Skip to consent to cookiesSkip navigation
Mandatory Photo Credit: Abel Arciniega :: @tequilagraphics

Upcoming Chicago Events

Check out what's happening all around Chicago.

Alice in Wonderland
Oct21
Theatre & Performing Arts

Alice in Wonderland

Follow Alice as she travels down the Rabbit Hole to the most amazing places!  Along her fantastic journey she’ll meet the Mad Hatter, March Hare,…

Tuesday, October 21st
10:30 a.m.11:30 p.m.

Tuesday Good Show
Oct21
Music & Comedy

Tuesday Good Show

Showcasing some of the best performers in the city, Tuesday Good Show is a free weekly variety show hosted by Nick Bonsignore and Keller Paulson.…

Tuesday, October 21st
7:00 p.m.8:30 p.m.
The Gallery Cabaret
2020 N Oakley Ave
Tate McRae – Miss Possessive Tour
Oct21
Music & Comedy

Tate McRae – Miss Possessive Tour

Tate McRae is bringing her Miss Possessive Tour, with Zara Larsson, to United Center on October 21, 2025! Singer, songwriter, and dancer triple threat Tate…

Tuesday, October 21st
7:00 p.m.11:00 p.m.
United Center
1901 W Madison St.
Tomato Throw Show at The Comedy Bar
Oct21
Music & Comedy

Tomato Throw Show at The Comedy Bar

2-Item Minimum Per Guest First Come, First Served Seating No Outside Food or Beverage Valid ID Required at Entry Join us for the most fun…

Tuesday, October 21st
7:30 p.m.9:00 p.m.
The Comedy Bar
500 N. LaSalle St.
Mr. Wolf
Oct21
Theatre & Performing Arts

Mr. Wolf

12 years ago, Theresa was stolen from her parents. Now a precocious 15-year-old, she has been rescued and returned to a family that had nearly…

Tuesday, October 21st
7:30 p.m.9:30 p.m.
Dermot Kennedy: 2025 North American Fall Tour
Oct21
Music & Comedy

Dermot Kennedy: 2025 North American Fall Tour

Dermot Kennedy will perform live at House Of Blues on Oct. 21, 2025.

Tuesday, October 21st
8:00 p.m.11:00 p.m.
The Sound of Music
Oct22
Theatre & Performing Arts

The Sound of Music

For 65 years, THE SOUND OF MUSIC has been one of our “favorite things.” With its timeless story and irresistibly charming score, this Rodgers & Hammerstein classic…

Wednesday, October 22nd
James M. Nederlander Theatre
24 W. Randolph St.
Alice in Wonderland
Oct22
Theatre & Performing Arts

Alice in Wonderland

Follow Alice as she travels down the Rabbit Hole to the most amazing places!  Along her fantastic journey she’ll meet the Mad Hatter, March Hare,…

Wednesday, October 22nd
10:30 a.m.11:30 p.m.

Crowd Work Wednesday at The Comedy Bar
Oct22
Music & Comedy

Crowd Work Wednesday at The Comedy Bar

2-Item Minimum Per Guest First Come, First Served Seating No Outside Food or Beverage Valid ID Required at Entry Crowd Work Wednesday is a weekly…

Wednesday, October 22nd
7:30 p.m.9:00 p.m.
The Comedy Bar
500 N. LaSalle St.
Mr. Wolf
Oct22
Theatre & Performing Arts

Mr. Wolf

12 years ago, Theresa was stolen from her parents. Now a precocious 15-year-old, she has been rescued and returned to a family that had nearly…

Wednesday, October 22nd
7:30 p.m.9:30 p.m.
Goody! An Immersive Folk-Horror Sketch Comedy Show
Oct22
Music & Comedy, Theatre & Performing Arts

Goody! An Immersive Folk-Horror Sketch Comedy Show

Hear ye, hear ye! Goody! is back by popular demand! This October, join the town elders of Brian’s Hollow in the meetinghouse for an immersive…

Wednesday, October 22nd
8:00 p.m.9:00 p.m.
The Annoyance Theatre
851 W. Belmont Ave.
The Book of Will
Oct22
Theatre & Performing Arts

The Book of Will

Without William Shakespeare, we wouldn’t have literary masterpieces like ROMEO AND JULIET. But without Henry Condell and John Heminges, we would have lost half of…

Wednesday, October 22nd
8:00 p.m.10:00 p.m.
The Den Theatre
1331 North Milwaukee Avenue
Hooch & Holler Comedy Show
Oct22
Music & Comedy, Theatre & Performing Arts

Hooch & Holler Comedy Show

Every Wednesday The Best Speakeasy In Chicago Hosts The Hottest Comedians The City Has To Offer! Indulge In Our Amazing Craft Cocktails And Enjoy An…

Wednesday, October 22nd
9:00 p.m.11:00 p.m.
Bordel Cocktail & Cabaret
1721 W Division
The Sound of Music
Oct23
Theatre & Performing Arts

The Sound of Music

For 65 years, THE SOUND OF MUSIC has been one of our “favorite things.” With its timeless story and irresistibly charming score, this Rodgers & Hammerstein classic…

Thursday, October 23rd
James M. Nederlander Theatre
24 W. Randolph St.
Alice in Wonderland
Oct23
Theatre & Performing Arts

Alice in Wonderland

Follow Alice as she travels down the Rabbit Hole to the most amazing places!  Along her fantastic journey she’ll meet the Mad Hatter, March Hare,…

Thursday, October 23rd
10:30 a.m.11:30 p.m.

Hundreds and Hundreds of Stars
Oct23
Theatre & Performing Arts

Hundreds and Hundreds of Stars

Motherhood, marijuana, and the multiverse collide in this Chicago-set story of family, immigration, and American identity. Like millions of Americans, Clara is doing her best…

Thursday, October 23rd
7:00 p.m.8:30 p.m.
Lookingglass Theatre Company
821 N. Michigan Ave.
Clued In: Where There’s a Will, There’s a Way
Oct23
Music & Comedy, Theatre & Performing Arts

Clued In: Where There’s a Will, There’s a Way

YOU’RE INVITED…to bear witness to a fully improvised murder mystery. Six improvisers find themselves trapped on stage with a murderer, and nobody knows who the…

Thursday, October 23rd
7:00 p.m.8:30 p.m.
The Second City
1616 N. Wells St.
Nate Bargatze – Big Dumb Eyes World Tour
Oct23
Music & Comedy

Nate Bargatze – Big Dumb Eyes World Tour

Nate Bargatze is bringing his Big Dumb Eyes World Tour to United Center on October 23 & 24, 2025!

Thursday, October 23rd
7:00 p.m.9:00 p.m.
United Center
1901 W Madison St.
Stars & Garters Presents “Stars & Garters After Dark”
Oct23
Theatre & Performing Arts

Stars & Garters Presents “Stars & Garters After Dark”

Chicago’s brand new Stars & Garters, 3914 N Clark St, presents Stars & Garters After Dark, every Thursday at 7 p.m. in the Rouge Room.…

Thursday, October 23rd
7:00 p.m.9:30 p.m.
Stars and Garters Club
3914 N Clark St
Teatro Zinzanni
Oct23
Music & Comedy, Theatre & Performing Arts

Teatro Zinzanni

Tickets are on sale Now at https://zinzanni.com/chicago/ for Love, Chaos, & Dinner ! Teatro Zinzanni returns to the vibrant Chicago Loop inside the velvet walls…

Thursday, October 23rd
7:00 p.m.10:00 p.m.
Spiegeltent – Cambria Hotel
32 W. Randolph
Duluth: An Improvised Midwest Murder
Oct23
Music & Comedy, Theatre & Performing Arts

Duluth: An Improvised Midwest Murder

Based on the hit FX show “Fargo”, Duluth takes audiences into the world of true crime in the Midwest. Each week, the cast of Duluth will improvise a…

Thursday, October 23rd
7:30 p.m.8:30 p.m.
iO Theater
1501 N. Kingsbury St.
Thursdays: OhJay Lamont at The comedy Bar
Oct23
Music & Comedy

Thursdays: OhJay Lamont at The comedy Bar

2-Item Minimum Per Guest First Come, First Served Seating No Outside Food or Beverage Valid ID Required at Entry OhJay Lamont, born and raised on…

Thursday, October 23rd
7:30 p.m.9:00 p.m.
The Comedy Bar
500 N. LaSalle St.
Ugly Lies The Bone
Oct23
Theatre & Performing Arts

Ugly Lies The Bone

Jonathan Berry is BACK and he’s directing Shattered Globe’s powerful season opener UGLY LIES THE BONE. After three tours in Afghanistan, Jess returns home to…

Thursday, October 23rd
7:30 p.m.9:00 p.m.
Theater Wit
Mr. Wolf
Oct23
Theatre & Performing Arts

Mr. Wolf

12 years ago, Theresa was stolen from her parents. Now a precocious 15-year-old, she has been rescued and returned to a family that had nearly…

Thursday, October 23rd
7:30 p.m.9:30 p.m.
bean-night

Explore Chicago hotels, flights, deals, and more

Plan your trip

Expedia
Expedia
Expedia
Expedia

CTA Newsletter

Chicago Newsletter

Stay in the know

Sign up

OVG25_enews_cover_for website footer

Chicago Visitors Guide

Start planning today

Get the guide