Things to do in Chicago, IL

1,899 events · Music, Comedy, Nightlife

Sunday, September 20

$15.77

Sun · Sep 20 · 7:30 PM

Starcharm Lana Leone Baby

Cole's Bar

Sun · Sep 20 · 7:30 PM

Shoshana Bean

Thalia Hall · Chicago

Nightlife

↻ Recurring

Sun · Sep 20 · 8:00 PM

SOUL MESSAGE

Green Mill Cocktail Lounge

Sun · Sep 20 · 8:00 PM

Gable Price And Friends

Beat Kitchen · Chicago

Sun · Sep 20 · 8:00 PM

Pleiades Series: 'Flagellent Songs' Film Screening, Gabi Vanek w/ Tina LeFauve + iph

Elastic Arts

Sun · Sep 20 · 8:00 PM

Kany Garcia: Puerta Abierta Tour

Cahn Auditorium · Evanston

Sun · Sep 20 · 8:00 PM

Sunday Night Live Ft. 5onny W/ Lil Keisha

Reggies Bananna's Shack · Chicago

Sun · Sep 20 · 8:30 PM

Luke Callen, Austin Cash & Nathan Smerage, Ultra Violet Archer

The Hideout

Sun · Sep 20 · 8:30 PM

Frequency Series Presents: Formosa Quartet

Constellation

Sun · Sep 20 · 9:00 PM

Three Grebes + Banana Acid

Hungry Brain

Sun · Sep 20 · 9:00 PM

Slug Nudger, Niã±O Chiflo, Tã¿Re Fã¿Re

Reggies Music Joint · Chicago

$16.99

Sun · Sep 20 · 9:00 PM

WILLIE BUCK

Buddy Guy's Legends

Nightlife

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Sun · Sep 20 · 9:00 PM

Open Mic Night

My Buddy's

Nightlife

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Sun · Sep 20 · 10:00 PM

Open Mic Night

Reed's Local

20↻ Recurring

Sun · Sep 20

1st Set With Andy Brown Quartet

Andy's Jazz Club

20↻ Recurring

Sun · Sep 20

Late Night Concert Series w/Sunday Soul

Andy's Jazz Club

20↻ Recurring

Sun · Sep 20

2nd Set With Andy Brown Quartet

Andy's Jazz Club

Monday, September 21

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Mon · Sep 21 · 6:30 PM

Trivia Night

City Winery Chicago

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Mon · Sep 21 · 7:00 PM

Trivia Night

Fatpour Tap Works - Wicker Park

Mon · Sep 21 · 7:30 PM

*SOLD OUT* Bella Kay: The Reckless Tour with Hailey Picardi

Thalia Hall · Chicago

Mon · Sep 21 · 8:00 PM

Kaya, Panic Priest

Reggies Rock Club · Chicago

Mon · Sep 21 · 8:00 PM

Industry Night w/ Lawn Brutic

Sleeping Village

Mon · Sep 21 · 8:00 PM

Spencer Thomas with Tyler Stock

Tack Room · Chicago

Mon · Sep 21 · 8:00 PM

Powers Rolin Duo

The Hideout

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Mon · Sep 21 · 8:00 PM

Open Mic Night

Riddles Comedy Club

Free

Mon · Sep 21 · 8:30 PM

Cole's Bar Jam Session

Cole's Bar

Nightlife

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Mon · Sep 21

JOEL PATERSON & FRIENDS

Green Mill Cocktail Lounge

20

Mon · Sep 21

2nd Set With The Tom Garling Jazz Orchestra

Andy's Jazz Club

Mon · Sep 21

Al Jarreau Tribute feat. Vocalist Bruce Henry

Jazz Showcase

20

Mon · Sep 21

1st Set With The Tom Garling Jazz Orchestra

Andy's Jazz Club

Tuesday, September 22

Tue · Sep 22 · 6:00 PM

Ryan Beatty - Arms Over Armor North American Tour '26

House of Blues Chicago · Chicago

Free

Tue · Sep 22 · 6:00 PM

Row Sham Bow

Cole's Bar

Tue · Sep 22 · 6:30 PM

All Time Low

The Salt Shed Outdoors (Fairgrounds) · Chicago

Tue · Sep 22 · 7:00 PM

wave to earth - the pieces tour

Aragon Ballroom · Chicago

Nightlife

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Tue · Sep 22 · 7:00 PM

Open Mic / Blues Jam

Gallery Cabaret

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Tue · Sep 22 · 7:00 PM

Trivia Night

Sheffield's Wine & Beer Garden

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Tue · Sep 22 · 7:00 PM

Trivia Night

Timothy O'Toole's Pub Chicago

Nightlife

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Tue · Sep 22 · 7:00 PM

Trivia Night

Punch Bowl Social Chicago

Tue · Sep 22 · 7:00 PM

WEEZER: The Gathering

United Center · Chicago

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Tue · Sep 22 · 7:00 PM

Trivia Night

Butch McGuire's

Nightlife

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Tue · Sep 22 · 7:00 PM

Trivia Night

Jake Melnick's Corner Tap

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Tue · Sep 22 · 7:00 PM

Trivia Night

Roscoe Village Pub

Tue · Sep 22 · 7:00 PM

Logic & G-Eazy: The Endless Summer Tour Part II

Huntington Bank Pavilion at Northerly Island · Chicago

Tue · Sep 22 · 7:15 PM

Iron Maiden: Run For Your Lives World Tour 2026

Credit Union 1 Amphitheatre · Tinley Park

Tue · Sep 22 · 7:30 PM

Igorrr - Ages 18+

Vic Theatre · Chicago

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Tue · Sep 22 · 7:30 PM

Open Mic Comedy

Harrigan's

Tue · Sep 22 · 8:00 PM

Elephant Stone w/ Diagonal

Sleeping Village

Tue · Sep 22 · 8:00 PM

John Pizzarelli

Old Town School of Folk Music

Tue · Sep 22 · 8:00 PM

Jason Ricci & The Bad Kind

SPACE · Evanston

Tue · Sep 22 · 8:00 PM

Sleeping Village Presents: Truck Violence at NOT NOT

Sleeping Village

Nightlife

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Tue · Sep 22 · 8:00 PM

CHICAGO CELLAR BOYS

Green Mill Cocktail Lounge

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Tue · Sep 22 · 8:00 PM

Open Mic Night

Emerald Isle

Tue · Sep 22 · 8:00 PM

Thundersmack

Garcia's Chicago · Chicago

Tue · Sep 22 · 8:30 PM

Dead Pink Radio

Reggies Music Joint · Chicago

$16.99↻ Recurring

Tue · Sep 22 · 9:00 PM

CHRIS O’LEARY

Buddy Guy's Legends

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Tue · Sep 22 · 9:00 PM

Open Mic Night

Vaughan's Pub

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Tue · Sep 22 · 9:00 PM

Open Mic Night

Cubby Bear · Chicago

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Tue · Sep 22 · 9:00 PM

Open Mic Night

Laugh Factory Chicago

Music

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Tue · Sep 22 · 10:00 PM

Open Mic Night

Subterranean · Chicago

20↻ Recurring

Tue · Sep 22

2nd Set With Tenor Time

Andy's Jazz Club

Tue · Sep 22

Jeremiah Hunt Quintet

Jazz Showcase

20↻ Recurring

Tue · Sep 22

1st Set With Tenor Time

Andy's Jazz Club

Wednesday, September 23

Wed · Sep 23 · 5:30 PM

Bobby Lewis Quintet - 90th Birthday Tour!

Winter's Jazz Club

Wed · Sep 23 · 6:00 PM

Staind: Break The Cycle 25th Anniversary Tour

Credit Union 1 Amphitheatre · Tinley Park

$96

Wed · Sep 23 · 6:15 PM

JEFF TWEEDY w/ special guest Max Subar at FITZGERALDS OUTDOORS

FITZGERALDS PATIO · Berwyn

Wed · Sep 23 · 6:30 PM

STRFKR

Outset · Chicago

Nightlife

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Wed · Sep 23 · 7:00 PM

Geeks Who Drink Trivia

Fado Irish Pub

Wed · Sep 23 · 7:00 PM

Buffalo Traffic Jam - Pictures of You Tour

House of Blues Chicago · Chicago

↻ Recurring

Wed · Sep 23 · 7:30 PM

Geeks Who Drink Trivia

Commonwealth Tavern

Wed · Sep 23 · 7:30 PM

Gadan

Old Town School of Folk Music

Wed · Sep 23 · 7:30 PM

A Winged Victory for the Sullen

Vic Theatre · Chicago

$32-$136

Wed · Sep 23 · 7:30 PM

LØLØ - God Forbid a Girl Goes on Tour

Bottom Lounge · Chicago

Wed · Sep 23 · 7:30 PM

Jacob Collier

Martin Theatre · Highland Park

Wed · Sep 23 · 7:30 PM

Knorrwood

North Theatre at North Shore Center for the Performing Arts · Skokie

↻ Recurring

Wed · Sep 23 · 8:00 PM

Trivia Night

Burwood Tap

Wed · Sep 23 · 8:00 PM

Volcandra, Graveripper, Beyond Deth

Reggies Music Joint · Chicago

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Wed · Sep 23 · 8:00 PM

Comedy Open Mic

Cole's Bar

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Wed · Sep 23 · 8:00 PM

Geeks Who Drink Trivia

Dante's Tavern

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Wed · Sep 23 · 8:00 PM

SOLD OUT - Son Volt

SPACE · Evanston

Nightlife

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Wed · Sep 23 · 8:00 PM

Karaoke Night

Sidekick's Entertainment Lounge

20

Wed · Sep 23 · 8:00 PM

John Coltrane's 100th Birthday with, Pat Mallinger Quartet

Martyrs'

$34-$492

Wed · Sep 23 · 8:00 PM

*CANCELLED* josh conway: the plum tour with special guest HOMESHAKE (solo)

Thalia Hall · Chicago

Wed · Sep 23 · 8:00 PM

YHWH Nailgun

Reggies Rock Club · Chicago

↻ Recurring

Wed · Sep 23 · 8:00 PM

Trivia Night

George Street Pub

Wed · Sep 23 · 8:00 PM

Charlie Hunter Trio

Garcia's Chicago · Chicago

Nightlife

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Wed · Sep 23 · 8:00 PM

ALFONSO PONTICELLI

Green Mill Cocktail Lounge

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Wed · Sep 23 · 8:00 PM

Karaoke Night

Rabbit Hole Wrigley

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Wed · Sep 23 · 8:00 PM

Trivia Night

Carol's Pub · Chicago

Wed · Sep 23 · 8:30 PM

Grayna Augucik Chicago Quintet: On The Way

Constellation

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Wed · Sep 23 · 9:00 PM

Karaoke Wednesdays

Replay Lakeview

Wed · Sep 23 · 9:00 PM

Bath Drawers Record Release with Spread Joy & Wulf Pac

The Hideout

$16.99↻ Recurring

Wed · Sep 23 · 9:00 PM

BROTHER JOHN – Host The Jam

Buddy Guy's Legends

10↻ Recurring

Wed · Sep 23

Late Night Concert Series w/Ben Paterson

Andy's Jazz Club

20↻ Recurring

Wed · Sep 23

1st Set With Charles Heath

Andy's Jazz Club

Wed · Sep 23

Willie Buck: A Chicago Blues Legend

Rosa's Lounge

20↻ Recurring

Wed · Sep 23

2nd Set With Charles Heath

Andy's Jazz Club

Thursday, September 24

Nightlife

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Thu · Sep 24 · 5:00 PM

ANDY BROWN

Green Mill Cocktail Lounge

$18

Thu · Sep 24 · 6:00 PM

Rico McFarland Blues Band/Joanna Connor Blues Band

Kingston Mines - Chicago Blues Center · Chicago

$96

Thu · Sep 24 · 6:15 PM

JEFF TWEEDY at FITZGERALDS OUTDOORS (Solo Acoustic) w/ special guest Official Claire

FITZGERALDS PATIO · Berwyn

Thu · Sep 24 · 6:30 PM

Monsieur Perine - Instrucciones Para Ser Feliz Tour

Outset · Chicago