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Caryn Caffarelli has appeared onstage in the US, Europe, and the Caribbean. Her performing career began in musical theatre and expanded to include a cappella singing, cabaret, standards, and jazz. Caryn 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 including The National Gallery and The Westin Grand Ballroom.

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


Come Fly With Me is a tribute to the community and history of the Cayman Islands. Caryn has performed her solos shows to benefit nonprofits in Grand Cayman including National Trust for the Cayman IslandsCayman Arts Festivaland has participated in Voices for Hospice to benefit Jasmine


In Chicago, Caryn was inspired to help nonprofit organizations with her time and talent performing with Acts Of Kindness Cabaret. She was also a founding member of the a cappella female 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 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:



Marriott Grand Ballroom, Grand Cayman

The National Gallery, 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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