Secret Sketch Show
Jan23
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…

Saturday January 23, 2027
9:00 p.m.10:30 p.m.
iO Theater
1501 N. Kingsbury St.
Best Of Annoyance Sketch
Jan23
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 January 23, 2027
9:30 p.m.10:30 p.m.
The Annoyance Theatre
851 W. Belmont Ave.
The 8th Dwarf
Jan24
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 January 24, 2027
2:00 p.m.3:00 p.m.
Bughouse Theater
1910 West Irving Park Road
Spamalot
Jan24
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 January 24, 2027
5:00 p.m.7:00 p.m.
CIBC Theatre
18 W. Monroe St. , Chicago, IL, 60602
Suffs
Jan24
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 January 24, 2027
7:00 p.m.9:30 p.m.
CIBC Theatre
18 W. Monroe St. , Chicago, IL, 60602
Water for Elephants
Jan24
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 January 24, 2027
7:00 p.m.10:00 p.m.
James M. Nederlander Theatre
24 W. Randolph St.
Spamalot
Jan26
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 January 26, 2027
5:00 p.m.7:00 p.m.
CIBC Theatre
18 W. Monroe St. , Chicago, IL, 60602
Tuesday Good Show
Jan26
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 January 26, 2027
7:00 p.m.8:30 p.m.
The Gallery Cabaret
2020 N Oakley Ave
Suffs
Jan26
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 January 26, 2027
7:00 p.m.9:30 p.m.
CIBC Theatre
18 W. Monroe St. , Chicago, IL, 60602
Water for Elephants
Jan26
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 January 26, 2027
7:00 p.m.10:00 p.m.
James M. Nederlander Theatre
24 W. Randolph St.
Hooch & Holler Comedy Show
Jan27
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 January 27, 2027
9:00 p.m.11:00 p.m.
Bordel Cocktail & Cabaret
1721 W Division
Spamalot
Jan28
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 January 28, 2027
5:00 p.m.7:00 p.m.
CIBC Theatre
18 W. Monroe St. , Chicago, IL, 60602
Suffs
Jan28
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 January 28, 2027
7:00 p.m.9:30 p.m.
CIBC Theatre
18 W. Monroe St. , Chicago, IL, 60602
Water for Elephants
Jan28
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 January 28, 2027
7:00 p.m.10:00 p.m.
James M. Nederlander Theatre
24 W. Randolph St.
Comedy Hour at Annoyance Theatre
Jan29
Jan30
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 January 29, 2027
12:00 a.m.Saturday January 30, 2027
1:00 a.m.
Annoyance Theatre & Bar
851 W. Belmont Ave., 2nd Fl.
Spamalot
Jan29
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 January 29, 2027
5:00 p.m.7:00 p.m.
CIBC Theatre
18 W. Monroe St. , Chicago, IL, 60602
The Infinite Wrench
Jan29
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 January 29, 2027
7:00 p.m.8:00 p.m.
The Neo-Futurist Theater
5153 N. Ashland Ave.
Suffs
Jan29
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 January 29, 2027
7:00 p.m.9:30 p.m.
CIBC Theatre
18 W. Monroe St. , Chicago, IL, 60602
Water for Elephants
Jan29
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 January 29, 2027
7:00 p.m.10:00 p.m.
James M. Nederlander Theatre
24 W. Randolph St.
Devil’s Daughter
Jan29
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 January 29, 2027
8:00 p.m.9:00 p.m.
iO Theater
1501 N. Kingsbury St.
3 Stages of Love Part 2: Simple Love/Unperfect Actor
Jan29
Theatre & Performing Arts

3 Stages of Love Part 2: Simple Love/Unperfect Actor

Love always makes for a good story because some part of it is always relatable. And what better way to explore all the various sides…

Friday January 29, 2027
8:00 p.m.9:00 p.m.
Mrs. Murphy & Sons Irish Bistro
3905 N Lincoln Ave
The Lincoln Lodge
Jan29
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 January 29, 2027
8:00 p.m.9:30 p.m.
The Lincoln Lodge Theater
2040 N. Milwaukee Ave.
Voila: The Improvised Musical
Jan29
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 January 29, 2027
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
Jan29
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 January 29, 2027
10:00 p.m.11:30 p.m.
Annoyance Theatre & Bar
851 W. Belmont Ave., 2nd Fl.