Unfortunately, the W City Center is in the heart of the business area called "the loop". There is not a ton of stuff nearby that will be open on the weekends, let alone later in the evening. Cabs are a plenty, so don't let distance stop you. The W itself has a fun bar called Whiskey Blue.

You will be not far from Randolph St., which is considered Restaurant Row, however, while there are a ton of restaurants (all of which have a bar area), there are not a ton of bars just for the drinking. Maybe Fulton Lounge? http://www.fultonlounge.com. Also, Greektown is close and there is a place called the Green Room, http://metromix.chicagotribune.com/d...0,163475.venue, you may want to try. Both are kind of swanky and sound like what you want. Not sure of the noise level in either place.