The Cruise Room Bar

Opened on December 6, 1933—the day after prohibition ended—The Cruise Room Bar was founded as a celebration of good booze, good times, and the endless promise of a late night. Now, more than 90 years later, the Union Station staple looks much as it always has. There have been a few renovations here and there to top off its elegance, but the historic landmark retains all the glamour and glitz of its post-prohibition heyday. 

Decorated by Gilbert Charles Jaka, who also designed a lounge on the luxury ocean liner RMS Queen Mary, the Cruise Room oozes sultry grandeur. A vintage jukebox spins tunes from velvety-voiced crooners, and the red-tinged room sports bas-relief panels and gilded details. Over the last century, the Cruise Room served as a watering hole for celebrities and artists, politicians, and entrepreneurs. The air almost feels thick with the accumulated century of the city’s juiciest gossip. 

Like any good speakeasy, the bar isn’t immediately obvious from the street. Instead, it lies hidden within the Oxford, a regal Victorian-era hotel that’s been around since 1890. Pull up a stool, listen to the moody fizz of champagne and low voices, and wave the waiter over. The wine list is good, as is the food, but this place is known for its cocktails. The gin martini and negroni both come highly recommended.