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Festivals, Fairs & Special Events, Music & Comedy

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October 16, 2026: Oct16
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.…
Lincoln Park
Event details
Friday, October 16th
7:30 p.m. – 9:00 p.m.
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iO Theater
1501 N. Kingsbury St.
Oct16
Music & Comedy
Brad Williams: The Tall Tales Tour
Brad Williams will bring the Tall Tales Tour to The Chicago Theatre on Friday, October 16.
Loop
Event details
Friday, October 16th
7:30 p.m. – 9:30 p.m.
The Chicago Theatre
175 N. State
Oct16
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.…
Lincoln Park
Event details
Friday, October 16th
8:00 p.m. – 9:00 p.m.
iO Theater
1501 N. Kingsbury St.
Oct16
Music & Comedy, Theatre & Performing Arts
Honk! A Short Form Improv Show
Honk! is a short form, game-based improv show that asks: what good is comedy if you can’t get a little silly? Comprised of some of…
Event details
Friday, October 16th
9:00 p.m. – 10:00 p.m.
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Malarkey Comedy Company
1501 N Kingsbury St
Oct16
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…
Event details
Friday, October 16th
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,
Oct16
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…
Lakeview
Event details
Friday, October 16th
10:00 p.m. – 11:30 p.m.
Annoyance Theatre & Bar
851 W. Belmont Ave., 2nd Fl.
October 17, 2026: Oct17
Music & Comedy
Stargazers Adventure Club
Blast off with Stargazers Adventure Club in Planetary Games, an interactive space spectacular where imagination fuels the fun! You’ll learn planetary facts from out-of-this-world host,…
Event details
Saturday, October 17th
10:00 a.m. – 11:30 a.m.
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Stars & Garters Theater
3914 N. Clark St.
Oct17
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…
Andersonville
Event details
Saturday, October 17th
7:00 p.m. – 8:00 p.m.
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The Neo-Futurist Theater
5153 N. Ashland Ave.
Oct17
Music & Comedy
Ben Schwartz & Friends
Ben Schwartz is bringing his “Ben Schwartz & Friends” tour to Chicago for a night of unscripted improv comedy in the fall of 2026.
Loop
Event details
Saturday, October 17th
7:00 p.m. – 10:00 p.m.
The Chicago Theatre
175 N. State
Oct17
Music & Comedy
Catch Your Breath – Not Broken Enough Tour
Catch Your Breath will perform live in Chicago on Saturday, October 17, 2026, as part of their “Not Broken Enough Tour”. Supporting Lineup: This heavy…
Event details
Saturday, October 17th
7:00 p.m. – 10:00 p.m.
The Vic Theatre
3145 N. Sheffield
Oct17
Music & Comedy, Theatre & Performing Arts
Baby Wants Candy! The Original Completely Improvised Musical
“CRITICS’ PICK. TRULY AMAZING!” – New York Times “BEST VISITING IMPROV COMEDY!”– TimeOut NY “HIGHLY RECOMMENDED!” – The Onion “★★★★★” THEY ARE AN ENTERTAINMENT PHENOMENON AND I…
Old Town
Event details
Saturday, October 17th
7:30 p.m. – 8:30 p.m.
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The Second City
1616 N. Wells St.
Oct17
Music & Comedy, Theatre & Performing Arts
Clued In
After getting a single suggestion, the cast of six professional comedians asks the audience to choose a detective. Enjoy as they invent a tale of…
Old Town
Event details
Saturday, October 17th
7:30 p.m. – 8:30 p.m.
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The Second City
1616 N. Wells St., Theater on the Second Floor
Oct17
Music & Comedy
Suki Waterhouse – The Loveland Tour
Suki Waterhouse will conclude her North American tour in Chicago on Saturday, October 17, 2026. This show at the Byline Bank Aragon Ballroom is part…
Uptown
Event details
Saturday, October 17th
7:30 p.m. – 10:30 p.m.
Aragon Ballroom
Oct17
Music & Comedy
Grupo Duelo – Gravedad Tour
Grupo Duelo is bringing their Gravedad Tour 2026 to the Rosemont Theatre on Saturday, October 17, 2026. The tour highlights the band’s signature norteño style…
Event details
Saturday, October 17th
8:00 p.m. – 11:00 p.m.
Rosemont Theatre
Oct17
Music & Comedy
Secret Sketch Show
Shhhhh! It’s a secret! Don’t tell anyone but your favorite iO performers are hosting a wild night of variety and sketch. Secret sketch show is…
Lincoln Park
Event details
Saturday, October 17th
9:00 p.m. – 10:30 p.m.
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iO Theater
1501 N. Kingsbury St.
Oct17
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…
Lakeview
Event details
Saturday, October 17th
9:30 p.m. – 10:30 p.m.
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The Annoyance Theatre
851 W. Belmont Ave.
October 18, 2026: Oct18
Music & Comedy
Movements – Happier Now USA Tour
Movements is headlining The Salt Shed Indoors on Sunday, October 18, 2026, as part of their “Happier Now USA Tour”. Special Guests: Balance and Composure,…
Event details
Sunday, October 18th
6:00 p.m. – 11:00 p.m.
The Salt Shed
1357 N Elston Ave, Chicago, IL
Oct18
Music & Comedy
Foos Gone Wild – 2026 Tour
Foos Gone Wild is bringing The FOOS GONE WILD Tour 2026 live to Chicago on Sunday, October 18, 2026, at the House of Blues Chicago.
River North
Event details
Sunday, October 18th
6:30 p.m. – 10:00 p.m.
House of Blues
October 19, 2026: Oct19
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…
Lincoln Park
Event details
Monday, October 19th
7:00 p.m. – 8:30 p.m.
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iO Theater
1501 N. Kingsbury St.
Oct19
Music & Comedy
Disney Descendants & Zombies: Worlds Collide
The all-new “Worlds Collide Concert Tour” brings together the worlds of “Descendants,” “ZOMBIES,” and for the very first time, “Camp Rock,”in an unforgettable new arena spectacular. A pop concert…
West Loop
Event details
Monday, October 19th
7:00 p.m. – 10:00 p.m.
United Center
1901 W Madison St,
October 20, 2026: Oct20
Music & Comedy
Tuesday Good Show
Showcasing some of the best performers in the city, Tuesday Good Show is a free weekly variety show hosted by Nick Bonsignore and Keller Paulson.…
Event details
Tuesday, October 20th
7:00 p.m. – 8:30 p.m.
The Gallery Cabaret
2020 N Oakley Ave
October 21, 2026: Oct21
Music & Comedy
Disney Descendants & Zombies: Worlds Collide
The all-new “Worlds Collide Concert Tour” brings together the worlds of “Descendants,” “ZOMBIES,” and for the very first time, “Camp Rock,”in an unforgettable new arena spectacular. A pop concert…
Event details
Wednesday, October 21st
7:00 p.m. – 10:00 p.m.
Allstate Arena
6920 Mannheim Road
Oct21
Music & Comedy, Theatre & Performing Arts
The Orbit
The Orbit is Chicago’s only improv show performed in the round. This 45-minute avant-garde experience takes the audience on a full-circle journey, showcasing a bold…
Lincoln Park
Event details
Wednesday, October 21st
9:00 p.m. – 10:30 p.m.
See all events in series
iO Theater
1501 N. Kingsbury St.
Oct21
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…
Event details
Wednesday, October 21st
9:00 p.m. – 11:00 p.m.
Bordel Cocktail & Cabaret
1721 W Division

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