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Festivals, Fairs & Special Events, Music & Comedy

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October 21, 2026: Oct21
Music & Comedy, Theatre & Performing Arts
The Fizz Show
Join iO house team Fizz for Chicago’s most carbonated improv show. Wednesdays at 10 p.m., Fizz cracks open a high-octane, full-sugar set of one-night-only scenes,…
Lincoln Park
Event details
Wednesday, October 21st
10:00 p.m. – 11:00 p.m.
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iO Theater
1501 N. Kingsbury St.
October 22, 2026: Oct22
Music & Comedy
Morgan’s Laugh Lounge
Laugh your way into your new favorite Thursday tradition at Morgan’s Laugh Lounge, Chicago’s newest comedy hotspot. Every Thursday night from 6:00–9:30 PM, the lounge…
Event details
Thursday, October 22nd
7:00 p.m. – 8:30 p.m.
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Morgan’s On Fulton
950 W Fulton Market
Oct22
Music & Comedy
Maher Zain – USA Tour 2026
Maher Zain is performing live in Chicago on Thursday, October 22, 2026, at The Auditorium Theatre as part of his USA Tour 2026.
Loop
Event details
Thursday, October 22nd
7:30 p.m. – 9:30 p.m.
Auditorium
50 East Ida B. Wells Drive
Oct22
Music & Comedy
The Buena Vista Orchestra
The Buena Vista Orchestra is scheduled to perform in Chicago, IL, on Thursday, October 22, 2026.
Event details
Thursday, October 22nd
7:30 p.m. – 10:30 p.m.
The Vic Theatre
3145 N. Sheffield
October 23, 2026: Oct23
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
Friday, October 23rd
7:00 p.m. – 8:00 p.m.
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The Neo-Futurist Theater
5153 N. Ashland Ave.
Oct23
Music & Comedy
Randy Feltface – Gimmick Tour
Australian comedian Randy Feltface is scheduled to perform in Chicago on Friday, October 23, 2026, as part of his “Gimmick” tour.
Event details
Friday, October 23rd
7:00 p.m. – 9:00 p.m.
The Vic Theatre
3145 N. Sheffield
Oct23
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 23rd
7:30 p.m. – 9:00 p.m.
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iO Theater
1501 N. Kingsbury St.
Oct23
Music & Comedy
Tedeschi Trucks Band – Future Soul 2026 Tour
Award-winning blues-rock powerhouse The Tedeschi Trucks Band will conclude their “Future Soul 2026 Tour” with a four-night stand in Chicago in October 2026.
Loop
Event details
Friday, October 23rd
7:30 p.m. – 10:30 p.m.
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The Chicago Theatre
175 N. State
Oct23
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 23rd
8:00 p.m. – 9:00 p.m.
iO Theater
1501 N. Kingsbury St.
Oct23
Music & Comedy
Sammy Rae & The Friends – The Album Tour
Sammy Rae & The Friends are scheduled to perform in Chicago on Friday, October 23, 2026, as part of “The Album Tour”. Special Guest: The…
Event details
Friday, October 23rd
8:00 p.m. – 11:00 p.m.
The Salt Shed
1357 N Elston Ave, Chicago, IL
Oct23
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 23rd
9:00 p.m. – 10:00 p.m.
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Malarkey Comedy Company
1501 N Kingsbury St
Oct23
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 23rd
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,
Oct23
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 23rd
10:00 p.m. – 11:30 p.m.
Annoyance Theatre & Bar
851 W. Belmont Ave., 2nd Fl.
October 24, 2026: Oct24
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 24th
10:00 a.m. – 11:30 a.m.
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Stars & Garters Theater
3914 N. Clark St.
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…
Andersonville
Event details
Saturday, October 24th
7:00 p.m. – 8:00 p.m.
See all events in series
The Neo-Futurist Theater
5153 N. Ashland Ave.
Oct24
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 24th
7:30 p.m. – 8:30 p.m.
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The Second City
1616 N. Wells St.
Oct24
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 24th
7:30 p.m. – 8:30 p.m.
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The Second City
1616 N. Wells St., Theater on the Second Floor
Oct24
Music & Comedy
Tedeschi Trucks Band – Future Soul 2026 Tour
Award-winning blues-rock powerhouse The Tedeschi Trucks Band will conclude their “Future Soul 2026 Tour” with a four-night stand in Chicago in October 2026.
Loop
Event details
Saturday, October 24th
7:30 p.m. – 10:30 p.m.
See all events in series
The Chicago Theatre
175 N. State
Oct24
Music & Comedy
Blondshell – Scaring Strangers Tour
Blondshell is scheduled to perform live in Chicago, Illinois on Saturday, October 24, 2026, as part of her newly announced “Scaring Strangers Tour”. Supporting Act:…
Event details
Saturday, October 24th
7:30 p.m. – 10:30 p.m.
The Vic Theatre
3145 N. Sheffield
Oct24
Music & Comedy
Lupillo Rivera – 90’s CORRIDOS TOUR
Lupillo Rivera is bringing his 90’s CORRIDOS TOUR to the Rosemont Theatre on Saturday, October 24, 2026. This concert features a nostalgic lineup of regional…
Event details
Saturday, October 24th
8:00 p.m. – 11:00 p.m.
Rosemont Theatre
Oct24
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 24th
9:00 p.m. – 10:30 p.m.
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iO Theater
1501 N. Kingsbury St.
Oct24
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 24th
9:30 p.m. – 10:30 p.m.
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The Annoyance Theatre
851 W. Belmont Ave.
October 25, 2026: Oct25
Music & Comedy, Theatre & Performing Arts
Malarkey Comedy Expo League
Welcome to Expo League, where competition and exhibition meet to make an entertaining and interactive experience you’ll never forget! Like the Savannah Bananas and Harlem…
Event details
Sunday, October 25th
6:00 p.m. – 7:30 p.m.
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Malarkey Comedy
1501 N. Kingsbury St.
Oct25
Music & Comedy, Theatre & Performing Arts
Improvised 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 with…
Event details
Sunday, October 25th
8:00 p.m. – 9:00 p.m.
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Malarkey Comedy Company
1501 N Kingsbury St

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