
Upcoming Chicago Events
Check out what's happening all around Chicago.
Search events
Events Search and Views Navigation
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 AvenueTheatre & 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, 60660Festivals, 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 StreetTheatre & 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 AvenueTheatre & 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, 60025Theatre & 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.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.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 StTheatre & 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 AvenueMusic & 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 DriveTheatre & 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 AvenueMusic & 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.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.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 FloorMusic & 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.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.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.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 19thCadillac Palace Theatre
151 W. Randolph St. , Chicago, IL, 60601Theatre & 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.”…
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 19thThe Harris Theater for Music and Dance
205 East Randolph StreetMuseums, 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…
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 RdFestivals, 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.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,…

Explore Chicago hotels, flights, deals, and more
Your Favorites
Quick access links
Made with in Chicago