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Upcoming Chicago Events

Check out what's happening all around Chicago.

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.
SCP Piano: Yunchan Lim
Oct19
Music & Comedy, Theatre & Performing Arts

SCP Piano: Yunchan Lim

Overview Yunchan Lim, who at 18 became the youngest-ever winner of the Van Cliburn Competition, climbs the summit of Baroque keyboard music in Bach’s Goldberg Variations. A…

Sunday, October 19th
3:00 p.m.4:30 p.m.
Chicago Symphony Center
220 S Michigan Ave
Kurbasy
Oct19
Music & Comedy

Kurbasy

Born from Lviv’s progressive Les Kurbas Theatre, Kurbasy channels ancient Ukrainian folklore through tight vocal harmonies, spectral instrumentation, and striking visual storytelling. Their performances are…

Sunday, October 19th
3:00 p.m.4:30 p.m.
Reva and David – Logan Center for the Arts
915 E 60th St
Clued In: Where There’s a Will, There’s a Way
Oct19
Music & Comedy, Theatre & Performing Arts

Clued In: Where There’s a Will, There’s a Way

YOU’RE INVITED…to bear witness to a fully improvised murder mystery. Six improvisers find themselves trapped on stage with a murderer, and nobody knows who the…

Sunday, October 19th
4:00 p.m.5:30 p.m.
The Second City
1616 N. Wells St.
Brian Hooks at The Comedy Bar
Oct19
Music & Comedy

Brian Hooks at The Comedy Bar

2-Item Minimum Per Guest Valid ID Required for Entry First Come, First Served Seating No Outside Food or Beverage Brian Hooks is a highly prolific…

Sunday, October 19th
7:00 p.m.8:30 p.m.
The Comedy Bar
500 N. LaSalle St.
Avatar: The Last Airbender in Concert
Oct19
Music & Comedy

Avatar: The Last Airbender in Concert

Avatar: The Last Airbender In Concert presents a live orchestral rendition of the series’ iconic soundtrack, paired with a two-hour special recap of the animated…

Sunday, October 19th
7:00 p.m.9:00 p.m.
Auditorium Theatre
50 East Ida B. Wells Drive
Wheel of Improv
Oct19
Music & Comedy, Theatre & Performing Arts

Wheel of Improv

Chicago’s top comedians battle it out for laughs, glory, and sweet sweet points in an interactive game show, featuring a live studio audience (that’s you!)…

Sunday, October 19th
7:30 p.m.8:30 p.m.
The Second City
1616 N. Wells St.
Ear Taxi Festival
Oct20
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,…

Monday, October 20th
Division Street Farmers Market
Oct20
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.

Monday, October 20th
7:00 a.m.12:00 p.m.
30 W. Division St.
30 W. Division St.
Boo! at the Zoo
Oct20
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,…

Monday, October 20th
10:00 a.m.5:00 p.m.
Brookfield Zoo Chicago
3300 Golf Rd
Magic Mondays
Oct20
Music & Comedy, Theatre & Performing Arts

Magic Mondays

Experience an unforgettable night of wonder at Magic Mondays!! Starring award-winning magician John Sturk, this monthly showcase features Chicago’s top conjurors performing mind-blowing illusions and…

Monday, October 20th
7:00 p.m.8:30 p.m.
iO Theater
1501 N. Kingsbury St.
CNN’s Abby Phillip in Conversation
Oct20
Festivals, Fairs & Special Events

CNN’s Abby Phillip in Conversation

Join CNN anchor and author Abby Phillip in conversation with bestselling writer and cultural critic Luvvie Ajayi Jones for a powerful look at Jesse Jackson’s…

Monday, October 20th
7:00 p.m.9:00 p.m.
First United Methodist Church at the Chicago Temple
77 W Washington St
Late Nite Mic With Vik Pandya at The Comedy Bar
Oct20
Music & Comedy

Late Nite Mic With Vik Pandya at The Comedy Bar

2-Item Minimum Per Guest First Come, First Served Seating No Outside Food or Beverage Valid ID Required at Entry Vik Pandya is a nationally touring…

Monday, October 20th
7:30 p.m.9:00 p.m.
The Comedy Bar
500 N. LaSalle St.
Adam Sandler: You’re My Best Friend Tour
Oct20
Music & Comedy

Adam Sandler: You’re My Best Friend Tour

Adam Sandler returns to Chicago! He is bringing his You’re My Best Friend Tour to United Center on October 20, 2025! Adam Sandler needs no…

Monday, October 20th
7:30 p.m.10:00 p.m.
United Center
1901 W Madison St.
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