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

Upcoming Chicago Events

Check out what's happening all around Chicago.

Here 4 A Bit *Naughty Improv
Oct25
Music & Comedy, Theatre & Performing Arts

Here 4 A Bit *Naughty Improv

Join us again for a whose line styled night of explosive laughter that will titillate your “funny” bone. Fast paced short form improv, hilarious songs,…

Saturday, October 25th
9:00 p.m.10:00 p.m.
The Second City
1616 N. Wells St., Theater on the Second Floor
Chicago’s Best Stand Up
Oct25
Music & Comedy

Chicago’s Best Stand Up

Welcome to Chicago’s Best Stand Up at The Laugh Factory – Chicago! Join us on October 25, 2025, at 9:15 PM for a night of…

Saturday, October 25th
9:15 p.m.11:15 p.m.
The Laugh Factory
175 N Broadway
Best Of Annoyance Sketch
Oct25
Music & Comedy, Theatre & Performing Arts

Best Of Annoyance Sketch

Enjoy the best sketch comedy Chicago has to offer! The Annoyance Theatre has been at the crux of the comedy scene in Chicago for over…

Saturday, October 25th
9:30 p.m.10:30 p.m.
The Annoyance Theatre
851 W. Belmont Ave.
Joke Sistas Chicago
Oct25
Music & Comedy

Joke Sistas Chicago

Joke Sistas is the unofficial sorority of the Black Women in Comedy Laff Fest with NYC as home and now DC/DMV & Chicago as Sista…

Saturday, October 25th
9:30 p.m.11:00 p.m.
The Lincoln Lodge Theater
2040 N. Milwaukee Ave.
LET’S PLAY A GAME: Chicago’s scariest short-form show
Oct25
Music & Comedy, Theatre & Performing Arts

LET’S PLAY A GAME: Chicago’s scariest short-form show

Who’s Line is it Anyways meets Fear Factor in LETS PLAY A GAME, a new short form show that’s a unique blend of comedy, chaos,…

Saturday, October 25th
10:00 p.m.11:00 p.m.
Annoyance Theatre & Bar
851 W. Belmont Ave., 2nd Fl.
Calvin Evans
Oct25
Oct26
Music & Comedy

Calvin Evans

Welcome to Zanies Comedy Club in Chicago, Illinois! Get ready to laugh the night away with the incredibly talented Calvin Evans on October 25, 2025,…

Saturday, October 25th
11:15 p.m.Sunday, October 26th
1:15 a.m.
Zanies Comedy Club
5437 Park Place
The Nasty Show: Tiny Thickemz
Oct25
Oct26
Music & Comedy

The Nasty Show: Tiny Thickemz

Welcome to The Nasty Show: Tiny Thickemz at The Laugh Factory – Chicago, featuring the incredibly talented Tiny Thickemz! Get ready for a night of…

Saturday, October 25th
11:30 p.m.Sunday, October 26th
1:30 a.m.
The Laugh Factory
175 N Broadway
The Sound of Music
Oct26
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…

Sunday, October 26th
James M. Nederlander Theatre
24 W. Randolph St.
Leo Lionni’s Frederick
Oct26
Theatre & Performing Arts

Leo Lionni’s Frederick

While other mice are gathering food for the winter, Frederick daydreams the summer away. But when fall weather comes, it is Frederick who has stored…

Sunday, October 26th
9:30 a.m.10:30 a.m.
Chicago Children’s Theatre
100 S Racine Ave
Woodland Creatures’ Halloween
Oct26
Theatre & Performing Arts

Woodland Creatures’ Halloween

Theater for Young Audiences @ Corn presents our newest show, perfect for young ones and the entire family! In Woodland Creatures’ Halloween, our friends are…

Sunday, October 26th
11:00 a.m.12:00 p.m.
Cornservatory
4210 N Lincoln Ave
A Family Magic Show
Oct26
Theatre & Performing Arts

A Family Magic Show

Looking for a family outing that’s out of this world? Our Family Cosmic Magic Show isn’t your typical “pull a rabbit out of a hat”…

Sunday, October 26th
1:00 p.m.2:00 p.m.
cosmic underground theater
3433 W Fullerton Ave
ABLE presents Frankenstein
Oct26
Theatre & Performing Arts

ABLE presents Frankenstein

Following a sold-out run at Chicago Shakespeare Theater, A.B.L.E.—Artists Breaking Limits & Expectations is thrilled to bring our critically acclaimed adaptation of Frankenstein back to…

Sunday, October 26th
1:00 p.m.2:30 p.m.
Theater Wit
Hundreds and Hundreds of Stars
Oct26
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…

Sunday, October 26th
2:00 p.m.3:30 p.m.
Lookingglass Theatre Company
821 N. Michigan Ave.
wyrd
Oct26
Theatre & Performing Arts

wyrd

Three ageless, timeless, deathless sisters in a basement in Bushwick One of them falls in love Another falls in hate The third tries to keep…

Sunday, October 26th
2:00 p.m.3:30 p.m.
Greenhouse Theater Center
2257 North Lincoln Avenue
The Neighborhood of the Loners
Oct26
Theatre & Performing Arts

The Neighborhood of the Loners

The Neighborhood of the Loners is a place where residents live without social interactions or contact with the world around them. This sanctuary of solitude…

Sunday, October 26th
2:00 p.m.4:00 p.m.
Mundelein Center For The Fine & Performing Arts
1020 W Sheridan Rd
Ugly Lies The Bone
Oct26
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…

Sunday, October 26th
3:00 p.m.4:30 p.m.
Theater Wit
Strange Cargo: The Doom of the Demeter
Oct26
Theatre & Performing Arts

Strange Cargo: The Doom of the Demeter

Based on Chapter Seven of Bram Stoker’s DRACULA, this gothic horror high seas adventure tells the shocking events aboard the cargo ship transporting Count Dracula’s belongings from…

Sunday, October 26th
3:00 p.m.5:30 p.m.
City Lit Theater
1020 W. Bryn Mawr, Chicago, IL, 60660
In Good Company – Chicago and Theatre Y
Oct26
Theatre & Performing Arts

In Good Company – Chicago and Theatre Y

What if democracy isn’t just a system—but a shared movement forward? Beginning Saturday, October 18th and running Saturdays and Sundays through November 9th, 2025, Theatre…

Sunday, October 26th
3:00 p.m.7:00 p.m.
3611 W Cermak Road
3611 W Cermak Road
In Good Company
Oct26
Theatre & Performing Arts

In Good Company

What if democracy isn’t just a system—but a shared movement forward? Beginning Saturday, October 18th and running Saturdays and Sundays through November 9th, 2025, Chicagoans are invited…

Sunday, October 26th
3:00 p.m.7:00 p.m.
Theatre Y
3611 W Cermak Rd
Lights, Camera, Create!
Oct26
Festivals, Fairs & Special Events, Theatre & Performing Arts

Lights, Camera, Create!

The stage is set at Chicago Actor’s Studio for Spooky Fun! Theatrical Skits & Pumpkin Decorating  – Be entertained while you bring your creative vision…

Sunday, October 26th
3:30 p.m.7:30 p.m.
Chicago Actor’s Studio
2040 N. Elston
Clued In: Where There’s a Will, There’s a Way
Oct26
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…

Sunday, October 26th
4:00 p.m.5:30 p.m.
The Second City
1616 N. Wells St.
Almost 24 Hours, Tricks & Treats: A Sketch Show
Oct26
Music & Comedy, Theatre & Performing Arts

Almost 24 Hours, Tricks & Treats: A Sketch Show

It’s almost Halloween and it is almost the end of our fundraising campaign! To give us a little boost, we have a brand new Almost…

Sunday, October 26th
5:00 p.m.6:30 p.m.
Cornservatory
4210 N Lincoln Ave
Chicago Climate Bash!
Oct26
Music & Comedy

Chicago Climate Bash!

Comedy! Music! Activism! More! Join us for a night of laughs and hot takes on our planetary crisis. It’s the hottest comedy show on the…

Sunday, October 26th
5:00 p.m.7:00 p.m.
The Lincoln Lodge
2040 North Milwaukee Avenue
Chicago’s Best Comedy Show
Oct26
Music & Comedy

Chicago’s Best Comedy Show

2-Item Minimum Per Guest Valid ID Required for Entry First Come, First Served Seating No Outside Food or Beverage Get ready for a night of…

Sunday, October 26th
7:00 p.m.9:00 p.m.
The Comedy Bar
500 N. LaSalle St.
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