Events in Chicago May




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Fri May 1 3:30am
Northwestern Wildcats vs. Indiana Hoosiers
Rocky Miller Park  •  Evanston, IL
Fri May 1 1:20pm
Chicago Cubs vs. Arizona Diamondbacks
Wrigley Field  •  Chicago, IL
Fri May 1 1:30pm
Chicago Symphony Orchestra: Karina Canellakis & Conrad Tao - Tchaikovsky, Bartok & Dvorak
Chicago Symphony Center  •  Chicago, IL
Fri May 1 6:00pm
Kenny Garrett
Garcias Chicago  •  Chicago, IL
Fri May 1 6:00pm
Evansville Purple Aces vs. Illinois-Chicago Flames
Charles H. Braun Stadium  •  Evansville, IN
Fri May 1 6:00pm
Cattle Decapitation
The Forge  •  Joliet, IL
Fri May 1 6:00pm
Creighton Bluejays vs. DePaul Blue Demons
Creighton Stadium  •  Omaha, NE
Fri May 1 6:00pm
South Chicago Dance Theatre
Harris Theater  •  Chicago, IL
Fri May 1 6:30pm
The Second City Mainstage 114th Revue
Mainstage at Second City  •  Chicago, IL
Fri May 1 6:40pm
San Diego Padres vs. Chicago White Sox
Petco Park  •  San Diego, CA
Fri May 1 7:00pm
Tom Papa
Rialto Square Theatre  •  Joliet, IL
Fri May 1 7:00pm
South Pacific
Paramount Theatre  •  Aurora, IL
Fri May 1 7:00pm
The Great Gatsby - Theatrical Production
Cadillac Palace  •  Chicago, IL
Fri May 1 7:00pm
Bilmuri
Byline Bank Aragon Ballroom  •  Chicago, IL
Fri May 1 7:00pm
Vana - Artist
Bottom Lounge  •  Chicago, IL
Fri May 1 7:00pm
Chris D'Elia
Chicago Improv  •  Schaumburg, IL
Fri May 1 7:00pm
Elmiene
House Of Blues  •  Chicago, IL
Fri May 1 7:00pm
Pat Tomasulo
Zanies Comedy Club  •  Rosemont, IL
Fri May 1 7:00pm
Laura Peek
Zanies Comedy Club  •  Chicago, IL
Fri May 1 7:00pm
The Merry Wives of Windsor
Courtyard Theater at Chicago Shakespeare Theatre  •  Chicago, IL
Fri May 1 7:00pm
Kelly Kellz
The Comedy Bar  •  Chicago, IL
Fri May 1 7:15pm
Rayna Greenberg
Heath Mainstage At The Den Theatre  •  Chicago, IL
Fri May 1 7:30pm
The Wedding Singer
Metropolis Performing Arts Centre  •  Arlington Heights, IL
Fri May 1 7:30pm
Ain't Misbehavin'
The Yard at Chicago Shakespeare Theatre  •  Chicago, IL
Fri May 1 7:30pm
LOKI - The End of the World Tour
Lifeline Theatre  •  Chicago, IL
Fri May 1 7:30pm
The Angel Next Door
North Theatre At North Shore Center For The Performing Arts  •  Skokie, IL
Fri May 1 7:30pm
Heartbreak Hotel
Marriott Theatre  •  Lincolnshire, IL
Fri May 1 7:30pm
Hasan Raheem
Thalia Hall  •  Chicago, IL
Fri May 1 7:30pm
Evren Ozel
Studebaker Theater  •  Chicago, IL
Fri May 1 7:30pm
Fault
The Yard at Chicago Shakespeare Theatre  •  Chicago, IL
Fri May 1 7:30pm
Jeff Mauro
City Winery  •  Chicago, IL
Fri May 1 7:30pm
The Movement You Need
Downstairs Theatre At Steppenwolf Theatre  •  Chicago, IL
Fri May 1 7:30pm
Windfall
Ensemble Theater At Steppenwolf Theatre  •  Chicago, IL
Fri May 1 7:30pm
Going Bacharach: The Songs of an Icon
Apollo Theater Main Stage  •  Chicago, IL
Fri May 1 8:00pm
Julio Iglesias Jr.
Arcada Theatre  •  Saint Charles, IL
Fri May 1 8:00pm
St. Paul and The Broken Bones
The Salt Shed Indoors  •  Chicago, IL
Fri May 1 8:00pm
Mike Reed's Chicago Inspirations
Chicago Symphony Center  •  Chicago, IL
Fri May 1 8:00pm
Demi Lovato
United Center  •  Chicago, IL
Fri May 1 8:00pm
Caroline Jones
Joe's Bar On Weed St.  •  Chicago, IL
Fri May 1 8:00pm
Reverend Horton Heat
Metro Chicago  •  Chicago, IL
Fri May 1 8:00pm
They Might Be Giants
Vic Theatre  •  Chicago, IL
Fri May 1 8:00pm
Steven Ho
Historic Main Stage at Athenaeum Center  •  Chicago, IL
Fri May 1 8:00pm
Hippie Sabotage
Riviera Theatre  •  Chicago, IL
Fri May 1 8:00pm
Anuv Jain
Park West  •  Chicago, IL
Fri May 1 8:00pm
The Back Alley
Lincoln Hall  •  Chicago, IL
Fri May 1 8:00pm
Your Neighbors
Beat Kitchen  •  Chicago, IL
Fri May 1 8:30pm
Kenny Garrett
Garcias Chicago  •  Chicago, IL
Fri May 1 8:30pm
Green TTea and The Tempos
Schubas  •  Chicago, IL
Fri May 1 8:30pm
Shamilton, The Improvised Hip-Hop American Musical
Donny's Skybox Theatre at Second City  •  Chicago, IL
Fri May 1 9:00pm
Kelly Kellz
The Comedy Bar  •  Chicago, IL
Fri May 1 9:00pm
Spinall
Outset  •  Chicago, IL
Fri May 1 9:15pm
Pat Tomasulo
Zanies Comedy Club  •  Rosemont, IL
Fri May 1 9:15pm
Laura Peek
Zanies Comedy Club  •  Chicago, IL
Fri May 1 9:30pm
Chris D'Elia
Chicago Improv  •  Schaumburg, IL
Fri May 1 9:30pm
Sango
Ramova Theatre  •  Chicago, IL
Fri May 1 9:30pm
Sunset Sinners
Carol's Pub  •  Chicago, IL
Fri May 1 9:30pm
The Second City Mainstage 114th Revue
Mainstage at Second City  •  Chicago, IL
Fri May 1 10:00pm
Noizu
Radius  •  Chicago, IL
Fri May 1 10:00pm
Giuseppe Ottaviani
Sound  •  Chicago, IL
Fri May 1 11:00pm
Diox
TAO Nightclub  •  Chicago, IL
Sat May 2 3:30am
Eintracht Frankfurt vs. Hamburger SV
Deutsche Bank Park  •  Frankfurt am Main, HE
Sat May 2 3:30am
Shipshewana on the Road - 2 Day Pass
Lake County Fairgrounds  •  Crown Point, IN
Sat May 2 9:00am
Shipshewana On the Road
Lake County Fairgrounds  •  Crown Point, IN
Sat May 2 11:00am
Dog Man - The Musical
George Van Dusen Theatre At North Shore Center For The Performing Arts  •  Skokie, IL
Sat May 2 12:00pm
Monster Truck Wars
Lake County Fairgrounds  •  Grayslake, IL
Sat May 2 1:20pm
Chicago Cubs vs. Arizona Diamondbacks
Wrigley Field  •  Chicago, IL
Sat May 2 2:00pm
The Wedding Singer
Metropolis Performing Arts Centre  •  Arlington Heights, IL
Sat May 2 2:00pm
Northwestern Wildcats vs. Indiana Hoosiers
Rocky Miller Park  •  Evanston, IL
Sat May 2 2:00pm
South Pacific
Paramount Theatre  •  Aurora, IL
Sat May 2 2:00pm
The Great Gatsby - Theatrical Production
Cadillac Palace  •  Chicago, IL
Sat May 2 2:00pm
Evansville Purple Aces vs. Illinois-Chicago Flames
Charles H. Braun Stadium  •  Evansville, IN
Sat May 2 2:00pm
Ballet Folklorico de Chicago: Tradiciones y Fiesta
Copernicus Center  •  Chicago, IL
Sat May 2 2:00pm
The Merry Wives of Windsor
Courtyard Theater at Chicago Shakespeare Theatre  •  Chicago, IL
Sat May 2 2:00pm
Creighton Bluejays vs. DePaul Blue Demons
Creighton Stadium  •  Omaha, NE
Sat May 2 2:30pm
Ain't Misbehavin'
The Yard at Chicago Shakespeare Theatre  •  Chicago, IL
Sat May 2 2:30pm
The Angel Next Door
North Theatre At North Shore Center For The Performing Arts  •  Skokie, IL
Sat May 2 2:30pm
Fault
The Yard at Chicago Shakespeare Theatre  •  Chicago, IL
Sat May 2 2:30pm
Going Bacharach: The Songs of an Icon
Apollo Theater Main Stage  •  Chicago, IL
Sat May 2 3:00pm
Dog Man - The Musical
George Van Dusen Theatre At North Shore Center For The Performing Arts  •  Skokie, IL
Sat May 2 3:00pm
The Movement You Need
Downstairs Theatre At Steppenwolf Theatre  •  Chicago, IL
Sat May 2 3:00pm
Windfall
Ensemble Theater At Steppenwolf Theatre  •  Chicago, IL
Sat May 2 4:00pm
Heartbreak Hotel
Marriott Theatre  •  Lincolnshire, IL
Sat May 2 5:00pm
Failure
Radius  •  Chicago, IL
Sat May 2 5:40pm
San Diego Padres vs. Chicago White Sox
Petco Park  •  San Diego, CA
Sat May 2 6:00pm
Monster Truck Wars
Lake County Fairgrounds  •  Grayslake, IL
Sat May 2 6:00pm
Rakim
City Winery  •  Chicago, IL
Sat May 2 6:30pm
Bloodywood
House Of Blues  •  Chicago, IL
Sat May 2 6:30pm
Pat Tomasulo
Zanies Comedy Club  •  Rosemont, IL
Sat May 2 6:30pm
The Second City Mainstage 114th Revue
Mainstage at Second City  •  Chicago, IL
Sat May 2 7:00pm
Josiah Queen
Byline Bank Aragon Ballroom  •  Chicago, IL
Sat May 2 7:00pm
South Pacific
Paramount Theatre  •  Aurora, IL
Sat May 2 7:00pm
Matteo Lane
The Chicago Theatre  •  Chicago, IL
Sat May 2 7:00pm
Chris D'Elia
Chicago Improv  •  Schaumburg, IL
Sat May 2 7:00pm
The Temptations and The Four Tops
Hard Rock Live Northern Indiana  •  Gary, IN
Sat May 2 7:00pm
Ballet Folklorico de Chicago: Epocas de Mexico
Copernicus Center  •  Chicago, IL
Sat May 2 7:00pm
Laura Peek
Zanies Comedy Club  •  Chicago, IL
Sat May 2 7:00pm
Arankai
Cobra Lounge  •  Chicago, IL
Sat May 2 7:00pm
The Merry Wives of Windsor
Courtyard Theater at Chicago Shakespeare Theatre  •  Chicago, IL
Sat May 2 7:00pm
AHL Central Division Semifinals: Chicago Wolves vs. Texas Stars - Home Game 1, Series Game 3
Allstate Arena  •  Rosemont, IL
Sat May 2 7:00pm
Aurie Styla
The Comedy Bar  •  Chicago, IL


Events in Chicago May 2026 schedule

May is an exciting month for sports and entertainment in Chicago, featuring a variety of major events at iconic venues. Baseball fans can enjoy a thrilling series of Chicago Cubs games at Wrigley Field, with home matchups against top teams such as the Arizona Diamondbacks, Cincinnati Reds, Milwaukee Brewers, and Houston Astros. The Cubs' schedule includes multiple games from May 1st through May 24th, with key dates like May 1st to May 3rd, where the team faces the Diamondbacks, and later matchups against the Reds from May 4th to May 7th, and against the Brewers from May 18th to May 20th. These games showcase some of the league's best players and are hosted at Wrigley Field, one of the most historic and beloved ballparks in Major League Baseball.

In addition to baseball, Chicago's vibrant May events include concerts, festivals, and cultural activities, particularly around the city's main venues such as the United Center and Millennium Park. While specific concert details are not provided, May often features performances by renowned artists and top performers, making it a prime time for live entertainment.

Whether you're a sports enthusiast or seeking cultural experiences, Chicago's May lineup offers something for everyone. Be sure to check the schedule for your favorite teams and artists, and enjoy the lively atmosphere that defines Chicago in spring.