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Water for Elephants
Oct22
Theatre & 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 22, 2026
7:00 p.m.10:00 p.m.
James M. Nederlander Theatre
24 W. Randolph St.
Comedy Hour at Annoyance Theatre
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…

Friday October 23, 2026
12:00 a.m.Saturday October 24, 2026
1:00 a.m.
Annoyance Theatre & Bar
851 W. Belmont Ave., 2nd Fl.
Spamalot
Oct23
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 23, 2026
5:00 p.m.7:00 p.m.
CIBC Theatre
18 W. Monroe St. , Chicago, IL, 60602
The Infinite Wrench
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…

Friday October 23, 2026
7:00 p.m.8:00 p.m.
The Neo-Futurist Theater
5153 N. Ashland Ave.
Suffs
Oct23
Theatre & 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…

Friday October 23, 2026
7:00 p.m.9:30 p.m.
CIBC Theatre
18 W. Monroe St. , Chicago, IL, 60602
Water for Elephants
Oct23
Theatre & 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…

Friday October 23, 2026
7:00 p.m.10:00 p.m.
James M. Nederlander Theatre
24 W. Randolph St.
Devil’s Daughter
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.…

Friday October 23, 2026
8:00 p.m.9:00 p.m.
iO Theater
1501 N. Kingsbury St.
The Lincoln Lodge
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…

Friday October 23, 2026
8:00 p.m.9:30 p.m.
The Lincoln Lodge Theater
2040 N. Milwaukee Ave.
Voila: The Improvised Musical
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…

Friday October 23, 2026
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,
Hitch*Cocktails
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…

Friday October 23, 2026
10:00 p.m.11:30 p.m.
Annoyance Theatre & Bar
851 W. Belmont Ave., 2nd Fl.
Spamalot
Oct24
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…

Saturday October 24, 2026
5:00 p.m.7:00 p.m.
CIBC Theatre
18 W. Monroe St. , Chicago, IL, 60602
The Infinite Wrench
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…

Saturday October 24, 2026
7:00 p.m.8:00 p.m.
The Neo-Futurist Theater
5153 N. Ashland Ave.
Suffs
Oct24
Theatre & 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…

Saturday October 24, 2026
7:00 p.m.9:30 p.m.
CIBC Theatre
18 W. Monroe St. , Chicago, IL, 60602
Water for Elephants
Oct24
Theatre & 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…

Saturday October 24, 2026
7:00 p.m.10:00 p.m.
James M. Nederlander Theatre
24 W. Randolph St.
Baby Wants Candy! The Original Completely Improvised Musical
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…

Saturday October 24, 2026
7:30 p.m.8:30 p.m.
The Second City
1616 N. Wells St.
Clued In
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…

Saturday October 24, 2026
7:30 p.m.8:30 p.m.
The Second City
1616 N. Wells St., Theater on the Second Floor
The Lincoln Lodge
Oct24
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 24, 2026
8:00 p.m.9:30 p.m.
The Lincoln Lodge Theater
2040 N. Milwaukee Ave.
Best Of Annoyance Sketch
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…

Saturday October 24, 2026
9:30 p.m.10:30 p.m.
The Annoyance Theatre
851 W. Belmont Ave.
Spamalot
Oct25
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…

Sunday October 25, 2026
5:00 p.m.7:00 p.m.
CIBC Theatre
18 W. Monroe St. , Chicago, IL, 60602
Suffs
Oct25
Theatre & 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 25, 2026
7:00 p.m.9:30 p.m.
CIBC Theatre
18 W. Monroe St. , Chicago, IL, 60602
Water for Elephants
Oct25
Theatre & 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 25, 2026
7:00 p.m.10:00 p.m.
James M. Nederlander Theatre
24 W. Randolph St.
Spamalot
Oct27
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 27, 2026
5:00 p.m.7:00 p.m.
CIBC Theatre
18 W. Monroe St. , Chicago, IL, 60602
Tuesday Good Show
Oct27
Music & 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 27, 2026
7:00 p.m.8:30 p.m.
The Gallery Cabaret
2020 N Oakley Ave
Suffs
Oct27
Theatre & 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 27, 2026
7:00 p.m.9:30 p.m.
CIBC Theatre
18 W. Monroe St. , Chicago, IL, 60602
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