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Gus Constantellis at The Comedy Bar
May10
Music & Comedy

Gus Constantellis at The Comedy Bar

Gus Constantellis (he/they) is a gay, first-generation Greek-American stand-up comedian and writer. His material deals heavily with his large immigrant family, his Greek heritage, raunchy…

Saturday, May 10th
7:00 p.m.8:30 p.m.
The Comedy Bar
500 N. LaSalle St.
Ali Siddiq: In The Shadows Tour
May10
Music & Comedy

Ali Siddiq: In The Shadows Tour

Ali Siddiq will bring the In The Shadows Tour to The Chicago Theatre on Saturday, May 10.

Saturday, May 10th
7:00 p.m.9:00 p.m.
The Chicago Theatre
175 N. State
Reimagining Cabaret presented by Black Voices in Cabaret
May10
Festivals, Fairs & Special Events, Music & Comedy, Theatre & Performing Arts

Reimagining Cabaret presented by Black Voices in Cabaret

Join us on May 10th as Reimagining Cabaret, the acclaimed series created, produced, and directed by Lynn Colbert-Jones, makes its debut at Freedom Hall in…

Saturday, May 10th
7:00 p.m.9:00 p.m.
Freedom Hall
410 Lakewood Blvd
Baby Wants Candy! The Original Completely Improvised Musical
May10
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 10th
7:30 p.m.8:30 p.m.
The Second City
1616 N. Wells St.
Clued In
May10
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 10th
7:30 p.m.8:30 p.m.
The Second City
1616 N. Wells St., Theater on the Second Floor
Ben Jones “Temptation”
May10
Festivals, Fairs & Special Events, Music & Comedy, Theatre & Performing Arts

Ben Jones “Temptation”

“One of the most unbelievable vocal instruments in the industry today.” – BroadwayWorld. Join award-winning vocalist Ben Jones and legendary pianist, composer, and music director…

Saturday, May 10th
7:30 p.m.9:30 p.m.
Hey Nonny
10 S. Vail Ave.
Rauw Alejandro – Cosa Nuestra World Tour
May10
Music & Comedy

Rauw Alejandro – Cosa Nuestra World Tour

Rauw Alejandro is bringing the Cosa Nuestra World Tour to United Center on May 9 & 10, 2025! Fans can expect an electrifying showcase of Rauw’s…

Saturday, May 10th
8:00 p.m.11:00 p.m.
United Center
1901 W Madison St.
Here 4 A Bit *Naughty Improv
May10
Music & Comedy, Theatre & Performing Arts

Here 4 A Bit *Naughty Improv

Join us again for a whose line styled night of explosive laughter that will titillate your “funny” bone. Fast paced short form improv, hilarious songs,…

Saturday, May 10th
9:00 p.m.10:00 p.m.
The Second City
1616 N. Wells St., Theater on the Second Floor
Gus Constantellis at The Comedy Bar
May10
Music & Comedy

Gus Constantellis at The Comedy Bar

Gus Constantellis (he/they) is a gay, first-generation Greek-American stand-up comedian and writer. His material deals heavily with his large immigrant family, his Greek heritage, raunchy…

Saturday, May 10th
9:00 p.m.10:30 p.m.
The Comedy Bar
500 N. LaSalle St.
Best Of Annoyance Sketch
May10
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 10th
9:30 p.m.10:30 p.m.
The Annoyance Theatre
851 W. Belmont Ave.
LET’S PLAY A GAME: Chicago’s scariest short-form show
May10
Music & Comedy, Theatre & Performing Arts

LET’S PLAY A GAME: Chicago’s scariest short-form show

Who’s Line is it Anyways meets Fear Factor in LETS PLAY A GAME, a new short form show that’s a unique blend of comedy, chaos,…

Saturday, May 10th
10:00 p.m.11:00 p.m.
Annoyance Theatre & Bar
851 W. Belmont Ave., 2nd Fl.
Teatro Zinzanni
May11
Music & Comedy, Theatre & Performing Arts

Teatro Zinzanni

Tickets are on sale Now at https://zinzanni.com/chicago/ for Love, Chaos, & Dinner ! Teatro Zinzanni returns to the vibrant Chicago Loop inside the velvet walls…

Sunday, May 11th
5:00 a.m.9:00 p.m.
Spiegeltent – Cambria Hotel
32 W. Randolph
Judy & Liza London Palladium Tribute
May11
Festivals, Fairs & Special Events, Music & Comedy, Theatre & Performing Arts

Judy & Liza London Palladium Tribute

Enjoy real life mother/daughter duo Nancy Hays and Mary Heffernan for a Mother’s Day brunch and a show as they lovingly recall the famed 1964…

Sunday, May 11th
12:00 p.m.1:15 p.m.
Le Piano
6970 N. Glenwood Ave.
Judy & Liza London Palladium Tribute, A Mother’s Day Concert
May11
Festivals, Fairs & Special Events, Music & Comedy, Theatre & Performing Arts

Judy & Liza London Palladium Tribute, A Mother’s Day Concert

Enjoy real life mother/daughter duo Nancy Hays and Mary Heffernan’s performance as they lovingly recall the famed 1964 concert of the legendary mother/daughter duo of…

Sunday, May 11th
4:30 p.m.6:00 p.m.
Fulton Street Collective
1821 W Hubbard St UNIT 307
Today’s Specials
May11
Music & Comedy, Theatre & Performing Arts

Today’s Specials

Today’s Specials is a variety show hosted by Asian Takeout Improv, featuring Chicago’s best comedians, musicians, performers and improvisers. We strive to highlight comedians and…

Sunday, May 11th
6:30 p.m.9:00 p.m.
Kamehachi Sushi
1531 N Wells St
Katy Perry – The Lifetimes Tour
May12
Music & Comedy

Katy Perry – The Lifetimes Tour

Katy Perry is bringing The Lifetimes Tour to United Center on May 12! Touring in support of her new album, 1432, the global pop superstar will…

Monday, May 12th
7:00 p.m.10:00 p.m.
United Center
1901 W Madison St.
Chicago Cabaret Professionals presents Musical Mondays—Cities of the World
May12
Festivals, Fairs & Special Events, Music & Comedy, Theatre & Performing Arts

Chicago Cabaret Professionals presents Musical Mondays—Cities of the World

We celebrate the great cities of the world in song. Selections include the romantic, humorous, well known, and those not as familiar. Join us to…

Monday, May 12th
7:30 p.m.9:30 p.m.
The Rhapsody Theater
1328 W Morse Ave
Tuesday Good Show
May13
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 13th
7:00 p.m.8:30 p.m.
The Gallery Cabaret
2020 N Oakley Ave
From Chicago to Paris with Love
May13
Festivals, Fairs & Special Events, Music & Comedy, Theatre & Performing Arts

From Chicago to Paris with Love

Claudia Hommel & friends are conjuring up the Seine while looking out at the Chicago River. Let flow the Chicago sounds and Paris melodies with…

Tuesday, May 13th
7:00 p.m.9:00 p.m.
Rockwell on the River
3057 North Rockwell Street
Beloved French Singer Joe Dassin’s Legacy Lives on in Salut! Tour
May13
Music & Comedy

Beloved French Singer Joe Dassin’s Legacy Lives on in Salut! Tour

Joe Dassin was a legendary 1960’s American- French singer, whose timeless melodies have touched generations. Joe Dassin’s greatest hits, including “Les Champs-Élysées” and “Et Si…

Tuesday, May 13th
8:00 p.m.10:00 p.m.
Copernicus Center
5216 W Lawrence Avenue
Comic Court: The Best Comedy Show in the World
May13
Music & Comedy, Theatre & Performing Arts

Comic Court: The Best Comedy Show in the World

Would you rather be able to fly or be able to turn invisible? Who are we more tired of: Ryan Reynolds or Dwayne Johnson? Would…

Tuesday, May 13th
9:00 p.m.10:30 p.m.
The Lincoln Lodge
2040 North Milwaukee Avenue
Dame Myra Hess Memorial Concerts | Adria Ye, Piano
May14
Festivals, Fairs & Special Events, Music & Comedy, Tours & Attractions

Dame Myra Hess Memorial Concerts | Adria Ye, Piano

DAME MYRA HESS MEMORIAL CONCERTS | ADRIA YE, PIANO    Program Lili Boulanger – Trois morceaux pour piano Leoš Janáček – In the Mists  Frederic…

Wednesday, May 14th
12:15 p.m.1:00 p.m.
Seventeenth Church of Christ, Scientist, Chicago
55 E. Wacker Drive
Lexa Maxa: Give Me Jazz!
May14
Festivals, Fairs & Special Events, Music & Comedy, Theatre & Performing Arts

Lexa Maxa: Give Me Jazz!

Lexa Maxa is back this Chicago Cabaret Week with her band but this time with brand new original jazz songs! Come listen to classical jazz…

Wednesday, May 14th
8:00 p.m.10:00 p.m.
Davenport’s Piano Bar & Cabaret
1383 N Milwaukee Ave
Hooch & Holler Comedy Show
May14
Music & 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 14th
9:00 p.m.11:00 p.m.
Bordel Cocktail & Cabaret
1721 W Division
bean-night

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