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Upcoming Chicago Events

Check out what's happening all around Chicago.

October 27, 2026: Oct27
Music & Comedy
SiM – Hooman After All World Tour
Japanese reggae-punk and metal band SiM is scheduled to perform live in Chicago, Illinois on Tuesday, October 27, 2026, as part of their newly announced…
River North
Event details
Tuesday, October 27th
6:30 p.m. – 9:30 p.m.
House of Blues
Oct27
Music & Comedy
Guy’z Nite Comedy Show at The Comedy Bar
Guy’z Nite is a wildly known weekly sold out comedy show headlined by Guy Reuven, starring NEW celebrity lineups of Hollywood’s BIGGEST comedians including Ismo,…
River North
Event details
Tuesday, October 27th
7:00 p.m. – 9:00 p.m.
The Comedy Bar
162 E Superior St, Chicago, IL 60611
Oct27
Music & Comedy
Joanne Mcnally – Pinotphile Tour
Joanne McNally is performing live in Chicago on Tuesday, October 27, 2026, as part of her hotly anticipated new North American stand-up comedy tour, “Pinotphile”.
Event details
Tuesday, October 27th
7:30 p.m. – 9:30 p.m.
The Vic Theatre
3145 N. Sheffield
Oct27
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
Tuesday, October 27th
7:30 p.m. – 10:30 p.m.
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The Chicago Theatre
main stage is located at 2550 N. Lincoln Ave., Chicago, IL 60614
Oct27
Music & Comedy
Sienna Spiro – My House Tour
Sienna Spiro is performing live in Chicago on Tuesday, October 27, 2026, at The Riviera Theatre as part of her massive My House Tour world…
Uptown
Event details
Tuesday, October 27th
7:30 p.m. – 10:30 p.m.
The Riveria Theater
4746 N Racine Ave
Oct27
Oct28
Music & Comedy
The 11pm Show
Continuing the rich tradition of late night improv, join the veteran cast of THE 11PM SHOW every Friday at 11PM as they perform late night, artistic improv…
Lincoln Park
Event details
Tuesday, October 27th
11:00 p.m. – Wednesday, October 28th
12:00 a.m.
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iO Theater
1501 N. Kingsbury St.
October 28, 2026: Oct28
Music & Comedy, Theatre & Performing Arts
Illinois Humanities Presents “THE PURSUIT: A People’s Salon”
Illinois Humanities is proud to present an evening of commissioned performances from comedian Lisa Beasley, choreographer/director INSÉKTA, Illinois Poet Laureate Mark Turcotte, former Chicago Poet Laureate avery r.…
Event details
Wednesday, October 28th
5:30 p.m. – 9:00 p.m.
Ramova Theatre
3520 S. Halsted St.
Oct28
Music & Comedy
Respawn Improv with Blue.0
A weekly improv show hosted by Blue.0 and featuring a rotating cast of indie teams formed right here at The iO Theater! Each Wednesday at…
Lincoln Park
Event details
Wednesday, October 28th
6:00 p.m. – 7:00 p.m.
See all events in series
iO Theater
1501 N. Kingsbury St.
Oct28
Music & Comedy
Chicago’s Best Comedy Show at The Comedy Bar
Join Chicago’s best comedians for a hilarious night of stand-up comedy, pizza, and nonstop laughs!
River North
Event details
Wednesday, October 28th
7:00 p.m. – 9:00 p.m.
The Comedy Bar
162 E Superior St, Chicago, IL 60611
Oct28
Music & Comedy, Theatre & Performing Arts
Omar
Where memory is preserved, legacy endures. MacArthur “Genius Grant” recipient Rhiannon Giddens and celebrated co-composer Michael Abels deliver a profoundly moving story about the strength…
Loop
Event details
Wednesday, October 28th
7:00 p.m. – 9:30 p.m.
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Lyric Opera of Chicago
20 N. Wacker Dr. , Chicago, IL, 60606
Oct28
Music & Comedy
Father Mike Schmitz – Parables: A Time of Reflection
Father Mike Schmitz will bring his popular live presentation, Parables: A Time of Reflection, to The Chicago Theatre in Chicago, Illinois, on Wednesday, October 28,…
Loop
Event details
Wednesday, October 28th
7:00 p.m. – 10:00 p.m.
The Chicago Theatre
main stage is located at 2550 N. Lincoln Ave., Chicago, IL 60614
Oct28
Music & Comedy
Play Time
A showcase of 3 short plays by select writing teams and featuring a cast of iO Theater performers. It’s experimental, it’s follow-the-fun, it’s Play Time. Plays…
Lincoln Park
Event details
Wednesday, October 28th
7:30 p.m. – 9:00 p.m.
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iO Theater
1501 N. Kingsbury St.
Oct28
Music & Comedy
Shakey Graves – Fondness, Etc. Tour
Shakey Graves will bring his Fondness, Etc. Tour to Chicago on Wednesday, October 28, 2026. Special Guest: New York indie-rock band Wild Pink will open…
Event details
Wednesday, October 28th
7:30 p.m. – 10:30 p.m.
The Vic Theatre
3145 N. Sheffield
Oct28
Music & Comedy
Eros Ramazzotti – Una Storia Importante World Tour
Eros Ramazzotti is bringing his Una Storia Importante World Tour to the Rosemont Theatre on Wednesday, October 28, 2026. This tour celebrates his 40-year career…
Event details
Wednesday, October 28th
8:00 p.m. – 11:00 p.m.
Rosemont Theatre
Oct28
Music & Comedy
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 28th
10:00 p.m. – 11:00 p.m.
See all events in series
iO Theater
1501 N. Kingsbury St.
Oct28
Oct29
Music & Comedy
The 11pm Show
Continuing the rich tradition of late night improv, join the veteran cast of THE 11PM SHOW every Friday at 11PM as they perform late night, artistic improv…
Lincoln Park
Event details
Wednesday, October 28th
11:00 p.m. – Thursday, October 29th
12:00 a.m.
See all events in series
iO Theater
1501 N. Kingsbury St.
October 29, 2026: Oct29
Music & Comedy
Best of Chicago Comedy – Chicago
Get ready for a night filled with laughter at the “Best of Chicago Comedy – Chicago,” where some of the city’s funniest talents take the…
Event details
Thursday, October 29th
The Foundation Room at House Of Blues – Chicago
329 N Dearborn St, Chicago,
Oct29
Music & Comedy
OhJay Lamont & Friends at The Comedy Bar
OhJay Lamont, born and raised on the west side of Chicago, started doing stand-up comedy in 2015. He has worked in many different areas of…
River North
Event details
Thursday, October 29th
7:00 p.m. – 9:00 p.m.
The Comedy Bar
162 E Superior St, Chicago, IL 60611
Oct29
Music & Comedy
Set In Chicago – Improvised Spooky Movie Sequels
It’s officially spooky season and there’s no better time to watch a scary movie. From slashers to thrashers, Halloween-themed and gore, we take your favorite…
Event details
Thursday, October 29th
7:30 p.m. – 8:30 p.m.
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de Maat Theatre at Second City
230 W North Ave
Oct29
Music & Comedy, Theatre & Performing Arts
Vape! The Grease Parody
Vape! lovingly pokes fun at all of the wonderful moments, sexual innuendos, outrageous characters, rivalries and secret romances from the original musical. The hair products may…
Event details
Thursday, October 29th
7:30 p.m. – 8:55 p.m.
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Apollo Theater
2550 N. Lincoln Ave.
Oct29
Music & Comedy
Improv The Play
With the help of some of Chicago’s best actors, Improv: The Play is a new, hybrid version of long form improv happening only at the…
Lincoln Park
Event details
Thursday, October 29th
7:30 p.m. – 9:00 p.m.
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iO Theater
1501 N. Kingsbury St.
Oct29
Music & Comedy
Thursday Night Improv Hosted by Cream Boy
If you’re looking for a date night, girls’ night out, or a mandatory work outing (that your staff will actually like) — Look no further!…
Lincoln Park
Event details
Thursday, October 29th
7:30 p.m. – 9:00 p.m.
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iO Theater
1501 N. Kingsbury St.
Oct29
Music & Comedy, Theatre & Performing Arts
Brahms Requiem
Brahms once called A German Requiem his “human requiem” — and it fits. The gently powerful score emphasizes consolation for the living rather than fiery judgment, and…
Loop
Event details
Thursday, October 29th
7:30 p.m. – 9:30 p.m.
See all events in series

220 S. Michigan Ave.
Oct29
Music & Comedy
The Airborne Toxic Event
Orchestral indie rock band The Airborne Toxic Event is scheduled to perform live in Chicago, Illinois on Thursday, October 29, 2026.
Event details
Thursday, October 29th
7:30 p.m. – 10:30 p.m.
The Vic Theatre
3145 N. Sheffield

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