I was a band geek in high school, and in my junior year went on a trip with the class for a competition that was being held in Chicago. I remember thinking that it was kind of boring (but that was because the year before we had gone to New York; the next year we went to Florida.) I don't really have a reason to visit there now, but if someone I knew wanted to go, and were willing to pay for my expenses to tag along, I'd go back. Chicago has a lot history, I know that much. Plus there's Oprah and pizza.