Non-Stop for less than $400 on Lufthansa is pretty killer, as a bonus there is also some good availability on jetBlue if you prefer to fly with them. Some great stacking discounts on Hotels and Rental cars with Expedia definitely help at least cover your gas from Milan (I would be heading to Chamonix personally!)
NY/NJ to Milan generally runs at least $750 during ski season — these cheap flight save you about 50% and get you there Non-Stop on Lufthansa.
I am keeping this one short since I am currently sitting in the Athens airport ($370RT from NYC on Emirates, I had to). That being said this is one to jump on if you have Europe on your list this winter, I SERIOUSLY doubt it will get any cheaper than this.
Ski + Snowboard
There are so many options within reach from Milan it's ridiculous BUT you will need a car. To that effect these trips match up well with Expedia's current 25% off coupon / link with Budget good for 25% off your car when booked with Expedia over here: 25% off with Budget Rental Cars on Expedia
The other thing that the above matches up nicely is a pretty killer coupon that Expedia is running on Hotel bookings: $25 off $250 2+ Nights with code: HOTEL25 on Expedia. While I don't have good enough Wifi at the moment to dig through the hotel listings, guaranteed there are some options — $25 is $25.
Hoping to fill in more dates but my flights boarding so this is all you guys get for now.