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Dutchman
Oct16
Theatre & Performing Arts

Dutchman

A searing examination of race, power, and social expectation, this explosive classic of American theatre surges with racial tension and sexual politics. Keith Surney revives…

Thursday, October 16th
8:00 p.m.9:15 p.m.
Trap Door Theatre
1655 W. Cortland St.
The Wolfman of Wrigleyville – Horror Comedy Play
Oct16
Music & Comedy, Theatre & Performing Arts

The Wolfman of Wrigleyville – Horror Comedy Play

This 70-minute comedy set in 1927 follows an investigative journalist and her ex-girlfriend, a private eye, as they look into a series of murders that…

Thursday, October 16th
8:00 p.m.9:30 p.m.
Annoyance Theatre & Bar
851 W. Belmont Ave., 2nd Fl.
wyrd
Oct16
Theatre & Performing Arts

wyrd

Three ageless, timeless, deathless sisters in a basement in Bushwick One of them falls in love Another falls in hate The third tries to keep…

Thursday, October 16th
8:00 p.m.9:30 p.m.
Greenhouse Theater Center
2257 North Lincoln Avenue
The Book of Will
Oct16
Theatre & Performing Arts

The Book of Will

Without William Shakespeare, we wouldn’t have literary masterpieces like ROMEO AND JULIET. But without Henry Condell and John Heminges, we would have lost half of…

Thursday, October 16th
8:00 p.m.10:00 p.m.
The Den Theatre
1331 North Milwaukee Avenue
Elvis Costello and The Imposters
Oct16
Music & Comedy

Elvis Costello and The Imposters

Elvis Costello and The Imposters with Charlie Sexton, will bring “Radio Soul!: The Early Songs of Elvis Costello” tour to The Chicago Theatre on October…

Thursday, October 16th
8:00 p.m.11:00 p.m.
The Chicago Theatre
175 N. State
Chicago Comedy Hour
Oct16
Music & Comedy, Theatre & Performing Arts

Chicago Comedy Hour

The Chicago Comedy hour is a comedy variety show featuring sketch, improv and stand up from some of the best up and coming comedians in…

Thursday, October 16th
8:30 p.m.9:30 p.m.
Donny’s Skybox
230 W North Ave
Composer Showcase Featuring Lakeshore Rush
Oct16
Festivals, Fairs & Special Events, Music & Comedy

Composer Showcase Featuring Lakeshore Rush

Ear Taxi Festival presents a Composer Showcase. Lakeshore Rush premieres new works by Illinois composers. Natasha Bogojevic writes a meditation on the effects of gun…

Thursday, October 16th
8:30 p.m.10:30 p.m.
Constellation
3111 N Western Ave
Sketch Playlist
Oct16
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, October 16th
9:30 p.m.10:30 p.m.
iO Theater
1501 N. Kingsbury St.
The Lion King
Oct17
Theatre & Performing Arts

The Lion King

Giraffes strut. Birds swoop. Gazelles leap. The entire Serengeti comes to life as never before. And as the music soars, Pride Rock slowly emerges from…

Friday, October 17th
Cadillac Palace Theatre
151 W. Randolph St. , Chicago, IL, 60601
The Book of Mormon
Oct17
Theatre & Performing Arts

The Book of Mormon

The New York Times calls it “the best musical of this century.” The Washington Post says, “It is the kind of evening that restores your faith in musicals.”…

Friday, October 17th
CIBC Theatre
18 W. Monroe St. , Chicago, IL, 60602
Comedy Hour at Annoyance Theatre
Oct17
Oct18
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 17th
12:00 a.m.Saturday, October 18th
1:00 a.m.
Annoyance Theatre & Bar
851 W. Belmont Ave., 2nd Fl.
A Night with Chicago Football Conference Champions: Brian Urlacher, Rex Grossman & Alex Brown
Oct17
Music & Comedy, Tours & Attractions

A Night with Chicago Football Conference Champions: Brian Urlacher, Rex Grossman & Alex Brown

Relive the 2006 season with legends aboard City Cruises Live! Celebrate one of the most unforgettable chapters in Chicago football history with the players who…

Friday, October 17th
6:00 p.m.10:00 p.m.
City Cruises Chicago – Navy Pier
600 E Grand Ave
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…

Friday, October 17th
7:00 p.m.8:00 p.m.
The Neo-Futurist Theater
5153 N. Ashland Ave.
ComedySportz Chicago
Oct17
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, October 17th
7:00 p.m.8:30 p.m.
Malarkey Comedy
1501 N. Kingsbury St.
ComedySportz Chicago
Oct17
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, October 17th
7:00 p.m.8:30 p.m.
Malarkey Comedy Company
1501 N Kingsbury St
Matty Chymbor at The Comedy Bar
Oct17
Music & Comedy

Matty Chymbor at The Comedy Bar

2-Item Minimum Per Guest First Come, First Served Seating No Outside Food or Beverage Valid ID Required at Entry Matty Chymbor is an LA based…

Friday, October 17th
7:00 p.m.8:30 p.m.
The Comedy Bar
500 N. LaSalle St.
Teatro Zinzanni
Oct17
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, October 17th
7:00 p.m.10:00 p.m.
Spiegeltent – Cambria Hotel
32 W. Randolph
Lainey Wilson: Whirlwind World Tour
Oct17
Music & Comedy

Lainey Wilson: Whirlwind World Tour

With special guests Muscadine Bloodline & Maddox Batson

Friday, October 17th
7:00 p.m.10:00 p.m.
Allstate Arena
6920 Mannheim Road
Morgan Jay – The Goofy Guy Tour
Oct17
Music & Comedy

Morgan Jay – The Goofy Guy Tour

Comedian Morgan Jay will perform live at The Chicago Theatre on Oct. 17, 2025.

Friday, October 17th
7:00 p.m.11:30 p.m.
The Chicago Theatre
175 N. State
Ashland Avenue
Oct17
Theatre & Performing Arts

Ashland Avenue

“You gotta start living your life right now. Because someday you’ll wake up and it’s over.” Pete’s TV and Video has served Chicagoland for 40+…

Friday, October 17th
7:30 p.m.
Goodman Albert Theatre
170 N. Dearborn, Chicago, IL, 60601
The Improvised Shakespeare Company®
Oct17
Theatre & Performing Arts

The Improvised Shakespeare Company®

The Improvised Shakespeare Company® proudly presents its critically-acclaimed, long-running hit show Improvised Shakespeare Chicago, now in its 19th year! Join us for an evening of…

Friday, October 17th
7:30 p.m.9:00 p.m.
iO Theater
1501 N. Kingsbury St.
Improvised Shakespeare
Oct17
Music & Comedy, Theatre & Performing Arts

Improvised Shakespeare

Critically-acclaimed improvised comedy featuring the language and themes of William Shakespeare

Friday, October 17th
7:30 p.m.9:00 p.m.
iO Theater
1501 N. Kingsbury St.
Gangsta Baby
Oct17
Theatre & Performing Arts

Gangsta Baby

The hit production from the London Pub Theatre scene – first production in the US Junior is a queer sex worker in Hastings suffering from…

Friday, October 17th
7:30 p.m.9:00 p.m.
Open Space Arts
1411 W. Wilson Ave, Chicago, IL, 60640
Belcea Quartet
Oct17
Music & Comedy

Belcea Quartet

Passion, precision, and pure emotion lie at the heart of Belcea’s Quartet performances. Featuring Romanian violinist Corina Belcea, Korean Australian violinist Suyeon Kang, Polish violist…

Friday, October 17th
7:30 p.m.9:00 p.m.
Mandel Hall, University of Chicago
1131 East 57th Street
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