Moving to New York City in 1982, he was privileged to work with many of the swing era's recognized greats, studying with both Remo Palmier and 4-string guitarist "Tiny" Grimes, while appearing at the West End Café with artists such as Eddie Durham, Eddie Barefield, Earle Warren, Joe Newman, and Haywood Henry. As a member of Benny Goodman's last band, his performances included the PBS television broadcast Let's Dance. With the Buck Clayton Orchestra he toured Europe in the summer of 1991, and played such venues as New York's Village Vanguard. Working regularly with clarinetist Kenny Davern, he recorded the newly released The Kenny Davern Quartet: In Concert at the Outpost Performance Space.

As "Fiddler" Claude Williams' guitarist of choice, he participated in President Clinton's inaugural festivities, and performed at Carnegie's Weill Recital Hall. He was also a charter member of the Smithsonian Jazz Masterworks Orchestra (1992-99) under the direction of David Baker and Gunther Schuller, and has performed with Bob Wilber and the Carnegie Hall Jazz Band directed by Jon Faddis. Working regularly with Jazz At Lincoln Center directed by Wynton Marsalis, he has played with Benny Carter, Frank Wess, and Paquito D'Rivera.

Having studied composition and arranging with John Carisi, he was honored to have premiered, with the composer on trumpet, Mr. Carisi's Counterpoise #2 for Electric Guitar and Trumpet, expressly written for Mr. Chirillo in 1991. The National Endowment for the Arts awarded him a 1995 Jazz Composition Grant for the Homage Concerto for Clarinet and Jazz Orchestra*, written for clarinetist Ken Peplowski and the Loren Schoenberg Jazz Orchestra. He composed/arranged the title track of Mr. Schoenberg's CD Manhattan Work Song (on Jazz Heritage - voted "worthy of wider recognition" by the Village Voice, 1993) and arranged the title track of Out Of This World (on TCB Records). He has also written arrangements for singers Daryl Sherman, the late Bobby Short, and is much in demand on NYC's free-lance scene, while continuing his studies with composer/arranger Bill Finegan.

His work as a writer has been featured on National Public Radio's Jazz At The Archives, and in April 2000 he was invited by the Cleveland Jazz Orchestra to conduct a program of his music, featuring the Homage Concerto with Mr. Peplowski as soloist. To celebrate their bi-centennial (spring of 2002), he premiered his Grainger Suite, written for and commissioned by the US Military Academy Jazz Knights. Recently, in Glasgow, Mr. Chirillo wrote for and conducted cornetist Warren Vaché with the Scottish Ensemble on his new release, Don’t Look Back, on the Arbors label. After performing on dozens of albums, he was invited by Nagel-Heyer Records to record his debut as leader --- Sultry Serenade --- selected by the director of the Institute of Jazz Studies at Rutgers University Dan Morgenstern as one of his top five Critics’ Picks for the Year 2000 in Jazz Times magazine, and as one of critic C. Michael Bailey's Top Ten List of Jazz Releases for 2000 at allaboutjazz.com.