The 8th Dwarf
May24
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, May 24th
2:00 p.m.3:00 p.m.
Bughouse Theater
1910 West Irving Park Road
Windfall
May24
Theatre & Performing Arts

Windfall

This is a story about money. Don’t let them fool you otherwise. When a father loses his child in a clash with the local police,…

Sunday, May 24th
3:00 p.m.5:00 p.m.
Steppenwolf Theatre Company
1650 N. Halsted St. , Chicago, IL, 60614
Spamalot
May24
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, May 24th
5:00 p.m.7:00 p.m.
CIBC Theatre
18 W. Monroe St. , Chicago, IL, 60602
Thornhill – The Mercia Tour
May24
Music & Comedy

Thornhill – The Mercia Tour

Australian alternative metal band Thornhill is scheduled to perform in Chicago on May 24 as part of The Mercia Tour. Supporting Acts: 156/Silence, Fox Lake,…

Sunday, May 24th
6:00 p.m.11:00 p.m.
The Vic Theatre
3145 N. Sheffield
Wheel of Improv
May24
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, May 24th
7:30 p.m.8:30 p.m.
The Second City
1616 N. Wells St.
Spamalot
May26
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, May 26th
5:00 p.m.7:00 p.m.
CIBC Theatre
18 W. Monroe St. , Chicago, IL, 60602
Tuesday Good Show
May26
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, May 26th
7:00 p.m.8:30 p.m.
The Gallery Cabaret
2020 N Oakley Ave
Comic Court: Chicago’s #1 Comedy Court Show
May26
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, May 26th
9:00 p.m.10:30 p.m.
The Lincoln Lodge
2040 North Milwaukee Avenue
Stories
May27
Theatre & Performing Arts

Stories

Join Cunning Folk Theatre Co. for a new play based on a tale by classic Yiddish author Y.L. Peretz (and the company’s Midwest debut!) In…

Wednesday, May 27th
7:00 p.m.8:20 p.m.
Athenaeum Center for Thought & Culture
2936 North Southport Avenue
Windfall
May27
Theatre & Performing Arts

Windfall

This is a story about money. Don’t let them fool you otherwise. When a father loses his child in a clash with the local police,…

Wednesday, May 27th
7:30 p.m.9:30 p.m.
Steppenwolf Theatre Company
1650 N. Halsted St. , Chicago, IL, 60614
A$AP Rocky – Don’t Be Dumb World Tour 2026
May27
Music & Comedy

A$AP Rocky – Don’t Be Dumb World Tour 2026

Hip-hop artist A$AP Rocky is scheduled to kick off his 42-date “Don’t Be Dumb World Tour” in Chicago on Wednesday, May 27, 2026. This tour…

Wednesday, May 27th
7:30 p.m.10:30 p.m.
United Center
1901 W Madison St,
Hooch & Holler Comedy Show
May27
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, May 27th
9:00 p.m.11:00 p.m.
Bordel Cocktail & Cabaret
1721 W Division
Spamalot
May28
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, May 28th
5:00 p.m.7:00 p.m.
CIBC Theatre
18 W. Monroe St. , Chicago, IL, 60602
Stories
May28
Theatre & Performing Arts

Stories

Join Cunning Folk Theatre Co. for a new play based on a tale by classic Yiddish author Y.L. Peretz (and the company’s Midwest debut!) In…

Thursday, May 28th
7:00 p.m.8:20 p.m.
Athenaeum Center for Thought & Culture
2936 North Southport Avenue
Stars & Garters Presents “Stars & Garters After Dark”
May28
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, May 28th
7:00 p.m.9:30 p.m.
Stars and Garters Club
3914 N Clark St
Windfall
May28
Theatre & Performing Arts

Windfall

This is a story about money. Don’t let them fool you otherwise. When a father loses his child in a clash with the local police,…

Thursday, May 28th
7:30 p.m.9:30 p.m.
Steppenwolf Theatre Company
1650 N. Halsted St. , Chicago, IL, 60614
Comedy Hour at Annoyance Theatre
May29
May30
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, May 29th
12:00 a.m.Saturday, May 30th
1:00 a.m.
Annoyance Theatre & Bar
851 W. Belmont Ave., 2nd Fl.
Spamalot
May29
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, May 29th
5:00 p.m.7:00 p.m.
CIBC Theatre
18 W. Monroe St. , Chicago, IL, 60602
The Infinite Wrench
May29
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, May 29th
7:00 p.m.8:00 p.m.
The Neo-Futurist Theater
5153 N. Ashland Ave.
The Improvised Shakespeare Company®
May29
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…

Friday, May 29th
7:30 p.m.9:00 p.m.
iO Theater
1501 N. Kingsbury St.
Devil’s Daughter
May29
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, May 29th
7:30 p.m.9:00 p.m.
iO Theater
1501 N. Kingsbury St.
Windfall
May29
Theatre & Performing Arts

Windfall

This is a story about money. Don’t let them fool you otherwise. When a father loses his child in a clash with the local police,…

Friday, May 29th
7:30 p.m.9:30 p.m.
Steppenwolf Theatre Company
1650 N. Halsted St. , Chicago, IL, 60614
Rilo Kiley Live In Concert
May29
Music & Comedy

Rilo Kiley Live In Concert

Rilo Kiley is scheduled to perform in Chicago, IL, on Friday, May 29, 2026, as part of their reunion tour.

Friday, May 29th
7:30 p.m.10:30 p.m.
The Chicago Theatre
175 N. State
Summer Walker – Still Finally Over It Tour 2026
May29
Music & Comedy

Summer Walker – Still Finally Over It Tour 2026

R&B star Summer Walker is scheduled to perform in Chicago on Friday, May 29, 2026, as part of her first major arena run, the “Still…

Friday, May 29th
7:30 p.m.10:30 p.m.
United Center
1901 W Madison St,