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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
7:00 p.m.8:30 p.m.
The Comedy Bar
500 N. LaSalle St.
Teatro Zinzanni
Oct18
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. Randolph
Halloween Chicago Hauntings Ghost Tour: Explore Paranormal Activity with American Ghost Walks
Oct18
Festivals, 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.
Baby Wants Candy! The Original Completely Improvised Musical
Oct18
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…

Saturday, October 18th
7:30 p.m.8:30 p.m.
The Second City
1616 N. Wells St.
Clued In
Oct18
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 Floor
Improvised Shakespeare
Oct18
Music & Comedy, Theatre & Performing Arts

Improvised Shakespeare

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

Saturday, October 18th
7:30 p.m.9:00 p.m.
iO Theater
1501 N. Kingsbury St.
Stir Friday Night Presents: The Best of Stir Friday Night! A 30th Anniversary Comedy Celebration
Oct18
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 Blvd
Chicago Symphony Orchestra: Mäkelä Conducts Symphonie fantastique
Oct18
Music & 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 Ave
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
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
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
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.
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.
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
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.
Glenwood Sunday Market in Rogers Park
Oct19
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…

Sunday, October 19th
9:00 a.m.2:00 p.m.
Glenwood Alfresco
Boo! at the Zoo
Oct19
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 Rd
Stitching Stories Asia from East to West
Oct19
Festivals, 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, 60609
The Fall West Loop Contemporary Fine Art Expo
Oct19
Festivals, 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.
bean-night

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