Cheap flights from Massachusetts to Italy from $261

The cheapest month to fly to Italy from Massachusetts is in February. Flight prices, which tend to average around $500, are often lower during this time because this is during the off-season. If you aren’t able to travel during the month of February, then book flights to Italy from Massachusetts during January instead. Flights to Italy in January, while not as cheap as those in February, still average around $542.

According to our data, Monday is the cheapest day to fly to Italy from Massachusetts. The lowest ticket price found for a Monday departure recently was $704. Keep in mind that prices can always vary depending on your route and whether or not you are flying domestic or international. When flying out on a Thursday, the most expensive travel day of the week, you can expect to see flight prices from Massachusetts to Italy for around $811.

Our data shows that the cheapest Massachusetts to Italy flights are usually those with departure times in the afternoon. Our users have found flights to Italy in the afternoon for as low as $749. In contrast, the most expensive time of day to depart to Italy is in the evening when prices are around $924.

Fly from Boston Logan Intl to Milan Malpensa for the best Massachusetts - Italy flight prices

You are more likely to see cheaper flights to Italy from Massachusetts when booking weeks ahead of your departure date. In general, you can expect to find flights to Italy for around $668 when searching weeks out. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Italy from Massachusetts for as low as $613 on momondo.

There are 3 cabin classes available to choose from on Massachusetts to Italy flights. Cabin price and availability will vary by airline so perform a search above to find the right deals for you.

TAP AIR PORTUGAL, LEVEL, and KLM are the most popular carriers operating from Massachusetts to Italy

ITA Airways, Delta and SWISS are the top three most popular airlines that fly to Italy from Massachusetts according to our data. ITA Airways is the first choice among our users, with 41% of people opting to fly with this airline when traveling to Italy. Keep in mind that there are 20 different airlines that fly to Italy on a routine basis, so you have a few additional options to choose from.

8 flights are operational daily from Massachusetts to Italy as of June 2026. The most popular departure time for this route is 4:00PM, with 76% of flights per day taking off in the afternoon.

The number of flights available between Massachusetts and Italy is 59 per week as of June 2026. The most frequent departure day is Mon, with 17% of weekly flights leaving on this day.