One of the nicer posh bars downtown is simply called Roof. It is located inside of the Wit Hotel on State street downtown. They serve both drinks and have quite a decent food menu. They have a nice unique decor that will remind you of the outdoors. It has an amazing view out to the Chicago skyscrapers and it kind of reminds you of a vegas night club. The drinks aren't very cheap but at a place like this it's what you would expect. Don't expect to reserve a table or get great service from one of the servers unless you plan on paying for bottle service. I would recommend checking out out during the week after work before you try going on the weekend.

The Wit Hotel
201 N State
Chicago, IL 60601
(312) 239-9501