Chicago Festivals Events

2025 Chicago Winter Whiskey Tasting Festival (January 25) AE

Downtown Chicago 25 Jan 2025

Espresso Martini Fest at Hubbard Inn - Tastings Included

Hubbard Inn 25 Jan 2025

Chicago Beefsteak 2025 [Two Nights]

DANK Haus German Cultural Center 24 Jan 2025

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

Stan's Donut Pop-Up 1 Feb 2025

Chi-Town Blues Festival

21 Mar 2025

NEW DATES! Zainab Johnson at Zanies Chicago

Zanies Comedy Club Chicago 21 Feb 2025

Stan's Donut Fest🍩 | 2025

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

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

Wrigleyville's Best Bars TBA 12 Apr 2025

Espresso Martini Fest at Hubbard Inn - Early Bird Tix Include 15 Tastings!

Hubbard Inn 25 Jan 2025

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

Barstool River North 1 Feb 2025

SAVE THE DATE: Blues at the Bean 2025

Forteza Fitness and Martial Arts 6 Jun 2025

Chicago Mimosa Fest 2025

Chicago, Illinois 23 Feb 2025

Gouge Away / Gumm

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

Chicago Wine Fest at Hubbard Inn - Wine Tastings Included

Hubbard Inn 8 Mar 2025

Pat Mallinger Quartet

Jazz Showcase 1 Feb 2025

Thrown / Varials / No Cure / Heavensgate

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

An Evening with the Bow Tides

Mayfair Theatre 28 Feb 2025

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

65 E Huron St 1 Mar 2025

The Ultimate Karaoke Event (en Español)

Simone's 26 Jan 2025

Christian Dillingham Quartet

Jazz Showcase 24 Jan 2025

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

South Chicago Dance Festival 2025

South Shore Cultural Center 15 Feb 2025

Dune Rats: If It Sucks, Turn It Up Tour

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

Chicago Chamoy Fest - $10 Early Bird Tix - Flamin' Hot, Pica, & Everything In-Between!

Moe's Cantina River North 3 May 2025

Chicago Artopia Presents: Avanti Guitar Trio

West Lawn Branch, Chicago Public Library 9 Feb 2025

Reggie Thomas & Trio Nexus

Jazz Showcase 7 Feb 2025

SNAPCASE w/ Barbarians of California, Racetraitor, and Absolute Truth

Bottom Lounge 15 Feb 2025

SATURDAY FEBRUARY 15: CHRIS BADER

The Comedy Bar - Chicago Main Stage 15 Feb 2025

Hot Clown Breakup Sex

The Newport Theater 14 Feb 2025

The Mackenzie O'Brien Band at Tin Roof Wrigleyville (Chicago)

Tin Roof Chicago 25 Jan 2025

Andersonville Coffee & Cocoa Crawl

Swedish American Museum 1 Feb 2025

Golden Hour featuring Fiesta Cuba

Epiphany Center for the Arts 25 Jan 2025

Demetrius Fields LIVE in Chicago

The Lincoln Lodge 15 Feb 2025

Shermanology

646 N Franklin St, Chicago, IL 15 Feb 2025

Love is LoveFest IV presented by Ritual Rhythms Chicago

The Newport Theater 22 Feb 2025

The Bi Wives Club: A Comedy Showcase

Dorothy 2 Feb 2025

Frequency Festival: Ensemble Dal Niente

3111 N Western Ave Chicago IL 60618 23 Feb 2025

Silverstein: 25 Years of Noise w/ Thursday

Concord Music Hall 11 Feb 2025

This Circus Called Life

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

Intimate Affairs-

Chicago Hope Academy 15 Feb 2025

Helmet: Betty 30th Anniversary Show

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

Champagne & Sparkling Wine Fest at Hubbard Inn - Tastings Included

Hubbard Inn 15 Feb 2025

Christian Dillingham Quartet

Jazz Showcase 23 Jan 2025

Aaron's Love Fest

The Edge Theater 14 Feb 2025

Psychostick with Arc Impulse & Secret Tape at Beat Kitchen

Beat Kitchen 25 Jan 2025

Free Documentary Screening of Most Likely to Succeed

Bennett Day School 6 Feb 2025

Kiran Deol LIVE in Chicago

The Lincoln Lodge 2 Mar 2025

Kumail Nanjiani: Live Special Taping

The Vic Theatre 15 Mar 2025

Pour Your Heart Out Fest

X - Fat Azz Cycling & Fitness Studio 7 Mar 2025

Jeremy Piven Live

The Vic Theatre 6 Jun 2025

HIS GIRL FRIDAY - New 4K Restoration

Music Box Theatre 1 Feb 2025

CHEAT CODES at Sound-Bar

226 W Ontario St, Chicago, IL 7 Feb 2025

SATURDAY MARCH 15: KRISTEN TOOMEY

The Comedy Bar - Chicago Main Stage 15 Mar 2025

Pat Mallinger Quartet

Jazz Showcase 30 Jan 2025

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

The Vic Theatre 22 Mar 2025

Christian Dillingham Quartet

Jazz Showcase 23 Jan 2025

Old Crow's Anti-Valentine's Day Party

Old Crow Smokehouse - Wrigleyville 14 Feb 2025

Free Throw: Those Days Are Gone 10 Year Anniversary Tour

Metro Chicago 11 Apr 2025

Pat Mallinger Quartet

Jazz Showcase 23 Feb 2025

Reggie Thomas & Trio Nexus

Jazz Showcase 6 Feb 2025

Butoh Artist Talk and Community Discussion with Joan Laage

Heritage Museum of Asian Art 22 Feb 2025

Golden Hour featuring Danielle Crim

Epiphany Center for the Arts 6 Feb 2025

Gully Boys / Skating Polly

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

Christian Dillingham Quartet

Jazz Showcase 26 Jan 2025

FRIDAY MARCH 14: KRISTEN TOOMEY

The Comedy Bar - Chicago Main Stage 14 Mar 2025

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

65 E Huron St 10 May 2025

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

Tin Roof Chicago 1 Mar 2025

Chicago Artopia Presents: Laura Snowden

West Lawn Branch, Chicago Public Library 30 Mar 2025

Golden Hour with Vivian Garcia

Epiphany Center for the Arts 20 Feb 2025

POP Cats Chicago

Artifact Events 1 Mar 2025

Golden Hour featuring Fiesta Cuba

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

Frequency Festival: Mabel Kwan & Beyond This Point

3111 N Western Ave Chicago IL 60618 19 Feb 2025

Kyle Swan Trio

Jazz Showcase 2 Mar 2025

THURSDAY FEBRUARY 13: CHRIS BADER

The Comedy Bar - Chicago Main Stage 13 Feb 2025

Mat Kerekes / Equipment / Bike Routes / Daybreaker

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

Subhumans w/ FEA

Reggie's Music Joint 6 Apr 2025

SATURDAY APRIL 5: BRADY MATTHEWS & STEVEN BRIGGS

The Comedy Bar - Chicago Main Stage 5 Apr 2025

The 19th Annual Chi-Town Blues Festival

Arie Crown Theater 22 Mar 2025

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

Seventeenth Church of Christ Scientist 29 Jan 2025

Chicago Arte Agave Tequila and Mezcal Festival

Sarabande Chicago 2 May 2025

Chicago African Restaurant Week 2025

Chicago 10 Jul 2025

Pat Mallinger Quartet

Jazz Showcase 2 Feb 2025

Tromblau&Friends Presents: Because We Love You

Dorothy 10 Feb 2025

Reading Your Resistance + Writing Your Resistance with StoryStudio Chicago

Women & Children First 21 Jan 2025

The Wrecks - Inside : Outside Tour

Concord Music Hall 4 May 2025

Comeback Kid "Wake The Dead" 20 Year Anniversary

Bottom Lounge 25 Feb 2025

JSTJR • TECHNO PLAYGROUND TOUR

226 W Ontario St, Chicago, IL 15 Mar 2025

LIL TEXAS • NEED FOR SPEED TOUR

226 W Ontario St, Chicago, IL 28 Feb 2025

THURSDAY FEBRUARY 20: MARC-ANTHONY SINAGOGA

The Comedy Bar - Chicago Main Stage 20 Feb 2025

Have Mercy / Flake

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

Christian Dillingham Quartet

Jazz Showcase 26 Jan 2025

Colter Wall and Friends

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

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

Frequency Series: a•pe•ri•od•ic (56): Bonnie Han Jones

Constellation Chicago 2 Mar 2025

Free Blues Friday featuring Dave Specter

Epiphany Center for the Arts 28 Feb 2025

Tobe Nwigwe

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

SATURDAY APRIL 5: BRADY MATTHEWS & STEVEN BRIGGS

The Comedy Bar - Chicago Main Stage 5 Apr 2025

FRIDAY APRIL 4: BRADY MATTHEWS & STEVEN BRIGGS

The Comedy Bar - Chicago Main Stage 4 Apr 2025

THE URBAN SHORT FILM FESTIVAL DOUBLE FEATURE EVENT PART 2

ACX Harper Theater- Hyde Park 15 Feb 2025

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

3111 N Western Ave Chicago IL 60618 18 Feb 2025