Red curtains all around and red lights abound. Red tables too–delicately lit in an evening of music, dining, and early 20^th century elegance. Surely a rift in the space-time continuum had transported us back to a New York City speakeasy in the 30s. Edith Piaf would be walking onto that stage any minute now…

As it turns out we were at the newly opened and exquisite St. Regis Chicago. The hotel recently hosted its inaugural restoration of Jack’s Club–a modern cabaret experience inspired by those timeless traditions of yesteryear. Serving to commemorate the one year anniversary of St. Regis’ newest luxury auberge, Jack’s Club drew on Chicago’s rich jazz tradition to deliver an unforgettable night of performance. 

Prior to doors opening, attendees were treated to champagne and a complimentary caviar bar, all while being serenaded by the trumpet stylings of Chicago’s own Marquis Hill. The party soon found itself in cabaret-style seating, being greeted by the dynamic performance artist Daphne Always. Bandleader and trumpeter Chris Norton paid homage to Louis Armstrong and jazz legends alike with an arrangement of vivacious ditties, while Grammy-nominated Bossa nova singer Bebel Gilberto mesmerized the crowd with her uniquely alluring tones. 

Lettuce Entertain You, the same restaurant group behind award-winning chef Evan Funke’s Tre Dita (housed within the St. Regis Chicago) provided the evening’s dining options: oysters, shrimp cocktails, and martinis for some Jazz Age flare, while miniature Chicago-style hot dogs added a regional touch. 

Named in honor of St. Regis founder John “Jack” Jacob Astor IV, the event brought together a diverse mix of guests to enjoy this reintroduction to a wonderful cabaret tradition like none other. Future Jack’s Club events are set to take place in St. Regis hotels around the world beginning in 2025.

Images courtesy St. Regis Hotels & Resorts.