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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 AveMusic & 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.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 DivisionTheatre & 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 11thBroadway Playhouse at Water Tower Place
175 E. Chestnut St .Chicago, IL 60611Theatre & 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 –…
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,…
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 AveMusic & 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. RandolphMusic & 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 FloorMusic & 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 AveTheatre & 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 AvenueMusic & 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.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, 60025Theatre & 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…
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 StreetMusic & 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 StMusic & 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.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 12thBroadway Playhouse at Water Tower Place
175 E. Chestnut St .Chicago, IL 60611Theatre & 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 –…
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.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 AveMusic & 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. RandolphMusic & 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.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.

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