Caryn Caffarelli is a professional singer and actress. She has appeared onstage in the US, Europe, and the Caribbean. Her career began in musical theatre and expanded to include standards, jazz, a cappella music, and cabaret. Caryn has performed as 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.


While performing with Acts Of Kindness CabaretCaryn was inspired to help nonprofit organizations with her time and talent. Her show, Come Fly With Me was created as a benefit for National Trust for the Cayman Islands whose mission is to preserve the history and biodiversity of the Cayman Islands. In Grand Cayman she has performed MOMufactured to benefit the Cayman Arts Festival and participated in Voices for Hospice to benefit Jasmine


In addition to her nonprofit work, Caryn was the 1st soprano for Route 66, Chicago’s premiere female a cappella quartet. She entertained at corporate and private parties, summer festivals, and holiday caroling 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 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.


Former Chicago Sun-Times’ theater critic, Hedy Weiss said Caryn has, “a lovely voice,” and the late Richard Christiansen of the Chicago Tribune enjoyed how she “fervently delivers the material.”


In addition to performing, Caryn offers coaching in vocal technique and song interpretation backed by years of experience teaching and performing, and with Master’s degrees in Education and Voice.  


To experience music in different ways, Caryn loves to take ballet, tap, hip hop, musical theater, and jazz dance classes.

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