I love Chicago, well the north side, at least. There is plenty to do there. The John Hancock observatory is just as good as the Sears tower, and you're closer to the lake. It's location (right on Michigan Avenue) is better. And if that black guy that they showed on The Real World, Chicago is still working there, he can tell you how to possibly get last minute tickets to the taping of Oprah's show. 😉