September 11th - 14th
St. Charles Jazz Weekend is a four-day event that showcases and promotes live jazz music at different St. Charles establishments. An array of St. Charles venues will take part in this year’s event featuring numerous jazz soloists, quintets, and big bands.
Patrons can enjoy jazz music starting mid-day through the evening, with the opportunity to visit multiple venues.
Please note: Some Jazz Weekend performances do require the purchase of tickets to attend. Please reference the Music Schedule to see which performances require tickets.
2025 Jazz Performers

Baker Memorial Church
Enjoy a concert featuring the marriage of classical and jazz music by the French composer Claude Bolling. This performance features special guest violinist James Martin, with bassist Cory Biggerstaff, Darren Scorza on drums, and pianist Richard Sladek performing Bolling’s Suite for Violin and Jazz Piano Trio.

Diego Rodriguez Big Band
The Diego Rodriguez Big Band, commonly known as the DRBB, emerged onto the Chicago jazz scene in December 2022 with a profound commitment to the art form and a dedicated to preserving the legacy of big band music.
Led by drummer Diego Rodriguez, this ensemble stands as a testament to the enduring traditions of Black American Music. Rooted in the greats who laid the foundations of this music, the DRBB reverently pays homage to their contributions while simultaneously aiming to create their own sound. Their repertoire is marked by a fusion of standard repertoire and original arrangements/compositions, encapsulating the essence of both the past and the present.

Gregory Hyde
Gregory Hyde, a Billboard award-winning Chicago-based Singer/Songwriter who has toured North America as an original artist, and as an entertainer for major corporate events.
Gregory has shared the stage with notable performers like Jay Leno, Jim Gaffigan, Pat Benatar, Barenaked Ladies, Soul Asylum, 10,000 Maniacs, Sister Hazel, Gin Blossoms, Los Lonely Boys, Toad the Wet Sprocket, The Smithereens, The Jayhawks, Edwin McCain, Tesla, America, Guster, The Fixx, Air Supply, Blood Sweat & Tears, Bo Bice, and many others.

John Wesley Experience
John Wesley III was born and raised in Chicago, where his father played trumpet and his mother directed and sang in the church choir. Music has played a large part in the Wesley household. At about age 12, John heard his first live jazz saxophone solo. It was love at first note. From there, his life as a musician began. From the Gallery 37 Jazz Band internship to the Chicago All-City Jazz Ensemble. From the ensemble came the creation of the John Wesley Experience (JWE), a group of musicians that come together to make people feel good. JWE is currently in residence at The Duplex in Chicago's Logan Square on the third Thursday of every month.

New Vintage Strings
New Vintage Strings is a contemporary string quartet known for its distinctive blend of jazz, classic rock, pop & alternative instrumental covers with a Classical touch. NVS presents the songs you love like you’ve never heard them before - modern takes on timeless classics. Their unique instrumentation (two violins, viola, double bass), blend of diverse genres and rotation of outstanding musicians sets NVS apart from the traditional string quartet. Classically-trained, experienced orchestral players and music educators, the members of NVS strive to share their passion for music with their community and bring the perfect balance of energy and elegance to any setting.

Sincerely Sinatra Big Band with Nick Pontarelli
Crooner Nick Pontarelli, with an 18-piece orchestra, is bringing his show to the Arcada stage. Nick is a crowd-favorite in our Club Arcada Speakeasy. Don’t miss your chance to hear him perform the music of Frank Sinatra LIVE on stage.
Opening the afternoon’s show will be Close To Karen, A Tribute to Karen Carpenter. Hear the beautiful songs of The Carpenters including “Rainy Days and Mondays”, “Close To You”, “We’ve Only Just Begun” and so many more!

Ten Cat Swing
Ten Cat Swing is a Chicago-based acoustic quartet, bringing a fresh twist to the jazz standards everyone loves. Our music captures the essence of gypsy jazz and beyond, offering the perfect blend of timeless melodies and innovative arrangements. Whether you’re a jazz aficionado or someone new to the genre, our tunes are engaging, easy to listen to, and will make you want to dance, swoon, or croon along with us! Ten Cat Swing performs at a variety of venues and events, from intimate gatherings to grand celebrations, bringing jazz to life wherever we play, and delivering an unforgettable musical experience that is truly “the cat's meow”!

Black and Blue Hearts
Jukebox JBC and Colleen Wild founded The Black and Blue Hearts two years ago. They started as a band writing jazzy and torchy tunes about unrequited love and murder. When it came time to release an EP, Henry and Colleen decided to do something a little different. Inspired by their love for old time radio, The Spectral Silhouette Radio Show was born; a musical and comedic homage to the golden age of radio. In time their humble little duo grew into a multifaceted collective featuring great musicians and artists from all over the Chicagoland area.

Elaine Dame Trio
Elaine Dame sings – and people stop and listen. Since 1996, the woman Time Out Chicago calls “a jazz dynamo” and “a gem in the city’s vocal jazz scene” has been turning heads and capturing attention at venerable jazz venues from coast to coast, bringing her unique, superlative interpretations to vintage vocal classics and modern standards alike. Originally from Toronto, Chris White has gained recognition as a leader with the albums Young at Heart and Tributaries. At home in a host of genres and settings, he has made his name as a go-to freelance pianist, arranger, and accompanist in the Chicago area. Bassist Joe Policastro is a Chicago-based performer, composer, educator, and bandleader. Originally from Cincinnati, OH, he spent time performing in Europe and settled in Chicago in early 2003. He is an in-demand bassist for vocalists, combos, and big bands alike. As a composer/arranger, he leads and contributes to a wide array of ensembles.

Haley Reinhart
A timeless voice outlasts eras. It feels just as at home in the sixties as it does in the TikTok age. It also resounds louder as time goes on. Haley Reinhart brandishes such a voice. Haley plays regularly with Robby Krieger of The Doors among other rock legends; she continues to keep her rock ‘n’ roll roots intact.
The gold-certified Chicago-born/Los Angeles-based singer and songwriter exudes an empowering level of charisma and confidence earned by a quiet, decade-long grind. Haley landed third place and became a fan favorite on season 10 of American Idol. She recently returned to AI, this time as a mentor, coaching contestants singing in the Soul Genre.

Kirby Fellis
Kirby Fellis is an accomplished performer, educator, composer and arranger. Born and raised in South Florida, Fellis attended both Performing Arts Schools at Parkway Middle and Dillard High studying under Melton Mustafa Jr. and Christopher Dorsey respectively. Currently, he is the Graduate Assistant in the Jazz Studies field at Northern Illinois University.

Cherry Poppin' Daddies
Initially rooted in the underground punk scene, the Cherry Poppin’ Daddies made waves with their unique fusion of swing-era jazz and modern rock elements, gaining a reputation for their explosive live performances. They burst into the mainstream in 1997 with the release of Zoot Suit Riot, an album that celebrated the swing revival of the late 1990s. The title track became an instant hit, propelling the band to international fame and selling over two million copies. Musically, the Cherry Poppin’ Daddies are hard to pin down. They fluidly navigate a range of styles, from the big band swing sound of Zoot Suit Riot to the ska-punk of albums like Kids on the Street and Rapid City Muscle Car. With roots in alternative and punk rock, the Daddies have always pushed boundaries, creating music that feels fresh and innovative. Their ability to seamlessly blend vintage swing with modern genres like ska and rock has allowed them to stand out in a crowded musical landscape, while appealing to a wide variety of listeners. The band’s vision, led by charismatic frontman Steve Perry, is grounded in a love for American music traditions and a rebellious spirit. Perry’s songwriting often tackles deep social issues, but with a playful, irreverent edge that keeps listeners hooked. Cherry Poppin’ Daddies have always been about more than nostalgia—they bring a modern sensibility to classic sounds, breathing new life into the swing genre while staying true to their punk roots. Their music speaks to both die-hard swing fans and those seeking something new and different. For new fans, Cherry Poppin’ Daddies offer an exciting journey through American music, on their new recording At The Pink Rat, a 12 song Swing high energy album experimenting with: 40’s Big Band, Ragtime Hot Jazz, salacious mid-century Bump and Grind, slap bass Rockabilly and much more.

Frank Catalano
Frank Catalano is a 3-time Grammy-winning, and 11-time Grammy-nominated jazz saxophone player who has been heard by millions of people all over the globe. He has recorded alongside notable artists such as Jennifer Lopez, Destiny's Child, and John Legend. His most recent album, “Tokyo No. 9” was recorded in collaboration with Jimmy Chamberlin, the drummer for the alternative rock band “The Smashing Pumpkins”.

Michael Shebar Trio
At the ripe old age of 17, Michael has already begun to establish himself as a formidable improvisor, ensemble player and all-around musician. He began studying with renowned saxophonist Gary Smulyan at the age of 12 and quickly began devouring every opportunity for selective school-aged jazz ensembles and competitions. For the past year, Michael has been studying with contemporary jazz alto sax phenom Sharel Cassity, and playing gigs around the Chicago area with various established performers from the Chicago jazz scene. Michael just returned from the ultra-selective Jazz at Lincoln Center two-week jazz program at Bard College in New York, where he was one of 40 students selected from an international pool of applicants to study with a faculty of internationally acclaimed jazz masters including bassist Professor Rodney Whitaker and guitarist Mark Whitfield. Michael is excited for his return to gigging in the Chicago area.

Shout Section Big Band
Formed in 2007, the Shout Section Big Band will be performing as a six person group at this year's Jazz Weekend, and has been entertaining audiences at swing dances, weddings, corporate events, city concerts, festivals and schools all over the Midwest. They’ve been featured on WGN TV, WBEZ radio, and on the nationally syndicated television show, “Vampire Diaries.” They were hired by Amazon.com to perform 1940’s swing for the opening of the Amazon Prime series “A League of Their Own.” Staffed by some of the best musicians in the Chicago Area, you’re going to love listening to and dancing to Shout Section Big Band!
2025 Jazz Weekend Sponsors
