air to italy

I’ve flown nonstop from Newark to Milan, and Newark to Rome, on United. Prices vary for the time of year. We flew to Milan in May of 2017 and that was less than Flying to Rome. Last February we flew to Rome for around $460.

matrix.itasoftware.com

You can explore your options with this site, operated by Google for the airlines. It doesn't sell tickets but its information is more complete than any other (including Google Flights, which does sell tickets.) No site covers everything.
Major American cities will show the cheapest trans-Atlantic fares because they have competition on the routes. New York, Atlanta, Chicago etc. are gateways. The connections can be on either side of the Atlantic (London, Amsterdam, Paris, Frankfurt etc. ) These days, non-stop flights may be a little more costly than routes with a change of planes, because of the demand -- they're faster and less stressful.
Do not try to piece together a series of flights yourself. Use the airlines' sites to find the routes for you, or agencies such as Expedia, Priceline, Cheapoair and many others.

Thank you both for your insight this will help quite a bit.

Most flights to Italy land in Milan (MXP) or Rome (FCO). New York (JFK) offers the greatest selection of nonstop flights. For example:

JFK - Milan on Air Italy, Emirates, or Delta.

JFK-Rome on Delta
Newark (EWR) to Miami on United
Newark (EWR) to Rome on Norwegian, and Brussels airlines
Boston - Rome on Alitalia
Dulles (IAD) to Rome on United
Atlanta (ATL) to Rome on Delta.

Note that many Delta bookings include flights on Alitalia, which is in bankruptcy. Alitalia has also had serious service issues over the years.

The JFK-Milan flights have been the cheapest in recent years.

We do not use JFK, even though we live 2.5 hours away. Our current favorite airline is Aerlingus, mainly since they fly direct from our home airport -Hartford (BDL) to Dublin. It is easy to connect in Dublin to Italy. Another nice feature of Aerlingus is that you can go through US customs and immigration in Dublin on the way home. Before the Hartford-Dublin flight started, we flew out of Boston and connected in Amsterdam or Paris on Delta or Air France.

Boston does have direct flights to Rome (current Alitalia but think it will continue just may change carriers in the future)
I imagine Newark / JFK will be lower cost and more options though.

For Italy Rome or Milan is usually your best option (most flights and lowest typically).
Venice is probably the only other one with any direct options but cannot imagine ever cheapest.

All above said, the cheaper option will almost always involve a connection somewhere else in Europe and once you do that your airport choices in Italy will be much greater and probably have little affect on the cost.

What is your home airport(s) from which you will be departing?
knowing which airport has the cheapest flights to Italy doesn’t help you if you don’t live near that airport.
Use any search engine like Kayak or Google flights.
Enter
from YOUR HOME AIRPORT
to: ITALIAN AIRPORT where you need to land.
These are some international Italian airports where most tourists go, in order of size (in parenthesis the airport code):
Rome (FCO)
Milan (MXP)
Venice (VCE)
Naples (NAP)
Bologna (BLQ)
Florence (FLR)

Note that only the first 3 (FCO, MXP, VCE) have non stop flights from/to North America, the others have only Intra European flights which require at least one change at a European hub.

Thanks for the recommendation of matrix.itasoftware.com

I had always used Kayak, which is pretty good, but Matrix is great because it doesn't even sell tickets. You can just do your research and know what you're dealing with before you go to buy directly from the airlines.

I agree with epltd .... Use the websites suggested to research flight options but buy direct from the airline or use a real live travel agent to purchase your tickets. The online sites that sell tickets will only be a barrier between you and the airline if there are any issues during your travels.

There are American direct flights from Philadelphia it Rome and Venice, these are USAir routes they took over.