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Upcoming Chicago Events

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October 3, 2025: Oct3
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…
Lakeview
Event details
Friday, October 3rd
9:00 p.m. – 10:00 p.m.
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ComedySportz Chicago
929 W. Belmont Ave.
Oct3
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 3rd
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,
Oct3
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 3rd
10:00 p.m. – 11:30 p.m.
Annoyance Theatre & Bar
851 W. Belmont Ave., 2nd Fl.
October 4, 2025: Oct4
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…
Loop
Event details
Saturday, October 4th
12:00 p.m. – 3:00 p.m.
Spiegeltent – Cambria Hotel
32 W. Randolph
Oct4
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…
Event details
Saturday, October 4th
6:00 p.m. – 7:30 p.m.
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Malarkey Comedy Company
1501 N Kingsbury St
Oct4
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…
Loop
Event details
Saturday, October 4th
6:00 p.m. – 10:00 p.m.
Spiegeltent – Cambria Hotel
32 W. Randolph
Oct4
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 4th
7:00 p.m. – 8:00 p.m.
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The Neo-Futurist Theater
5153 N. Ashland Ave.
Oct4
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 4th
7:30 p.m. – 8:30 p.m.
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The Second City
1616 N. Wells St.
Oct4
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 4th
7:30 p.m. – 8:30 p.m.
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The Second City
1616 N. Wells St., Theater on the Second Floor
Oct4
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
Saturday, October 4th
8:00 p.m. – 9:30 p.m.
See all events in series
The Lincoln Lodge Theater
2040 N. Milwaukee Ave.
Oct4
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…
Event details
Saturday, October 4th
8:00 p.m. – 9:30 p.m.
See all events in series
Malarkey Comedy Company
1501 N Kingsbury St
Oct4
Music & Comedy, Theatre & Performing Arts
Here 4 A Bit *Naughty Improv
Join us again for a whose line styled night of explosive laughter that will titillate your “funny” bone. Fast paced short form improv, hilarious songs,…
Old Town
Event details
Saturday, October 4th
9:00 p.m. – 10:00 p.m.
See all events in series
The Second City
1616 N. Wells St., Theater on the Second Floor
Oct4
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 4th
9:30 p.m. – 10:30 p.m.
The Annoyance Theatre
851 W. Belmont Ave.
Oct4
Music & Comedy, Theatre & Performing Arts
LET’S PLAY A GAME: Chicago’s scariest short-form show
Who’s Line is it Anyways meets Fear Factor in LETS PLAY A GAME, a new short form show that’s a unique blend of comedy, chaos,…
Lakeview
Event details
Saturday, October 4th
10:00 p.m. – 11:00 p.m.
See all events in series
Annoyance Theatre & Bar
851 W. Belmont Ave., 2nd Fl.
October 5, 2025: Oct5
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…
Loop
Event details
Sunday, October 5th
5:00 a.m. – 9:00 p.m.
Spiegeltent – Cambria Hotel
32 W. Randolph
October 7, 2025: Oct7
Theatre & Performing Arts
Alice in Wonderland
Follow Alice as she travels down the Rabbit Hole to the most amazing places! Along her fantastic journey she’ll meet the Mad Hatter, March Hare,…
Event details
Tuesday, October 7th
10:30 a.m. – 11:30 p.m.
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October 8, 2025: Oct8
Theatre & Performing Arts
Alice in Wonderland
Follow Alice as she travels down the Rabbit Hole to the most amazing places! Along her fantastic journey she’ll meet the Mad Hatter, March Hare,…
Event details
Wednesday, October 8th
10:30 a.m. – 11:30 p.m.
See all events in series

Oct8
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 8th
9:00 p.m. – 11:00 p.m.
Bordel Cocktail & Cabaret
1721 W Division
October 9, 2025: Oct9
Theatre & Performing Arts
Alice in Wonderland
Follow Alice as she travels down the Rabbit Hole to the most amazing places! Along her fantastic journey she’ll meet the Mad Hatter, March Hare,…
Event details
Thursday, October 9th
10:30 a.m. – 11:30 p.m.
See all events in series

Oct9
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…
Loop
Event details
Thursday, October 9th
6:00 p.m. – 10:00 p.m.
Spiegeltent – Cambria Hotel
32 W. Randolph
Oct9
Music & Comedy, Theatre & Performing Arts
Improvsed 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 every…
Event details
Thursday, October 9th
8:00 p.m. – 9:00 p.m.
See all events in series
Malarkey Comedy Company
1501 N Kingsbury St
October 10, 2025: Oct10
Oct11
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 10th
12:00 a.m. – Saturday, October 11th
1:00 a.m.
See all events in series
Annoyance Theatre & Bar
851 W. Belmont Ave., 2nd Fl.
Oct10
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…
Loop
Event details
Friday, October 10th
6:00 p.m. – 10:00 p.m.
Spiegeltent – Cambria Hotel
32 W. Randolph
Oct10
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 10th
7:00 p.m. – 8:00 p.m.
See all events in series
The Neo-Futurist Theater
5153 N. Ashland Ave.

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