This is my first post about deals and bargains from the US to Italy! I’ve found a cheap roundtrip ticket from New York City to Milan and you should book right now because the departure is in less than a month!
648$. October 6-14, fly with Air Canada and stop in Toronto. Book on Expedia.com.
What can you visit other than Milan? You can get the best from this week in Italy by visiting Verona and Venice for a day trip. There are frequent trains with Trenitalia.it and if you book in advance you can save a little.