Here are The Traveling Professor's tips for getting cheap airfares to Italy.
Fly into Milan: Without a doubt, Milan is consistently the cheapest gateway into Italy. From there, take the train to any of Italy's major cities like Rome, Florence or Italy. Last year, I was quoted an $1,100 R/T fare to/from Rome from New York. Instead, I flew into Milan for $678. For about $75 I took the train from Milan to Rome. Is it worth the hassle? This is how I figured it: I was arriving in Italy early in the morning, whether I flew to Rome or Milan, too early to check into the hotel. So, instead of waiting in the Rome hotel lobby to check into my room, I was on a pleasant train ride from Milan to Rome. Similar bargains on airfare can sometimes be found into Bologna.
Find Best Airfares: If you have been a regular reader of my blog posts, you know that matrix.itasoftware.com is hands down, the best way to find inexpensive airfares to Europe. It's better than Expedia, better than Orbitz, better than anything else out there. Do a search on this website to find a tutorial on how to use this powerful airline search engine.
Avoid Alitalia: One of the worst airlines we have seen in terms of losing/delaying luggage and customer service. It's not that inexpensive either.
Consider Discount Airlines: I avoid Ryanair and EasyJet, but more established "discount" airlines like Icelandair, AirBerlin and Norwegian Airlines do offer flights into Italy with top-quality service on great equipment. By the way, their premium seating is often near the cost of coach seating on legacy airlines like American or Delta.