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Music & Comedy
Dermot Kennedy: 2025 North American Fall Tour
Dermot Kennedy will perform live at House Of Blues on Oct. 21, 2025.
Tuesday, October 21st
8:00 p.m. – 11:00 p.m.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,…
Wednesday, October 22ndThe 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.
Wednesday, October 22nd
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,…
Wednesday, October 22nd
10:00 a.m. – 5:00 p.m.Brookfield Zoo Chicago
3300 Golf RdMusic & Comedy
Crowd Work Wednesday at The Comedy Bar
2-Item Minimum Per Guest First Come, First Served Seating No Outside Food or Beverage Valid ID Required at Entry Crowd Work Wednesday is a weekly…
Wednesday, October 22nd
7:30 p.m. – 9:00 p.m.The Comedy Bar
500 N. LaSalle St.Music & Comedy, Theatre & Performing Arts
Goody! An Immersive Folk-Horror Sketch Comedy Show
Hear ye, hear ye! Goody! is back by popular demand! This October, join the town elders of Brian’s Hollow in the meetinghouse for an immersive…
Wednesday, October 22nd
8:00 p.m. – 9:00 p.m.The Annoyance Theatre
851 W. Belmont Ave.Festivals, Fairs & Special Events, Tours & Attractions
Halloween Chicago Ghost Tour & Hunt: Lincoln Park Hauntings by American Ghost Walks
Join American Ghost Walks on a spine-chilling Chicago Ghost Tour & Ghost Hunt in Lincoln Park, known for its eerie hauntings and chilling history. Dive…
Wednesday, October 22nd
8:00 p.m. – 10:00 p.m.Meeting Point: In front of the Chicago History Museum
1601 N Clark St.Music & Comedy, Theatre & Performing Arts
Hooch & Holler Comedy Show
Every Wednesday The Best Speakeasy In Chicago Hosts The Hottest Comedians The City Has To Offer! Indulge In Our Amazing Craft Cocktails And Enjoy An…
Wednesday, October 22nd
9:00 p.m. – 11:00 p.m.Bordel Cocktail & Cabaret
1721 W DivisionFestivals, 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,…
Thursday, October 23rdThe 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.
Thursday, October 23rd
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,…
Thursday, October 23rd
10:00 a.m. – 5:00 p.m.Brookfield Zoo Chicago
3300 Golf RdMusic & 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
Nate Bargatze – Big Dumb Eyes World Tour
Nate Bargatze is bringing his Big Dumb Eyes World Tour to United Center on October 23 & 24, 2025!
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…
Thursday, October 23rd
7:00 p.m. – 10:00 p.m.Spiegeltent – Cambria Hotel
32 W. RandolphMusic & Comedy, Theatre & Performing Arts
Duluth: An Improvised Midwest Murder
Based on the hit FX show “Fargo”, Duluth takes audiences into the world of true crime in the Midwest. Each week, the cast of Duluth will improvise a…
Music & Comedy
Thursdays: OhJay Lamont at The comedy Bar
2-Item Minimum Per Guest First Come, First Served Seating No Outside Food or Beverage Valid ID Required at Entry OhJay Lamont, born and raised on…
Music & Comedy, Theatre & Performing Arts
Chicago Symphony Orchestra: The Soldier’s Tale
Overview Step into the engrossing world of Stravinsky’s The Soldier’s Tale — a Faustian fable about a soldier-fiddler who makes a pact with the devil — in…
Thursday, October 23rd
7:30 p.m. – 9:40 p.m.Chicago Symphony Center
220 S Michigan AveMusic & Comedy, Theatre & Performing Arts
Improvsed DCOM
Dive into the nostalgia of Disney Channel Original Movies with the cast of Improvised DCOM! This All Star cast is bringing screen to stage every…
Thursday, October 23rd
8:00 p.m. – 9:00 p.m.Malarkey Comedy Company
1501 N Kingsbury StMusic & Comedy, Theatre & Performing Arts
The Wolfman of Wrigleyville – Horror Comedy Play
This 70-minute comedy set in 1927 follows an investigative journalist and her ex-girlfriend, a private eye, as they look into a series of murders that…
Thursday, October 23rd
8:00 p.m. – 9:30 p.m.Annoyance Theatre & Bar
851 W. Belmont Ave., 2nd Fl.Festivals, Fairs & Special Events, Tours & Attractions
Halloween Chicago Ghost Tour & Hunt: Lincoln Park Hauntings by American Ghost Walks
Join American Ghost Walks on a spine-chilling Chicago Ghost Tour & Ghost Hunt in Lincoln Park, known for its eerie hauntings and chilling history. Dive…
Thursday, October 23rd
8:00 p.m. – 10:00 p.m.Meeting Point: In front of the Chicago History Museum
1601 N Clark St.Music & Comedy, Theatre & Performing Arts
Chicago Comedy Hour
The Chicago Comedy hour is a comedy variety show featuring sketch, improv and stand up from some of the best up and coming comedians in…
Music & Comedy, Theatre & Performing Arts
Sketch Playlist
Sketch Playlist is a weekly sketch show on Thursdays at 9:30pm at iO Theater (1501 N Kingsbury Street, Chicago 60642) that will feature brand-new material…
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,…
Friday, October 24thThe 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.
Friday, October 24th
7:00 a.m. – 12:00 p.m.30 W. Division St.
30 W. Division St.

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