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Upcoming Chicago Events

Check out what's happening all around Chicago.

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.
Boo! at the Zoo
Oct24
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,…

Friday, October 24th
10:00 a.m.5:00 p.m.
Brookfield Zoo Chicago
3300 Golf Rd
Wicker Park Bucktown’s “First Fridays” Art Walk
Oct24
Festivals, Fairs & Special Events, Museums, Galleries & Exhibitions

Wicker Park Bucktown’s “First Fridays” Art Walk

The “First Fridays Art Walk,” organized by the Wicker Park Bucktown Chamber of Commerce, welcomes art enthusiasts to explore the neighborhoods’ vibrant arts scene. All…

Friday, October 24th
6:00 p.m.8:00 p.m.
Jackson Junge Gallery
1389 N Milwaukee Ave
Adults Night Out: Howl-o-ween at Lincoln Park Zoo
Oct24
Festivals, Fairs & Special Events

Adults Night Out: Howl-o-ween at Lincoln Park Zoo

Adults Night Out: Howl-o-ween is a 21+ Halloween party at the zoo that includes a haunted trail, Halloween-themed animal chats, free face-painting, a live DJ,…

Friday, October 24th
6:30 p.m.10:00 p.m.
The Infinite Wrench
Oct24
Music & Comedy, Theatre & Performing Arts

The Infinite Wrench

Don’t miss the longest running late-night show in Chicago! At The Infinite Wrench you’ll see 30 original plays in 60 minutes written and performed by…

Friday, October 24th
7:00 p.m.8:00 p.m.
The Neo-Futurist Theater
5153 N. Ashland Ave.
ComedySportz Chicago
Oct24
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…

Friday, October 24th
7:00 p.m.8:30 p.m.
Malarkey Comedy
1501 N. Kingsbury St.
ComedySportz Chicago
Oct24
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…

Friday, October 24th
7:00 p.m.8:30 p.m.
Malarkey Comedy Company
1501 N Kingsbury St
Nate Bargatze – Big Dumb Eyes World Tour
Oct24
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!

Friday, October 24th
7:00 p.m.9:00 p.m.
United Center
1901 W Madison St.
Teatro Zinzanni
Oct24
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…

Friday, October 24th
7:00 p.m.10:00 p.m.
Spiegeltent – Cambria Hotel
32 W. Randolph
Improvised Shakespeare
Oct24
Music & Comedy, Theatre & Performing Arts

Improvised Shakespeare

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

Friday, October 24th
7:30 p.m.9:00 p.m.
iO Theater
1501 N. Kingsbury St.
Alarm Will Sound
Oct24
Music & Comedy

Alarm Will Sound

“Überhip” (Entertainment Weekly) 20-member band Alarm Will Sound takes on music from the arch-modernist to the pop-influenced. Committed to innovative performances and recordings of today’s…

Friday, October 24th
7:30 p.m.9:00 p.m.
Reva and David – Logan Center for the Arts
915 E 60th St
Chicago Symphony Orchestra: The Soldier’s Tale
Oct24
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…

Friday, October 24th
7:30 p.m.9:40 p.m.
Chicago Symphony Center
220 S Michigan Ave
A Royal Affair – Where Wakanda Meets Bridgerton
Oct24
Festivals, Fairs & Special Events

A Royal Affair – Where Wakanda Meets Bridgerton

Join us for books, banter, great food and music, with a little cosplay at the Alhambra Palace Restaurant! Come dressed in your amazing African garment,…

Friday, October 24th
7:30 p.m.11:00 p.m.
Alhambra Palace Restaurant
1240 West Randolph Street
Devil’s Daughter
Oct24
Music & Comedy

Devil’s Daughter

The hottest show in town Devil’s Daughter features a cast of seasoned comedians who have performed together in Chicago and around the country for over a decade.…

Friday, October 24th
8:00 p.m.9:00 p.m.
iO Theater
1501 N. Kingsbury St.
Missed Call Sketch Comedy Show
Oct24
Music & Comedy, Theatre & Performing Arts

Missed Call Sketch Comedy Show

Missed Call is a premier Chicago comedy group that writes and performs an entirely new sketch show every Friday — inspired by the audience’s suggestion!

Friday, October 24th
8:00 p.m.9:00 p.m.
The Annoyance Theatre
851 W. Belmont Ave.
An Evening with Chris Thile
Oct24
Music & Comedy, Theatre & Performing Arts

An Evening with Chris Thile

Overview MacArthur Fellow and Grammy Award-winning mandolinist, singer, songwriter and composer Chris Thile, hailed as “an all-round musician” (The Guardian), brings his genre-spanning artistry to…

Friday, October 24th
8:00 p.m.9:30 p.m.
Chicago Symphony Center
220 S Michigan Ave
Penn & Teller: 50th Anniversary Tour
Oct24
Music & Comedy

Penn & Teller: 50th Anniversary Tour

Penn & Teller will bring their 50th Anniversary tour to The Chicago Theatre on Friday, October 24.

Friday, October 24th
8:00 p.m.10:00 p.m.
The Chicago Theatre
175 N. State
Halloween Chicago Ghost Tour & Hunt: Lincoln Park Hauntings by American Ghost Walks
Oct24
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…

Friday, October 24th
8:00 p.m.10:00 p.m.
Meeting Point: In front of the Chicago History Museum
1601 N Clark St.
Trapped in a Musical – an improvised musical
Oct24
Music & Comedy, Theatre & Performing Arts

Trapped in a Musical – an improvised musical

Trapped in a Musical is a completely improvised Broadway-style show created before your very eyes. It’s the opening and closing night of a brand new…

Friday, October 24th
9:00 p.m.10:00 p.m.
Voila: The Improvised Musical
Oct24
Music & Comedy, Theatre & Performing Arts

Voila: The Improvised Musical

iO Chicago presents: a fully made-up, off-off-off Broadway style musical every Friday at 10pm in the Fremont Theater. Spend your Friday night with us. See…

Friday, October 24th
10:00 p.m.11:30 p.m.
The iO Theater, 1501 N Kingsbury St, Chicago, IL 60642, USA,
The iO Theater, 1501 N Kingsbury St, Chicago, IL 60642, USA,
Hitch*Cocktails
Oct24
Music & Comedy, Theatre & Performing Arts

Hitch*Cocktails

A Chicago based improv comedy show and drinking game based on the works of Alfred Hitchcock. Based on an audience suggestion, the cast weave together…

Friday, October 24th
10:00 p.m.11:30 p.m.
Annoyance Theatre & Bar
851 W. Belmont Ave., 2nd Fl.
Ear Taxi Festival
Oct25
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,…

Saturday, October 25th
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