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

Upcoming Chicago Events

Check out what's happening all around Chicago.

420 Shakespeare
Dec21
Music & Comedy, Theatre & Performing Arts

420 Shakespeare

Chicago’s Own Shakespeare-friendly Comedy Show! What happens when five actors attempt to perform one of Shakespeare’s hit plays while one or more of them get……

Saturday, December 21st
7:00 p.m.8:30 p.m.
Your Budz
3722 N Southport Ave
Stand-Up Comedy: Sophie Buddle
Dec21
Music & Comedy

Stand-Up Comedy: Sophie Buddle

Sophie Buddle is a stand-up, a TV writer, and a podcaster. She has appeared on “The Tonight Show”, “The Late Late Show with James Corden”,…

Saturday, December 21st
7:00 p.m.9:00 p.m.
Zanies Comedy Club
1548 N. Wells St.
Slava Komissarinko Comedy Show
Dec21
Music & Comedy

Slava Komissarinko Comedy Show

Slava Komissarenko is back in the USA! The famous Belarusian stand-up comedian will present a tour featuring a program of new jokes and entirely fresh…

Saturday, December 21st
7:00 p.m.10:00 p.m.
Christian Heritage Academy
315 Waukegan Rd
Baby Wants Candy! The Original Completely Improvised Musical
Dec21
Music & Comedy, Theatre & Performing Arts

Baby Wants Candy! The Original Completely Improvised Musical

“CRITICS’ PICK. TRULY AMAZING!” – New York Times “BEST VISITING IMPROV COMEDY!”– TimeOut NY “HIGHLY RECOMMENDED!” – The Onion “★★★★★” THEY ARE AN ENTERTAINMENT PHENOMENON AND I…

Saturday, December 21st
7:30 p.m.8:30 p.m.
The Second City
230 West North Avenue
Clued In
Dec21
Music & Comedy, Theatre & Performing Arts

Clued In

After getting a single suggestion, the cast of six professional comedians asks the audience to choose a detective. Enjoy as they invent a tale of…

Saturday, December 21st
7:30 p.m.8:30 p.m.
The Second City
1616 N. Wells St., Theater on the Second Floor
The Kensingtons: An Improvised Soap Opera
Dec21
Music & Comedy, Theatre & Performing Arts

The Kensingtons: An Improvised Soap Opera

About the Show Fresh off of their sold out run as The Davenports, these fan faves are back as…The Kensingtons! Showcasing an improvised style family…

Saturday, December 21st
7:30 p.m.8:30 p.m.
The Second City
1616 N. Wells St., Theater on the Second Floor
Little Orphan Boy The Musical!
Dec21
Music & Comedy

Little Orphan Boy The Musical!

The critically acclaimed original musical returns one more time to the Annoyance Theater just in time for the holiday season. Come enjoy some of Chicago’s…

Saturday, December 21st
8:00 p.m.9:30 p.m.
Annoyance Theatre & Bar
851 W. Belmont Ave., 2nd Fl.
The Improvised Shakespeare Company®
Dec21
Music & Comedy, Theatre & Performing Arts

The Improvised Shakespeare Company®

The Improvised Shakespeare Company® proudly presents its critically-acclaimed, long-running hit show Improvised Shakespeare Chicago now in it’s 18th year!  Join us for an evening of off-the-ruff…

Saturday, December 21st
8:00 p.m.9:30 p.m.
iO Theater
1501 N. Kingsbury St.
Hartfelt Family Christmas with Chapel Hart
Dec21
Music & Comedy

Hartfelt Family Christmas with Chapel Hart

Presented by Chop Shop. All Ages Lineup Doors open ― 7:00 PM Chapel Hart

Saturday, December 21st
8:00 p.m.11:30 p.m.
1st Ward at Chop Shop
2033 W. North Ave
Here 4 A Bit *Naughty Improv
Dec21
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, December 21st
9:00 p.m.10:00 p.m.
The Second City
1616 N. Wells St., Theater on the Second Floor
Stand-Up Comedy: Sophie Buddle
Dec21
Music & Comedy

Stand-Up Comedy: Sophie Buddle

Sophie Buddle is a stand-up, a TV writer, and a podcaster. She has appeared on “The Tonight Show”, “The Late Late Show with James Corden”,…

Saturday, December 21st
9:15 p.m.11:15 p.m.
Zanies Comedy Club
1548 N. Wells St.
Best Of Annoyance Sketch
Dec21
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, December 21st
9:30 p.m.10:30 p.m.
The Annoyance Theatre
851 W. Belmont Ave.
LET’S PLAY A GAME: Chicago’s scariest short-form show
Dec21
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, December 21st
10:00 p.m.11:00 p.m.
Annoyance Theatre & Bar
851 W. Belmont Ave., 2nd Fl.
Teatro Zinzanni
Dec22
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…

Sunday, December 22nd
5:00 a.m.9:00 p.m.
Spiegeltent – Cambria Hotel
32 W. Randolph
Woodland Critter Christmas
Dec22
Music & Comedy, Theatre & Performing Arts

Woodland Critter Christmas

The woodland critters have a yearly celebration where they gather to celebrate the winter solstice as friends. This has worked for the majority of the…

Sunday, December 22nd
11:00 a.m.12:00 p.m.
Cornservatory
4210 N Lincoln Ave
Join the Festive Fun at Roosevelt Collection Shops with Carolers and an Elf!
Dec22
Festivals, Fairs & Special Events, Music & Comedy

Join the Festive Fun at Roosevelt Collection Shops with Carolers and an Elf!

Roosevelt Collection Shops will be welcoming an incredible Quartet of carolers for special live performances and plenty of cheer! A playful elf will also be…

Sunday, December 22nd
11:00 a.m.4:00 p.m.
Roosevelt Collection Shops
150 W Roosevelt Rd
Don’t Let the Pigeon Drive the Bus!
Dec22
Music & Comedy, Theatre & Performing Arts

Don’t Let the Pigeon Drive the Bus!

Mo Willems’ Pigeon Sparks Holiday Havoc! CHICAGO – Building on two years of outstanding reviews, sold-out performances, and extraordinary attendance at weekday school matinees, The Young…

Sunday, December 22nd
1:00 p.m.2:00 p.m.
Greenhouse Theater Center
2257 North Lincoln Avenue
Little Orphan Boy The Musical!
Dec22
Music & Comedy

Little Orphan Boy The Musical!

The critically acclaimed original musical returns one more time to the Annoyance Theater just in time for the holiday season. Come enjoy some of Chicago’s…

Sunday, December 22nd
3:00 p.m.4:30 p.m.
Annoyance Theatre & Bar
851 W. Belmont Ave., 2nd Fl.
Straight No Chaser: Top Shelf Tour
Dec22
Music & Comedy

Straight No Chaser: Top Shelf Tour

Chart-topping a cappella group Straight No Chaser will perform live at The Chicago Theatre on Dec. 22, 2024.

Sunday, December 22nd
3:00 p.m.6:00 p.m.
The Chicago Theatre
175 N. State
Trans-Siberian Orchestra -The Lost Christmas Eve
Dec23
Music & Comedy

Trans-Siberian Orchestra -The Lost Christmas Eve

This year’s tour marks the grand return of “THE LOST CHRISTMAS EVE” to the stage for the first time since 2013. Expect an all-new, dazzling…

Monday, December 23rd
3:00 p.m.11:00 p.m.
Allstate Arena
6920 Mannheim Road
Tuesday Good Show
Dec24
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, December 24th
7:00 p.m.8:30 p.m.
The Gallery Cabaret
2020 N Oakley Ave
Hooch & Holler Comedy Show
Dec25
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, December 25th
9:00 p.m.11:00 p.m.
Bordel Cocktail & Cabaret
1721 W Division
Matt Rife: ProbleMATTic World Tour
Dec26
Music & Comedy

Matt Rife: ProbleMATTic World Tour

Comedian Matt Rife will perform live at The Chicago Theatre on Dec. 26-30, 2024.

Thursday, December 26th
8:00 a.m.5:00 p.m.
The Chicago Theatre
175 N. State
Teatro Zinzanni
Dec26
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, December 26th
6:00 p.m.10:00 p.m.
Spiegeltent – Cambria Hotel
32 W. Randolph
bean-night

Explore hotels, flights, deals, and more

Plan your trip

Expedia
Expedia
Expedia
Expedia

CTA Newsletter

Chicago Newsletter

Stay in the know

Sign up

visitors_guide_2024_cover

Visitors Guide

Start planning today

Get the guide