Water for Elephants
Oct17
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 17, 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
Oct17
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 17, 2026
7:30 p.m.8:30 p.m.
The Second City
1616 N. Wells St.
Clued In
Oct17
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 17, 2026
7:30 p.m.8:30 p.m.
The Second City
1616 N. Wells St., Theater on the Second Floor
The Lincoln Lodge
Oct17
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 17, 2026
8:00 p.m.9:30 p.m.
The Lincoln Lodge Theater
2040 N. Milwaukee Ave.
Best Of Annoyance Sketch
Oct17
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 17, 2026
9:30 p.m.10:30 p.m.
The Annoyance Theatre
851 W. Belmont Ave.
Teatro Zinzanni
Oct18
Music & Comedy, Theatre & Performing Arts

Teatro Zinzanni

Tickets are on sale now at https://zinzanni.com/chicago/tickets/ “Best Night Out” – CS Magazine | “You must see to believe!” – Forbes Teatro ZinZanni, Chicago’s most…

Sunday October 18, 2026
4:00 p.m.7:00 p.m.
Spiegeltent – Cambria Hotel
32 W. Randolph
Spamalot
Oct18
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 18, 2026
5:00 p.m.7:00 p.m.
CIBC Theatre
18 W. Monroe St. , Chicago, IL, 60602
Suffs
Oct18
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 18, 2026
7:00 p.m.9:30 p.m.
CIBC Theatre
18 W. Monroe St. , Chicago, IL, 60602
Water for Elephants
Oct18
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 18, 2026
7:00 p.m.10:00 p.m.
James M. Nederlander Theatre
24 W. Randolph St.
Magic Mondays
Oct19
Music & Comedy, Theatre & Performing Arts

Magic Mondays

Experience an unforgettable night of wonder at Magic Mondays!! Starring award-winning magician John Sturk, this monthly showcase features Chicago’s top conjurors performing mind-blowing illusions and…

Monday October 19, 2026
7:00 p.m.8:30 p.m.
iO Theater
1501 N. Kingsbury St.
Spamalot
Oct20
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 20, 2026
5:00 p.m.7:00 p.m.
CIBC Theatre
18 W. Monroe St. , Chicago, IL, 60602
Tuesday Good Show
Oct20
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 20, 2026
7:00 p.m.8:30 p.m.
The Gallery Cabaret
2020 N Oakley Ave
Suffs
Oct20
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 20, 2026
7:00 p.m.9:30 p.m.
CIBC Theatre
18 W. Monroe St. , Chicago, IL, 60602
Water for Elephants
Oct20
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…

Tuesday October 20, 2026
7:00 p.m.10:00 p.m.
James M. Nederlander Theatre
24 W. Randolph St.
Hooch & Holler Comedy Show
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…

Wednesday October 21, 2026
9:00 p.m.11:00 p.m.
Bordel Cocktail & Cabaret
1721 W Division
Spamalot
Oct22
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…

Thursday October 22, 2026
5:00 p.m.7:00 p.m.
CIBC Theatre
18 W. Monroe St. , Chicago, IL, 60602
Suffs
Oct22
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…

Thursday October 22, 2026
7:00 p.m.9:30 p.m.
CIBC Theatre
18 W. Monroe St. , Chicago, IL, 60602
Teatro Zinzanni
Oct22
Music & Comedy, Theatre & Performing Arts

Teatro Zinzanni

Tickets are on sale now at https://zinzanni.com/chicago/tickets/ “Best Night Out” – CS Magazine | “You must see to believe!” – Forbes Teatro ZinZanni, Chicago’s most…

Thursday October 22, 2026
7:00 p.m.10:00 p.m.
Teatro ZinZanni – Cambria Hotel
32 W Randolph St
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
Teatro Zinzanni
Oct23
Music & Comedy, Theatre & Performing Arts

Teatro Zinzanni

Tickets are on sale now at https://zinzanni.com/chicago/tickets/ “Best Night Out” – CS Magazine | “You must see to believe!” – Forbes Teatro ZinZanni, Chicago’s most…

Friday October 23, 2026
7:00 p.m.10:00 p.m.
Teatro ZinZanni – Cambria Hotel
32 W Randolph St