Events in Chicago, Illinois

Sat, May 23 · 12:00 AM

Chicago Architecture Center River Cruise

Chicago's First Lady Cruises

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May 23

Sat · 12:00 AM

Chicago Architecture Center River Cruise

Chicago's First Lady Cruises · Chicago, IL

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Sat, May 23 · 9:30 AM

Goodnight Moon

Chicago Children's Theatre

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May 23

Sat · 9:30 AM

Goodnight Moon

Chicago Children's Theatre · Chicago, IL

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Sat, May 23 · 10:59 AM

2026 Suenos - 2 Day Pass (5/23-5/24) (J Balvin, Kali Uchis, Fuerza Regida)

Hutchinson Field Grant Park

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May 23

Sat · 10:59 AM

2026 Suenos - 2 Day Pass (5/23-5/24) (J Balvin, Kali Uchis, Fuerza Regida)

Hutchinson Field Grant Park · Chicago, IL

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Sat, May 23 · 11:30 AM

Goodnight Moon

Chicago Children's Theatre

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May 23

Sat · 11:30 AM

Goodnight Moon

Chicago Children's Theatre · Chicago, IL

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Sat, May 23 · 12:00 PM

2026 Suenos - Saturday (J Balvin, Kali Uchis)

Hutchinson Field Grant Park

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May 23

Sat · 12:00 PM

2026 Suenos - Saturday (J Balvin, Kali Uchis)

Hutchinson Field Grant Park · Chicago, IL

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Sat, May 23 · 12:00 PM

Minnesota Lynx at Chicago Sky

Wintrust Arena

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May 23

Sat · 12:00 PM

Minnesota Lynx at Chicago Sky

Wintrust Arena · Chicago, IL

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Sat, May 23 · 1:20 PM

Houston Astros at Chicago Cubs

Wrigley Field

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May 23

Sat · 1:20 PM

Houston Astros at Chicago Cubs

Wrigley Field · Chicago, IL

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Sat, May 23 · 2:00 PM

Monty Python's Spamalot - Musical

CIBC Theatre

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May 23

Sat · 2:00 PM

Monty Python's Spamalot - Musical

CIBC Theatre · Chicago, IL

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Sat, May 23 · 2:00 PM

Les Miserables

Cadillac Palace

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May 23

Sat · 2:00 PM

Les Miserables

Cadillac Palace · Chicago, IL

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Sat, May 23 · 2:30 PM

Fault - Play

The Yard - Chicago Shakespeare Theater

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May 23

Sat · 2:30 PM

Fault - Play

The Yard - Chicago Shakespeare Theater · Chicago, IL

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Sat, May 23 · 2:30 PM

LOKI - The End of the World Tour

Lifeline Theatre

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May 23

Sat · 2:30 PM

LOKI - The End of the World Tour

Lifeline Theatre · Chicago, IL

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Sat, May 23 · 3:00 PM

Best of The Second City

Second City Chicago - UP Comedy Club

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May 23

Sat · 3:00 PM

Best of The Second City

Second City Chicago - UP Comedy Club · Chicago, IL

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Sat, May 23 · 3:00 PM

Drunk Romeo and Juliet

The Lion Theatre - Chicago

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May 23

Sat · 3:00 PM

Drunk Romeo and Juliet

The Lion Theatre - Chicago · Chicago, IL

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Sat, May 23 · 6:00 PM

2026 Slide Away (17+ Event)

Byline Bank Aragon Ballroom

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May 23

Sat · 6:00 PM

2026 Slide Away (17+ Event)

Byline Bank Aragon Ballroom · Chicago, IL

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Sat, May 23 · 7:00 PM

Decibel Magazine Tour: Cryptopsy, Spirit Adrift & Blood Monolith

Bottom Lounge

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May 23

Sat · 7:00 PM

Decibel Magazine Tour: Cryptopsy, Spirit Adrift & Blood Monolith

Bottom Lounge · Chicago, IL

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Sat, May 23 · 7:00 PM

Kurt Rosenwinkel

Garcias Chicago

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May 23

Sat · 7:00 PM

Kurt Rosenwinkel

Garcias Chicago · Chicago, IL

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Sat, May 23 · 7:15 PM

David Koechner

The Den Theatre

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May 23

Sat · 7:15 PM

David Koechner

The Den Theatre · Chicago, IL

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Sat, May 23 · 7:30 PM

Chicago Symphony Orchestra - Pekka Kuusisto

Orchestra Hall At Chicago Symphony Center

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May 23

Sat · 7:30 PM

Chicago Symphony Orchestra - Pekka Kuusisto

Orchestra Hall At Chicago Symphony Center · Chicago, IL

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Sat, May 23 · 7:30 PM

Monty Python's Spamalot - Musical

CIBC Theatre

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May 23

Sat · 7:30 PM

Monty Python's Spamalot - Musical

CIBC Theatre · Chicago, IL

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Sat, May 23 · 7:30 PM

Toronto FC at Chicago Fire FC

Soldier Field

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May 23

Sat · 7:30 PM

Toronto FC at Chicago Fire FC

Soldier Field · Chicago, IL

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Sat, May 23 · 7:30 PM

Les Miserables

Cadillac Palace

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May 23

Sat · 7:30 PM

Les Miserables

Cadillac Palace · Chicago, IL

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Sat, May 23 · 7:30 PM

Yves

Copernicus Center

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May 23

Sat · 7:30 PM

Yves

Copernicus Center · Chicago, IL

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Sat, May 23 · 7:30 PM

Fault - Play

The Yard - Chicago Shakespeare Theater

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May 23

Sat · 7:30 PM

Fault - Play

The Yard - Chicago Shakespeare Theater · Chicago, IL

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Sat, May 23 · 7:30 PM

LOKI - The End of the World Tour

Lifeline Theatre

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May 23

Sat · 7:30 PM

LOKI - The End of the World Tour

Lifeline Theatre · Chicago, IL

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Sat, May 23 · 8:00 PM

Trap Bingo

House of Blues - Chicago

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May 23

Sat · 8:00 PM

Trap Bingo

House of Blues - Chicago · Chicago, IL

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Sat, May 23 · 9:30 PM

David Koechner

The Den Theatre

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May 23

Sat · 9:30 PM

David Koechner

The Den Theatre · Chicago, IL

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Sat, May 23 · 9:30 PM

Kurt Rosenwinkel

Garcias Chicago

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May 23

Sat · 9:30 PM

Kurt Rosenwinkel

Garcias Chicago · Chicago, IL

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Sun, May 24 · 12:00 AM

Chicago Architecture Center River Cruise

Chicago's First Lady Cruises

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May 24

Sun · 12:00 AM

Chicago Architecture Center River Cruise

Chicago's First Lady Cruises · Chicago, IL

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Sun, May 24 · 9:30 AM

Goodnight Moon

Chicago Children's Theatre

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May 24

Sun · 9:30 AM

Goodnight Moon

Chicago Children's Theatre · Chicago, IL

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Sun, May 24 · 11:30 AM

Goodnight Moon

Chicago Children's Theatre

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May 24

Sun · 11:30 AM

Goodnight Moon

Chicago Children's Theatre · Chicago, IL

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Sun, May 24 · 12:00 PM

2026 Suenos - Sunday (Fuerza Regida)

Hutchinson Field Grant Park

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May 24

Sun · 12:00 PM

2026 Suenos - Sunday (Fuerza Regida)

Hutchinson Field Grant Park · Chicago, IL

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Sun, May 24 · 12:00 PM

Bluegrass Brunch with Mudflapps (21+ Event)

Garcias Chicago

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May 24

Sun · 12:00 PM

Bluegrass Brunch with Mudflapps (21+ Event)

Garcias Chicago · Chicago, IL

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Sun, May 24 · 1:00 PM

Monty Python's Spamalot - Musical

CIBC Theatre

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May 24

Sun · 1:00 PM

Monty Python's Spamalot - Musical

CIBC Theatre · Chicago, IL

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Sun, May 24 · 1:00 PM

Les Miserables

Cadillac Palace

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May 24

Sun · 1:00 PM

Les Miserables

Cadillac Palace · Chicago, IL

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Sun, May 24 · 1:20 PM

Houston Astros at Chicago Cubs

Wrigley Field

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May 24

Sun · 1:20 PM

Houston Astros at Chicago Cubs

Wrigley Field · Chicago, IL

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Sun, May 24 · 2:30 PM

LOKI - The End of the World Tour

Lifeline Theatre

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May 24

Sun · 2:30 PM

LOKI - The End of the World Tour

Lifeline Theatre · Chicago, IL

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Sun, May 24 · 3:00 PM

Chicago Symphony Orchestra - Hilary Hahn

Orchestra Hall At Chicago Symphony Center

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May 24

Sun · 3:00 PM

Chicago Symphony Orchestra - Hilary Hahn

Orchestra Hall At Chicago Symphony Center · Chicago, IL

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Sun, May 24 · 3:00 PM

Best of The Second City

Second City Chicago - UP Comedy Club

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May 24

Sun · 3:00 PM

Best of The Second City

Second City Chicago - UP Comedy Club · Chicago, IL

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Sun, May 24 · 3:00 PM

Drunk Romeo and Juliet

The Lion Theatre - Chicago

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May 24

Sun · 3:00 PM

Drunk Romeo and Juliet

The Lion Theatre - Chicago · Chicago, IL

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Sun, May 24 · 6:00 PM

Thornhill

Vic Theatre

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May 24

Sun · 6:00 PM

Thornhill

Vic Theatre · Chicago, IL

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Sun, May 24 · 6:30 PM

Monty Python's Spamalot - Musical

CIBC Theatre

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May 24

Sun · 6:30 PM

Monty Python's Spamalot - Musical

CIBC Theatre · Chicago, IL

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Sun, May 24 · 7:00 PM

Murphy Lee and Kyjuan

City Winery - Chicago

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May 24

Sun · 7:00 PM

Murphy Lee and Kyjuan

City Winery - Chicago · Chicago, IL

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Sun, May 24 · 7:30 PM

Diva Bleach (17+ Event)

Beat Kitchen

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May 24

Sun · 7:30 PM

Diva Bleach (17+ Event)

Beat Kitchen · Chicago, IL

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Mon, May 25 · 12:00 AM

Chicago Architecture Center River Cruise

Chicago's First Lady Cruises

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May 25

Mon · 12:00 AM

Chicago Architecture Center River Cruise

Chicago's First Lady Cruises · Chicago, IL

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Mon, May 25 · 1:10 PM

Minnesota Twins at Chicago White Sox

Rate Field

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May 25

Mon · 1:10 PM

Minnesota Twins at Chicago White Sox

Rate Field · Chicago, IL

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Mon, May 25 · 7:00 PM

Drunk Romeo and Juliet

The Lion Theatre - Chicago

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May 25

Mon · 7:00 PM

Drunk Romeo and Juliet

The Lion Theatre - Chicago · Chicago, IL

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Mon, May 25 · 8:00 PM

Best of The Second City

Second City Chicago - UP Comedy Club

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May 25

Mon · 8:00 PM

Best of The Second City

Second City Chicago - UP Comedy Club · Chicago, IL

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Tue, May 26 · 12:00 AM

Chicago Architecture Center River Cruise

Chicago's First Lady Cruises

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May 26

Tue · 12:00 AM

Chicago Architecture Center River Cruise

Chicago's First Lady Cruises · Chicago, IL

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Tue, May 26 · 6:40 PM

Minnesota Twins at Chicago White Sox

Rate Field

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May 26

Tue · 6:40 PM

Minnesota Twins at Chicago White Sox

Rate Field · Chicago, IL

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Tue, May 26 · 7:00 PM

Monty Python's Spamalot - Musical

CIBC Theatre

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May 26

Tue · 7:00 PM

Monty Python's Spamalot - Musical

CIBC Theatre · Chicago, IL

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