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Upcoming Chicago Events

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Dumb and Drummer
Aug20
Music & Comedy, Theatre & Performing Arts

Dumb and Drummer

Chicago’s best comedians doing their best material over live jazz! Every third Thursday at The Lincoln Lodge Theatre, Hosted by Jamaal Sanders, Hunter Hirsch, and…

Thursday August 20, 2026
7:30 p.m.9:00 p.m.
The Lincoln Lodge Theater
2040 N. Milwaukee Ave.
Comedy Hour at Annoyance Theatre
Aug21
Aug22
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 August 21, 2026
12:00 a.m.Saturday August 22, 2026
1:00 a.m.
Annoyance Theatre & Bar
851 W. Belmont Ave., 2nd Fl.
Spamalot
Aug21
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 August 21, 2026
5:00 p.m.7:00 p.m.
CIBC Theatre
18 W. Monroe St. , Chicago, IL, 60602
The Infinite Wrench
Aug21
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 August 21, 2026
7:00 p.m.8:00 p.m.
The Neo-Futurist Theater
5153 N. Ashland Ave.
Suffs
Aug21
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 August 21, 2026
7:00 p.m.9:30 p.m.
CIBC Theatre
18 W. Monroe St. , Chicago, IL, 60602
Teatro Zinzanni
Aug21
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…

Friday August 21, 2026
7:00 p.m.10:00 p.m.
Spiegeltent – Cambria Hotel
32 W. Randolph
Water for Elephants
Aug21
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 August 21, 2026
7:00 p.m.10:00 p.m.
James M. Nederlander Theatre
24 W. Randolph St.
Devil’s Daughter
Aug21
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 August 21, 2026
8:00 p.m.9:00 p.m.
iO Theater
1501 N. Kingsbury St.
The Lincoln Lodge
Aug21
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 August 21, 2026
8:00 p.m.9:30 p.m.
The Lincoln Lodge Theater
2040 N. Milwaukee Ave.
Voila: The Improvised Musical
Aug21
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 August 21, 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
Aug21
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 August 21, 2026
10:00 p.m.11:30 p.m.
Annoyance Theatre & Bar
851 W. Belmont Ave., 2nd Fl.
Spamalot
Aug22
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 August 22, 2026
5:00 p.m.7:00 p.m.
CIBC Theatre
18 W. Monroe St. , Chicago, IL, 60602
The Infinite Wrench
Aug22
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 August 22, 2026
7:00 p.m.8:00 p.m.
The Neo-Futurist Theater
5153 N. Ashland Ave.
Suffs
Aug22
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 August 22, 2026
7:00 p.m.9:30 p.m.
CIBC Theatre
18 W. Monroe St. , Chicago, IL, 60602
Water for Elephants
Aug22
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 August 22, 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
Aug22
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 August 22, 2026
7:30 p.m.8:30 p.m.
The Second City
1616 N. Wells St.
Clued In
Aug22
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 August 22, 2026
7:30 p.m.8:30 p.m.
The Second City
1616 N. Wells St., Theater on the Second Floor
The Lincoln Lodge
Aug22
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 August 22, 2026
8:00 p.m.9:30 p.m.
The Lincoln Lodge Theater
2040 N. Milwaukee Ave.
Best Of Annoyance Sketch
Aug22
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 August 22, 2026
9:30 p.m.10:30 p.m.
The Annoyance Theatre
851 W. Belmont Ave.
Spamalot
Aug23
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 August 23, 2026
5:00 p.m.7:00 p.m.
CIBC Theatre
18 W. Monroe St. , Chicago, IL, 60602
Suffs
Aug23
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 August 23, 2026
7:00 p.m.9:30 p.m.
CIBC Theatre
18 W. Monroe St. , Chicago, IL, 60602
Water for Elephants
Aug23
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 August 23, 2026
7:00 p.m.10:00 p.m.
James M. Nederlander Theatre
24 W. Randolph St.
Wheel of Improv
Aug23
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 August 23, 2026
7:30 p.m.8:30 p.m.
The Second City
1616 N. Wells St.
Spamalot
Aug25
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 August 25, 2026
5:00 p.m.7:00 p.m.
CIBC Theatre
18 W. Monroe St. , Chicago, IL, 60602
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