Upcoming Chicago Events
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Music & Comedy
Music & Comedy
The Head and The Heart – 15th Anniversary Tour
The Head and The Heart /w special guests The Brudi Brothers will perform live at Auditorium Theatre on May 2, 2026.
Music & Comedy, Theatre & Performing Arts
moonwatchers
It is Rocco and Allen’s job to watch the moon, and it is really quite boring. Night after night, they time the sequences exactly –…
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…
Music & Comedy
Aurie Styla at The Comedy Bar
2-Item Minimum Per Guest Valid ID Required for Entry First Come, First Served Seating No Outside Food or Beverage Aurie Styla is an award-winning comedian,…
Music & Comedy
Saturday Night in the Sidebar w/ Push Puppets
Push Puppets bring their dual-vocal attack to Fitzgerald’s Sidebar for a FREE SHOW! Their critically acclaimed 2025 release Tethered Together has drawn comparisons to Squeeze,…
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…
Music & Comedy
Chicago Comedy Hour
The Chicago Comedy hour is a comedy variety show featuring sketch, improv and stand up from some of the best up and coming comedians in…
Music & Comedy
Top Shelf Comedy
Top Shelf Comedy is all in the name! Join us every first Saturday of the month for an incredible night of laughs! Our production team’s…
Music & Comedy
Top Shelf Comedy
Top Shelf Comedy is all in the name! Join us every first Saturday of the month for an incredible night of laughs! Our production team’s…
Music & Comedy
Chicago Jazz Orchestra Presents: A Tribute to Roy Eldridge Featuring Jon Faddis with Alyssa Allgood
Join the Chicago Jazz Orchestra as they celebrate the legacy of jazz icon Roy Eldridge, one of the first black musicians to become part of…
Music & Comedy, Theatre & Performing Arts
HighQ
Is it a cannabis-themed game show or an uproarious, electively interactive live theatrical experience? Why can’t it be both? HighQ is an uplifting blend of…
Music & Comedy
SatchVai Band: Joe Satriani & Steve Vai & Animals As Leaders
The SatchVai Band, featuring iconic rock guitarists Joe Satriani and Steve Vai, is scheduled to perform in Chicago, IL, on Sunday, May 3, 2026, as…
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!)…
Music & Comedy, Theatre & Performing Arts
“Going Bacharach” Presents the Greatest Hits of Bacharach at the Apollo Theater
Rediscover the soundtrack of a lifetime with GOING BACHARACH, a vibrant new revue, direct from a sold-out run in New York, celebrating the legacy of…
Music & Comedy
Caifanes: 2026 Tour
Legendary Mexican rock band Caifanes is scheduled to perform in Chicago on Sunday, May 3, 2026.
Music & Comedy
Barry Brewer at The Comedy Bar
Join Comedian Barry Brewer for a fun night of stand up comedy with a mix of crowd collaboration and conversation. Barry Brewer hails as one…
Music & Comedy
They Might Be Giants – The Bigger Show Tour
They Might Be Giants are scheduled to perform a three-night residency in Chicago from Friday, May 1, through Sunday, May 3, 2026. These are their…
Music & Comedy, Theatre & Performing Arts
moonwatchers
It is Rocco and Allen’s job to watch the moon, and it is really quite boring. Night after night, they time the sequences exactly –…
Music & Comedy
Late Nite Mic with Vik Pandya at The Comedy Bar
2-Item Minimum Per Guest First Come, First Served Seating No Outside Food or Beverage Valid ID Required at Entry Vik Pandya is a nationally touring…
Music & Comedy, Theatre & Performing Arts
“Going Bacharach” Presents the Greatest Hits of Bacharach at the Apollo Theater
Rediscover the soundtrack of a lifetime with GOING BACHARACH, a vibrant new revue, direct from a sold-out run in New York, celebrating the legacy of…
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.…
Music & Comedy
Tomato Throw Show at The Comedy Bar
2-Item Minimum Per Guest First Come, First Served Seating No Outside Food or Beverage Valid ID Required at Entry Join us for the most fun…
Music & Comedy, Theatre & Performing Arts
“Going Bacharach” Presents the Greatest Hits of Bacharach at the Apollo Theater
Rediscover the soundtrack of a lifetime with GOING BACHARACH, a vibrant new revue, direct from a sold-out run in New York, celebrating the legacy of…
Music & Comedy
Iron & Wine Live In Chicago
Indie folk songwriter Iron & Wine will perform two shows in Chicago, IL, at Thalia Hall in May 2026.
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