The 8th Dwarf
Oct25
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 Road
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 25th
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 25th
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 25th
7:00 p.m.10:00 p.m.
James M. Nederlander Theatre
24 W. Randolph St.
Matt Rife Live In Chicago – Stay Golden 2025-26 World Tour
Oct25
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,
American Prophets: Writers, Religion, and Culture
Oct26
Museums, Galleries & Exhibitions

American Prophets: Writers, Religion, and Culture

American Prophets journeys through the pages of American history to explore the influence of religion and spirituality on writers and culture, with interactive displays incorporating…

Monday, October 26th
10:00 a.m.5:00 p.m.
American Writers Museum
180 N. Michigan Ave.
Tedeschi Trucks Band – Future Soul 2026 Tour
Oct26
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.

Monday, October 26th
7:30 p.m.10:30 p.m.
The Chicago Theatre
175 N. State
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 27th
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 27th
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 27th
7:00 p.m.9:30 p.m.
CIBC Theatre
18 W. Monroe St. , Chicago, IL, 60602
Water for Elephants
Oct27
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 27th
7:00 p.m.10:00 p.m.
James M. Nederlander Theatre
24 W. Randolph St.
Tedeschi Trucks Band – Future Soul 2026 Tour
Oct27
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.

Tuesday, October 27th
7:30 p.m.10:30 p.m.
The Chicago Theatre
175 N. State
Comic Court: Chicago’s #1 Comedy Court Show
Oct27
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 Avenue
Hooch & Holler Comedy Show
Oct28
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 28th
9:00 p.m.11:00 p.m.
Bordel Cocktail & Cabaret
1721 W Division
American Prophets: Writers, Religion, and Culture
Oct29
Museums, Galleries & Exhibitions

American Prophets: Writers, Religion, and Culture

American Prophets journeys through the pages of American history to explore the influence of religion and spirituality on writers and culture, with interactive displays incorporating…

Thursday, October 29th
10:00 a.m.5:00 p.m.
American Writers Museum
180 N. Michigan Ave.
Spamalot
Oct29
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 29th
5:00 p.m.7:00 p.m.
CIBC Theatre
18 W. Monroe St. , Chicago, IL, 60602
Suffs
Oct29
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 29th
7:00 p.m.9:30 p.m.
CIBC Theatre
18 W. Monroe St. , Chicago, IL, 60602
Water for Elephants
Oct29
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 29th
7:00 p.m.10:00 p.m.
James M. Nederlander Theatre
24 W. Randolph St.
Comedy Hour at Annoyance Theatre
Oct30
Oct31
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.
American Prophets: Writers, Religion, and Culture
Oct30
Museums, Galleries & Exhibitions

American Prophets: Writers, Religion, and Culture

American Prophets journeys through the pages of American history to explore the influence of religion and spirituality on writers and culture, with interactive displays incorporating…

Friday, October 30th
10:00 a.m.5:00 p.m.
American Writers Museum
180 N. Michigan Ave.
Spamalot
Oct30
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, 60602
The Infinite Wrench
Oct30
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 30th
7:00 p.m.8:00 p.m.
The Neo-Futurist Theater
5153 N. Ashland Ave.
Suffs
Oct30
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 30th
7:00 p.m.9:30 p.m.
CIBC Theatre
18 W. Monroe St. , Chicago, IL, 60602
Water for Elephants
Oct30
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 30th
7:00 p.m.10:00 p.m.
James M. Nederlander Theatre
24 W. Randolph St.