Chicago Holiday Events

Durango Fest 2025 - Plaza Garibaldi - Chicago, IL.

Plaza Garibaldi Chicago IL 17 Aug 2025

10cc in Chicago

Park West 5 Sep 2025

Boulet Brothers' Dragula: Season 666 Tour

The Vic Theatre 21 Aug 2025

AVLI NIGHTS IN MYKONOS - WHITE ATTIRE PARTY

Avli on The Park (Chicago) 6 Sep 2025

Baila Habibi All White Yacht Party

Anita Dee Yacht Charters 29 Aug 2025

The Pilsen Cruise 2 (The Finale) Latin Beats Boat Party and Fireworks Show!

Summer of George - Chicago Lakefront Cruises 16 Aug 2025

Chicago Halloween Party Cruise | Pier Pressure® Black Pearl

Spirit of Chicago Yacht 31 Oct 2025

11th Annual Arts in the Dark Halloween Parade 2025

State Street 18 Oct 2025

102ND YEAR ANNIVERSARY COMMUNITY OUTREACH & BACK 2 SCHOOL RALLY

True Light Baptist Church 24 Aug 2025

Nightmare on Chicago Street 2025

E Chicago St, Elgin, IL 60120, United States 25 Oct 2025

My Momma’s Era

Greenwood Oasis 27 Sep 2025

Air & Water Show Yacht Cruise (Anita Dee 1) Chicago

Anita Dee Yacht Charters 17 Aug 2025

Mannheim Steamroller Christmas at Nederlander Theatre Chicago

Nederlander Theatre Chicago 20 Dec 2025

BLISS The Ultimate Caribbean Rooftop Day Party

The Wild Hare & Singing Armadillo Frog Sanctuary 17 Aug 2025

Diwali Celebration Party

Alhambra Palace Restaurant 24 Oct 2025

CVS White Party 2025

436 E 47th St 30 Aug 2025

Turnpike Troubadours, Old Crow Medicine Show, Ken Pomeroy in Chicago

The Salt Shed Outdoors (Fairgrounds) 28 Aug 2025

Chicago Day of The Dead Bar Crawl - Dia De Muertos

Chicago 1 Nov 2025

Daft Disko Halloween: Chicago @ Navy Pier

Bar Sol Navy Pier 31 Oct 2025

Hanumankind in Chicago

Thalia Hall 28 Aug 2025

The Boos & Booze Chicago Halloween Bar Crawl | Lake View

Neon Gardens 25 Oct 2025

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

The Salt Shed Outdoors (Fairgrounds) 11 Sep 2025

The Mighty Ducks Meet & Greet

Sluggers World Class Sports Bar and Grill & Dueling Pianos 31 Aug 2025

INDIA Independence Day- Rooftop Party

Azul 15 Aug 2025

Pups & Palomas

Somerset Patio 23 Aug 2025

Bad Pluma: Reggaeton, Banda and Corridos Dance Party

Simone's 16 Aug 2025

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

Women & Children First 13 Sep 2025

Invite Only: Celeste Venue Showcase

Celeste 27 Aug 2025

Chicago Halloween Bar Crawl

Chicago 25 Oct 2025

Pole Night - Latinx Heritage

Provocateur 19 Sep 2025

The Crab Pad's 9th Anniversary Chill Celebration

The Crab Pad 18 Aug 2025

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

Chicago, IL 5 Sep 2025

Summer Tropical Social Party | 08/16

600 W Roosevelt, Chicago, IL, United States, Illinois 60607 16 Aug 2025

The Boos & Booze Chicago Halloween Bar Crawl | Wicker Park

Chop Shop 25 Oct 2025

Rituals of Remembering: Living Altars

4910 W Quincy St 20 Sep 2025

Christmas Wonderland Mini Photoshoots | Chicago, IL

Chicago, IL 27 Sep 2025

Karaoke SupaStarz VIP - Masquerade Yacht Soiree Powered by DJ Rock Hell

3155 S DuSable Lake Shore Dr 16 Aug 2025

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

Old Crow Smokehouse - Wrigleyville 6 Dec 2025

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

Old Crow Smokehouse - Wrigleyville 20 Dec 2025

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

Old Crow Smokehouse - Wrigleyville 27 Dec 2025

WHITE & SILVER (Grown & Sexy) PARTY

Row 24 Chicago 15 Aug 2025

Vienna Boys Choir: Christmas in Vienna

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

Shannon Rovers 99th Annual Dinner Dance

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

AHEE in Chicago

Concord Music Hall 22 Nov 2025

40+ Christians Mixer: Pairing Party

Prāzbar 6 Sep 2025

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

Old Crow Smokehouse - Wrigleyville 19 Dec 2025

Finish Strong: 90-Day Blitz to Close More Deals Before Year-End

6348 N Cicero Ave 21 Aug 2025

Chicago SantaCon 2025

PB&J: Pizza Beer and Jukebox 20 Dec 2025

Beach Vibes: Sunday Funday Edition

Whispers at Oak Street Beach 24 Aug 2025

The Chicago Art Girls Holiday Pop-Up Shop

Alexander Graham Bell Elementary School 13 Dec 2025

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

Everybody's Coffee (Wilson Abbey) 5 Sep 2025

Christian Singles Meet & Greet in Chicago!

Pinstripes 5 Sep 2025

Ava Max vs. Dua Lipa Drag Brunch

Lark 16 Aug 2025

Too Hype Crew at DeKalb Corn Fest with Rob Base, Color Me Badd & Young MC!

Chicago, IL, United States, Illinois 23 Aug 2025

Chicago Santa Bar Crawl

PB&J: Pizza Beer and Jukebox 20 Dec 2025

The Official Christmas Bar Crawl - Chicago

SPIN 20 Dec 2025

Hells Kitchen - Musical by Alicia Keys at Nederlander Theatre Chicago

Nederlander Theatre Chicago 14 Nov 2025

LDW SUNDAY NIGHT - Afrobeats, Amapiano & More @ Masada

To Be Announced 31 Aug 2025

Alumni Gathering | Chicago Cubs

Wrigley Field 27 Sep 2025

2025 Chicago Halloween Bar Crawl

Chicago 1 Nov 2025

Fizz Band Night ft The Joshua Jern Orchestra!

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

Weird Al Animal Mask Circle Pit

Douglass Park 19 Sep 2025

Labor Day Weekend Drag Brunch

Lark 30 Aug 2025

Annual PACC Boat Outing

900 S Wells St, Chicago, IL 60607, United States 17 Aug 2025

Carnivale's 20th Anniversary Party!

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

LAVISH THE ULTIMATE VIRGO CELEBRATION!!!! WHITE & GOLD AFFAIR

Juliana Restaurant 30 Aug 2025

Martha Mae Studio Sale | Art Supplies + Oil Paint

1727 W Grand Ave 13 Sep 2025

Just Dance!: Lady Gaga Nite [Chicago]

Subterranean 18 Oct 2025

SUMMER VIBES 2 - Yacht Party

Anita Dee Yacht Charters 7 Sep 2025

Golden Hour featuring Jackson Jay Kidder

Epiphany Center for the Arts 4 Sep 2025

Labor Day Sunday Funday Sunset Cruise!

Chicago Lakefront Cruises 31 Aug 2025

THE CHICAGO STEPPERS HOMECOMING WEEK

Hyatt Regency Downtown Chicago 31 Aug 2025

The Boos & Booze Chicago Halloween Bar Crawl | River North

Headquarters Beercade 25 Oct 2025

Home Alone in Concert

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

IN CULINARY CONVERSATION WITH CHEF MATTHEW SKOLARUS

Boelter Foodservice Design, Equipment & Supply 24 Sep 2025

The Boos & Booze Chicago Halloween Bar Crawl | West Loop

Punch Bowl Social 25 Oct 2025

Gabby's Dollhouse Live!

The Chicago Theatre 15 Nov 2025

A Spirited Affair: A Private Pour Series with LALO Tequila

The Gwen, a Luxury Collection Hotel, Michigan Avenue Chicago 14 Aug 2025

Pizza and Cocktail Dinner at Ranalli's in West Loop

Ranalli's Pizza Bar - West Loop, Chicago 21 Aug 2025

The Cinderella Escape in Chicago

Chicago 20 Sep 2025

POP UP SHOP - LABOR DAY WEEKEND

Da Dip 30 Aug 2025

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

2301 S Prairie Ave 19 Sep 2025

the quiet part by Keegon Schuett

The Understudy Coffee and Books 18 Aug 2025

Santa Hustle Chicago 5K, 10K, Kids Dash

Soldier Field 6 Dec 2025

Stardew Valley - Symphony of Seasons - Chicago

The Chicago Theatre 11 Oct 2025

Merry Merry Chicago at Chicago Symphony Center

Chicago Symphony Center 19 Dec 2025

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

Old Crow Smokehouse - Wrigleyville 13 Dec 2025

Boys Night Out

Bottom Lounge 31 Oct 2025

Day Drip Day Party

Park Tavern 24 Aug 2025

A Christmas Carol

Albert Ivar Goodman Theatre 14 Nov 2025

Harvest Ball

Ballroom Dance Chicago 18 Oct 2025

Hatch Chile Roast with Jewel-Osco!

Jewel-Osco (2940 N Ashland Ave, Chicago) 30 Aug 2025

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

Old Crow Smokehouse - Wrigleyville 12 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 5 Dec 2025

Candlelight: The Best of Hans Zimmer

Stan Mansion 21 Aug 2025

Adult Prom Scholarship Fundraiser

Purcell Hall 25 Oct 2025

Mannheim Steamroller Christmas

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

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

Headquarters Beercade 27 Dec 2025

Galena Country Fair

Galena IL 11 Oct 2025