Things to do in Chicago, IL

2,043 events · Music, Comedy, Theater, Food & Drink, Nightlife

Tuesday, October 20

Tue · Oct 20 · 8:00 PM

LowDown Brass Band & Fonville x Fribush

Garcia's Chicago · Chicago

Nightlife

↻ Recurring

Tue · Oct 20 · 8:00 PM

CHICAGO CELLAR BOYS

Green Mill Cocktail Lounge

$18↻ Recurring

Tue · Oct 20 · 8:30 PM

Perfect Mash: A Dating

Cole's Bar

↻ Recurring

Tue · Oct 20 · 9:00 PM

Open Mic Night

Laugh Factory Chicago

↻ Recurring

Tue · Oct 20 · 9:00 PM

Open Mic Night

Vaughan's Pub

↻ Recurring

Tue · Oct 20 · 9:00 PM

Open Mic Night

Cubby Bear · Chicago

Music

↻ Recurring

Tue · Oct 20 · 10:00 PM

Open Mic Night

Subterranean · Chicago

↻ Recurring

Tue · Oct 20

Petra's Recession Seven

Jazz Showcase

Wednesday, October 21

Wed · Oct 21 · 4:00 PM

Russell P. Johnson - "Beyond Civility in Social Conflict" - Marvin Wickware

Seminary Co-op Bookstore

Wed · Oct 21 · 6:00 PM

The Army, The Navy

Chop Shop · Chicago

Nightlife

↻ Recurring

Wed · Oct 21 · 7:00 PM

Geeks Who Drink Trivia

Fado Irish Pub

↻ Recurring

Wed · Oct 21 · 7:00 PM

The Black Keys: PEACHES 'N KREAM

The Salt Shed Indoors (Shed) · Chicago

Wed · Oct 21 · 7:00 PM

Disney Descendants, ZOMBIES & Camp Rock: Worlds Collide Concert Tour

Allstate Arena · Rosemont

Wed · Oct 21 · 7:30 PM

DJ Shadow (18+)

Vic Theatre · Chicago

Wed · Oct 21 · 7:30 PM

Furious Desire

Old Town School of Folk Music

Wed · Oct 21 · 7:30 PM

Beat

Copernicus Center · Chicago

$21-$34

Wed · Oct 21 · 7:30 PM

The Lowest Pair w. The Spine Stealers

SPACE · Evanston

↻ Recurring

Wed · Oct 21 · 7:30 PM

Geeks Who Drink Trivia

Commonwealth Tavern

$30-$221

Wed · Oct 21 · 8:00 PM

JEFFREY FOCAULT @ FITZGERALDS HISTORIC NIGHTCLUB

FITZGERALDS NIGHTCLUB · Berwyn

Wed · Oct 21 · 8:00 PM

Herakleion, Wraith, Morbidity

Reggies Music Joint · Chicago

↻ Recurring

Wed · Oct 21 · 8:00 PM

Trivia Night

Carol's Pub · Chicago

Nightlife

↻ Recurring

Wed · Oct 21 · 8:00 PM

Karaoke Night

Sidekick's Entertainment Lounge

↻ Recurring

Wed · Oct 21 · 8:00 PM

Trivia Night

George Street Pub

Wed · Oct 21 · 8:00 PM

Pain of Truth, 100 Demons, Shattered Realm, Killing Pace

Bottom Lounge · Chicago

↻ Recurring

Wed · Oct 21 · 8:00 PM

Karaoke Night

Rabbit Hole Wrigley

↻ Recurring

Wed · Oct 21 · 8:00 PM

Comedy Open Mic

Cole's Bar

↻ Recurring

Wed · Oct 21 · 8:00 PM

Geeks Who Drink Trivia

Dante's Tavern

↻ Recurring

Wed · Oct 21 · 8:00 PM

Trivia Night

Burwood Tap

Nightlife

↻ Recurring

Wed · Oct 21 · 8:00 PM

ALFONSO PONTICELLI

Green Mill Cocktail Lounge

Wed · Oct 21 · 8:00 PM

2026-27 TAEMIN WORLD TOUR <LiMiNaL> in Chicago

Wintrust Arena · Chicago

$16.99↻ Recurring

Wed · Oct 21 · 9:00 PM

BROTHER JOHN – Host The Jam

Buddy Guy's Legends

↻ Recurring

Wed · Oct 21 · 9:00 PM

Karaoke Wednesdays

Replay Lakeview

Wed · Oct 21 · 9:00 PM

Eleventh Dream Day

The Hideout

↻ Recurring

Wed · Oct 21

Christian Dillingham Quartet

Jazz Showcase

Wed · Oct 21

Fox and Bones with Haley Johnsen

Uncommon Ground

Thursday, October 22

Nightlife

↻ Recurring

Thu · Oct 22 · 5:00 PM

ANDY BROWN

Green Mill Cocktail Lounge

$18↻ Recurring

Thu · Oct 22 · 6:00 PM

TBD/TBD

Kingston Mines - Chicago Blues Center · Chicago

Nightlife

↻ Recurring

Thu · Oct 22 · 7:00 PM

Open Mic Night

Whiskey Girl Tavern

$24-$190

Thu · Oct 22 · 7:00 PM

SCOTT LIGON'S ALL STAR FREAKOUT w/ special guests CHRIS LIGON & The Problems and RAMI & The Reliables

FITZGERALDS NIGHTCLUB · Berwyn

Thu · Oct 22 · 7:30 PM

Jonas Brothers: The Burning Up Tour All Over Again

Allstate Arena · Rosemont

Thu · Oct 22 · 7:30 PM

Maher Zain - USA Tour 2026

Cahn Auditorium · Evanston

Free

Thu · Oct 22 · 7:30 PM

Road to GLDS: The Oracle, Mortlach, Terran Wretch

Cole's Bar

Thu · Oct 22 · 7:30 PM

Buena Vista Orchestra

Vic Theatre · Chicago

Thu · Oct 22 · 7:30 PM

Whitney w/ Greg Mendez

Metro · Chicago

$29

Thu · Oct 22 · 7:30 PM

Every Avenue x In Her Own Words - Perfectly Unfamiliar Tour

Bottom Lounge · Chicago

↻ Recurring

Thu · Oct 22 · 7:30 PM

Jeopardy! Bar League

Guthries Tavern

↻ Recurring

Thu · Oct 22 · 7:30 PM

Sleeping Beauty & Dvor??k Cello Concerto

Symphony Center-IL · Chicago

15

Thu · Oct 22 · 7:30 PM

The Unknown Pleasures - The Music of Joy Division, Matt North - Record Release!

Martyrs'

↻ Recurring

Thu · Oct 22 · 8:00 PM

Trivia Night

Bucktown Pub

$41-$134

Thu · Oct 22 · 8:00 PM

Maggie Rose: Half Moon Tour

SPACE · Evanston

Thu · Oct 22 · 8:00 PM

Houseplant

Garcia's Chicago · Chicago

Thu · Oct 22 · 8:00 PM

Sylvan Esso presented by Jack Daniel's

The Salt Shed Indoors (Shed) · Chicago

Nightlife

↻ Recurring

Thu · Oct 22 · 8:00 PM

ALAN GRESIK'S SWING ORCHESTRA

Green Mill Cocktail Lounge

Thu · Oct 22 · 8:00 PM

Isabel LaRosa

Reggies Rock Club · Chicago

Thu · Oct 22 · 8:30 PM

Clever

Subterranean · Chicago

$16.99↻ Recurring

Thu · Oct 22 · 9:00 PM

TBA

Buddy Guy's Legends

Thu · Oct 22

Rita Bliss and The Sweet Maries

Uncommon Ground

Thu · Oct 22

Lenard Simpson Quartet

Jazz Showcase

Friday, October 23

Nightlife

↻ Recurring

Fri · Oct 23 · 1:00 AM

GREEN MILL JAM SESSION with MARQUIS HILL

Green Mill Cocktail Lounge

Fri · Oct 23 · 4:00 PM

Jonathan González - "Ways to Move: Black Insurgent Grammars" - Anna Martine Whitehead

Seminary Co-op Bookstore

Nightlife

↻ Recurring

Fri · Oct 23 · 5:00 PM

Chris Foreman

Green Mill Cocktail Lounge

Fri · Oct 23 · 6:00 PM

This Wild Life w/ Nate Bergman

Chop Shop · Chicago

Fri · Oct 23 · 7:00 PM

This Wild Life

Chop Shop · Chicago

Fri · Oct 23 · 7:00 PM

Rebecca Black - Exhibitionism on Tour

House of Blues Chicago · Chicago

$23↻ Recurring

Fri · Oct 23 · 7:00 PM

TBD/TBD

Kingston Mines - Chicago Blues Center · Chicago

↻ Recurring

Fri · Oct 23 · 7:30 PM

Tedeschi Trucks Band: Future Soul 2026 Tour

The Chicago Theatre · Chicago

↻ Recurring

Fri · Oct 23 · 8:00 PM

Open Mic Night

O'Donnell's

Fri · Oct 23 · 8:00 PM

William Elliott Whitmore, Meg & the Wheelers

Reggies Rock Club · Chicago

↻ Recurring

Fri · Oct 23 · 8:00 PM

Judy Collins

Old Town School of Folk Music

Fri · Oct 23 · 8:00 PM

La Diosa

George Van Dusen Theatre at North Shore Center · Skokie

Fri · Oct 23 · 8:00 PM

Maggie Rose

Garcia's Chicago · Chicago

$26-$129

Fri · Oct 23 · 8:00 PM

Austin Snell - Colors Tour 2026

Joe's on Weed Street · Chicago

Fri · Oct 23 · 8:00 PM

Gilla Band

Bottom Lounge · Chicago

Fri · Oct 23 · 8:00 PM

Fort Frances

The Hideout

$32

Fri · Oct 23 · 8:00 PM

Gilla Band, Piss

Bottom Lounge · Chicago

$34

Fri · Oct 23 · 8:00 PM

Vincent Neil Emerson

SPACE · Evanston

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

$17

Fri · Oct 23 · 8:30 PM

The Ron Burgundy's

Joe's Live Rosemont · Rosemont

$16

Fri · Oct 23 · 8:30 PM

Glimmer Daarling Bursting

Cole's Bar

Fri · Oct 23 · 9:00 PM

¥ØU$UK ¥UK1MAT$U: Autumn 2026 Tour

Aragon Ballroom · Chicago

$27.30

Fri · 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

$8

Fri · Oct 23 · 9:30 PM

The Messengers

Carol's Pub · Chicago

Fri · Oct 23 · 10:00 PM

Grabbitz

Outset · Chicago

Fri · Oct 23

Buffalo Rose

Uncommon Ground

Saturday, October 24

Nightlife

↻ Recurring

Sat · Oct 24 · 1:00 AM

RIGHTEOUS ROOSTER ORGAN TRIO

Green Mill Cocktail Lounge

Nightlife

↻ Recurring

Sat · Oct 24 · 3:00 PM

PAPER MACHETE

Green Mill Cocktail Lounge

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↻ Recurring

Sat · Oct 24 · 7:00 PM

TBD/TBD

Kingston Mines - Chicago Blues Center · Chicago

Sat · Oct 24 · 7:30 PM

The Smiley Tillmon Band with Billy Flynn

Beverly Arts Center

↻ Recurring

Sat · 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

↻ Recurring

Sat · 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