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Upcoming Chicago Events

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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
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
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
7:00 p.m.11:30 p.m.
The Chicago Theatre
175 N. State
Christmas Karen 3
Dec26
Music & Comedy

Christmas Karen 3

Christmas Karen 3 is a new original multi-media play written by Elizabeth Fulton and is the trilogy no one asked for but everyone needed. Picking…

Thursday, December 26th
9:30 p.m.10:30 p.m.
Annoyance Theatre & Bar
851 W. Belmont Ave., 2nd Fl.
Teatro Zinzanni
Dec27
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 27th
6:00 p.m.10:00 p.m.
Spiegeltent – Cambria Hotel
32 W. Randolph
Little Orphan Boy The Musical!
Dec27
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 27th
6:30 p.m.8:00 p.m.
Annoyance Theatre & Bar
851 W. Belmont Ave., 2nd Fl.
The Infinite Wrench
Dec27
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 27th
7:00 p.m.8:00 p.m.
The Neo-Futurist Theater
5153 N. Ashland Ave.
Stand-Up Comedy: Michael Longfellow
Dec27
Music & Comedy

Stand-Up Comedy: Michael Longfellow

Michael Longfellow is a cast member on Saturday Night Live. He joined as one of the new featured players of the show’s current 48th season.…

Friday, December 27th
7:00 p.m.8:45 p.m.
Zanies Comedy Club
1548 N. Wells St.
Matt Rife: ProbleMATTic World Tour
Dec27
Music & Comedy

Matt Rife: ProbleMATTic World Tour

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

Friday, December 27th
7:00 p.m.11:30 p.m.
The Chicago Theatre
175 N. State
Devil’s Daughter
Dec27
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 27th
8:00 p.m.9:00 p.m.
iO Theater
1501 N. Kingsbury St.
Improvised Sitcom
Dec27
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 27th
8:30 p.m.9:30 p.m.
The Second City
230 W North Ave., 2nd Floor
The Sleighover
Dec27
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 27th
8:30 p.m.9:30 p.m.
Annoyance Theatre & Bar
851 W. Belmont Ave., 2nd Fl.
Stand-Up Comedy: Michael Longfellow
Dec27
Music & Comedy

Stand-Up Comedy: Michael Longfellow

Michael Longfellow is a cast member on Saturday Night Live. He joined as one of the new featured players of the show’s current 48th season.…

Friday, December 27th
9:15 p.m.11:00 p.m.
Zanies Comedy Club
1548 N. Wells St.
Voila: The Improvised Musical
Dec27
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 27th
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,
bean-night

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