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

Upcoming Chicago Events

Check out what's happening all around Chicago.

Teatro Zinzanni
Dec20
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…

Friday, December 20th
6:00 p.m.10:00 p.m.
Spiegeltent – Cambria Hotel
32 W. Randolph
Little Orphan Boy The Musical!
Dec20
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…

Friday, December 20th
6:30 p.m.8:00 p.m.
Annoyance Theatre & Bar
851 W. Belmont Ave., 2nd Fl.
The Infinite Wrench
Dec20
Music & Comedy, Theatre & Performing Arts

The Infinite Wrench

Don’t miss the longest running late-night show in Chicago! At The Infinite Wrench you’ll see 30 original plays in 60 minutes written and performed by…

Friday, December 20th
7:00 p.m.8:00 p.m.
The Neo-Futurist Theater
5153 N. Ashland Ave.
420 Shakespeare
Dec20
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……

Friday, December 20th
7:00 p.m.8:30 p.m.
Your Budz
3722 N Southport Ave
Stand-Up Comedy: Sophie Buddle
Dec20
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”,…

Friday, December 20th
7:00 p.m.9:00 p.m.
Zanies Comedy Club
1548 N. Wells St.
Ugly Sweater Party at Schubas w/ Josh Spinner
Dec20
Music & Comedy

Ugly Sweater Party at Schubas w/ Josh Spinner

Get ready for an ugly sweater extravaganza with Josh Spinner! Come on down to Schubas December 20th for an indie pop show you will not…

Friday, December 20th
7:30 p.m.9:00 p.m.
Schubas Tavern
3159 N Southport Ave
Onward and Overwhelmed
Dec20
Music & Comedy, Theatre & Performing Arts

Onward and Overwhelmed

Onward and… Overwhelmed! is a continuation of the show “Onward and Off My Parents’ Health Insurance”.  The show features original sketch comedy, songs, musical improv,…

Friday, December 20th
7:30 p.m.9:00 p.m.
The Second City
230 West North Avenue
Happy Holly-Daze Performance
Dec20
Music & Comedy, Theatre & Performing Arts

Happy Holly-Daze Performance

Year after year, Corn Productions brings the holiday magic in a tradition spanning over a decade. Happy Holly-Daze is a sketch comedy show about all…

Friday, December 20th
7:30 p.m.9:00 p.m.
Cornservatory
4210 N Lincoln Ave
Devil’s Daughter
Dec20
Music & Comedy

Devil’s Daughter

The hottest show in town Devil’s Daughter features a cast of seasoned comedians who have performed together in Chicago and around the country for over a decade.…

Friday, December 20th
8:00 p.m.9:00 p.m.
iO Theater
1501 N. Kingsbury St.
The Improvised Shakespeare Company®
Dec20
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…

Friday, December 20th
8:00 p.m.9:30 p.m.
iO Theater
1501 N. Kingsbury St.
Samara Joy – A Joyful Holiday
Dec20
Music & Comedy

Samara Joy – A Joyful Holiday

Don’t miss Samara Joy’s A Joyful Holiday performance at The Chicago Theatre on December 20.

Friday, December 20th
8:00 p.m.11:00 p.m.
The Chicago Theatre
175 N. State
Improvised Sitcom
Dec20
Music & Comedy, Theatre & Performing Arts

Improvised Sitcom

Cue the laugh track- it’s a very special episode of your favorite long running tv show! The gang gets up to the same ‘ol wacky…

Friday, December 20th
8:30 p.m.9:30 p.m.
The Second City
230 W North Ave., 2nd Floor
The Sleighover
Dec20
Music & Comedy

The Sleighover

In this world-premiere comedy from the comedic minds of Sage Huston and Riley Woollen, holiday cheer meets absolute chaos as three families are trapped in…

Friday, December 20th
8:30 p.m.9:30 p.m.
Annoyance Theatre & Bar
851 W. Belmont Ave., 2nd Fl.
Tvvin + KOLLA + NEIV + ATV – In the round
Dec20
Music & Comedy

Tvvin + KOLLA + NEIV + ATV – In the round

Presented by Chop Shop. This is an 18+ event Lineup Doors open ― 8:00 PM Tvvin KOLLA NEIV

Friday, December 20th
9:00 p.m.11:30 p.m.
1st Ward at Chop Shop
2033 W. North Ave
Stand-Up Comedy: Sophie Buddle
Dec20
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”,…

Friday, December 20th
9:15 p.m.11:15 p.m.
Zanies Comedy Club
1548 N. Wells St.
Voila: The Improvised Musical
Dec20
Music & Comedy, Theatre & Performing Arts

Voila: The Improvised Musical

iO Chicago presents: a fully made-up, off-off-off Broadway style musical every Friday at 10pm in the Fremont Theater. Spend your Friday night with us. See…

Friday, December 20th
10:00 p.m.11:30 p.m.
The iO Theater, 1501 N Kingsbury St, Chicago, IL 60642, USA,
The iO Theater, 1501 N Kingsbury St, Chicago, IL 60642, USA,
Hitch*Cocktails
Dec20
Music & Comedy, Theatre & Performing Arts

Hitch*Cocktails

A Chicago based improv comedy show and drinking game based on the works of Alfred Hitchcock. Based on an audience suggestion, the cast weave together…

Friday, December 20th
10:00 p.m.11:30 p.m.
Annoyance Theatre & Bar
851 W. Belmont Ave., 2nd Fl.
Don’t Let the Pigeon Drive the Bus!
Dec21
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…

Saturday, December 21st
10:00 a.m.11:00 a.m.
Greenhouse Theater Center
2257 North Lincoln Avenue
Woodland Critter Christmas
Dec21
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…

Saturday, December 21st
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!
Dec21
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…

Saturday, December 21st
11:00 a.m.4:00 p.m.
Roosevelt Collection Shops
150 W Roosevelt Rd
Teatro Zinzanni
Dec21
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…

Saturday, December 21st
12:00 p.m.3:00 p.m.
Spiegeltent – Cambria Hotel
32 W. Randolph
Don’t Let the Pigeon Drive the Bus!
Dec21
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…

Saturday, December 21st
1:00 p.m.2:00 p.m.
Greenhouse Theater Center
2257 North Lincoln Avenue
Teatro Zinzanni
Dec21
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…

Saturday, December 21st
6:00 p.m.10:00 p.m.
Spiegeltent – Cambria Hotel
32 W. Randolph
The Infinite Wrench
Dec21
Music & Comedy, Theatre & Performing Arts

The Infinite Wrench

Don’t miss the longest running late-night show in Chicago! At The Infinite Wrench you’ll see 30 original plays in 60 minutes written and performed by…

Saturday, December 21st
7:00 p.m.8:00 p.m.
The Neo-Futurist Theater
5153 N. Ashland Ave.
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