Fly nonstop from New York to Milan for $657 round-trip on Delta/Alitalia.
Seen below, we found seats departing JFK on Wednesday, April 22, returning from MXP on Thursday, April 30.
Other dates are also available for travel in winter/spring through mid-May.
If you don't mind connecting, you'll find slightly lower flights (at $638 round-trip) available on Air Canada.
Need a room in Milan? Here's a look at what's available on Hotelwatchdog for the above travel dates.
You'll also find rooms going for $91/night at the Starhotels Anderson currently featured on Jetsetter.