Chicago Festivals Events

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

Headquarters Beercade 29 Nov 2025

AfroSocaLove : Chicago One Love Festival (Feat Maga Stories )

The Venue Chicago 6 Dec 2025

Chicago SantaCon 2025

PB&J: Pizza Beer and Jukebox 20 Dec 2025

All Inclusive New Year's Eve 2026 Fireworks Cruise aboard Anita Dee II

Anita Dee II TEMPORARILY LOCATED at BURNHAM HARBOR (See directions below) 31 Dec 2025

Cumbia Catedral 3 - Cumbia Festival

Epiphany Center for the Arts 6 Dec 2025

The Official Christmas Bar Crawl - Chicago

SPIN 20 Dec 2025

FESTIVAL OF LIGHTS CHANUKAH SOIREE

The Old Post Office 14 Dec 2025

Bridgerton Ball

Ballroom Dance Chicago 10 Jan 2026

Renegade Chicago

Morgan Manufacturing 20 Dec 2025

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

West Lawn Branch, Chicago Public Library 13 Dec 2025

2026 Chicago Winter Whiskey Tasting Festival (January 24)

Downtown Chicago 24 Jan 2026

Chicago Official Ugly Sweater Bar Crawl

PB&J: Pizza Beer and Jukebox 20 Dec 2025

Chicago St. Patrick's Day Bar Crawl

Chicago 14 Mar 2026

DeffJam - Celebrating the Life of Ryan Deffet @ Thalia Hall

Thalia Hall 3 Jan 2026

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

IO Godfrey Rooftop Lounge 6 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

DKV Trio *Night One*

Elastic Arts 26 Dec 2025

The Chicago Cookie Market

Christmas Club Pop-Up Bar 14 Dec 2025

Espresso Martini Fest at Hubbard Inn, Chicago - Tastings Included

Hubbard Inn 27 Sep 2025

2026 Chicago Beer Fest

The Field Museum 28 Feb 2026

2026 Chicago Winter Tequila Tasting Festival (February 14)

Downtown Chicago 14 Feb 2026

Chicago Santa Bar Crawl

PB&J: Pizza Beer and Jukebox 20 Dec 2025

C2E2: Chicago Comic and Entertainment Expo - Friday

McCormick Place 26 Mar 2026

New Year's Eve Sunset Cocktail Cruise on Wednesday, December 31st

Anita Dee II TEMPORARILY LOCATED at BURNHAM HARBOR (See directions below) 31 Dec 2025

Nate Craig - Live in Chicago - 2026

The Lincoln Lodge 9 Jan 2026

Broken Robots w/ Corn On My Dinner Plate at Martyrs'

3855 N Lincoln Ave, Chicago, IL, United States, Illinois 60613 10 Jan 2026

Eve of the Eve Lake Cocktail Cruise on Tuesday, December 30th

Anita Dee II TEMPORARILY LOCATED at BURNHAM HARBOR (See directions below) 30 Dec 2025

CALCIUM at Sound-Bar

226 W Ontario St, Chicago, IL 20 Dec 2025

Cristela Alonzo: The Midlife Mixtape Tour

The Vic Theatre 31 Jan 2026

Performance | Reduction 11

220 E Chicago Ave, Chicago, IL, United States, Illinois 60611 19 Dec 2025

Afrofusion Friday : Afrobeats, Hiphop, Dancehall, Soca (Free Entry)

BASSLINE 19 Dec 2025

Share the Love WinterFest

6402 S Honore St 13 Dec 2025

Steph Tolev at Zanies Chicago

1548 N Wells St, Chicago, IL, United States, Illinois 60610 11 Dec 2025

Sandy Film Festival

Blanc 13 Dec 2025

Future Artists

The Edge Theater 17 Jan 2026

MONDAY DECEMBER 22: LATE NITE MIC WITH VIK PANDYA

The Comedy Bar - Chicago Main Stage 22 Dec 2025

Jeff Libman with Max Morton

UncommonGround - Lakeview 18 Dec 2025

Chanukah Winter Wonderland

NEWCITY 21 Dec 2025

Dirty Soda Fest - Unlimited Dirty Sodas, Cookies & Pretzel Bites

Chicago's BEST Bars TBA 31 Jan 2026

Free Blues Friday featuring Ivy Ford

Epiphany Center for the Arts 19 Dec 2025

Rempis/Abrams/Ra + Baker

2319 W Belmont Ave Chicago IL 60618 28 Dec 2025

MONDAY DECEMBER 29: LATE NITE MIC WITH VIK PANDYA

The Comedy Bar - Chicago Main Stage 29 Dec 2025

The Lawrence Arms 11th Annual War on X-Mas

Metro Chicago 5 Dec 2025

DJ Ca$h Era at Dorothy

Dorothy 12 Dec 2025

Godfrey Wine Fest - Wine Tasting at I|O Godfrey Rooftop in Chicago

IO Godfrey Rooftop Lounge 12 Apr 2025

13th Annual Krampus Fest at Martyrs'

3855 N Lincoln Ave, Chicago, IL, United States, Illinois 60613 13 Dec 2025

Raks Inferno: Holiday Cirque Burlesque

The Newport Theater 12 Dec 2025

Ravenswood Light Up Nights Festival + Holiday Market

Ravenswood, Chicago 6 Dec 2025

Golden Hour Featuring Brother Jacob With Chris Christmas

Epiphany Center for the Arts 13 Dec 2025

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

Martyrs' 26 Dec 2025

Newport Peek-Easy: Burlesque, Drag, and Variety Show

The Newport Theater 11 Jun 2021

Sulzer Comic & Arts Festival

Conrad Sulzer Regional Library 6 Dec 2025

JG Shadid + Nicole Miglis

3111 N Western Ave Chicago IL 60618 11 Dec 2025

Karl Denson's Tiny Universe

Garcia's Chicago 30 Dec 2025

Merry Merry Chicago at Chicago Symphony Center

Chicago Symphony Center 19 Dec 2025

Ana Everling & Grażyna Auguścik: Pagan Carols From The East

201 S. Ashland Avenue, Chicago, IL, United States, Illinois 60607 12 Dec 2025

HEALTH + CARPENTER BRUT w/ Desire at The Salt Shed

The Salt Shed 11 Apr 2026

Anarchotech, Voltaic Planes, Tatv Gral, DJ Veganinblack/ Fri 12.26.2025/ The Burlington Chicago

Burlington Bar 26 Dec 2025

Leftover Salmon

Garcia's Chicago 6 Mar 2026

Afrofusion Friday : Afrobeats, Hiphop, Dancehall, Soca (Free Entry)

BASSLINE 16 Jan 2026

Struggle Bus: A Comedy Show About Suffering

The Lincoln Lodge 12 Dec 2025

David Drake At The Lincoln Lodge

The Lincoln Lodge 27 Feb 2026

ROFest Trends Chicago 2025

AMC River East 21 6 Dec 2025

Robin Watson and Will Washington

201 S. Ashland Avenue, Chicago, IL, United States, Illinois 60607 7 Dec 2025

Frosty Fest

Downtown West Chicago, West Chicago, United States 6 Dec 2025

Tax Fairy’s Holiday Festival

4056 W Division St 6 Dec 2025

The Christkindlmarket 2025 | Chicago

Daley Plaza 20 Nov 2025

Fanfare for the New Year

North Shore Baptist Church - Chicago, IL 13 Dec 2025

Frequency Series Presents: Daniel Schlosberg + Jamie Jordan

3111 N Western Ave Chicago IL 60618 25 Jan 2026

Rematch / When The Sun Sets / 5ever

235 N Ashland Ave, Chicago, IL 60607, USA 20 Dec 2025

Demo & Dine: Holiday Desserts

Eataly Chicago 12 Dec 2025

Volpe Family Christmas!

235 N Ashland Ave, Chicago, IL 60607, USA 13 Dec 2025

Suenos Music Festival - 2 Day Pass

Hutchinson Field Grant Park 22 May 2026

Rough House Puppet Arts: Nasty, Brutish & Short

3111 N Western Ave. Chicago IL 60618 23 Jan 2026

ZERO HOUR: NYE Music Festival at Everything Bar

1601 W Grand Ave 31 Dec 2025

Chicago Immigrant Orchestra

201 S. Ashland Avenue, Chicago, IL, United States, Illinois 60607 21 Dec 2025

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

Lincoln Park 14 Mar 2026

GRUM at Sound-Bar

226 W Ontario St, Chicago, IL 30 Jan 2026

Chicago, IL: David Nihill at The Den Theatre

The Den Theatre 13 Feb 2026

Restorative Yoga Soundbath Chicago (90 minutes)

4007 N. Broadway #202, Chicago, IL, Illinois 60613 12 Dec 2025

Leftover Salmon

Garcia's Chicago 7 Mar 2026

GHENGAR at Ramova Theatre

Ramova Theatre 24 Jan 2026

Mac Obrien and Band at BarStool Sports River North Chicago

Barstool River North 12 Dec 2025

Elon Gold Live in Chicago, IL - Modi: Big Deal Comedy Fest

Auditorium Theatre 18 Dec 2025

MONDAY DECEMBER 15: LATE NITE MIC WITH VIK PANDYA

The Comedy Bar - Chicago Main Stage 15 Dec 2025

Rang De Christmas

Fame Nightclub 19 Dec 2025

Big Richard

Garcia's Chicago 31 Jan 2026

El Ultimo Sueno de Frida y Diego at Lyric Opera House

Lyric Opera House 21 Mar 2026

NYE at Liar's Club with Bev Rage & the Drinks / Yada Yada

Liar's Club 31 Dec 2025

Catalytic Sound Festival

3111 N Western Ave Chicago IL 60618 6 Dec 2025

PBR - Unleash the Beast - 2 Day Pass at United Center

United Center 19 Dec 2025

WINTERFEST: Chicago Roots Music 2026

Artifact Events 24 Jan 2026

SPACE ECHO

RADIUS, CHICAGO 2 May 2026

Deff Jam at Thalia Hall

Thalia Hall 3 Jan 2026

STAY H: Trinket Fest Holiday Special!

4325 N Ravenswood Ave 14 Dec 2025

NBGC's Frosty Fest

2501 W Irving Park Rd, Chicago, IL, United States, Illinois 60618 6 Dec 2025

All Your Friends

235 N Ashland Ave, Chicago, IL 60607, USA 9 Jan 2026

The High Kings - The Rocky Road Tour

The Vic Theatre 21 Mar 2026

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

IO Godfrey Rooftop Lounge 13 Dec 2025