Baby Wants Candy! The Original Completely Improvised Musical
May9
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…

Saturday, May 9th
7:30 p.m.8:30 p.m.
The Second City
1616 N. Wells St.
Clued In
May9
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 Floor
Peso Pluma – Dinastia Tour 2026
May9
Music & 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…

Saturday, May 9th
8:00 p.m.11:00 p.m.
United Center
1901 W Madison St,
moonwatchers
May9
May26
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 Avenue
Alejandro Fernandez – de Rey a Rey Tour
May9
Music & 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 Road
Gus Constantellis at The Comedy Bar
May9
Music & 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 60611
Secret Sketch Show
May9
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…

Saturday, May 9th
9:00 p.m.10:30 p.m.
iO Theater
1501 N. Kingsbury St.
Best Of Annoyance Sketch
May9
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.
Sonia Oyola & Bob Solone – Love Songs for You
May10
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.
Mother’s Day Celebration with Tamela Mann
May10
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 St
Disclosure: Spring 2026 North America Tour
May10
Music & 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, IL
Wheel of Improv
May10
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!)…

Sunday, May 10th
7:30 p.m.8:30 p.m.
The Second City
1616 N. Wells St.
Zoé Soteres — Does This Song Make Me Look Dramatic? A New One-Woman Show
May10
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 Road
Diljit Dosanjh – Aura Tour
May10
Music & 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 Road
moonwatchers
May10
May27
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 10th
8:00 p.m.Wednesday, May 27th
2:30 p.m.
Greenhouse Theater Center
2257 North Lincoln Avenue
Chicago Cabaret Professionals presents Musical Mondays: Tony Bennett at 100
May11
Festivals, 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 Ave
Girls Like Us — It’s My Party: Celebrating the Girls and the Groups of the 1960s
May12
Festivals, 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 Avenue
Tuesday Good Show
May12
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 12th
7:00 p.m.8:30 p.m.
The Gallery Cabaret
2020 N Oakley Ave
The Beaus — Mashups and More
May12
Festivals, 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 St
Comic Court: Chicago’s #1 Comedy Court Show
May12
Festivals, 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 Avenue
Hilary Ann Feldman — The Life & Laughs of Carol Burnett
May13
Festivals, 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 Ave
24WORDS Production —The Day Before Remember When: An Equal Rights journey
May13
Festivals, 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 Road
Rodrigo Y Gabriela – 20th Anniversary Tour
May13
Music & 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. State
Triumph Live In Chicago – 50th Anniversary Tour
May13
Music & 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