Comedy Hour at Annoyance Theatre
Oct16
Oct17
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, October 16th
12:00 a.m.Saturday, October 17th
1:00 a.m.
Annoyance Theatre & Bar
851 W. Belmont Ave., 2nd Fl.
The Infinite Wrench
Oct16
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, October 16th
7:00 p.m.8:00 p.m.
The Neo-Futurist Theater
5153 N. Ashland Ave.
Jekyll& Hyde
Oct16
Theatre & Performing Arts

Jekyll& Hyde

Kokandy Productions’ critically acclaimed revival of the 10-time 2025 Jeff Award–nominated musical JEKYLL & HYDE will make its Broadway In Chicago debut at the Broadway Playhouse at…

Friday, October 16th
7:00 p.m.10:00 p.m.
Broadway Playhouse at Water Tower Place
175 E. Chestnut St .Chicago, IL 60611
Redtwist Theatre’s “‘Night Mother” By Marsha Norman
Oct16
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, October 16th
7:30 p.m.9:30 p.m.
Redtwist Theatre
1044 W. Bryn Mawr Ave
OFF BOOK: The Improvised Musical Podcast
Oct16
Theatre & Performing Arts

OFF BOOK: The Improvised Musical Podcast

Off Book: The Improvised Musical Podcast is performing live in Chicago on Friday, October 16, 2026. Hosted by Zach Reino and Jessica McKenna, this live…

Friday, October 16th
7:30 p.m.9:30 p.m.
The Vic Theatre
3145 N. Sheffield
3 Stages of Love Part 2: Simple Love/Unperfect Actor
Oct16
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, October 16th
8:00 p.m.9:00 p.m.
Mrs. Murphy & Sons Irish Bistro
3905 N Lincoln Ave
The Lincoln Lodge
Oct16
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, October 16th
8:00 p.m.9:30 p.m.
The Lincoln Lodge Theater
2040 N. Milwaukee Ave.
Honk! A Short Form Improv Show
Oct16
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, October 16th
9:00 p.m.10:00 p.m.
Malarkey Comedy Company
1501 N Kingsbury St
Voila: The Improvised Musical
Oct16
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, October 16th
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
Oct16
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, October 16th
10:00 p.m.11:30 p.m.
Annoyance Theatre & Bar
851 W. Belmont Ave., 2nd Fl.
The 8th Dwarf
Oct17
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, October 17th
2:00 p.m.3:00 p.m.
Bughouse Theater
1910 West Irving Park Road
The Infinite Wrench
Oct17
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, October 17th
7:00 p.m.8:00 p.m.
The Neo-Futurist Theater
5153 N. Ashland Ave.
FreakShow & Tell
Oct17
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, October 17th
7:00 p.m.8:30 p.m.
Stars & Garters Theater
3914 N. Clark St.
The Séance
Oct17
Theatre & Performing Arts

The Séance

The Séance is an original stage show that recreates an authentic Victorian-era séance. We investigate the history, tell the stories of the participants, and demonstrate…

Saturday, October 17th
7:00 p.m.8:30 p.m.
Stars & Garters
3914 N Clark St
Jekyll& Hyde
Oct17
Theatre & Performing Arts

Jekyll& Hyde

Kokandy Productions’ critically acclaimed revival of the 10-time 2025 Jeff Award–nominated musical JEKYLL & HYDE will make its Broadway In Chicago debut at the Broadway Playhouse at…

Saturday, October 17th
7:00 p.m.10:00 p.m.
Broadway Playhouse at Water Tower Place
175 E. Chestnut St .Chicago, IL 60611
Baby Wants Candy! The Original Completely Improvised Musical
Oct17
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, October 17th
7:30 p.m.8:30 p.m.
The Second City
1616 N. Wells St.
Clued In
Oct17
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, October 17th
7:30 p.m.8:30 p.m.
The Second City
1616 N. Wells St., Theater on the Second Floor
Redtwist Theatre’s “‘Night Mother” By Marsha Norman
Oct17
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…

Saturday, October 17th
7:30 p.m.9:30 p.m.
Redtwist Theatre
1044 W. Bryn Mawr Ave
The Lincoln Lodge
Oct17
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…

Saturday, October 17th
8:00 p.m.9:30 p.m.
The Lincoln Lodge Theater
2040 N. Milwaukee Ave.
Best Of Annoyance Sketch
Oct17
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 17th
9:30 p.m.10:30 p.m.
The Annoyance Theatre
851 W. Belmont Ave.
The 8th Dwarf
Oct18
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, October 18th
2:00 p.m.3:00 p.m.
Bughouse Theater
1910 West Irving Park Road
Don Giovanni
Oct18
Music & Comedy, Theatre & Performing Arts

Don Giovanni

The path to damnation never sounded so sweet The 2026/27 Season kicks off with a thrilling fable of deceit and retribution. Sharp humor, high drama,…

Sunday, October 18th
2:00 p.m.5:30 p.m.
Lyric Opera of Chicago
20 N. Wacker Dr. , Chicago, IL, 60606
Jekyll& Hyde
Oct18
Theatre & Performing Arts

Jekyll& Hyde

Kokandy Productions’ critically acclaimed revival of the 10-time 2025 Jeff Award–nominated musical JEKYLL & HYDE will make its Broadway In Chicago debut at the Broadway Playhouse at…

Sunday, October 18th
7:00 p.m.10:00 p.m.
Broadway Playhouse at Water Tower Place
175 E. Chestnut St .Chicago, IL 60611
Magic Mondays
Oct19
Music & Comedy, Theatre & Performing Arts

Magic Mondays

Experience an unforgettable night of wonder at Magic Mondays!! Starring award-winning magician John Sturk, this monthly showcase features Chicago’s top conjurors performing mind-blowing illusions and…

Monday, October 19th
7:00 p.m.8:30 p.m.
iO Theater
1501 N. Kingsbury St.