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Caryn Caffarelli has appeared onstage in the US, Europe, and the Caribbean. Genres include musical theater, cabaret, a cappella, standards and jazz. She has been a soloist at venues in Chicago including Victory Gardens Theater, Davenport’s Cabaret, The Cliffdweller’s Club, and The Skokie Theatre, and in Grand Cayman at The National Gallery, The Harquail Theatre, and the Kimpton Grand Ballroom.

Caryn's solo show MOMufactured is a funny and poignant insider’s look at parenting. She and her husband, Craig are grateful parents to two daughters. Caryn’s recording, "Journey" is about her path to motherhood and is available at her live events.


Caryn has a passion for helping nonprofits with benefit performances. She created Come Fly With Me as a tribute to Grand Cayman's community and history for the National Trust for the Cayman Islands. She collaborated with survivors of domestic abuse, weaving their stories into a set of songs for the Crisis Center Cayman Islands 20th anniversary gala. Her performances have also benefitted the Cayman Arts Festival and Jasmine Hospice CareIn Chicago she performed for many years with Acts Of Kindness Cabaret and served on their board.

Caryn was a founding member of Chicago’s premier female a cappella quartet, Route 66, performing at venues like Soldier’s Field, the Museum of Science and Industry, and the United Center. 


As a proud member of Actors Equity Association, Caryn has been seen in regional theater productions of Sweeney Todd at Marriott’s Lincolnshire Theater and in Maury Yeston's Phantom. Favorite roles include Anne Egerman in A Little Night Music, Velma Kelly in Chicago, and Molly Brown in The Unsinkable Molly Brown.


Caryn has been praised in the Chicago Sun-Times as having “a lovely voice,” and in the Chicago Tribune as she “fervently delivers the material.”

Venues played include:



Kimpton Grand Ballroom, Grand Cayman

Marriott Grand Ballroom, Grand Cayman

The National Gallery, Grand Cayman

Next Door, Grand Cayman

Westin Grand Ballroom, Grand Cayman


Chopin Theatre, Chicago, IL USA

Cliffdweller's Club, Chicago, IL USA

Davenport's Cabaret, Chicago, IL USA

DePaul University, Chicago, IL USA

Drew's on Halsted, Chicago, IL USA

Fairmont Hotel, Chicago, IL USA

Museum of Science & Industry, Chicago, IL USA

Park West, Chicago, IL USA

Skokie Theatre, Skokie, IL USA

Soldier Field, Chicago, IL USA

Victory Gardens Theater, Chicago, IL USA

Elspe Festival, Elspe, Germany

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