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He'll have to cross the Atlantic - Gina Marie Trio
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The Very Thought of You - Gina Marie Trio
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Penthouse Serenade
Who Walks In When I Walk Out? - Gina DeGregorio & Hal Smith- Penthouse Serenade
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You Started Me Dreaming - Gina DeGregorio & Hal Smith feat. Paul Asaro- Penthouse Serenade
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Biography

 

Chicago-based artist Gina Marie DeGregorio has evolved as a formidable voice in early jazz. Gina has developed a uniquely “bold yet soothing sound evoking memories of 1930s lounges with a fresh homage to italian-american crooning styles.”

 

Gina’s curative style has been in high-demand on Chicago’s bustling jazz scene and world wide at venues such as Chicago’s Green Mill, Caveu de Hutchette in Paris, Spirit de Milan, Cafe Diablo in Quito, The Three Muses in New Orleans, The Iguana NYC, and beyond. She is equally at home entertaining distinguished audiences including international delegations in Washington DC and festival audiences abroad. 

 

Gina's Uptown Swingtet delivers upbeat swing with authentic 30's/40's stylings designed with dancers in mind. For intimate settings, the trio evokes the class and sophistication of old Hollywood.

Upcoming Events

  • Sep 18, 2025, 8:00 PM – Sep 19, 2025, 12:00 AM
    Chicago, 4802 N Broadway, Chicago, IL 60640, USA
    Thursdays at the Green Mill mean high‑energy big band, a timeless Uptown ambiance, and a night where both your feet and the past can't help but swing. Don’t miss it—dust off your dancing shoes, grab some cash, and tap into Chicago’s golden jazz era as the music comes alive in the room where swing s
  • Thu, Jul 31
    Jul 31, 2025, 9:00 AM – Aug 03, 2025, 1:00 PM
    Davenport, 7077 Elmore Avenue, Davenport, IA 52807, USA
    🎺 BixFest in Davenport is a must for trad jazz lovers—live bands, swing dancing, and vintage vibes all weekend long in Bix Beiderbecke’s hometown. Celebrate where the legend began!
  • Jul 12, 2025, 7:00 PM – 11:00 PM
    Arlington Heights, 10 S Vail Ave, Arlington Heights, IL 60005, USA
  • Jul 04, 2025, 3:30 PM – Jul 05, 2025, 12:00 AM
    Location is TBD
    🎺✨ Chicago’s Vintage Block Bash is the ultimate throwback street fest for those in the know—live vintage music, street dancing, retro vendors, and a fireworks finale. Dress up, show out, and celebrate Chicago’s coolest scene!
  • Jul 03, 2025, 8:00 PM – Jul 04, 2025, 12:00 AM
    Chicago, 4802 N Broadway, Chicago, IL 60640, USA
    Step back in time with the Alan Gresik Swing Orchestra at the legendary Green Mill! Vintage charts, hot rhythms, and vocals by Gina Marie DeGregorio—every Thursday night, it’s 1938 all over again. Don’t miss the swing!
  • Jun 05, 2025, 8:00 PM – Jun 06, 2025, 12:00 AM
    Chicago, 4802 N Broadway, Chicago, IL 60640, USA
    Classic songs of the 30s and 40s in the iconic green mill cocktail lounge
  • Fri, May 30
    May 30, 2025, 9:00 PM – May 31, 2025, 12:00 AM
    Chicago, 140 E Walton Pl, Chicago, IL 60611, USA
    Gina Marie returns to the Historic Drake hotel in the intimate Coq D'Or lounge FREE no cover!
  • Thu, May 29
    May 29, 2025, 9:00 PM – May 30, 2025, 12:00 AM
    Chicago, 4802 N Broadway, Chicago, IL 60640, USA
    Gina Marie returns to the iconic Green Mill Cocktail Lounge backed by the Alan Gresik Swing Orchestra for the Big Band Radio Hour
  • Thu, May 15
    May 15, 2025, 8:00 PM – May 16, 2025, 12:00 AM
    Chicago, 4802 N Broadway, Chicago, IL 60640, USA
    Gina Marie returns to the Green Mill Cocktail Lounge backed by the Alan Gresik Swing Orchestra for Big Band Radio Hour
  • May 10, 2025, 9:00 PM – May 11, 2025, 12:00 AM
    Chicago, 140 E Walton Pl, Chicago, IL 60611, USA
    Gina Marie returns to the intimate Coq D'Or Lounge in the Drake hotel to sing the best American Songbook tunes from the 20's through the 40's As part of the Supperclub Series presented by Biossat Custom Productions
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