Maybe I'm not getting the definition of clean/dirty in this context but well, Chicago probably has the prettiest downtown among the major US cities. Keeping it clean and green has been one of Mayor Daley's top priorities and I would say he's been fairly successful... Obviously, it's a huge city, so not every part is as rosy. But the downtown is. Oys is right... Chicago has a lot of highrises (including, the tallest building in the US?), some with very fascinating architecture. Not sure about the wind in Connecticut but unless you really measured it in a scientific way and can tell with certainty, I think Chicago is the windiest, too :-p