Chicago Festivals Events

Festivals Happening Next in Chicago, IL

2025 Chicago Winter Whiskey Tasting Festival (January 25) AE

Downtown Chicago 25 Jan 2025
FOOD-DRINKS USD 0 TO 400

Espresso Martini Fest at Hubbard Inn - Tastings Included

Hubbard Inn 25 Jan 2025
FESTIVALS USD 31 TO 58

Chicago Beefsteak 2025 [Two Nights]

DANK Haus German Cultural Center 24 Jan 2025
SPORTS USD 223 TO 235

Stan's Donut Fest - Chicago’s Tastiest Party!

Stan's Donut Pop-Up 1 Feb 2025
FESTIVALS USD 25 TO 35

Chi-Town Blues Festival

21 Mar 2025
FESTIVALS USD 72 TO 193

NEW DATES! Zainab Johnson at Zanies Chicago

Zanies Comedy Club Chicago 21 Feb 2025
COMEDY

Stan's Donut Fest🍩 | 2025

155 W Kinzie St, Chicago, IL 60654-4514, United States 1 Feb 2025
FESTIVALS

Chicago Pickle Fest: Live Bands, Beer and Everything Pickle!

Wrigleyville's Best Bars TBA 12 Apr 2025
FESTIVALS USD 16 TO 40

The Mackenzie O'Brien Band at Barstool River North (Chicago)

Barstool River North 1 Feb 2025
MUSIC

SAVE THE DATE: Blues at the Bean 2025

Forteza Fitness and Martial Arts 6 Jun 2025
FESTIVALS

Chicago Mimosa Fest 2025

Chicago, Illinois 23 Feb 2025
FESTIVALS

Gouge Away / Gumm

235 N Ashland Ave, Chicago, IL 60607, USA 8 Feb 2025
FESTIVALS

Chicago Wine Fest at Hubbard Inn - Wine Tastings Included

Hubbard Inn 8 Mar 2025
FESTIVALS USD 31 TO 58

Pat Mallinger Quartet

Jazz Showcase 1 Feb 2025
ENTERTAINMENT USD 30 TO 46

Thrown / Varials / No Cure / Heavensgate

235 N Ashland Ave, Chicago, IL 60607, USA 1 Mar 2025
FESTIVALS

An Evening with the Bow Tides

Mayfair Theatre 28 Feb 2025
MUSIC USD 25

The CBASO & the CBA Chorus in Concert at St James Cathedral

65 E Huron St 1 Mar 2025
MUSIC USD 13 TO 18

The Ultimate Karaoke Event (en Español)

Simone's 26 Jan 2025
MUSIC FREE

Christian Dillingham Quartet

Jazz Showcase 24 Jan 2025
ENTERTAINMENT USD 30 TO 46

Saturday Night Fireworks Cruise on Lake Michigan | 21+ | Live DJ | Full Bar

Sightseer Boat located at Monroe Harbor (See map and directions at bottom of page for exact location) 7 Jun 2025
FIREWORKS USD 37 TO 59

South Chicago Dance Festival 2025

South Shore Cultural Center 15 Feb 2025
FESTIVALS FREE

Dune Rats: If It Sucks, Turn It Up Tour

235 N Ashland Ave, Chicago, IL 60607, USA 22 Feb 2025
FESTIVALS

Chicago Artopia Presents: Avanti Guitar Trio

West Lawn Branch, Chicago Public Library 9 Feb 2025
MUSIC FREE

Reggie Thomas & Trio Nexus

Jazz Showcase 7 Feb 2025
ENTERTAINMENT USD 30 TO 46

SATURDAY FEBRUARY 15: CHRIS BADER

The Comedy Bar - Chicago Main Stage 15 Feb 2025
COMEDY USD 39 TO 52

Hot Clown Breakup Sex

The Newport Theater 14 Feb 2025
FESTIVALS USD 23

Andersonville Coffee & Cocoa Crawl

Swedish American Museum 1 Feb 2025
FESTIVALS

Golden Hour featuring Fiesta Cuba

Epiphany Center for the Arts 25 Jan 2025
MUSIC FREE

Demetrius Fields LIVE in Chicago

The Lincoln Lodge 15 Feb 2025
COMEDY USD 30

Shermanology

646 N Franklin St, Chicago, IL 15 Feb 2025
FESTIVALS

Love is LoveFest IV presented by Ritual Rhythms Chicago

The Newport Theater 22 Feb 2025
ART USD 29 TO 45

The Bi Wives Club: A Comedy Showcase

Dorothy 2 Feb 2025
COMEDY USD 16

Frequency Festival: Ensemble Dal Niente

3111 N Western Ave Chicago IL 60618 23 Feb 2025
ENTERTAINMENT

Silverstein: 25 Years of Noise w/ Thursday

Concord Music Hall 11 Feb 2025
FESTIVALS

This Circus Called Life

201 S. Ashland Avenue, Chicago, IL, United States, Illinois 60607 25 Jan 2025
MUSIC

Intimate Affairs-

Chicago Hope Academy 15 Feb 2025
VALENTINES-DAY USD 29 TO 162

Helmet: Betty 30th Anniversary Show

235 N Ashland Ave, Chicago, IL 60607, USA 12 Mar 2025
FESTIVALS

Champagne & Sparkling Wine Fest at Hubbard Inn - Tastings Included

Hubbard Inn 15 Feb 2025
FESTIVALS USD 31 TO 58

Christian Dillingham Quartet

Jazz Showcase 23 Jan 2025
ENTERTAINMENT USD 25 TO 40

Aaron's Love Fest

The Edge Theater 14 Feb 2025
FESTIVALS USD 8 TO 15

Free Documentary Screening of Most Likely to Succeed

Bennett Day School 6 Feb 2025
ENTERTAINMENT FREE

Kiran Deol LIVE in Chicago

The Lincoln Lodge 2 Mar 2025
COMEDY USD 30

Kumail Nanjiani: Live Special Taping

The Vic Theatre 15 Mar 2025
ENTERTAINMENT

Pour Your Heart Out Fest

X - Fat Azz Cycling & Fitness Studio 7 Mar 2025
FESTIVALS USD 23 TO 189

Jeremy Piven Live

The Vic Theatre 6 Jun 2025
ENTERTAINMENT

HIS GIRL FRIDAY - New 4K Restoration

Music Box Theatre 1 Feb 2025
FESTIVALS

CHEAT CODES at Sound-Bar

226 W Ontario St, Chicago, IL 7 Feb 2025
ART

SATURDAY MARCH 15: KRISTEN TOOMEY

The Comedy Bar - Chicago Main Stage 15 Mar 2025
COMEDY USD 30 TO 45

Pat Mallinger Quartet

Jazz Showcase 30 Jan 2025
ENTERTAINMENT USD 25 TO 40

CHIODOS: 20 Years of All’s Well That Ends Well

The Vic Theatre 22 Mar 2025
FESTIVALS

Christian Dillingham Quartet

Jazz Showcase 23 Jan 2025
ENTERTAINMENT USD 25 TO 40

Old Crow's Anti-Valentine's Day Party

Old Crow Smokehouse - Wrigleyville 14 Feb 2025
PARTIES USD 10 TO 22

Free Throw: Those Days Are Gone 10 Year Anniversary Tour

Metro Chicago 11 Apr 2025
FESTIVALS

Pat Mallinger Quartet

Jazz Showcase 23 Feb 2025
ENTERTAINMENT USD 30 TO 46

Reggie Thomas & Trio Nexus

Jazz Showcase 6 Feb 2025
ENTERTAINMENT USD 25 TO 40

Butoh Artist Talk and Community Discussion with Joan Laage

Heritage Museum of Asian Art 22 Feb 2025
ART FREE

Golden Hour featuring Danielle Crim

Epiphany Center for the Arts 6 Feb 2025
MUSIC FREE

Gully Boys / Skating Polly

235 N Ashland Ave, Chicago, IL 60607, USA 8 Mar 2025
FESTIVALS

Christian Dillingham Quartet

Jazz Showcase 26 Jan 2025
ENTERTAINMENT USD 30 TO 46

FRIDAY MARCH 14: KRISTEN TOOMEY

The Comedy Bar - Chicago Main Stage 14 Mar 2025
COMEDY USD 30 TO 45

The CBASO & the CBA Chorus in Concert at St James Cathedral

65 E Huron St 10 May 2025
MUSIC USD 13 TO 18

The Mackenzie OBrien Band at The Tin Roof Wrigleyville (Chicago)

Tin Roof Chicago 1 Mar 2025
ENTERTAINMENT

Chicago Artopia Presents: Laura Snowden

West Lawn Branch, Chicago Public Library 30 Mar 2025
MUSIC FREE

Golden Hour with Vivian Garcia

Epiphany Center for the Arts 20 Feb 2025
MUSIC FREE

POP Cats Chicago

Artifact Events 1 Mar 2025
FESTIVALS

Golden Hour featuring Fiesta Cuba

201 S. Ashland Avenue, Chicago, IL, United States, Illinois 60607 22 Feb 2025
MUSIC

Frequency Festival: Mabel Kwan & Beyond This Point

3111 N Western Ave Chicago IL 60618 19 Feb 2025
ENTERTAINMENT

Kyle Swan Trio

Jazz Showcase 2 Mar 2025
ENTERTAINMENT USD 30 TO 46

THURSDAY FEBRUARY 13: CHRIS BADER

The Comedy Bar - Chicago Main Stage 13 Feb 2025
COMEDY USD 33 TO 45

Mat Kerekes / Equipment / Bike Routes / Daybreaker

235 N Ashland Ave, Chicago, IL 60607, USA 10 Feb 2025
FESTIVALS

Subhumans w/ FEA

Reggie's Music Joint 6 Apr 2025
FESTIVALS

SATURDAY APRIL 5: BRADY MATTHEWS & STEVEN BRIGGS

The Comedy Bar - Chicago Main Stage 5 Apr 2025
COMEDY USD 33 TO 52

The 19th Annual Chi-Town Blues Festival

Arie Crown Theater 22 Mar 2025
FESTIVALS

DAME MYRA HESS MEMORIAL CONCERTS | JI-HYANG GWAK, piano

Seventeenth Church of Christ Scientist 29 Jan 2025
CONCERTS FREE

Chicago Arte Agave Tequila and Mezcal Festival

Sarabande Chicago 2 May 2025
FESTIVALS USD 82 TO 146

Chicago African Restaurant Week 2025

Chicago 10 Jul 2025
FOOD-DRINKS FREE

Pat Mallinger Quartet

Jazz Showcase 2 Feb 2025
ENTERTAINMENT USD 30 TO 46

Tromblau&Friends Presents: Because We Love You

Dorothy 10 Feb 2025
ENTERTAINMENT FREE

The Wrecks - Inside : Outside Tour

Concord Music Hall 4 May 2025
FESTIVALS

Comeback Kid "Wake The Dead" 20 Year Anniversary

Bottom Lounge 25 Feb 2025
FESTIVALS

JSTJR • TECHNO PLAYGROUND TOUR

226 W Ontario St, Chicago, IL 15 Mar 2025
FESTIVALS

LIL TEXAS • NEED FOR SPEED TOUR

226 W Ontario St, Chicago, IL 28 Feb 2025
FESTIVALS

THURSDAY FEBRUARY 20: MARC-ANTHONY SINAGOGA

The Comedy Bar - Chicago Main Stage 20 Feb 2025
COMEDY USD 33 TO 45

Have Mercy / Flake

235 N Ashland Ave, Chicago, IL 60607, USA 13 Mar 2025
FESTIVALS

Christian Dillingham Quartet

Jazz Showcase 26 Jan 2025
ENTERTAINMENT USD 30 TO 46

Colter Wall and Friends

50 E Ida B Wells Dr, Chicago, IL, United States, Illinois 60605 19 Feb 2025
MUSIC

St. Patrick's Day Friday Night River Cruise on Fri, March 14

Anita Dee ONE Boarding at Dusable Harbor (See map and directions at bottom of page for exact location) 14 Mar 2025
SAINT-PATRICKS-DAY USD 26 TO 42

Free Blues Friday featuring Dave Specter

Epiphany Center for the Arts 28 Feb 2025
MUSIC FREE

Tobe Nwigwe

4746 N Racine Ave, Chicago, IL, United States, Illinois 60640 22 Mar 2025
ENTERTAINMENT

SATURDAY APRIL 5: BRADY MATTHEWS & STEVEN BRIGGS

The Comedy Bar - Chicago Main Stage 5 Apr 2025
COMEDY USD 33 TO 52

FRIDAY APRIL 4: BRADY MATTHEWS & STEVEN BRIGGS

The Comedy Bar - Chicago Main Stage 4 Apr 2025
COMEDY USD 33 TO 52

THE URBAN SHORT FILM FESTIVAL DOUBLE FEATURE EVENT PART 2

ACX Harper Theater- Hyde Park 15 Feb 2025
ENTERTAINMENT USD 18

Frequency Festival: McCowen&Greenstone, Varo Quartet & ~Nois

3111 N Western Ave Chicago IL 60618 18 Feb 2025
FESTIVALS