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Upcoming Chicago Events

Check out what's happening all around Chicago.

Dermot Kennedy: 2025 North American Fall Tour
Oct21
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.
Ear Taxi Festival
Oct22
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 22nd
Division Street Farmers Market
Oct22
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.

Wednesday, October 22nd
7:00 a.m.12:00 p.m.
30 W. Division St.
30 W. Division St.
Boo! at the Zoo
Oct22
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 Rd
Crowd Work Wednesday at The Comedy Bar
Oct22
Music & 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.
Goody! An Immersive Folk-Horror Sketch Comedy Show
Oct22
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.
Halloween Chicago Ghost Tour & Hunt: Lincoln Park Hauntings by American Ghost Walks
Oct22
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.
Hooch & Holler Comedy Show
Oct22
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 Division
Ear Taxi Festival
Oct23
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,…

Thursday, October 23rd
Division Street Farmers Market
Oct23
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.

Thursday, October 23rd
7:00 a.m.12:00 p.m.
30 W. Division St.
30 W. Division St.
Boo! at the Zoo
Oct23
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 Rd
Clued In: Where There’s a Will, There’s a Way
Oct23
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…

Thursday, October 23rd
7:00 p.m.8:30 p.m.
The Second City
1616 N. Wells St.
Nate Bargatze – Big Dumb Eyes World Tour
Oct23
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!

Thursday, October 23rd
7:00 p.m.9:00 p.m.
United Center
1901 W Madison St.
Teatro Zinzanni
Oct23
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. Randolph
Duluth: An Improvised Midwest Murder
Oct23
Music & 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…

Thursday, October 23rd
7:30 p.m.8:30 p.m.
iO Theater
1501 N. Kingsbury St.
Thursdays: OhJay Lamont at The comedy Bar
Oct23
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…

Thursday, October 23rd
7:30 p.m.9:00 p.m.
The Comedy Bar
500 N. LaSalle St.
Chicago Symphony Orchestra: The Soldier’s Tale
Oct23
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 Ave
Improvsed DCOM
Oct23
Music & 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 St
The Wolfman of Wrigleyville – Horror Comedy Play
Oct23
Music & 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.
Halloween Chicago Ghost Tour & Hunt: Lincoln Park Hauntings by American Ghost Walks
Oct23
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.
Chicago Comedy Hour
Oct23
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…

Thursday, October 23rd
8:30 p.m.9:30 p.m.
Donny’s Skybox
230 W North Ave
Sketch Playlist
Oct23
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…

Thursday, October 23rd
9:30 p.m.10:30 p.m.
iO Theater
1501 N. Kingsbury St.
Ear Taxi Festival
Oct24
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 24th
Division Street Farmers Market
Oct24
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.

Friday, October 24th
7:00 a.m.12:00 p.m.
30 W. Division St.
30 W. Division St.
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