
Upcoming Chicago Events
Check out what's happening all around Chicago.
Search events
Events Search and Views Navigation
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.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.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 AveMusic & 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 StMusic & 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…
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.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 DriveMusic & 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!)…
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 20thThe Harris Theater for Music and Dance
205 East Randolph StreetFestivals, 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.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 RdMusic & 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…
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 StMusic & 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…
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.

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