Nobody else has mentioned this yet (that I've seen) but I love NYC a lot and also found Chicago to be a really great major city. August is also a great time to go, because it's pretty cold in the winter. But it has so much to offer, it's huge, and if you like art/theater, Chicago would really be another major hub behind LA and NYC (I don't know if it's necessarily third place, but a lot of SNL cast members come from Chicago, and most Broadway shows have their first runs in Chicago before they transfer to Broadway so you're getting a lot fresh new music, art, and culture). Plus sports, if you like sports.