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.

MOMufactured is Caryn's 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.


Caryn was inspired to help nonprofit organizations with her time and talent while performing with Acts Of Kindness Cabaret. She created Come Fly With Me as a benefit for the National Trust for the Cayman Islands whose mission is to preserve the history and biodiversity of the Cayman Islands. Caryn has performed MOMufactured to benefit nonprofits in Grand Cayman including the Cayman Arts Festival as well as the National Trust and has also participated in Voices for Hospice to benefit Jasmine


Making a cappella music with Route 66, Chicago’s premiere female a cappella quartet took Caryn to venues like Soldier’s Field, the Museum of Science and Industry, and the United Center entertaining at corporate and private parties, summer festivals, and holiday caroling. 


As a proud member of Actors Equity Association, Caryn has performed in productions of Maury Yeston's Phantom at the former Candlelight Dinner Playhouse, and Sweeney Todd at Marriott’s Lincolnshire Theater. 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 that 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

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