Best Of Annoyance Sketch
Jan9
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 January 9, 2027
9:30 p.m.10:30 p.m.
The Annoyance Theatre
851 W. Belmont Ave.
Maybe Happy Ending
Jan10
Theatre & Performing Arts

Maybe Happy Ending

Winner of 6 Tony Awards, including Best musical, Maybe Happy Ending tells the deeply human story of a chance encounter that sparks connection, adventure, and maybe…

Sunday January 10, 2027
CIBC Theatre
18 W. Monroe St. , Chicago, IL, 60602
The 8th Dwarf
Jan10
Theatre & Performing Arts

The 8th Dwarf

Binkley, an outsider dwarf from the Kingdom of Magical Land, is quiet, timid and scared of the dark — not exactly the best characteristics for…

Sunday January 10, 2027
2:00 p.m.3:00 p.m.
Bughouse Theater
1910 West Irving Park Road
Maybe Happy Ending
Jan11
Theatre & Performing Arts

Maybe Happy Ending

Winner of 6 Tony Awards, including Best musical, Maybe Happy Ending tells the deeply human story of a chance encounter that sparks connection, adventure, and maybe…

Monday January 11, 2027
CIBC Theatre
18 W. Monroe St. , Chicago, IL, 60602
Maybe Happy Ending
Jan12
Theatre & Performing Arts

Maybe Happy Ending

Winner of 6 Tony Awards, including Best musical, Maybe Happy Ending tells the deeply human story of a chance encounter that sparks connection, adventure, and maybe…

Tuesday January 12, 2027
CIBC Theatre
18 W. Monroe St. , Chicago, IL, 60602
Maybe Happy Ending
Jan13
Theatre & Performing Arts

Maybe Happy Ending

Winner of 6 Tony Awards, including Best musical, Maybe Happy Ending tells the deeply human story of a chance encounter that sparks connection, adventure, and maybe…

Wednesday January 13, 2027
CIBC Theatre
18 W. Monroe St. , Chicago, IL, 60602
The Orbit
Jan13
Music & Comedy, Theatre & Performing Arts

The Orbit

The Orbit is Chicago’s only improv show performed in the round. This 45-minute avant-garde experience takes the audience on a full-circle journey, showcasing a bold…

Wednesday January 13, 2027
9:00 p.m.10:30 p.m.
iO Theater
1501 N. Kingsbury St.
Hooch & Holler Comedy Show
Jan13
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 January 13, 2027
9:00 p.m.11:00 p.m.
Bordel Cocktail & Cabaret
1721 W Division
The Fizz Show
Jan13
Music & Comedy, Theatre & Performing Arts

The Fizz Show

Join iO house team Fizz for Chicago’s most carbonated improv show. Wednesdays at 10 p.m., Fizz cracks open a high-octane, full-sugar set of one-night-only scenes,…

Wednesday January 13, 2027
10:00 p.m.11:00 p.m.
iO Theater
1501 N. Kingsbury St.
Maybe Happy Ending
Jan14
Theatre & Performing Arts

Maybe Happy Ending

Winner of 6 Tony Awards, including Best musical, Maybe Happy Ending tells the deeply human story of a chance encounter that sparks connection, adventure, and maybe…

Thursday January 14, 2027
CIBC Theatre
18 W. Monroe St. , Chicago, IL, 60602
Redtwist Theatre’s “‘Night Mother” By Marsha Norman
Jan14
Theatre & Performing Arts

Redtwist Theatre’s “‘Night Mother” By Marsha Norman

Award-winning Redtwist Theatre announces the cast and creative team for ‘night Mother, April 16 – May 24, by Marsha Norman and directed by Executive Artistic…

Thursday January 14, 2027
7:30 p.m.9:30 p.m.
Redtwist Theatre
1044 W. Bryn Mawr Ave
Maybe Happy Ending
Jan15
Theatre & Performing Arts

Maybe Happy Ending

Winner of 6 Tony Awards, including Best musical, Maybe Happy Ending tells the deeply human story of a chance encounter that sparks connection, adventure, and maybe…

Friday January 15, 2027
CIBC Theatre
18 W. Monroe St. , Chicago, IL, 60602
Comedy Hour at Annoyance Theatre
Jan15
Jan16
Theatre & Performing Arts

Comedy Hour at Annoyance Theatre

Each week, Chicago comics bring the freshest, most experimental new material to the Annoyance for the Comedy Hour. The weekly show is an eclectic mix…

Friday January 15, 2027
12:00 a.m.Saturday January 16, 2027
1:00 a.m.
Annoyance Theatre & Bar
851 W. Belmont Ave., 2nd Fl.
The Infinite Wrench
Jan15
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 January 15, 2027
7:00 p.m.8:00 p.m.
The Neo-Futurist Theater
5153 N. Ashland Ave.
Redtwist Theatre’s “‘Night Mother” By Marsha Norman
Jan15
Theatre & Performing Arts

Redtwist Theatre’s “‘Night Mother” By Marsha Norman

Award-winning Redtwist Theatre announces the cast and creative team for ‘night Mother, April 16 – May 24, by Marsha Norman and directed by Executive Artistic…

Friday January 15, 2027
7:30 p.m.9:30 p.m.
Redtwist Theatre
1044 W. Bryn Mawr Ave
3 Stages of Love Part 2: Simple Love/Unperfect Actor
Jan15
Theatre & Performing Arts

3 Stages of Love Part 2: Simple Love/Unperfect Actor

Love always makes for a good story because some part of it is always relatable. And what better way to explore all the various sides…

Friday January 15, 2027
8:00 p.m.9:00 p.m.
Mrs. Murphy & Sons Irish Bistro
3905 N Lincoln Ave
The Lincoln Lodge
Jan15
Theatre & Performing Arts

The Lincoln Lodge

The Lincoln Lodge stand-up comedy and variety showcase plays every Friday and Saturday night in Chicago’s glamorous Logan Square! In addition to The Lodge’s rotating…

Friday January 15, 2027
8:00 p.m.9:30 p.m.
The Lincoln Lodge Theater
2040 N. Milwaukee Ave.
Honk! A Short Form Improv Show
Jan15
Music & Comedy, Theatre & Performing Arts

Honk! A Short Form Improv Show

Honk! is a short form, game-based improv show that asks: what good is comedy if you can’t get a little silly? Comprised of some of…

Friday January 15, 2027
9:00 p.m.10:00 p.m.
Malarkey Comedy Company
1501 N Kingsbury St
Voila: The Improvised Musical
Jan15
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 January 15, 2027
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
Jan15
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 January 15, 2027
10:00 p.m.11:30 p.m.
Annoyance Theatre & Bar
851 W. Belmont Ave., 2nd Fl.
Maybe Happy Ending
Jan16
Theatre & Performing Arts

Maybe Happy Ending

Winner of 6 Tony Awards, including Best musical, Maybe Happy Ending tells the deeply human story of a chance encounter that sparks connection, adventure, and maybe…

Saturday January 16, 2027
CIBC Theatre
18 W. Monroe St. , Chicago, IL, 60602
The 8th Dwarf
Jan16
Theatre & Performing Arts

The 8th Dwarf

Binkley, an outsider dwarf from the Kingdom of Magical Land, is quiet, timid and scared of the dark — not exactly the best characteristics for…

Saturday January 16, 2027
2:00 p.m.3:00 p.m.
Bughouse Theater
1910 West Irving Park Road
The Infinite Wrench
Jan16
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 January 16, 2027
7:00 p.m.8:00 p.m.
The Neo-Futurist Theater
5153 N. Ashland Ave.
FreakShow & Tell
Jan16
Theatre & Performing Arts

FreakShow & Tell

21+ ONLY Brianna Wellen, Chicago Reader: Sideshow entertainer Thom Britton’s solo show is part performance, part demonstration. Britton is a charismatic performer who appears genuinely…

Saturday January 16, 2027
7:00 p.m.8:30 p.m.
Stars & Garters Theater
3914 N. Clark St.