Airfare

Try looking on Kayak.

In general lowest airfares will happen at airports with the most competition. The two largest in Italy would be Milan and Rome.

Air fare is higher this year than I have ever see it. Usually the airlines hub are the cheapest. For instance we are flying United out of San Francisco. Through Frankfurt a Star Alliance airline, and returning through Dullas in DC a United hub. I did a lot of looking this year for May and there so far was not too much give on these prices. Now that the airlines have consolidated, not too many deals. And also sometimes the airlines that comes from the country you are flying too many be a better price too. Air France, France British airlines, England

Try Skyscanner. Much better than Kayak.

I can only speak for flights from the northern part of the midwest (Indianapolis/Chicago and Cincinnati) but I've found the least expensive flights are usually via Newark NJ to Milan.

Its impractical (at least to me) to fly back home from Milan though because you lose so much time traveling back north via train...so I've made the costly decision to still fly back from Rome, even though it adds several hundred per ticket (but gives us an additional 1-2 days of sightseeing, so its well worth it to us).

If you search Kayak and do a "multi city" ticket search Nashville to Newark NJ to Milan with return flights from your final city (Rome for example) with return to Nashville you'll probably find the lowest price using this multi city option (since airlines will discount a bit if you book all the flight legs through them)... it seems like booking the different legs separately always ends up costing more.

We are flying from Charleston, SC in March and I searched and searched and compared time and lay-overs and finally decided USAir had the best offer. We are flying USAir Charleston to Philly and direct to Rome from Philly getting in at 7:55 in the morning. It wasn't worth the savings to fly other airlines and stop more than once. Hope this helps. We did do Kayak, Watchdog. liligo and several others before deciding. Good luck.