Things to do in Chicago, IL
Music, Comedy, Food & Drink, Parks & Outdoors · afternoon/evening Clear
Area
1,502 events · Music, Comedy, Food & Drink, Parks & Outdoors · afternoon/evening
Friday, October 23
Fri · Oct 23 · 8:00 PM
PLAYGRND SERIES CHICAGO
Thalia Hall · Chicago
Fri · Oct 23 · 8:00 PM
Silvis, Everyday Fantastic, Om In Gold
Reggies Bananna's Shack · Chicago
Fri · Oct 23 · 8:00 PM
Menudo 50
Rosemont Theatre · Rosemont
Fri · Oct 23 · 8:00 PM
Austin Snell (21+ Event)
Joe's on Weed Street · Chicago
Fri · Oct 23 · 8:00 PM
Sammy Rae & The Friends with special guest Melt
The Salt Shed Indoors (Shed) · Chicago
$17Fri · Oct 23 · 8:30 PM
The Ron Burgundy's
Joe's Live Rosemont · Rosemont
Fri · Oct 23 · 9:00 PM
¥ØU$UK ¥UK1MAT$U: Autumn 2026 Tour
Aragon Ballroom · Chicago
$27.30Fri · Oct 23 · 9:00 PM
RAY FULLER
Buddy Guy's Legends
Fri · Oct 23 · 9:00 PM
MJT the Band, Desmond Jones, When We Was Kids
Reggies Music Joint · Chicago
$8Fri · Oct 23 · 9:30 PM
The Messengers
Carol's Pub · Chicago
Fri · Oct 23 · 10:00 PM
Grabbitz
Outset · Chicago
Saturday, October 24
Free↻ Recurring
Sat · Oct 24 · 1:00 PM
Daily Ranger Guided Tours
Pullman National Historical Park
Sat · Oct 24 · 3:00 PM
Rowenna Miller - "The Dancer and the Dream Thief"
Seminary Co-op Bookstore
Sat · Oct 24 · 4:00 PM
The Wrecks - Finally : OUTSIDE Tour
House of Blues Chicago · Chicago
Sat · Oct 24 · 6:30 PM
Badluv, Dan Vallejo, KR!S Cortez, Freshman
Reggies Bananna's Shack · Chicago
$23↻ RecurringSat · Oct 24 · 7:00 PM
TBD/TBD
Kingston Mines - Chicago Blues Center · Chicago
↻ RecurringSat · Oct 24 · 7:30 PM
Sleeping Beauty & Dvor??k Cello Concerto
Symphony Center-IL · Chicago
Sat · Oct 24 · 7:30 PM
Shane Dawson Live!
Vic Theatre · Chicago
↻ RecurringSat · Oct 24 · 7:30 PM
Tedeschi Trucks Band: Future Soul 2026 Tour
The Chicago Theatre · Chicago
Sat · Oct 24 · 8:00 PM
Mobb Deep x Talib Kweli (18 and Over)
Ramova Theatre · Chicago
$20-$33Sat · Oct 24 · 8:00 PM
Emo Night LIVE with All American Throwbacks
Joe's Live Rosemont · Rosemont
Sat · Oct 24 · 8:00 PM
Oh He Dead
Garcia's Chicago · Chicago
Sat · Oct 24 · 8:00 PM
Authority Zero, Counterpunch, the Run Around
Reggies Music Joint · Chicago
$40Sat · Oct 24 · 8:00 PM
Tank and The Bangas - The Last Balloon Tour with Ariel J. and Zeus
Thalia Hall · Chicago
Sat · Oct 24 · 8:00 PM
Fruit Bats with Matthew Logan Vasquez
The Salt Shed Indoors (Shed) · Chicago
$32-$187Sat · Oct 24 · 8:00 PM
Shawn James – Flew Too Close To The Sun Tour
Bottom Lounge · Chicago
Sat · Oct 24 · 8:00 PM
90's CORRIDOS TOUR
Rosemont Theatre · Rosemont
Sat · Oct 24 · 8:00 PM
Shawn James
Bottom Lounge · Chicago
↻ RecurringSat · Oct 24 · 8:00 PM
Judy Collins
Old Town School of Folk Music
Sat · Oct 24 · 8:00 PM
Authority Zero w/ Counterpunch
Reggies Music Joint · Chicago
$24-$159Sat · Oct 24 · 8:30 PM
ALICIA BLUE at FITZGERALDS Nightclub
FITZGERALDS NIGHTCLUB · Berwyn
Sat · Oct 24 · 9:00 PM
CircuitMOM & Uncle Present Haunted Hollywood ft Erik Vilar and Ed Wood
House of Blues Chicago · Chicago
Sat · Oct 24 · 9:00 PM
The Brokes, St. Marlboro
Reggies Rock Club · Chicago
$27.30Sat · Oct 24 · 9:00 PM
COREY DENNISON
Buddy Guy's Legends
$12-$28Sat · Oct 24 · 9:30 PM
Chasen Wayne & The Honky Tonk Machine - Chicago Album Release
Carol's Pub · Chicago
Sat · Oct 24 · 10:00 PM
Steven Castillo
The Hideout
Sunday, October 25
Free↻ Recurring
Sun · Oct 25 · 1:00 PM
Daily Ranger Guided Tours
Pullman National Historical Park
↻ RecurringSun · Oct 25 · 3:00 PM
Sleeping Beauty & Dvor??k Cello Concerto
Symphony Center-IL · Chicago
↻ RecurringSun · Oct 25 · 3:00 PM
The Hoyle Brothers
Martyrs'
$18↻ RecurringSun · Oct 25 · 5:30 PM
TBD/TBD
Kingston Mines - Chicago Blues Center · Chicago
Sun · Oct 25 · 7:00 PM
Streetlight Manifesto: The Presence of the Past Tour
House of Blues Chicago · Chicago
$32Sun · Oct 25 · 7:00 PM
Icon For Hire: Scripted 15 Year Anniversary Tour
Bottom Lounge · Chicago
↻ RecurringSun · Oct 25 · 7:00 PM
Judy Collins
Old Town School of Folk Music
Sun · Oct 25 · 7:00 PM
Sleeping With Sirens: An Ending In Itself Tour
The Salt Shed Indoors (Shed) · Chicago
Sun · Oct 25 · 7:30 PM
The Longest Johns
Vic Theatre · Chicago
25Sun · Oct 25 · 7:30 PM
An Intimate Evening with Pamela Des Barres, Author "I'm With The Band"
Martyrs'
Sun · Oct 25 · 7:30 PM
Jackopierce
SPACE · Evanston
$16.99↻ RecurringSun · Oct 25 · 9:00 PM
TBA
Buddy Guy's Legends
Monday, October 26
↻ RecurringMon · Oct 26 · 6:30 PM
Trivia Night
City Winery Chicago
↻ RecurringMon · Oct 26 · 7:00 PM
Trivia Night
Guinness Open Gate Brewery
↻ RecurringMon · Oct 26 · 7:00 PM
Trivia Night
Pilot Project Brewing - Logan Square
Mon · Oct 26 · 7:00 PM
She Wants Revenge
House of Blues Chicago · Chicago
↻ RecurringMon · Oct 26 · 7:30 PM
Tedeschi Trucks Band: Future Soul 2026 Tour
The Chicago Theatre · Chicago
Mon · Oct 26 · 7:30 PM
Vitamin String Quartet
George Van Dusen Theatre at North Shore Center · Skokie
$21Mon · Oct 26 · 8:00 PM
MADMAN CHYNO w. Nvrmnd st Sylas and Peez Alchemy
SPACE · Evanston
↻ RecurringMon · Oct 26 · 8:00 PM
Open Mic Night
Riddles Comedy Club
Tuesday, October 27
Tue · Oct 27 · 6:30 PM
SiM - HOOMAN WORLD TOUR
House of Blues Chicago · Chicago
↻ RecurringTue · Oct 27 · 7:30 PM
Tedeschi Trucks Band: Future Soul 2026 Tour
The Chicago Theatre · Chicago
Tue · Oct 27 · 7:30 PM
Sienna Spiro
Riviera Theatre- IL · Chicago
Tue · Oct 27 · 8:00 PM
Tth w/ William Alexander
Sleeping Village
Tue · Oct 27 · 8:00 PM
The Empty Pockets
Garcia's Chicago · Chicago
Tue · Oct 27 · 8:00 PM
Dylan Gossett - Live In Concert
The Salt Shed Indoors (Shed) · Chicago
Tue · Oct 27 · 8:00 PM
*SOLD OUT* This Is Lorelei with @
Thalia Hall · Chicago
$34-$41Tue · Oct 27 · 8:00 PM
The Arcadian Wild - Make It Out Alive Tour w. Addison Agen
SPACE · Evanston
Tue · Oct 27 · 8:00 PM
Colin Miller
The Hideout
↻ RecurringTue · Oct 27 · 9:00 PM
Open Mic Night
Cubby Bear · Chicago
↻ RecurringTue · Oct 27 · 9:00 PM
Open Mic Night
Laugh Factory Chicago
↻ Recurring
Tue · Oct 27 · 10:00 PM
Open Mic Night
Subterranean · Chicago
Wednesday, October 28
Free↻ Recurring
Wed · Oct 28 · 1:00 PM
Daily Ranger Guided Tours
Pullman National Historical Park
Wed · Oct 28 · 4:00 PM
Gautham Rao - "White Power: Policing American Slavery" - Alison L. LaCroix
Seminary Co-op Bookstore
Wed · Oct 28 · 7:30 PM
Shakey Graves w/ Wild Pink
Vic Theatre · Chicago
Wed · Oct 28 · 7:30 PM
Día de los Muertos (Day of the Dead)
Old Town School of Folk Music
Wed · Oct 28 · 8:00 PM
Phillip Phillips - Let’s Go Far Tour with Katie Lynne Sharbaugh
Thalia Hall · Chicago
↻ RecurringWed · Oct 28 · 8:00 PM
Trivia Night
Carol's Pub · Chicago
$16.99↻ RecurringWed · Oct 28 · 9:00 PM
JIMMY BURNS – Host The Jam
Buddy Guy's Legends
Thursday, October 29
Free↻ Recurring
Thu · Oct 29 · 1:00 PM
Daily Ranger Guided Tours
Pullman National Historical Park
$18↻ RecurringThu · Oct 29 · 6:00 PM
TBD/TBD
Kingston Mines - Chicago Blues Center · Chicago
Thu · Oct 29 · 6:00 PM
ESTEMAN & DANIELA SPALLA - AMORIO USA TOUR
House of Blues Chicago · Chicago
Thu · Oct 29 · 7:00 PM
Gavn!, Tba
Reggies Rock Club · Chicago
Thu · Oct 29 · 7:30 PM
Infinite 80s: Play The Cure
SPACE · Evanston
↻ RecurringThu · Oct 29 · 7:30 PM
Brahms Requiem
Symphony Center-IL · Chicago
Thu · Oct 29 · 7:30 PM
The Airborne Toxic Event
Vic Theatre · Chicago
$12-$22Thu · Oct 29 · 8:00 PM
Iris Marlowe
Carol's Pub · Chicago
Thu · Oct 29 · 8:00 PM
The Tallest Man On Earth with Gwenifer Raymond
Thalia Hall · Chicago
Thu · Oct 29 · 8:00 PM
Alicia Villarreal - Bendita Locura Tour 2026
Cahn Auditorium · Evanston
Thu · Oct 29 · 8:00 PM
Alice In Chains "Dirt", Pearl Jam "VS"
Reggies Music Joint · Chicago
Thu · Oct 29 · 8:00 PM
Tommy Lefroy
The Hideout
Thu · Oct 29 · 8:00 PM
The Dresden Dolls
The Salt Shed Indoors (Shed) · Chicago
15Thu · Oct 29 · 8:00 PM
The Clearwater Swimmers, Pebbles Inc
Martyrs'
Thu · Oct 29 · 8:00 PM
The Tallest Man on Earth
Thalia Hall · Chicago
Thu · Oct 29 · 8:00 PM
Little Barrie
Old Town School of Folk Music
Thu · Oct 29 · 9:00 PM
Flamingosis w/ Pure Colors
Sleeping Village
$16.99Thu · Oct 29 · 9:00 PM
NIGEL MACK
Buddy Guy's Legends
Thu · Oct 29 · 9:00 PM
Paul Bielatowicz's Nosferatu Live
Reggies Bananna's Shack · Chicago
Friday, October 30
Free↻ Recurring
Fri · Oct 30 · 1:00 PM
Daily Ranger Guided Tours
Pullman National Historical Park
↻ RecurringFri · Oct 30 · 1:30 PM
Brahms Requiem
Symphony Center-IL · Chicago
↻ RecurringFri · Oct 30 · 5:00 PM
Dom Dolla
Navy Pier · Chicago
Fri · Oct 30 · 6:00 PM
Periphery - A Pale White Dot US Tour
Ramova Theatre · Chicago
↻ RecurringFri · Oct 30 · 6:30 PM
Weston Estate
Outset · Chicago
$23↻ RecurringFri · Oct 30 · 7:00 PM
TBD/TBD
Kingston Mines - Chicago Blues Center · Chicago