Things to do in Chicago, IL
Music, Comedy, Nightlife Clear
Area
1,899 events · Music, Comedy, Nightlife
Sunday, October 11
Monday, October 12
↻ RecurringMon · Oct 12 · 6:30 PM
Trivia Night
City Winery Chicago
Mon · Oct 12 · 6:30 PM
INOHA
Metro · Chicago
↻ RecurringMon · Oct 12 · 7:00 PM
Olivia Rodrigo: The Unraveled Tour
United Center · Chicago
↻ RecurringMon · Oct 12 · 7:00 PM
Trivia Night
Fatpour Tap Works - Wicker Park
Mon · Oct 12 · 7:30 PM
Indigenous Peoples' Day
Old Town School of Folk Music
↻ RecurringMon · Oct 12 · 8:00 PM
Open Mic Night
Riddles Comedy Club
Mon · Oct 12
Carmen Sings Monk
Jazz Showcase
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Mon · Oct 12
JOEL PATERSON & FRIENDS
Green Mill Cocktail Lounge
Tuesday, October 13
Tue · Oct 13 · 6:30 PM
SLIFT
Outset · Chicago
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Tue · Oct 13 · 7:00 PM
Trivia Night
Jake Melnick's Corner Tap
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Trivia Night
Butch McGuire's
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Tue · Oct 13 · 7:00 PM
Trivia Night
Punch Bowl Social Chicago
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Trivia Night
Sheffield's Wine & Beer Garden
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Trivia Night
Timothy O'Toole's Pub Chicago
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Tue · Oct 13 · 7:00 PM
Open Mic / Blues Jam
Gallery Cabaret
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Trivia Night
Roscoe Village Pub
$41Tue · Oct 13 · 7:30 PM
White Denim w. Arc Iris
SPACE · Evanston
↻ RecurringTue · Oct 13 · 7:30 PM
Open Mic Comedy
Harrigan's
Free↻ RecurringTue · 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
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Tue · Oct 13 · 8:00 PM
CHICAGO CELLAR BOYS
Green Mill Cocktail Lounge
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Open Mic Night
Emerald Isle
Tue · Oct 13 · 8:00 PM
Will Varley, Beans On Toast
Reggies Bananna's Shack · Chicago
↻ RecurringTue · Oct 13 · 9:00 PM
Open Mic Night
Vaughan's Pub
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Open Mic Night
Laugh Factory Chicago
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Open Mic Night
Cubby Bear · Chicago
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Tue · Oct 13 · 10:00 PM
Open Mic Night
Subterranean · Chicago
Tue · Oct 13
WDCB 90.9FM feat. George Fludas & Trio Nexus in a Centennial Celebration of Ray Brown
Jazz Showcase
Wednesday, October 14
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Wed · Oct 14 · 7:00 PM
Geeks Who Drink Trivia
Fado Irish Pub
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
↻ RecurringWed · 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
↻ RecurringWed · Oct 14 · 8:00 PM
Geeks Who Drink Trivia
Dante's Tavern
↻ RecurringWed · Oct 14 · 8:00 PM
Comedy Open Mic
Cole's Bar
Wed · Oct 14 · 8:00 PM
Deraps, Reflexicon
Reggies Music Joint · Chicago
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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
↻ RecurringWed · 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
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Wed · Oct 14 · 8:00 PM
ALFONSO PONTICELLI
Green Mill Cocktail Lounge
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Trivia Night
Burwood Tap
Wed · Oct 14 · 8:00 PM
Joshua Burnside
Old Town School of Folk Music
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Trivia Night
George Street Pub
↻ RecurringWed · Oct 14 · 8:00 PM
Trivia Night
Carol's Pub · Chicago
$16.99↻ RecurringWed · Oct 14 · 9:00 PM
JIMMY BURNS – Host The Jam
Buddy Guy's Legends
↻ RecurringWed · Oct 14 · 9:00 PM
Karaoke Wednesdays
Replay Lakeview
↻ RecurringWed · Oct 14
Jazz Links Jam Session
Jazz Showcase
Thursday, October 15
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Thu · Oct 15 · 5:00 PM
ANDY BROWN
Green Mill Cocktail Lounge
$18↻ RecurringThu · Oct 15 · 6:00 PM
TBD/TBD
Kingston Mines - Chicago Blues Center · Chicago
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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
Thu · Oct 15 · 7:30 PM
Laura Veirs w. Karl Blau
SPACE · Evanston
↻ RecurringThu · 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
$42Thu · Oct 15 · 7:30 PM
Osees ft. Brigid Dawson with Traps PS
Thalia Hall · Chicago
↻ RecurringThu · 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-$119Thu · 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
↻ RecurringThu · Oct 15 · 8:00 PM
Trivia Night
Bucktown Pub
Thu · Oct 15 · 8:00 PM
Camilo
Rosemont Theatre · Rosemont
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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-$190Thu · Oct 15 · 8:30 PM
JESSE ROPER Returns to FITZGERALDS Nightclub!
FITZGERALDS NIGHTCLUB · Berwyn
Thu · Oct 15 · 9:00 PM
Salin
Sleeping Village
$16.99Thu · Oct 15 · 9:00 PM
ROCK ATLAS
Buddy Guy's Legends
↻ RecurringThu · Oct 15 · 9:00 PM
Subtronics (18 and Over)
Radius - Chicago · Chicago
Thu · Oct 15
Vibraphonist Thaddeus Tukes Quintet
Jazz Showcase
Friday, October 16
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Fri · Oct 16 · 1:00 AM
GREEN MILL JAM SESSION with MARQUIS HILL
Green Mill Cocktail Lounge
↻ RecurringFri · Oct 16 · 1:30 PM
Guerrero Leads Fandangos & Enigma Variations
Symphony Center-IL · Chicago
Fri · Oct 16 · 4:00 PM
Charlotte de Witte at East End at Navy Pier
Navy Pier · Chicago
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Fri · Oct 16 · 5:00 PM
Chris Foreman
Green Mill Cocktail Lounge
$23↻ RecurringFri · Oct 16 · 7:00 PM
TBD/TBD
Kingston Mines - Chicago Blues Center · Chicago
Fri · Oct 16 · 7:00 PM
Fugu Dugu
Old Town School of Folk Music
Fri · Oct 16 · 7:00 PM
Medium Build w/ Bella White
Metro · Chicago
Fri · Oct 16 · 7:00 PM
Capacity X Hidden Ideas: Umru + EQ
Outset · Chicago
Fri · Oct 16 · 7:00 PM
King's X
House of Blues Chicago · Chicago
Fri · Oct 16 · 7:30 PM
*SOLD OUT* Osees ft. Brigid Dawson with Traps PS
Thalia Hall · Chicago
Fri · Oct 16 · 7:30 PM
Summer Walker
Credit Union 1 Arena at UIC · Chicago
$33-$88Fri · Oct 16 · 8:00 PM
Willow Avalon - Pink Pocket Pistol Tour
Joe's Live Rosemont · Rosemont
$35Fri · Oct 16 · 8:00 PM
HEY, NOTHING – THE HOUND TOUR
Bottom Lounge · Chicago
Fri · Oct 16 · 8:00 PM
Scathing Torment, Snugglebunzzz, Convulsis, Dead and Buried
Reggies Music Joint · Chicago
$39-$52↻ RecurringFri · Oct 16 · 8:00 PM
Duane Betts & Palmetto Motel
SPACE · Evanston
Fri · Oct 16 · 8:00 PM
Grateful String Band
Garcia's Chicago · Chicago
↻ RecurringFri · Oct 16 · 8:00 PM
Open Mic Night
O'Donnell's
Fri · Oct 16 · 8:00 PM
V.V. Lightbody Album Release - Night 2!
The Hideout
Fri · Oct 16 · 8:00 PM
TINASHE - ONE NIGHT WITH A POPSTAR
The Salt Shed Indoors (Shed) · Chicago
Fri · Oct 16 · 8:00 PM
Branford Marsalis & Dianne Reeves Celebrate John Coltrane
Symphony Center-IL · Chicago
15Fri · Oct 16 · 8:30 PM
Todd Snider Get Together
Martyrs'
$35-$252Fri · Oct 16 · 8:30 PM
Friday Night in the Club w/ FUNKHOUSE!
FITZGERALDS NIGHTCLUB · Berwyn
$28Fri · Oct 16 · 9:00 PM
DISTANT MATTER - ‘VIVID NOSTALGIA - PHASE II’
Three Top Lounge · Chicago
Fri · Oct 16 · 9:00 PM
Metro Presents… RES – How i Do 25th Anniversary ** DJ set by Quinnette
Sleeping Village