 2025

Holiday Family Salsa Pop-Up Party!

2617 W Division St 28 Dec 2025

Holiday Ice Adventure Camp

1801 W. Jackson St., Chicago, IL, United States, Illinois 60612 22 Dec 2025

Holiday Gala Social: Christmas & New Year's Latin Dance Bash

Dennis PaSamba Dance Company | Chicago 24 Jan 2026

Custom Candle Making Workshop for Christmas Gifts

Three Cities Social Club - Wicker Park 21 Jan 2026

Holiday Beewax Candle Making Class

Wild Blossom Meadery and Winery 23 Dec 2025

L|Glamour Holiday Party

Tijuanas bar & Grill Chicago 3 Jan 2026

Holiday Comedy Show

CineCity Studios Chicago 27 Dec 2025

Ina Mae Tavern in Wicker Park Christmas Pop-Up Friday Happy Hour from 4-6PM

Ina Mae 5 Dec 2025

Strollin' Down MLK

Timothy Center 17 Jan 2026

2025 Christmas of Lights Holiday Concert

The CityLight Church 21 Dec 2025

Family Winter Origami Workshop - Fold a Heart-Shaped Gift Box!

Japanese Culture Center 5 Feb 2026

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

230 N Clark St 14 Mar 2026

Holiday Of Horror 2025 Edition

Reggie's Rock Club 26 Dec 2025

Chicago West Side Chamber Paint & Sip Workshop & Holiday Vintage

Front Porch Arts Center 30 Dec 2025

Suminagashi: Holiday Marbling Workshop at Dovetail Brewery

Dovetail Brewery 23 Dec 2025

Christmas Lessons and Carols Sing Along

St. Michael in Old Town 4 Jan 2026

Mac’s Wood Grilled is Open Christmas Day!

Mac's Wood Grilled 25 Dec 2025

Holiday Tournament Series | Reverse Coed 4's Tournament at St. Andrew Gym in Chicago ⛄

St. Andrew's School Gymnasium 5 Jan 2026

Christmas Workshop

2003 W 35th St 30 Nov 2025

#DiorChristmas

5353 W North Ave 20 Jan 2026

Christmas Eve for the Animals at CACC 2025

Chicago Animal Care and Control 24 Dec 2025

Dia de los Reyes Holiday Party

La Villa Restaurant Lounge and Banquets 9 Jan 2026