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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…
Saturday, October 24th
7:30 p.m. – 8:30 p.m.The Second City
1616 N. Wells St., Theater on the Second FloorMusic & 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.
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…
Saturday, October 24th
8:00 p.m. – 9:30 p.m.The Lincoln Lodge Theater
2040 N. Milwaukee Ave.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…
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…
Saturday, October 24th
9:30 p.m. – 10:30 p.m.The Annoyance Theatre
851 W. Belmont Ave.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…
Sunday, October 25th
2:00 p.m. – 3:00 p.m.Bughouse Theater
1910 West Irving Park RoadTheatre & Performing Arts
Spamalot
THE SHOW THAT SET BROADWAY BACK 1,000 YEARS…RETURNS! TOURING ACROSS AMERICA THE TONY AWARD-WINNING BEST MUSICAL COMEDY MONTY PYTHON’S SPAMALOT Peter Marks of The Washington…
Sunday, October 25th
5:00 p.m. – 7:00 p.m.CIBC Theatre
18 W. Monroe St. , Chicago, IL, 60602Theatre & Performing Arts
Suffs
BEHIND EVERY POWERFUL WOMAN… ARE MORE POWERFUL WOMEN. Direct from Broadway, comes the acclaimed Tony Award®-winning musical Suffs about the brilliant, passionate, and funny American…
Sunday, October 25th
7:00 p.m. – 9:30 p.m.CIBC Theatre
18 W. Monroe St. , Chicago, IL, 60602Theatre & Performing Arts
Water for Elephants
“Many wonders await audiences in this gorgeously imaginative Broadway musical.” – The New York Times The critically acclaimed bestselling novel comes to “thrilling, dazzling” life (Time…
Sunday, October 25th
7:00 p.m. – 10:00 p.m.James M. Nederlander Theatre
24 W. Randolph St.Music & Comedy
Matt Rife Live In Chicago – Stay Golden 2025-26 World Tour
Comedian Matt Rife will perform live at Chicago’s United Center on Oct. 25, 2026.
Sunday, October 25th
8:00 p.m. – 10:00 p.m.United Center
1901 W Madison St,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.
Theatre & Performing Arts
Spamalot
THE SHOW THAT SET BROADWAY BACK 1,000 YEARS…RETURNS! TOURING ACROSS AMERICA THE TONY AWARD-WINNING BEST MUSICAL COMEDY MONTY PYTHON’S SPAMALOT Peter Marks of The Washington…
Tuesday, October 27th
5:00 p.m. – 7:00 p.m.CIBC Theatre
18 W. Monroe St. , Chicago, IL, 60602Music & 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.…
Tuesday, October 27th
7:00 p.m. – 8:30 p.m.The Gallery Cabaret
2020 N Oakley AveTheatre & Performing Arts
Suffs
BEHIND EVERY POWERFUL WOMAN… ARE MORE POWERFUL WOMEN. Direct from Broadway, comes the acclaimed Tony Award®-winning musical Suffs about the brilliant, passionate, and funny American…
Tuesday, October 27th
7:00 p.m. – 9:30 p.m.CIBC Theatre
18 W. Monroe St. , Chicago, IL, 60602Theatre & Performing Arts
Water for Elephants
“Many wonders await audiences in this gorgeously imaginative Broadway musical.” – The New York Times The critically acclaimed bestselling novel comes to “thrilling, dazzling” life (Time…
Tuesday, October 27th
7:00 p.m. – 10:00 p.m.James M. Nederlander Theatre
24 W. Randolph St.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.
Festivals, Fairs & Special Events, Music & Comedy, Theatre & Performing Arts
Comic Court: Chicago’s #1 Comedy Court Show
Order in the court!Comic Court is back at The Lincoln Lodge every 2nd & 4th Tuesday at 9PM. Comedians argue ridiculous cases like actual lawyers,…
Tuesday, October 27th
9:00 p.m. – 10:30 p.m.The Lincoln Lodge
2040 North Milwaukee AvenueMusic & 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…
Wednesday, October 28th
9:00 p.m. – 11:00 p.m.Bordel Cocktail & Cabaret
1721 W DivisionTheatre & Performing Arts
Spamalot
THE SHOW THAT SET BROADWAY BACK 1,000 YEARS…RETURNS! TOURING ACROSS AMERICA THE TONY AWARD-WINNING BEST MUSICAL COMEDY MONTY PYTHON’S SPAMALOT Peter Marks of The Washington…
Thursday, October 29th
5:00 p.m. – 7:00 p.m.CIBC Theatre
18 W. Monroe St. , Chicago, IL, 60602Theatre & Performing Arts
Suffs
BEHIND EVERY POWERFUL WOMAN… ARE MORE POWERFUL WOMEN. Direct from Broadway, comes the acclaimed Tony Award®-winning musical Suffs about the brilliant, passionate, and funny American…
Thursday, October 29th
7:00 p.m. – 9:30 p.m.CIBC Theatre
18 W. Monroe St. , Chicago, IL, 60602Theatre & Performing Arts
Water for Elephants
“Many wonders await audiences in this gorgeously imaginative Broadway musical.” – The New York Times The critically acclaimed bestselling novel comes to “thrilling, dazzling” life (Time…
Thursday, October 29th
7:00 p.m. – 10:00 p.m.James M. Nederlander Theatre
24 W. Randolph St.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…
Friday, October 30th
12:00 a.m. – Saturday, October 31st
1:00 a.m.Annoyance Theatre & Bar
851 W. Belmont Ave., 2nd Fl.Theatre & Performing Arts
Spamalot
THE SHOW THAT SET BROADWAY BACK 1,000 YEARS…RETURNS! TOURING ACROSS AMERICA THE TONY AWARD-WINNING BEST MUSICAL COMEDY MONTY PYTHON’S SPAMALOT Peter Marks of The Washington…
Friday, October 30th
5:00 p.m. – 7:00 p.m.CIBC Theatre
18 W. Monroe St. , Chicago, IL, 60602Music & 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…
Friday, October 30th
7:00 p.m. – 8:00 p.m.The Neo-Futurist Theater
5153 N. Ashland Ave.

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