I've lived in Chicago for a couple of years and found all kinds of different places that I enjoy (everything from Pili-Pili to Kasey's). It seems, however, that I keep heading back to the same ones.
I'd like to go somewhere new tonight, for drinks and/or dinner (perhaps two places) near dowtown. Although I don't mind paying for good food, I tend to prefer simpler places to extravagant ones. Someplace hip and fun, but not ultra-cool... When I lived in London, I spent most of my time at gastropubs.