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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…
Sunday, May 3rd
8:00 p.m. – 9:30 p.m.The Comedy Bar
162 E Superior St, Chicago, IL 60611Music & 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 –…
Sunday, May 3rd
8:00 p.m. – Wednesday, May 20th
2:30 p.m.Greenhouse Theater Center
2257 North Lincoln AvenueMusic & 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…
Monday, May 4th
7:00 p.m. – 9:00 p.m.The Comedy Bar
162 E Superior St, Chicago, IL 60611Music & 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.…
Tuesday, May 5th
7:00 p.m. – 8:30 p.m.The Gallery Cabaret
2020 N Oakley AveMusic & 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…
Tuesday, May 5th
7:00 p.m. – 8:30 p.m.The Comedy Bar
162 E Superior St, Chicago, IL 60611Music & 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.
Tuesday, May 5th
8:00 p.m. – 11:00 p.m.Thalia Hall
"1621 Central Ave, Suite 330 Cheyenne, WY 82001"Music & Comedy
Crowd Work Wednesday at The Comedy Bar
2-Item Minimum Per Guest First Come, First Served Seating No Outside Food or Beverage Valid ID Required at Entry Crowd Work Wednesday is a weekly…
Wednesday, May 6th
7:00 p.m. – 8:30 p.m.The Comedy Bar
162 E Superior St, Chicago, IL 60611Music & Comedy
NewDad
Welcome to the iconic Metro Chicago, where on May 6, 2026, the indie-rock sensation NewDad will be taking the stage at 7:30 PM. Hailing from…
Wednesday, May 6th
7:30 p.m. – 9:30 p.m.Metro ChicagoMusic & 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.
Wednesday, May 6th
8:00 p.m. – 11:00 p.m.Thalia Hall
"1621 Central Ave, Suite 330 Cheyenne, WY 82001"Music & Comedy
Alan Doyle Live In Concert
Alan Doyle is performing in Chicago on Wednesday, May 6, 2026, at the Athenaeum Center for Thought & Culture. The concert is part of his…
Wednesday, May 6th
8:00 p.m. – 11:00 p.m.Historic Main Stage at Athenaeum Center
2936 N. Southport AveMusic & Comedy, Theatre & Performing Arts
Hooch & Holler Comedy Show
Every Wednesday The Best Speakeasy In Chicago Hosts The Hottest Comedians The City Has To Offer! Indulge In Our Amazing Craft Cocktails And Enjoy An…
Wednesday, May 6th
9:00 p.m. – 11:00 p.m.Bordel Cocktail & Cabaret
1721 W DivisionMusic & Comedy, Theatre & Performing Arts
The Fizz Show
Join iO house team Fizz for Chicago’s most carbonated improv show. Wednesdays at 10 p.m., Fizz cracks open a high-octane, full-sugar set of one-night-only scenes,…
Music & Comedy
Morgan’s Laugh Lounge
Laugh your way into your new favorite Thursday tradition at Morgan’s Laugh Lounge, Chicago’s newest comedy hotspot. Every Thursday night from 6:00–9:30 PM, the lounge…
Music & Comedy
OhJay Lamont & Friends at The Comedy Bar
2-Item Minimum Per Guest First Come, First Served Seating No Outside Food or Beverage Valid ID Required at Entry OhJay Lamont, born and raised on…
Thursday, May 7th
7:00 p.m. – 8:30 p.m.The Comedy Bar
162 E Superior St, Chicago, IL 60611Music & Comedy, Theatre & Performing Arts
Dark Side of the Pillow Sketch Comedy Show
The thoughts you have at 2 a.m.? We put them on stage. Looking for a night out that feels unmistakably Chicago? Dark Side of the…
Thursday, May 7th
7:30 p.m. – 8:30 p.m.The De Matt Theater at The Second City
230 W North AveMusic & 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
DiDonato Performs Neruda Songs
In her final program as 2025/26 CSO Artist-in-Residence, Joyce DiDonato — one of today’s most compelling operatic storytellers — brings extraordinary emotional depth to Neruda Songs,…
Thursday, May 7th
7:30 p.m. – 9:30 p.m.Chicago Symphony Center
220 S Michigan AveMusic & Comedy
Mika – Spinning Out Tour North America
Internationally acclaimed pop artist Mika is scheduled to perform in Chicago on Thursday, May 7, 2026, as part of the “Spinning Out Tour North America”.
Thursday, May 7th
7:30 p.m. – 10:30 p.m.The Riveria Theater
4746 N Racine AveMusic & Comedy
Cosmic Comedy Hour
Cosmic Comedy Hour is a one-hour live comedy show that combines magic, improv, and theatrical comedy into one fast-paced experience. Unlike traditional comedy shows, this…
Thursday, May 7th
8:00 p.m. – 9:00 p.m.cosmic underground theater
3433 W Fullerton AveMusic & Comedy
Sooshi Mango – The Home Made World Tour 2026
The Australian comedy trio Sooshi Mango is scheduled to perform in Chicago, IL, on Thursday, May 7, 2026, as part of their “The Home Made…
Thursday, May 7th
8:00 p.m. – 10:00 p.m.Historic Main Stage at Athenaeum Center
2936 N. Southport Ave

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