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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…
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…
Saturday, October 18th
7:00 p.m. – 10:00 p.m.Spiegeltent – Cambria Hotel
32 W. RandolphFestivals, Fairs & Special Events, Tours & Attractions
Halloween Chicago Hauntings Ghost Tour: Explore Paranormal Activity with American Ghost Walks
Join the acclaimed Original Chicago Hauntings Ghost Tour by American Ghost Walks. Discover the city’s most haunted sites, including the tragic Eastland disaster location and…
Saturday, October 18th
7:00 p.m. – 10:00 p.m.Meeting Point: Inside the bar at the Congress Plaza Hotel
520 S Michigan Ave.Music & Comedy, Theatre & Performing Arts
Baby Wants Candy! The Original Completely Improvised Musical
“CRITICS’ PICK. TRULY AMAZING!” – New York Times “BEST VISITING IMPROV COMEDY!”– TimeOut NY “HIGHLY RECOMMENDED!” – The Onion “★★★★★” THEY ARE AN ENTERTAINMENT PHENOMENON AND I…
Music & Comedy, Theatre & Performing Arts
Clued In
After getting a single suggestion, the cast of six professional comedians asks the audience to choose a detective. Enjoy as they invent a tale of…
Saturday, October 18th
7:30 p.m. – 8:30 p.m.The Second City
1616 N. Wells St., Theater on the Second FloorMusic & Comedy, Theatre & Performing Arts
Improvised Shakespeare
Critically-acclaimed improvised comedy featuring the language and themes of William Shakespeare
Music & Comedy, Theatre & Performing Arts
Stir Friday Night Presents: The Best of Stir Friday Night! A 30th Anniversary Comedy Celebration
Cheers to 30 years! This October, Stir Friday Night, Chicago’s longest-running AAPI comedy team, is celebrating three decades of groundbreaking comedy. Featuring favorite sketches from…
Saturday, October 18th
7:30 p.m. – 9:30 p.m.American Blues Theater
5627 N Lincoln BlvdMusic & Comedy, Theatre & Performing Arts
Chicago Symphony Orchestra: Mäkelä Conducts Symphonie fantastique
Overview Love, witchcraft, murder — it’s all packed into Symphonie fantastique, Berlioz’s thriller about a lovesick artist obsessed with a young actress. Zell Music Director Designate…
Saturday, October 18th
7:30 p.m. – 9:40 p.m.Chicago Symphony Center
220 S Michigan AveFestivals, 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 StreetMusic & 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 StMusic & 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 DriveMusic & 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.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.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 StreetFestivals, 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,…
Festivals, Fairs & Special Events
Glenwood Sunday Market in Rogers Park
The nonprofit Rogers Park Business Alliance (RPBA) announces 23 local vendors for the 16th anniversary season of the Glenwood Sunday Market, which will operate every…
Festivals, Fairs & Special Events
Boo! at the Zoo
Get ready for a fang-tastic time at BOO! at the Zoo, Brookfield Zoo Chicago’s family-friendly Halloween celebration. This event is packed with not-so-scary thrills, festive decorations,…
Sunday, October 19th
10:00 a.m. – 5:00 p.m.Brookfield Zoo Chicago
3300 Golf RdFestivals, Fairs & Special Events, Museums, Galleries & Exhibitions
Stitching Stories Asia from East to West
As part of Journey Chicago and Open House Chicago, the Heritage Museum of Asian Art—together with the Abrahamic Center for Cultural Education and Japanese Culture…
Sunday, October 19th
11:00 a.m. – 5:00 p.m.Heritage Museum of Asian Art
3FL, 3500 S Morgan St, Chicago, IL, 60609Festivals, Fairs & Special Events, Museums, Galleries & Exhibitions
The Fall West Loop Contemporary Fine Art Expo
An Art Expo unlike any in Chicagoland! The Fall West Loop Contemporary Fine Art Expo is a curated boutique expo showcasing over 40 invitation-only fine…
Sunday, October 19th
11:00 a.m. – 7:00 p.m.Stephen M Bailey Auditorium, Plumbers Hall
1340 West Washington Blvd.

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