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Music & Comedy, Theatre & Performing Arts
Baby Wants Candy! The Original Completely Improvised Musical
“CRITICS’ PICK. TRULY AMAZING!” – New York Times “BEST VISITING IMPROV COMEDY!”– TimeOut NY “HIGHLY RECOMMENDED!” – The Onion “★★★★★” THEY ARE AN ENTERTAINMENT PHENOMENON AND I…
Music & Comedy, Theatre & Performing Arts
Clued In
After getting a single suggestion, the cast of six professional comedians asks the audience to choose a detective. Enjoy as they invent a tale of…
Saturday, May 9th
7:30 p.m. – 8:30 p.m.The Second City
1616 N. Wells St., Theater on the Second FloorMusic & Comedy
Peso Pluma – Dinastia Tour 2026
Mexican music star Peso Pluma is scheduled to perform in Chicago on May 8-9, 2026, as the grand finale of his North American “DINASTÍA by…
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 –…
Saturday, May 9th
8:00 p.m. – Tuesday, May 26th
2:30 p.m.Greenhouse Theater Center
2257 North Lincoln AvenueMusic & Comedy
Alejandro Fernandez – de Rey a Rey Tour
Alejandro Fernández is bringing his de Rey a Rey tour, a tribute to the music of his late father, the legendary Vicente Fernández, to Allstate…
Saturday, May 9th
8:30 p.m. – 11:30 p.m.Allstate Arena
6920 Mannheim RoadMusic & Comedy
Gus Constantellis at The Comedy Bar
2-Item Minimum Per Guest First Come, First Served Seating No Outside Food or Beverage Valid ID Required at Entry Gus Constantellis (he/they) is a gay,…
Saturday, May 9th
9:00 p.m. – 10:30 p.m.The Comedy Bar
162 E Superior St, Chicago, IL 60611Music & 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, 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…
Saturday, May 9th
9:30 p.m. – 10:30 p.m.The Annoyance Theatre
851 W. Belmont Ave.Festivals, Fairs & Special Events, Music & Comedy, Theatre & Performing Arts
Sonia Oyola & Bob Solone – Love Songs for You
Sonia Oyola and Bob Solone are excited to share more of their favorite love songs and duets in English/Spanish. Their shows always feature an eclectic,…
Sunday, May 10th
4:00 p.m. – 6:00 p.m.Le Piano
6970 N. Glenwood Ave.Music & Comedy
Mother’s Day Celebration with Tamela Mann
COME CELEBRATE MOTHERS DAY AT THE HOUSE OF HOPE. Come to The Mothers Day Celebration at The House Of Hope. Treat the Mother In Your…
Sunday, May 10th
6:00 p.m. – 11:00 p.m.House Of Hope
752 E 114th StMusic & Comedy
Disclosure: Spring 2026 North America Tour
Multi-Platinum duo Disclosure will perform live at The Salt Shed Outdoors on May 8-10, 2026.
Sunday, May 10th
6:30 p.m. – 9:30 p.m.The Salt Shed
1357 N Elston Ave, Chicago, ILMusic & 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!)…
Festivals, Fairs & Special Events, Music & Comedy, Theatre & Performing Arts
Zoé Soteres — Does This Song Make Me Look Dramatic? A New One-Woman Show
After being named Chicago Cabaret Professional’s 2025 Best New Chicago Cabaret Vocalist, Zoé Soteres is proud to present her first one-woman cabaret, partnering with Kyle…
Sunday, May 10th
7:30 p.m. – 8:35 p.m.The Labyrinth Club
3658 North Pulaski RoadMusic & Comedy
Diljit Dosanjh – Aura Tour
Global Punjabi superstar Diljit Dosanjh will perform at the Allstate Arena in Rosemont, Illinois, on Sunday, May 10, 2026, as part of his 13-city Aura…
Sunday, May 10th
8:00 p.m. – 11:00 p.m.Allstate Arena
6920 Mannheim RoadMusic & 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 10th
8:00 p.m. – Wednesday, May 27th
2:30 p.m.Greenhouse Theater Center
2257 North Lincoln AvenueFestivals, Fairs & Special Events, Music & Comedy, Theatre & Performing Arts
Chicago Cabaret Professionals presents Musical Mondays: Tony Bennett at 100
Join us as we celebrate the 100th birthday of the one and only Tony Bennett! This Chicago Cabaret Week show highlights his incredible musical legacy,…
Monday, May 11th
7:30 p.m.The Rhapsody Theater
1328 W Morse AveFestivals, Fairs & Special Events, Music & Comedy, Theatre & Performing Arts
Girls Like Us — It’s My Party: Celebrating the Girls and the Groups of the 1960s
When we talk about music of the 1960s, most people think of Bob Dylan, The Beatles, Jimi Hendrix and the Rolling Stones — but that’s…
Tuesday, May 12th
7:00 p.m.PianoForte Chicago
1335 South Michigan AvenueMusic & 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 12th
7:00 p.m. – 8:30 p.m.The Gallery Cabaret
2020 N Oakley AveFestivals, Fairs & Special Events, Music & Comedy, Theatre & Performing Arts
The Beaus — Mashups and More
Prepare to be captivated by the harmonious melodies and infectious energy of The Beaus, Chicago’s favorite MAN-band. Their tight harmonies resonate through the room, enveloping…
Tuesday, May 12th
7:00 p.m. – 10:00 p.m.Stars & Garters
3914 N Clark StFestivals, Fairs & Special Events, Music & Comedy, Theatre & Performing Arts
Comic Court: Chicago’s #1 Comedy Court Show
Order in the court!Comic Court is back at The Lincoln Lodge every 2nd & 4th Tuesday at 9PM. Comedians argue ridiculous cases like actual lawyers,…
Tuesday, May 12th
9:00 p.m. – 10:30 p.m.The Lincoln Lodge
2040 North Milwaukee AvenueFestivals, Fairs & Special Events, Music & Comedy, Theatre & Performing Arts
Hilary Ann Feldman — The Life & Laughs of Carol Burnett
The world has loved Carol Burnett for over fifty years. Her fearless character acting and self-effacing personality made her Lucille Ball’s successor as the Queen…
Wednesday, May 13th
7:00 p.m.Borelli’s Pizza
2124 W Lawrence AveFestivals, Fairs & Special Events, Music & Comedy, Theatre & Performing Arts
24WORDS Production —The Day Before Remember When: An Equal Rights journey
Vibrant, funny, and inspirational, The Day Before Remember When is a cabaret about a 300-year odyssey to achieve Equality. With 15 original songs based on…
Wednesday, May 13th
7:30 p.m. – 9:30 p.m.Bughouse Theater
1910 West Irving Park RoadMusic & Comedy
Rodrigo Y Gabriela – 20th Anniversary Tour
Rodrigo y Gabriela are scheduled to perform in Chicago, IL, on Wednesday, May 13, 2026, as part of their “20th Anniversary Tour”.
Wednesday, May 13th
7:30 p.m. – 10:30 p.m.The Chicago Theatre
175 N. StateMusic & Comedy
Triumph Live In Chicago – 50th Anniversary Tour
Canadian rock legends Triumph /w special guests April Wine will perform live at Rosemont Theatre on May 13, 2026.
Wednesday, May 13th
8:00 p.m. – 10:00 p.m.Rosemont Theatre

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