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Spamalot
Jun6
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 June 6, 2026
5:00 p.m.7:00 p.m.
CIBC Theatre
18 W. Monroe St. , Chicago, IL, 60602
The Infinite Wrench
Jun6
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 June 6, 2026
7:00 p.m.8:00 p.m.
The Neo-Futurist Theater
5153 N. Ashland Ave.
Teatro Zinzanni
Jun6
Music & Comedy, Theatre & Performing Arts

Teatro Zinzanni

Tickets are on sale Now at https://zinzanni.com/chicago/ for Love, Chaos, & Dinner ! Teatro Zinzanni returns to the vibrant Chicago Loop inside the velvet walls…

Saturday June 6, 2026
7:00 p.m.10:00 p.m.
Spiegeltent – Cambria Hotel
32 W. Randolph
Baby Wants Candy! The Original Completely Improvised Musical
Jun6
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 June 6, 2026
7:30 p.m.8:30 p.m.
The Second City
1616 N. Wells St.
Clued In
Jun6
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 June 6, 2026
7:30 p.m.8:30 p.m.
The Second City
1616 N. Wells St., Theater on the Second Floor
The Improvised Shakespeare Company®
Jun6
Theatre & Performing Arts

The Improvised Shakespeare Company®

The Improvised Shakespeare Company® proudly presents its critically-acclaimed, long-running hit show Improvised Shakespeare Chicago, now in its 19th year! Join us for an evening of…

Saturday June 6, 2026
7:30 p.m.9:00 p.m.
iO Theater
1501 N. Kingsbury St.
The Lincoln Lodge
Jun6
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 June 6, 2026
8:00 p.m.9:30 p.m.
The Lincoln Lodge Theater
2040 N. Milwaukee Ave.
Best Of Annoyance Sketch
Jun6
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 June 6, 2026
9:30 p.m.10:30 p.m.
The Annoyance Theatre
851 W. Belmont Ave.
The 79th Annual 57th Street Art Fair
Jun7
Festivals, Fairs & Special Events

The 79th Annual 57th Street Art Fair

The 79th Annual 57th Street Art Fair returns June 6, 11 AM–6 PM, and Sunday, June 7, 10 AM–5 PM, featuring nearly 200 artists and…

Sunday June 7, 2026
10:00 a.m.5:00 p.m.
57th Street, Hyde Park
57th Street, Hyde Park, IL
Spamalot
Jun7
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 June 7, 2026
5:00 p.m.7:00 p.m.
CIBC Theatre
18 W. Monroe St. , Chicago, IL, 60602
Wheel of Improv
Jun7
Music & Comedy, Theatre & Performing Arts

Wheel of Improv

Chicago’s top comedians battle it out for laughs, glory, and sweet sweet points in an interactive game show, featuring a live studio audience (that’s you!)…

Sunday June 7, 2026
7:30 p.m.8:30 p.m.
The Second City
1616 N. Wells St.
Kinky Boots
Jun9
Theatre & Performing Arts

Kinky Boots

The boots are back! Kinky Boots will lift your spirits to high-heeled heights! Celebrated with six Tony Awards®, including Best Musical, a Grammy Award® for Best Musical…

Tuesday June 9, 2026
James M. Nederlander Theatre
24 W. Randolph St.
Spamalot
Jun9
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 June 9, 2026
5:00 p.m.7:00 p.m.
CIBC Theatre
18 W. Monroe St. , Chicago, IL, 60602
Tuesday Good Show
Jun9
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 June 9, 2026
7:00 p.m.8:30 p.m.
The Gallery Cabaret
2020 N Oakley Ave
Kinky Boots
Jun10
Theatre & Performing Arts

Kinky Boots

The boots are back! Kinky Boots will lift your spirits to high-heeled heights! Celebrated with six Tony Awards®, including Best Musical, a Grammy Award® for Best Musical…

Wednesday June 10, 2026
James M. Nederlander Theatre
24 W. Randolph St.
Hooch & Holler Comedy Show
Jun10
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 June 10, 2026
9:00 p.m.11:00 p.m.
Bordel Cocktail & Cabaret
1721 W Division
Kinky Boots
Jun11
Theatre & Performing Arts

Kinky Boots

The boots are back! Kinky Boots will lift your spirits to high-heeled heights! Celebrated with six Tony Awards®, including Best Musical, a Grammy Award® for Best Musical…

Thursday June 11, 2026
James M. Nederlander Theatre
24 W. Randolph St.
Spamalot
Jun11
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 June 11, 2026
5:00 p.m.7:00 p.m.
CIBC Theatre
18 W. Monroe St. , Chicago, IL, 60602
Stars & Garters Presents “Stars & Garters After Dark”
Jun11
Theatre & Performing Arts

Stars & Garters Presents “Stars & Garters After Dark”

Chicago’s brand new Stars & Garters, 3914 N Clark St, presents Stars & Garters After Dark, every Thursday at 7 p.m. in the Rouge Room.…

Thursday June 11, 2026
7:00 p.m.9:30 p.m.
Stars and Garters Club
3914 N Clark St
Teatro Zinzanni
Jun11
Music & Comedy, Theatre & Performing Arts

Teatro Zinzanni

Tickets are on sale Now at https://zinzanni.com/chicago/ for Love, Chaos, & Dinner ! Teatro Zinzanni returns to the vibrant Chicago Loop inside the velvet walls…

Thursday June 11, 2026
7:00 p.m.10:00 p.m.
Spiegeltent – Cambria Hotel
32 W. Randolph
Kinky Boots
Jun12
Theatre & Performing Arts

Kinky Boots

The boots are back! Kinky Boots will lift your spirits to high-heeled heights! Celebrated with six Tony Awards®, including Best Musical, a Grammy Award® for Best Musical…

Friday June 12, 2026
James M. Nederlander Theatre
24 W. Randolph St.
Comedy Hour at Annoyance Theatre
Jun12
Jun13
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 June 12, 2026
12:00 a.m.Saturday June 13, 2026
1:00 a.m.
Annoyance Theatre & Bar
851 W. Belmont Ave., 2nd Fl.
Spamalot
Jun12
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 June 12, 2026
5:00 p.m.7:00 p.m.
CIBC Theatre
18 W. Monroe St. , Chicago, IL, 60602
The Infinite Wrench
Jun12
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 June 12, 2026
7:00 p.m.8:00 p.m.
The Neo-Futurist Theater
5153 N. Ashland Ave.
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