I've spent a lot of time working in Chicago over the years, and consider it to be one of my favorite cities in the whole country... from about the end of April until the middle of October.

That said, the food scene is great, the night life is great, and the city just has a nice, chill vibe in general. For somebody who likes, or can tolerate, cold winters, it's probably a great place to live. For the rest of us, it's a great place to visit.