Mandatory Photo Credit: Abel Arciniega :: @tequilagraphics

Upcoming Chicago Events

Name: Windfall
Start: 2026-05-19T19:30:00-05:00
End: 2026-05-19T21:30:00-05:00
Location: Steppenwolf Ensemble Theater

Check out what's happening all around Chicago.

May 16, 2026: May16
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…
Event details
Saturday, May 16th
8:00 p.m. – 9:30 p.m.
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The Lincoln Lodge Theater
2040 N. Milwaukee Ave.
May16
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…
Lincoln Park
Event details
Saturday, May 16th
9:00 p.m. – 10:30 p.m.
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iO Theater
1501 N. Kingsbury St.
May16
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…
Lakeview
Event details
Saturday, May 16th
9:30 p.m. – 10:30 p.m.
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The Annoyance Theatre
851 W. Belmont Ave.
May 17, 2026: May17
Theatre & Performing Arts
Les Misérables
STILL THE WORLD’S MOST POPULAR MUSICAL Cameron Mackintosh’s acclaimed production of Alain Boublil and Claude-Michel Schönberg’s Tony Award-winning musical phenomenon, Les Misérables, makes a triumphant return…
Loop
Event details
Sunday, May 17th
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Cadillac Palace Theatre
151 W. Randolph St. , Chicago, IL, 60601
May17
Museums, Galleries & Exhibitions
By A Thread: Nature’s Resilience
By A Thread: Nature’s Resilience dives into the science of biodiversity and what it takes to protect it—showcasing the research, conservation, and education work happening…
Lincoln Park
Event details
Sunday, May 17th
10:00 a.m. – 4:00 p.m.
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Peggy Notebaert Nature Museum
2430 N. Cannon Dr.
May17
Museums, Galleries & Exhibitions
Illinois Holocaust Museum presents Experience360
Illinois Holocaust Museum presents Experience360 provides a panoramic view through history and truth, inviting visitors of all backgrounds to witness stories of survival, ask questions, and reflect…
Event details
Sunday, May 17th
10:00 a.m. – 5:00 p.m.
See all events in series
Illinois Holocaust Museum presents Experience360
360 N State St
May17
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…
Loop
Event details
Sunday, May 17th
10:00 a.m. – 5:00 p.m.
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American Writers Museum
180 N. Michigan Ave.
May17
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…
Event details
Sunday, May 17th
2:00 p.m. – 3:00 p.m.
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Bughouse Theater
1910 West Irving Park Road
May17
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,…
Lincoln Park
Event details
Sunday, May 17th
3:00 p.m. – 5:00 p.m.
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Steppenwolf Theatre Company
1650 N. Halsted St. , Chicago, IL, 60614
May17
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!)…
Old Town
Event details
Sunday, May 17th
7:30 p.m. – 8:30 p.m.
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The Second City
1616 N. Wells St.
May17
Music & Comedy
Good Kid – Can We Hang Out? 2026 Tour
Toronto indie rock band Good Kid /w special guest Inoha will perform live at Chicago’s Riviera Theatre on May 17, 2026.
Uptown
Event details
Sunday, May 17th
7:30 p.m. – 10:30 p.m.
The Riveria Theater
4746 N Racine Ave
May17
Music & Comedy
Bruno Mars – The Romantic Tour
16-time Grammy winner Bruno Mars /w special guests Leon Thomas & DJ Pee.Wee will perform live at Chicago’s Soldier Field on May 16-17, 2026.
South Loop
Event details
Sunday, May 17th
7:30 p.m. – 11:30 p.m.
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Soldier Field
1410 Special Olympics Drive
May 18, 2026: May18
Theatre & Performing Arts
Les Misérables
STILL THE WORLD’S MOST POPULAR MUSICAL Cameron Mackintosh’s acclaimed production of Alain Boublil and Claude-Michel Schönberg’s Tony Award-winning musical phenomenon, Les Misérables, makes a triumphant return…
Loop
Event details
Monday, May 18th
See all events in series
Cadillac Palace Theatre
151 W. Randolph St. , Chicago, IL, 60601
May18
Museums, Galleries & Exhibitions
By A Thread: Nature’s Resilience
By A Thread: Nature’s Resilience dives into the science of biodiversity and what it takes to protect it—showcasing the research, conservation, and education work happening…
Lincoln Park
Event details
Monday, May 18th
10:00 a.m. – 4:00 p.m.
See all events in series
Peggy Notebaert Nature Museum
2430 N. Cannon Dr.
May18
Museums, Galleries & Exhibitions
Illinois Holocaust Museum presents Experience360
Illinois Holocaust Museum presents Experience360 provides a panoramic view through history and truth, inviting visitors of all backgrounds to witness stories of survival, ask questions, and reflect…
Event details
Monday, May 18th
10:00 a.m. – 5:00 p.m.
See all events in series
Illinois Holocaust Museum presents Experience360
360 N State St
May18
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…
Loop
Event details
Monday, May 18th
10:00 a.m. – 5:00 p.m.
See all events in series
American Writers Museum
180 N. Michigan Ave.
May18
Music & Comedy, Theatre & Performing Arts
Magic Mondays
Experience an unforgettable night of wonder at Magic Mondays!! Starring award-winning magician John Sturk, this monthly showcase features Chicago’s top conjurors performing mind-blowing illusions and…
Lincoln Park
Event details
Monday, May 18th
7:00 p.m. – 8:30 p.m.
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iO Theater
1501 N. Kingsbury St.
May 19, 2026: May19
Theatre & Performing Arts
Les Misérables
STILL THE WORLD’S MOST POPULAR MUSICAL Cameron Mackintosh’s acclaimed production of Alain Boublil and Claude-Michel Schönberg’s Tony Award-winning musical phenomenon, Les Misérables, makes a triumphant return…
Loop
Event details
Tuesday, May 19th
See all events in series
Cadillac Palace Theatre
151 W. Randolph St. , Chicago, IL, 60601
May19
Museums, Galleries & Exhibitions
By A Thread: Nature’s Resilience
By A Thread: Nature’s Resilience dives into the science of biodiversity and what it takes to protect it—showcasing the research, conservation, and education work happening…
Lincoln Park
Event details
Tuesday, May 19th
10:00 a.m. – 4:00 p.m.
See all events in series
Peggy Notebaert Nature Museum
2430 N. Cannon Dr.
May19
Museums, Galleries & Exhibitions
Illinois Holocaust Museum presents Experience360
Illinois Holocaust Museum presents Experience360 provides a panoramic view through history and truth, inviting visitors of all backgrounds to witness stories of survival, ask questions, and reflect…
Event details
Tuesday, May 19th
10:00 a.m. – 5:00 p.m.
See all events in series
Illinois Holocaust Museum presents Experience360
360 N State St
May19
Music & Comedy
Chaos and Carnage: Thy Art Is Murder, Carnifex & Bodysnatcher
The Chaos and Carnage 2026 tour will be at the Ramova Theatre in Chicago on Tuesday, May 19, 2026. This year’s installment features a massive…
Event details
Tuesday, May 19th
4:45 p.m. – 10:00 p.m.
Ramova Theatre
3520 S. Halsted St.
May19
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…
Loop
Event details
Tuesday, May 19th
5:00 p.m. – 7:00 p.m.
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CIBC Theatre
18 W. Monroe St. , Chicago, IL, 60602
May19
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.…
Event details
Tuesday, May 19th
7:00 p.m. – 8:30 p.m.
The Gallery Cabaret
2020 N Oakley Ave
May19
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,…
Lincoln Park
Event details
Tuesday, May 19th
7:30 p.m. – 9:30 p.m.
See all events in series
Steppenwolf Theatre Company
1650 N. Halsted St. , Chicago, IL, 60614