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May Events and Things to do in Chicago, IL

Prime Time - Chicago's hottest comedy showcase
Sat, May 2, 9:00 PM + 4 more
Chicago · The Lincoln Lodge
Prime Time - Chicago's hottest comedy showcase
Sat, May 2, 9:00 PM + 4 more
Chicago · The Lincoln Lodge
R&B BRUNCH YACHT CRUISE
Sun, May 3, 1:30 PM
Chicago · 200 N Breakwater Access
R&B BRUNCH YACHT CRUISE
Sun, May 3, 1:30 PM
Chicago · 200 N Breakwater Access
the first hngout
Fri, May 8, 6:30 PM
Chicago · 3001 W Peterson Ave
the first hngout
Fri, May 8, 6:30 PM
Chicago · 3001 W Peterson Ave
Taylor Wolfe, "Just a Busy Season" Book Tour
Fri, May 1, 7:00 PM
Chicago · Everybody's Coffee (Wilson Abbey)
Taylor Wolfe, "Just a Busy Season" Book Tour
Fri, May 1, 7:00 PM
Chicago · Everybody's Coffee (Wilson Abbey)
Stitch 'n Bitch @ Night
Tue, May 12, 7:00 PM + 1 more
Chicago · Inclement Craft's Studio
Stitch 'n Bitch @ Night
Tue, May 12, 7:00 PM + 1 more
Chicago · Inclement Craft's Studio
FIND YOUR THING at the Spring 2026 Volunteer Fair!
Sun, May 3, 12:00 PM
Chicago · River Room at Burning Bush Brewery
FIND YOUR THING at the Spring 2026 Volunteer Fair!
Sun, May 3, 12:00 PM
Chicago · River Room at Burning Bush Brewery
Booked! A Stand Up Comedy Show.
Sat, May 9, 7:45 PM
Chicago · Passages Wine and Books
Booked! A Stand Up Comedy Show.
Sat, May 9, 7:45 PM
Chicago · Passages Wine and Books
CHICAGO OFFICIAL R&B BRUNCH AND DAY PARTY SERIES!
Sun, May 3, 12:00 PM + 4 more
Chicago · 1612 W Division St
CHICAGO OFFICIAL R&B BRUNCH AND DAY PARTY SERIES!
Sun, May 3, 12:00 PM + 4 more
Chicago · 1612 W Division St
Book Event: Fat Swim by Emma Copley Eisenberg
Tue, May 5, 7:00 PM
Chicago · Haymarket House
Book Event: Fat Swim by Emma Copley Eisenberg
Tue, May 5, 7:00 PM
Chicago · Haymarket House
Dime Saturday's
Sat, May 2, 10:00 PM + 4 more
Chicago · The Dime
Dime Saturday's
Sat, May 2, 10:00 PM + 4 more
Chicago · The Dime
KERRYN FEEHAN - ONE NIGHT ONLY AT THE LINCOLN LODGE 5/2/26
Sat, May 2, 11:00 PM
Chicago · The Lincoln Lodge
KERRYN FEEHAN - ONE NIGHT ONLY AT THE LINCOLN LODGE 5/2/26
Sat, May 2, 11:00 PM
Chicago · The Lincoln Lodge
Celebrating Jazz at Seviin
Sat, May 9, 5:00 PM + 7 more
Chicago · 5921 S State St
Celebrating Jazz at Seviin
Sat, May 9, 5:00 PM + 7 more
Chicago · 5921 S State St
Almost full
MooMoos and Margaritas
Sun, May 3, 3:00 PM
Chicago · Reserv
Almost full
MooMoos and Margaritas
Sun, May 3, 3:00 PM
Chicago · Reserv
Ladylike
Wed, May 6, 8:00 PM
Chicago · The Lincoln Lodge
Ladylike
Wed, May 6, 8:00 PM
Chicago · The Lincoln Lodge
Latte art for beginners - Mother's Day edition!
Sun, May 10, 1:30 PM
Chicago · Sip Society Coffee Education Center
Latte art for beginners - Mother's Day edition!
Sun, May 10, 1:30 PM
Chicago · Sip Society Coffee Education Center
SILENT PARTY CHICAGO| SLOW JAMZ VS JUKEFEST EDITION
Fri, May 8, 9:00 PM
Chicago · BASSLINE || 2239 - CHICAGO
SILENT PARTY CHICAGO| SLOW JAMZ VS JUKEFEST EDITION
Fri, May 8, 9:00 PM
Chicago · BASSLINE || 2239 - CHICAGO
Derby Day at Hubbard Inn
Sat, May 2, 4:00 PM
Chicago · Hubbard Inn
Derby Day at Hubbard Inn
Sat, May 2, 4:00 PM
Chicago · Hubbard Inn
Read & Run Chicago Turns 5: A Chicago Cookbook Potluck
Wed, May 13, 6:00 PM
Chicago · Fabrik Chicago
Read & Run Chicago Turns 5: A Chicago Cookbook Potluck
Wed, May 13, 6:00 PM
Chicago · Fabrik Chicago
Brews and Bad Movies: Mac & Me
Thu, May 7, 7:30 PM
Chicago · The Lincoln Lodge
Brews and Bad Movies: Mac & Me
Thu, May 7, 7:30 PM
Chicago · The Lincoln Lodge
Afro Fusion South Loop Edition - FREE/RSVP
Fri, May 15, 10:00 PM
Chicago · BASSLINE
Afro Fusion South Loop Edition - FREE/RSVP
Fri, May 15, 10:00 PM
Chicago · BASSLINE

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