Chicago Holiday Events

Saturday, 31st of October, 2026: Annual Nocturna All Hallows’ Eve Ball w/ DJ Scary Lady Sarah + more

Metro Chicago 31 Oct 2026

Chicago Halloween Party Cruise | Pier Pressure® Black Pearl

Spirit of Chicago Yacht 31 Oct 2026

Celebrate the Great Tree Lighting

111 N State St 7 Nov 2026

Wintrust Magnificent Mile Lights Festival®

The Magnificent Mile 21 Nov 2026

CHICAGO ZOMBIE CRAWL - Wrigleyville - Halloween Bar Crawl - Oct 30th & 31st

Almost Home Tavern 30 Oct 2026

Chicago Halloween Bar Crawl 2026

PB&J: Pizza Beer and Jukebox 31 Oct 2026

Volunteers Needed! 92nd Chicago Thanksgiving Parade 2026

HI Chicago, The J. Ira and Nicki Harris Family Hostel 26 Nov 2026

Chicago - Holiday Cocktail Tasting Festival - November 14

Utopian Tailgate 14 Nov 2026

Blue Man Group - A New Holiday Surprise

CIBC Theatre 29 Nov 2026

R&B Fest Is Coming To Chicago!

Sound-Bar 14 Nov 2026

Chicago Social and Language Exchange (Make New Friends) ✨

Timothy O'Toole's Pub Chicago 24 Apr 2026

Chicago Official Thanksgiving Eve Bar Crawl 2026

Downtown Chicago 25 Nov 2026

Blue Man Group - A New Holiday Surprise at CIBC Theatre

CIBC Theatre 24 Nov 2026

River North Pole - A family fun indoor event with Santa and Mrs. Claus!

Trump International Hotel & Tower® Chicago 21 Nov 2026

Chicago Riverwalk Secrets Quest

Michigan Avenue & East Wacker Place 28 Oct 2026

R&B Fest - Chicago

Sound Bar 14 Nov 2026

Jinkx and DeLa Holiday Show at Auditorium Theatre Chicago

Auditorium Theatre Chicago 6 Dec 2026

Broadway In Chicago - Blue Man Group "A New Holiday Surprise"

CIBC Theatre 25 Nov 2026

Crawl to Christkindlmarket: A Holiday Pub Crawl to Christkindlmarket

River North's BEST Bars On Your Way to Christkindlmarket 27 Nov 2026

Holiday Magic Kickoff

111 N State St 21 Nov 2026

Black Wednesday @ PARLAY RIVER NORTH

Parlay River North 25 Nov 2026

Free Community Holiday Family Giveaway

10300 S Eberhart Ave 21 Nov 2026

Black Wednesday @ PARLAY LINCOLN PARK

Parlay Lincoln Park 25 Nov 2026

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

Headquarters Beercade 4 Dec 2026

Parranda Bar Crawl en Wrigleyville | Tix Include Brunch Buffet & 2 Shots!

Wrigleyville's Best Bars TBA 28 Nov 2026

Breakfast with Santa Neiman Marcus Chicago Saturday, December 5, 8:30am

737 N Michigan Ave 5 Dec 2026

Godfrey Holiday Cocktail Fest - Cocktail Tasting at I|O Godfrey Rooftop

IO Godfrey Rooftop Lounge 5 Dec 2026

Love Actually In Concert

Auditorium Theatre 12 Dec 2026

Merry, Merry Chicago!

220 S Michigan Ave, Chicago, IL, United States, Illinois 60604 18 Dec 2026

Soulful Holiday Lights Trolley Celebrating Motown, R& B & House

230 W North Ave 28 Nov 2026

Fa La La Fabulous Holiday Market - Chicago

3656 N Halsted St, Chicago, IL, United States, Illinois 60613 14 Nov 2026

4TH ANNUAL FREEDOM CONCERT & Early Voter Accompaniment !

Willye B. White Park 1 Nov 2026

Future Travel World™ Chicago — International Travel & Experience Show

Marriott Marquis Chicago 29 Oct 2026

The Naughty List Bar Crawl - Chicago

Black Hole Bar 28 Nov 2026

Dr. Seuss’ How the Grinch Stole Christmas! The Musical

James M. Nederlander Theatre 9 Dec 2026

Breakfast with Santa Neiman Marcus Chicago Saturday, December 12, 8:30am

737 N Michigan Ave 12 Dec 2026

Chicago SantaCon Bar Crawl 2026

PB&J: Pizza Beer and Jukebox 19 Dec 2026

Chicago Wicker Park Naughty Santa Bar Crawl

DSTRKT and Wicker Park Venues 5 Dec 2026

Chicago, IL - First Taste Holiday @ Punch Bowl Social

Punch Bowl Social 6 Nov 2026

Thanksgiving Weekend: Feast

Bassline 28 Nov 2026

Theater on the Lake Presents: Burning Red's 4th Annual Christmas Birth-TAY

Theater on the Lake 12 Dec 2026

Ornament Paint & Sip

Cafe Con Leche, North Milwaukee Avenue, Chicago, IL, USA 10 Dec 2026

The Christmas Bar Crawl - Chicago

SPIN 19 Dec 2026

Chicago Vinyl Connection 028 NORTHSIDE

Emporium Arcade Bar 8 Nov 2026

Inward Day Wellness Retreat

Movement on Montrose 7 Nov 2026

Leftovers & Laughs: A Cooking Class & Comedy Night!

Cooking with Cass 13 Nov 2026

Renegade Chicago

Bridgeport Art Center 18 Dec 2026

The Holiday Gift Shop Opens · Lincoln Square

4645 N Rockwell St 1 Nov 2026

WONDERLAND 2027 NYE PARTY

BASSLINE || 2239 - CHICAGO 31 Dec 2026

Home Alone 2: Lost In New York - Live In Concert

50 E Ida B Wells Dr, Chicago, IL, United States, Illinois 60605 19 Dec 2026

HERE: for the holidays

The Newport Theater 2 Nov 2026

The Chicago Art Girls Holiday Pop-Up Shop

Alexander Graham Bell Elementary School 12 Dec 2026

Holiday Winter Dash Beer Run | 2026 Illinois Brewery Running Series

Goose Island Taproom 6 Dec 2026

Thanksgiving Dinner Buffet at The Ambassador Room

Ambassador Gold Coast - The Chicago Hotel Collection 26 Nov 2026

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

Lincoln Park 13 Mar 2027

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

Headquarters Beercade 13 Mar 2027

Holiday Soirèe

ICA GreenRise 13 Nov 2026

A Holiday Cabaret with The Uptones

UncommonGround - Lakeview 5 Dec 2026

Hallmark Christmas Experience

The Loop 27 Nov 2026

St. Patrick's Day Lucky Charms Wrigleyville Bar Crawl

Blue Bayou 13 Mar 2027

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

West Loop 13 Mar 2027

Once Upon a Holiday

111 N State St 5 Dec 2026

PROMCHELLA: The Art of Becoming — A Holiday Fashion Show

6330 S Stony Island Ave 7 Nov 2026

The Trashy Holiday Market '26

Mrs. Murphy & Sons Irish Bistro 27 Nov 2026

Mariah Bottomless Holiday Drag Brunch

Lark 14 Nov 2026

Halloween Trick-or-Treat in Northcenter!

Northcenter Town Square 31 Oct 2026

Cosmo Rotary Social at Mag Mile Holiday Lights Parade

875 North Michigan Avenue 21 Nov 2026

2026 Lycée French Market

1929 W Wilson Ave, Chicago, IL, United States, Illinois 60640 14 Nov 2026

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

River North 13 Mar 2027

Contemporary Holiday Styling Event

111 N State St 14 Nov 2026

The Balzekas Museum Guild Holiday Craft Fair

Balzekas Museum Of Lithuanian Culture, South Pulaski Road, Chicago, IL, USA 21 Nov 2026

Jo Ann Daugherty Jazz Trio | Printmaker Deborah Maris Lader

Artifact Events 13 Dec 2026

J-MORG ENTERTAINMENT PRESENTS: CROWN: THE BLACK ATTIRE GALA

Renaissance Chicago Downtown Hotel 28 Nov 2026

Cocktail Class at TRUCE: Holiday Cocktail Lab

TRUCE 1 Dec 2026

Felt Decor- Friday, December 4th

Revolution Brewing - Brewery & Taproom 4 Dec 2026

FashionCamp: WINTER HOLIDAY EDITION 2026

FashionBar (Level 3) 12 Dec 2026

Colvin Concerts: Kevin Wood's Be Dazzled

Colvin House 5 Dec 2026

Markets for Makers Chicago Holiday Market

Artifact Events 21 Nov 2026

The Nutcracker: Symphony of Lights | Chicago

Harris Theater for Music and Dance 19 Nov 2026

Tree Lighting and Cultural Festival

Griffin Museum of Science and Industry 7 Nov 2026

It's A Wonderful Life: A Live Radio Play at Paradiso at Athenaeum Theatre - IL

The Chicago Theatre 11 Dec 2026

Guided Tasting: Cheese for your Holiday Table

Eataly Chicago 24 Nov 2026

Candlelight House Tour 2026

Pullman Exhibit Hall 13 Dec 2026

“Santa Baby” Pole Experience

Bombshell Movement Studio 11 Dec 2026

The Shops - Holiday Edition #1

Water Tower Place (Level 3 Next to JJill and White House Black Market) 12 Dec 2026

Tony P's Ugly Sweater Holiday Party @ The Scout: Wednesday December 9th

The Scout Waterhouse + Kitchen 9 Dec 2026

Chicago Tinker Day

Cindy's Rooftop 28 Oct 2026

Gourd Ornament Decorating with Abeni Pierson

DuSable Black History Museum and Education Center 8 Nov 2026

Get Lit: Santa's Book Fair

American Writers Museum 9 Dec 2026

Jingle Jammies: A Holiday Pajamas Dance Party For Kids

Mathew Bieszczat Volunteer Resource Center 13 Dec 2026

Roo's Very Merry Pet Market

Fairlie 339 North Bell Chicago 13 Dec 2026

The Shops - Holiday Edition #2 - Final 2026 Pop-up!

Water Tower Place (Level 3 Next to JJill and White House Black Market) 19 Dec 2026

DeeJayVu Black Wednesday at Vu Rooftop

VU 25 Nov 2026

Vino Days Wine Around

Eataly Chicago 17 Nov 2026

Cosmo Rotary Holiday Bar Crawl Social

The Gage 11 Dec 2026

Make the Yuletide Gay at LVPC!

Lake View Presbyterian Church 18 Dec 2026

Paint your Butter Dish!

3849 N Lincoln Ave, Chicago, IL 60613 7 Nov 2026

Nia OA Design Pop-Up at Ponnopozz

Ponnopozz 21 Nov 2026

Veterans Day Dedication

Veteran’s Triangle – 55th St., Narragansett & Archer Ave. 11 Nov 2026

Sip & Savor: Wine & Cheese for the Holidays

Eataly Chicago 5 Dec 2026