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Monstrous
Oct18
Theatre & Performing Arts

Monstrous

written by Stephanie Lewis, directed by Rachel Borgo After a merciless punishment, Medusa loses her way—and her memory—traveling to the Underworld. She awakens at The…

Saturday, October 18th
7:30 p.m.10:00 p.m.
The Den Theatre
1331 North Milwaukee Avenue
Strange Cargo: The Doom of the Demeter
Oct18
Theatre & Performing Arts

Strange Cargo: The Doom of the Demeter

Based on Chapter Seven of Bram Stoker’s DRACULA, this gothic horror high seas adventure tells the shocking events aboard the cargo ship transporting Count Dracula’s belongings from…

Saturday, October 18th
7:30 p.m.10:00 p.m.
City Lit Theater
1020 W. Bryn Mawr, Chicago, IL, 60660
Ear Taxi Festival presents Invictus & An African American Requiem
Oct18
Festivals, Fairs & Special Events, Music & Comedy

Ear Taxi Festival presents Invictus & An African American Requiem

This culminating concert of the 2025 Ear Taxi Festival features the world premiere of Stacy Garrop’s Invictus and Midwestern premiere of Damien Geter’s powerful An…

Saturday, October 18th
7:30 p.m.10:00 p.m.
Harris Theater
205 E. Randolph Street
“The Shortlist: A Refracted Festival”
Oct18
Theatre & Performing Arts

“The Shortlist: A Refracted Festival”

Award-winning Refracted Theatre Company announces The Shortlist: A Refracted Festival, September 19 – October 18, at the Den Theatre, 1331 N. Milwaukee Ave. The Shortlist…

Saturday, October 18th
7:30 p.m.10:00 p.m.
The Den Theatre
1331 North Milwaukee Avenue
Oil Lamp Theater Presents “Gaslight”
Oct18
Theatre & Performing Arts

Oil Lamp Theater Presents “Gaslight”

Oil Lamp Theater is proud to present Gaslight (Angel Street), October 2 – November 2, by Patrick Hamilton and directed by Susan Gorman at Oil…

Saturday, October 18th
7:30 p.m.10:00 p.m.
Oil Lamp Theater
1723 Glenview Rd, Glenview, IL, 60025
Dutchman
Oct18
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…

Saturday, October 18th
8:00 p.m.9:15 p.m.
Trap Door Theatre
1655 W. Cortland St.
The Lincoln Lodge
Oct18
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 18th
8:00 p.m.9:30 p.m.
The Lincoln Lodge Theater
2040 N. Milwaukee Ave.
ComedySportz Chicago
Oct18
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…

Saturday, October 18th
8:00 p.m.9:30 p.m.
Malarkey Comedy Company
1501 N Kingsbury St
wyrd
Oct18
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…

Saturday, October 18th
8:00 p.m.9:30 p.m.
Greenhouse Theater Center
2257 North Lincoln Avenue
Sarah Millican – Late Bloomer Tour
Oct18
Music & Comedy

Sarah Millican – Late Bloomer Tour

When Sarah Millican was a child, she wouldn’t say boo to a goose. Quiet at school, not many friends, no boobs ‘til she was 16. Now? NOW she…

Saturday, October 18th
8:00 p.m.10:00 p.m.
Auditorium Theatre
50 East Ida B. Wells Drive
The Book of Will
Oct18
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…

Saturday, October 18th
8:00 p.m.10:00 p.m.
The Den Theatre
1331 North Milwaukee Avenue
Brandy & Monica: The Boy Is Mine Tour
Oct18
Music & Comedy

Brandy & Monica: The Boy Is Mine Tour

The highly anticipated The Boy Is Mine Tour is coming to United Center on October 18! The iconic GRAMMY Award-winning artists, Brandy and Monica, will…

Saturday, October 18th
8:00 p.m.11:00 p.m.
United Center
1901 W Madison St.
Sweetest Day Comedy Jam: Lavell Crawford, Bill Bellamy, & T.I. (TIP Harris)
Oct18
Theatre & Performing Arts

Sweetest Day Comedy Jam: Lavell Crawford, Bill Bellamy, & T.I. (TIP Harris)

The Sweetest Day Comedy Jam, featuring Lavell Crawford, Bill Bellamy, & T.I. (TIP Harris), is coming to Chicago.

Saturday, October 18th
8:00 p.m.11:00 p.m.
Here 4 A Bit *Naughty Improv
Oct18
Music & Comedy, Theatre & Performing Arts

Here 4 A Bit *Naughty Improv

Join us again for a whose line styled night of explosive laughter that will titillate your “funny” bone. Fast paced short form improv, hilarious songs,…

Saturday, October 18th
9:00 p.m.10:00 p.m.
The Second City
1616 N. Wells St., Theater on the Second Floor
Matty Chymbor at The Comedy Bar
Oct18
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…

Saturday, October 18th
9:00 p.m.10:30 p.m.
The Comedy Bar
500 N. LaSalle St.
Best Of Annoyance Sketch
Oct18
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 18th
9:30 p.m.10:30 p.m.
The Annoyance Theatre
851 W. Belmont Ave.
LET’S PLAY A GAME: Chicago’s scariest short-form show
Oct18
Music & Comedy, Theatre & Performing Arts

LET’S PLAY A GAME: Chicago’s scariest short-form show

Who’s Line is it Anyways meets Fear Factor in LETS PLAY A GAME, a new short form show that’s a unique blend of comedy, chaos,…

Saturday, October 18th
10:00 p.m.11:00 p.m.
Annoyance Theatre & Bar
851 W. Belmont Ave., 2nd Fl.
The Lion King
Oct19
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…

Sunday, October 19th
Cadillac Palace Theatre
151 W. Randolph St. , Chicago, IL, 60601
The Book of Mormon
Oct19
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.”…

Sunday, October 19th
CIBC Theatre
18 W. Monroe St. , Chicago, IL, 60602
Ear Taxi Festival
Oct19
Festivals, Fairs & Special Events

Ear Taxi Festival

The Ear Taxi Festival 2025, themed “The Composer’s Voice,” is a landmark event showcasing contemporary concert music across Chicagoland from October 3 through November 2,…

Sunday, October 19th
Pumpkin Lights & Playful Frights
Oct19
Museums, Galleries & Exhibitions

Pumpkin Lights & Playful Frights

Step into WNDR this October for a seasonal spectacle like never before. Celebrate fall fun at WNDR Museum next month where treats, surprises, entertainment and…

Sunday, October 19th
wndr museum
1130 W Monroe St.
Wolff’s Flea Market Opening Day
Oct19
Festivals, Fairs & Special Events

Wolff’s Flea Market Opening Day

Wolff’s Flea Market announces opening day April 20, 2025. Join us for our 34th season outdoors at the Allstate Arena, Rosemont. Sundays 6am-2pm through October…

Sunday, October 19th
6:00 a.m.2:00 p.m.
Wolff’s Flea Market
6920 N Mannheim Rd
Division Street Farmers Market
Oct19
Festivals, Fairs & Special Events

Division Street Farmers Market

Fresh seasonal produce, flowers, prepared foods, unique Chicago-made products and rare finds are available at the Division Street Farmers Market.

Sunday, October 19th
7:00 a.m.12:00 p.m.
30 W. Division St.
30 W. Division St.
Open House Chicago 2025
Oct19
Festivals, Fairs & Special Events

Open House Chicago 2025

Each October, the Chicago Architecture Center (CAC) hosts Open House Chicago (OHC), a free public festival that offers rare behind-the-scenes access to sites of architectural,…

Sunday, October 19th
Chicago Architecture Center
111 E. Wacker Dr.
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