Something's always happening at the Roosevelt.
Calendar

Something's always happening at the Roosevelt.

Live cabaret, close-up magic, classic film screenings, pool parties, and more — across every venue, every week.

All EventsFilmPool Parties
Classic Cinema Night
WEDBiweekly
Cinegrill Theater

Classic Cinema Night

A classic film retrospective hosted by renowned film critic Jose Ignacio Cuenca. Cinegrill Theater pays homage to its roots.

Every Other Wednesday · 7 PMTickets →
Down the Rabbit Hole
SATBiweekly
Cinegrill Theater

Down the Rabbit Hole

Tucked behind a bookcase, this immersive cabaret reimagines Alice in Wonderland through Old Hollywood indulgence — burlesque, surrealist visuals, and high-glam fashion. Created by Tableau Productions, directed by Tracy Phillips.

Every Other Saturday · 8 PM · 18+Tickets →
Magic at the Library Bar
SUNWeekly
Library Bar

Magic at the Library Bar

Close-up magic with the renowned HUBB, known from The Magic Castle and The Chicago Magic Lounge. An intimate, unforgettable evening of sophisticated illusions.

Every Sunday · 6 PMTickets →
Poster for Chess & Jazz at The Spare Room, showing a chessboard in a dark, wood-panelled lounge, Monday, September 7, 2026, 7–11 PM
MONMonthly
Spare Room

Chess and Jazz

First Monday of Every Month