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Upcoming Chicago Events

Check out what's happening all around Chicago.

October 19, 2026: Oct19
Theatre & Performing Arts
Jekyll& Hyde
Kokandy Productions’ critically acclaimed revival of the 10-time 2025 Jeff Award–nominated musical JEKYLL & HYDE will make its Broadway In Chicago debut at the Broadway Playhouse at…
Event details
Monday, October 19th
7:00 p.m. – 10:00 p.m.
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Broadway Playhouse at Water Tower Place
175 E. Chestnut St .Chicago, IL 60611
October 20, 2026: Oct20
Theatre & Performing Arts
Jekyll& Hyde
Kokandy Productions’ critically acclaimed revival of the 10-time 2025 Jeff Award–nominated musical JEKYLL & HYDE will make its Broadway In Chicago debut at the Broadway Playhouse at…
Event details
Tuesday, October 20th
7:00 p.m. – 10:00 p.m.
See all events in series
Broadway Playhouse at Water Tower Place
175 E. Chestnut St .Chicago, IL 60611
October 21, 2026: Oct21
Music & Comedy, Theatre & Performing Arts
Don Giovanni
The path to damnation never sounded so sweet The 2026/27 Season kicks off with a thrilling fable of deceit and retribution. Sharp humor, high drama,…
Loop
Event details
Wednesday, October 21st
2:00 p.m. – 5:30 p.m.
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Lyric Opera of Chicago
20 N. Wacker Dr. , Chicago, IL, 60606
Oct21
Theatre & Performing Arts
Jekyll& Hyde
Kokandy Productions’ critically acclaimed revival of the 10-time 2025 Jeff Award–nominated musical JEKYLL & HYDE will make its Broadway In Chicago debut at the Broadway Playhouse at…
Event details
Wednesday, October 21st
7:00 p.m. – 10:00 p.m.
See all events in series
Broadway Playhouse at Water Tower Place
175 E. Chestnut St .Chicago, IL 60611
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.
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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
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
Theatre & Performing Arts
Jekyll& Hyde
Kokandy Productions’ critically acclaimed revival of the 10-time 2025 Jeff Award–nominated musical JEKYLL & HYDE will make its Broadway In Chicago debut at the Broadway Playhouse at…
Event details
Thursday, October 22nd
7:00 p.m. – 10:00 p.m.
See all events in series
Broadway Playhouse at Water Tower Place
175 E. Chestnut St .Chicago, IL 60611
Oct22
Theatre & Performing Arts
Redtwist Theatre’s “‘Night Mother” By Marsha Norman
Award-winning Redtwist Theatre announces the cast and creative team for ‘night Mother, April 16 – May 24, by Marsha Norman and directed by Executive Artistic…
Edgewater
Event details
Thursday, October 22nd
7:30 p.m. – 9:30 p.m.
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Redtwist Theatre
1044 W. Bryn Mawr Ave
October 23, 2026: Oct23
Oct24
Theatre & Performing Arts
Comedy Hour at Annoyance Theatre
Each week, Chicago comics bring the freshest, most experimental new material to the Annoyance for the Comedy Hour. The weekly show is an eclectic mix…
Lakeview
Event details
Friday, October 23rd
12:00 a.m. – Saturday, October 24th
1:00 a.m.
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Annoyance Theatre & Bar
851 W. Belmont Ave., 2nd Fl.
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.
See all events in series
The Neo-Futurist Theater
5153 N. Ashland Ave.
Oct23
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
Friday, October 23rd
7:00 p.m. – 9:30 p.m.
See all events in series
Lyric Opera of Chicago
20 N. Wacker Dr. , Chicago, IL, 60606
Oct23
Theatre & Performing Arts
Jekyll& Hyde
Kokandy Productions’ critically acclaimed revival of the 10-time 2025 Jeff Award–nominated musical JEKYLL & HYDE will make its Broadway In Chicago debut at the Broadway Playhouse at…
Event details
Friday, October 23rd
7:00 p.m. – 10:00 p.m.
See all events in series
Broadway Playhouse at Water Tower Place
175 E. Chestnut St .Chicago, IL 60611
Oct23
Theatre & Performing Arts
Redtwist Theatre’s “‘Night Mother” By Marsha Norman
Award-winning Redtwist Theatre announces the cast and creative team for ‘night Mother, April 16 – May 24, by Marsha Norman and directed by Executive Artistic…
Edgewater
Event details
Friday, October 23rd
7:30 p.m. – 9:30 p.m.
See all events in series
Redtwist Theatre
1044 W. Bryn Mawr Ave
Oct23
Theatre & Performing Arts
3 Stages of Love Part 2: Simple Love/Unperfect Actor
Love always makes for a good story because some part of it is always relatable. And what better way to explore all the various sides…
Event details
Friday, October 23rd
8:00 p.m. – 9:00 p.m.
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Mrs. Murphy & Sons Irish Bistro
3905 N Lincoln Ave
Oct23
Theatre & Performing Arts
The Lincoln Lodge
The Lincoln Lodge stand-up comedy and variety showcase plays every Friday and Saturday night in Chicago’s glamorous Logan Square! In addition to The Lodge’s rotating…
Event details
Friday, October 23rd
8:00 p.m. – 9:30 p.m.
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The Lincoln Lodge Theater
2040 N. Milwaukee Ave.
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
Theatre & Performing Arts
A Random Memory
A Random Memory is a close-up magic show about memories, connection, and bringing people together to experience magic. In this highly interactive hour of card…
Event details
Friday, October 23rd
9:00 p.m. – 10:00 p.m.
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Stars & Garters
3914 N Clark 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
Theatre & Performing Arts
The 8th Dwarf
Binkley, an outsider dwarf from the Kingdom of Magical Land, is quiet, timid and scared of the dark — not exactly the best characteristics for…
Event details
Saturday, October 24th
2:00 p.m. – 3:00 p.m.
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Bughouse Theater
1910 West Irving Park Road
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
Theatre & Performing Arts
FreakShow & Tell
21+ ONLY Brianna Wellen, Chicago Reader: Sideshow entertainer Thom Britton’s solo show is part performance, part demonstration. Britton is a charismatic performer who appears genuinely…
Event details
Saturday, October 24th
7:00 p.m. – 8:30 p.m.
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Stars & Garters Theater
3914 N. Clark St.
Oct24
Theatre & Performing Arts
The Séance
The Séance is an original stage show that recreates an authentic Victorian-era séance. We investigate the history, tell the stories of the participants, and demonstrate…
Event details
Saturday, October 24th
7:00 p.m. – 8:30 p.m.
See all events in series
Stars & Garters
3914 N Clark St

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