Things to do in Chicago, IL

1,787 events · Music, Theater, Food & Drink, Nightlife · morning/afternoon/evening

Saturday, October 10

Sat · Oct 10 · 9:00 PM

Orange Dog Club, Tba

Reggies Music Joint · Chicago

$27.30

Sat · Oct 10 · 9:00 PM

DEMETRIA TAYLOR

Buddy Guy's Legends

Sat · Oct 10 · 9:30 PM

Alice Smith

Garcia's Chicago · Chicago

$12

Sat · Oct 10 · 9:30 PM

Riplock

Carol's Pub · Chicago

Sat · Oct 10 · 10:00 PM

BUMP. DISCO w/ NAOMI SMALLS

Sleeping Village

Sat · Oct 10 · 10:00 PM

Hamdi (18 and Over with Valid Government ID)

Radius - Chicago · Chicago

Sunday, October 11

Sun · Oct 11 · 11:30 AM

5th ANNUAL HONKY TONKTOBERFEST Hosted by WILD EARP

FitzGerald's · Berwyn

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Sun · Oct 11 · 3:00 PM

The Hoyle Brothers

Martyrs'

Sun · Oct 11 · 3:00 PM

Third Coast Symphony: Rhapsody in Blue & A World Premiere

George Van Dusen Theatre at North Shore Center · Skokie

$18↻ Recurring

Sun · Oct 11 · 5:30 PM

TBD/TBD

Kingston Mines - Chicago Blues Center · Chicago

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Sun · Oct 11 · 5:30 PM

Open Mic Night

aliveOne

Sun · Oct 11 · 6:00 PM

TASTE OF CHAOS

Aragon Ballroom · Chicago

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Sun · Oct 11 · 7:00 PM

Olivia Rodrigo: The Unraveled Tour

United Center · Chicago

Sun · Oct 11 · 7:00 PM

Heavy Temple, Crystal Spiders, Shadow of Jupiter

Reggies Music Joint · Chicago

Sun · Oct 11 · 7:00 PM

Interpol - North America Tour 2026 with DIIV

The Salt Shed Outdoors (Fairgrounds) · Chicago

$40-$148

Sun · Oct 11 · 7:30 PM

EMEI - Night at the Opera Tour with googly eyes

Thalia Hall · Chicago

Sun · Oct 11 · 7:30 PM

EMEI - Night at the Opera Tour

Thalia Hall · Chicago

$15.77

Sun · Oct 11 · 7:45 PM

Biitchseat Empty Heaven Molly O'Malley

Cole's Bar

Nightlife

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Sun · Oct 11 · 8:00 PM

SOUL MESSAGE

Green Mill Cocktail Lounge

Sun · Oct 11 · 8:00 PM

Metaphor: ReFantazio Orchestra Concert

Cahn Auditorium · Evanston

Sun · Oct 11 · 8:00 PM

An Evening With Steve Dawson with special guests Jason Adasiewicz, Jason Roebke, Diane Christiansen and Alton Smith

SPACE · Evanston

Sun · Oct 11 · 8:00 PM

Big Fat Head, Heavy Sleeper, Shy Bronco

The Hideout

Nightlife

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Sun · Oct 11 · 9:00 PM

Open Mic Night

My Buddy's

$16.99

Sun · Oct 11 · 9:00 PM

LUKE PYTEL

Buddy Guy's Legends

$56

Sun · Oct 11 · 10:00 PM

Paul Banks (DJ Set)

Three Top Lounge · Chicago

Nightlife

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Sun · Oct 11 · 10:00 PM

Open Mic Night

Reed's Local

Monday, October 12

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Mon · Oct 12 · 6:30 PM

Trivia Night

City Winery Chicago

Mon · Oct 12 · 6:30 PM

INOHA

Metro · Chicago

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Mon · Oct 12 · 7:00 PM

Olivia Rodrigo: The Unraveled Tour

United Center · Chicago

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Mon · Oct 12 · 7:00 PM

Trivia Night

Fatpour Tap Works - Wicker Park

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Mon · Oct 12 · 7:00 PM

Trivia Night

Guinness Open Gate Brewery

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Mon · Oct 12 · 7:00 PM

Trivia Night

Pilot Project Brewing - Logan Square

Mon · Oct 12 · 7:30 PM

Indigenous Peoples' Day

Old Town School of Folk Music

Tuesday, October 13

Tue · Oct 13 · 6:30 PM

SLIFT

Outset · Chicago

Nightlife

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Tue · Oct 13 · 7:00 PM

Trivia Night

Jake Melnick's Corner Tap

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Tue · Oct 13 · 7:00 PM

Trivia Night

Butch McGuire's

Nightlife

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Tue · Oct 13 · 7:00 PM

Trivia Night

Punch Bowl Social Chicago

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Tue · Oct 13 · 7:00 PM

Trivia Night

Sheffield's Wine & Beer Garden

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Tue · Oct 13 · 7:00 PM

Trivia Night

Timothy O'Toole's Pub Chicago

Nightlife

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Tue · Oct 13 · 7:00 PM

Open Mic / Blues Jam

Gallery Cabaret

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Tue · Oct 13 · 7:00 PM

Trivia Night

Roscoe Village Pub

$41

Tue · Oct 13 · 7:30 PM

White Denim w. Arc Iris

SPACE · Evanston

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Tue · Oct 13 · 7:30 PM

Open Mic Comedy

Harrigan's

Free↻ Recurring

Tue · Oct 13 · 7:30 PM

rocknite presents!

Cole's Bar

Tue · Oct 13 · 8:00 PM

2026 MONSTA X WORLD TOUR [THE X : NEXUS] IN ROSEMONT

Rosemont Theatre · Rosemont

Tue · Oct 13 · 8:00 PM

Jessie Ware: The Superbloom Tour

Aragon Ballroom · Chicago

Tue · Oct 13 · 8:00 PM

FREE TUESDAY w/ Hell Is Real & Degenerate Synapse [presented by Still Austin Whiskey Co.]

Sleeping Village

Nightlife

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Tue · Oct 13 · 8:00 PM

CHICAGO CELLAR BOYS

Green Mill Cocktail Lounge

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Tue · Oct 13 · 8:00 PM

Open Mic Night

Emerald Isle

Tue · Oct 13 · 8:00 PM

Will Varley, Beans On Toast

Reggies Bananna's Shack · Chicago

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Tue · Oct 13 · 9:00 PM

Open Mic Night

Vaughan's Pub

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Tue · Oct 13 · 9:00 PM

Open Mic Night

Cubby Bear · Chicago

Music

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Tue · Oct 13 · 10:00 PM

Open Mic Night

Subterranean · Chicago

Wednesday, October 14

Wed · Oct 14 · 4:00 PM

Martha C. Nussbaum - "The Republic of Love" - Douglas Baird

Seminary Co-op Bookstore

Nightlife

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Wed · Oct 14 · 7:00 PM

Geeks Who Drink Trivia

Fado Irish Pub

Wed · Oct 14 · 7:00 PM

Joe Dombrowski

The Den Theatre

Wed · Oct 14 · 7:30 PM

The Bolero Project

Old Town School of Folk Music

Wed · Oct 14 · 7:30 PM

Michael Franti

Park West · Chicago

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Wed · Oct 14 · 7:30 PM

Geeks Who Drink Trivia

Commonwealth Tavern

Wed · Oct 14 · 8:00 PM

Acid Mothers Temple, Magick Potion, Spiral Galaxy

Reggies Rock Club · Chicago

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Wed · Oct 14 · 8:00 PM

Geeks Who Drink Trivia

Dante's Tavern

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Wed · Oct 14 · 8:00 PM

Comedy Open Mic

Cole's Bar

Wed · Oct 14 · 8:00 PM

Deraps, Reflexicon

Reggies Music Joint · Chicago

Nightlife

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Wed · Oct 14 · 8:00 PM

Karaoke Night

Sidekick's Entertainment Lounge

Wed · Oct 14 · 8:00 PM

ALVARO DIAZ - OMAKASE TOUR

Riviera Theatre- IL · Chicago

Wed · Oct 14 · 8:00 PM

The Smashing Pumpkins: The Rats In A Cage Tour

United Center · Chicago

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Wed · Oct 14 · 8:00 PM

Karaoke Night

Rabbit Hole Wrigley

Wed · Oct 14 · 8:00 PM

CHRONO TRIGGER Orchestra Concert: Melodies Across Time

Cahn Auditorium · Evanston

Nightlife

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Wed · Oct 14 · 8:00 PM

ALFONSO PONTICELLI

Green Mill Cocktail Lounge

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Wed · Oct 14 · 8:00 PM

Trivia Night

Burwood Tap

Wed · Oct 14 · 8:00 PM

Joshua Burnside

Old Town School of Folk Music

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Wed · Oct 14 · 8:00 PM

Trivia Night

George Street Pub

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Wed · Oct 14 · 8:00 PM

Trivia Night

Carol's Pub · Chicago

$16.99↻ Recurring

Wed · Oct 14 · 9:00 PM

JIMMY BURNS – Host The Jam

Buddy Guy's Legends

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Wed · Oct 14 · 9:00 PM

Karaoke Wednesdays

Replay Lakeview

Thursday, October 15

Thu · Oct 15 · 12:00 PM

East Asia by the Book! CEAS Author Talks ft. Julia Alekseyeva

Seminary Co-op Bookstore

Thu · Oct 15 · 4:00 PM

Stephanie Soileau - "Should the Waters Take Us"

Seminary Co-op Bookstore

Nightlife

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Thu · Oct 15 · 5:00 PM

ANDY BROWN

Green Mill Cocktail Lounge

$18↻ Recurring

Thu · Oct 15 · 6:00 PM

TBD/TBD

Kingston Mines - Chicago Blues Center · Chicago

Nightlife

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Thu · Oct 15 · 7:00 PM

Open Mic Night

Whiskey Girl Tavern

Thu · Oct 15 · 7:00 PM

MAR SOLIS - TU TUTU TOUR 2026

House of Blues Chicago · Chicago

$21-$34

Thu · Oct 15 · 7:30 PM

Laura Veirs w. Karl Blau

SPACE · Evanston

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Thu · Oct 15 · 7:30 PM

Guerrero Leads Fandangos & Enigma Variations

Symphony Center-IL · Chicago

Thu · Oct 15 · 7:30 PM

Dadi Freyr (18+)

Vic Theatre · Chicago

$42

Thu · Oct 15 · 7:30 PM

Osees ft. Brigid Dawson with Traps PS

Thalia Hall · Chicago

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Thu · Oct 15 · 7:30 PM

Jeopardy! Bar League

Guthries Tavern

Thu · Oct 15 · 7:30 PM

ROBERT PLANT WITH SAVING GRACE and SUZI DIAN

The Chicago Theatre · Chicago

$26-$119

Thu · Oct 15 · 8:00 PM

Blake Whiten - Something To Say Tour

Joe's on Weed Street · Chicago

Thu · Oct 15 · 8:00 PM

Carbon Leaf

Garcia's Chicago · Chicago

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Thu · Oct 15 · 8:00 PM

Trivia Night

Bucktown Pub

Thu · Oct 15 · 8:00 PM

Camilo

Rosemont Theatre · Rosemont

Nightlife

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Thu · Oct 15 · 8:00 PM

ALAN GRESIK'S SWING ORCHESTRA

Green Mill Cocktail Lounge

Thu · Oct 15 · 8:00 PM

Will Dempsey - Carry The Weight Tour with Gavin Hughes

Carol's Pub · Chicago

Thu · Oct 15 · 8:00 PM

V.V. Lightbody Album Release - Night 1!

The Hideout

Thu · Oct 15 · 8:00 PM

Insomniac, Krononaut, the Waterfall King

Reggies Music Joint · Chicago

$24-$190

Thu · Oct 15 · 8:30 PM

JESSE ROPER Returns to FITZGERALDS Nightclub!

FITZGERALDS NIGHTCLUB · Berwyn

Thu · Oct 15 · 9:00 PM

Salin

Sleeping Village

$16.99

Thu · Oct 15 · 9:00 PM

ROCK ATLAS

Buddy Guy's Legends

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Thu · Oct 15 · 9:00 PM

Subtronics (18 and Over)

Radius - Chicago · Chicago