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“I Don’t Want to Play Myself” A Solo Show Written and Performed by Toccara Castleman
Sep10
Theatre & Performing Arts

“I Don’t Want to Play Myself” A Solo Show Written and Performed by Toccara Castleman

Six original characters – seven if you count code switching – explore the journey of an impressionable young woman who tried again and again…and again…

Wednesday, September 10th
7:30 p.m.8:30 p.m.
Red Twist Theatre
1044 W Bryn Mawr Ave
The Annoyance Sketch Show: Late Stage Everything
Sep10
Music & Comedy, Theatre & Performing Arts

The Annoyance Sketch Show: Late Stage Everything

The trains are late, the apps are broken, the bees are dying, and the algorithm knows your deepest fears. So what do we do? We…

Wednesday, September 10th
8:00 p.m.9:30 p.m.
The Annoyance Theatre
851 W. Belmont Ave.
Hooch & Holler Comedy Show
Sep10
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, September 10th
9:00 p.m.11:00 p.m.
Bordel Cocktail & Cabaret
1721 W Division
Dungeons & Dragons: The Twenty-Sided Tavern
Sep11
Theatre & Performing Arts

Dungeons & Dragons: The Twenty-Sided Tavern

Direct from New York City, the tavern returns to Chicago with an all new production! The global phenomenon that is DUNGEONS & DRAGONS is now…

Thursday, September 11th
Broadway Playhouse at Water Tower Place
175 E. Chestnut St .Chicago, IL 60611
Babes With Blades Theatre Company’s “Fighting Words Festival”
Sep11
Theatre & Performing Arts

Babes With Blades Theatre Company’s “Fighting Words Festival”

Babes With Blades Theatre Company’s (BWBTC) 2025 season opens with an extended run of its new works festival, the Fighting Words Festival, September 6 –…

Thursday, September 11th
Bramble Arts Loft
Alice in Wonderland
Sep11
Theatre & Performing Arts

Alice in Wonderland

Follow Alice as she travels down the Rabbit Hole to the most amazing places!  Along her fantastic journey she’ll meet the Mad Hatter, March Hare,…

Thursday, September 11th
10:30 a.m.11:30 p.m.

Redtwist Theatre’s “How To Transcend a Happy Marriage”
Sep11
Theatre & Performing Arts

Redtwist Theatre’s “How To Transcend a Happy Marriage”

Award-winning Redtwist Theatre launches its 21st season, “Defiant Femmes,” with  How to Transcend a Happy Marriage, by Sarah Ruhl, directed by Elizabeth Swanson and movement…

Thursday, September 11th
5:00 p.m.7:00 p.m.
Redtwist Theatre
1044 W. Bryn Mawr Ave
Teatro Zinzanni
Sep11
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, September 11th
6:00 p.m.10:00 p.m.
Spiegeltent – Cambria Hotel
32 W. Randolph
Love Is Improvised
Sep11
Music & Comedy, Theatre & Performing Arts

Love Is Improvised

An improvised take on a hit reality-TV show that dares to ask… is love truly improvised? A cast of 10 improvisers will embark on a…

Thursday, September 11th
7:00 p.m.8:00 p.m.
The Second City
230 W North Ave., 2nd Floor
Olympus Has Fallen (And It Can’t Get Up)
Sep11
Music & Comedy, Theatre & Performing Arts

Olympus Has Fallen (And It Can’t Get Up)

Olympus Has Fallen (And it Can’t Get Up) is a sketchy retelling of your favorite Greek myths. As educational as it is explicit, this hour-long…

Thursday, September 11th
7:30 p.m.8:30 p.m.
The De Matt Theater at The Second City
230 W North Ave
Tom & Eliza
Sep11
Theatre & Performing Arts

Tom & Eliza

Tom & Eliza is a dual meditation on the choices we make (and those we don’t) in a world that spins relentlessly into the future. Performed…

Thursday, September 11th
7:30 p.m.8:40 p.m.
TUTA Theatre
4670 N. Manor Avenue
BULL
Sep11
Music & Comedy, Theatre & Performing Arts

BULL

This original comedic play follows unproven jokesters Scott and Bryce, who find themselves at the pinnacle of the basketball world — the 1996 Chicago Bulls.…

Thursday, September 11th
7:30 p.m.9:00 p.m.
The Annoyance Theatre
851 W. Belmont Ave.
Oil Lamp Theater Presents “Side by Side by Sondheim”
Sep11
Theatre & Performing Arts

Oil Lamp Theater Presents “Side by Side by Sondheim”

 Oil Lamp Theater, which recently opened the Oil Lamp Theater’s SPARK CENTER for the Performing Arts, is proud to present, Side by Side by Sondheim,…

Thursday, September 11th
7:30 p.m.9:30 p.m.
Oil Lamp Theater
1723 Glenview Rd, Glenview, IL, 60025
Mr. Wolf
Sep11
Theatre & Performing Arts

Mr. Wolf

14 years ago, the infant Theresa was stolen from her parents. Now, the precocious 15-year-old has been rescued, and quickly returned to a family that…

Thursday, September 11th
7:30 p.m.9:30 p.m.
A New Brain
Sep11
Theatre & Performing Arts

A New Brain

Gordon Schwinn is a talented yet frustrated composer who is working on a children’s TV show and is having a hard time composing a song…

Thursday, September 11th
7:30 p.m.10:00 p.m.
Hoover-Leppen Theatre
3656 North Halsted Street
Improvsed DCOM
Sep11
Music & Comedy, Theatre & Performing Arts

Improvsed DCOM

Dive into the nostalgia of Disney Channel Original Movies with the cast of Improvised DCOM! This All Star cast is bringing screen to stage every…

Thursday, September 11th
8:00 p.m.9:00 p.m.
Malarkey Comedy Company
1501 N Kingsbury St
Sketch Playlist
Sep11
Music & Comedy, Theatre & Performing Arts

Sketch Playlist

Sketch Playlist is a weekly sketch show on Thursdays at 9:30pm at iO Theater (1501 N Kingsbury Street, Chicago 60642) that will feature brand-new material…

Thursday, September 11th
9:30 p.m.10:30 p.m.
iO Theater
1501 N. Kingsbury St.
Dungeons & Dragons: The Twenty-Sided Tavern
Sep12
Theatre & Performing Arts

Dungeons & Dragons: The Twenty-Sided Tavern

Direct from New York City, the tavern returns to Chicago with an all new production! The global phenomenon that is DUNGEONS & DRAGONS is now…

Friday, September 12th
Broadway Playhouse at Water Tower Place
175 E. Chestnut St .Chicago, IL 60611
Babes With Blades Theatre Company’s “Fighting Words Festival”
Sep12
Theatre & Performing Arts

Babes With Blades Theatre Company’s “Fighting Words Festival”

Babes With Blades Theatre Company’s (BWBTC) 2025 season opens with an extended run of its new works festival, the Fighting Words Festival, September 6 –…

Friday, September 12th
Bramble Arts Loft
Comedy Hour at Annoyance Theatre
Sep12
Sep13
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, September 12th
12:00 a.m.Saturday, September 13th
1:00 a.m.
Annoyance Theatre & Bar
851 W. Belmont Ave., 2nd Fl.
Redtwist Theatre’s “How To Transcend a Happy Marriage”
Sep12
Theatre & Performing Arts

Redtwist Theatre’s “How To Transcend a Happy Marriage”

Award-winning Redtwist Theatre launches its 21st season, “Defiant Femmes,” with  How to Transcend a Happy Marriage, by Sarah Ruhl, directed by Elizabeth Swanson and movement…

Friday, September 12th
5:00 p.m.7:00 p.m.
Redtwist Theatre
1044 W. Bryn Mawr Ave
Teatro Zinzanni
Sep12
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, September 12th
6:00 p.m.10:00 p.m.
Spiegeltent – Cambria Hotel
32 W. Randolph
The Infinite Wrench
Sep12
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, September 12th
7:00 p.m.8:00 p.m.
The Neo-Futurist Theater
5153 N. Ashland Ave.
ComedySportz Chicago
Sep12
Music & Comedy, Theatre & Performing Arts

ComedySportz Chicago

Chicago’s longest running and best interactive improv comedy experience. ComedySportz is comedy played as a sport, not comedy ABOUT sports (whew). Refs, fouls, points, games…

Friday, September 12th
7:00 p.m.8:30 p.m.
Malarkey Comedy
1501 N. Kingsbury St.
bean-night

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