Cheap flights from Boston to Italy from $222

The cheapest month to fly to Italy from Boston is in January. Flight prices, which tend to average around $539, are often lower during this time because this is during the off-season. If you aren’t able to travel during the month of January, then book flights to Italy from Boston during November instead. Flights to Italy in November, while not as cheap as those in January, still average around $558.

According to our data, Monday is the cheapest day to fly to Italy from Boston. The lowest ticket price found for a Monday departure recently was $693. 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 Friday, the most expensive travel day of the week, you can expect to see flight prices from Boston to Italy for around $806.

Our data shows that the cheapest Boston to Italy flights are usually those with departure times in the evening. Our users have found flights to Italy in the evening for as low as $732. In contrast, the most expensive time of day to depart to Italy is in the afternoon when prices are around $746.

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

You are more likely to see cheaper flights to Italy from Boston when booking week ahead of your departure date. In general, you can expect to find flights to Italy for around $668 when searching week out. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Italy from Boston for as low as $611 on momondo.

Icelandair, LEVEL, and SWISS are the most popular carriers operating from Boston Logan Intl to Italy

ITA Airways, Delta and SWISS are the top three most popular airlines that fly to Italy from Boston according to our data. ITA Airways is the first choice among our users, with 42% of people opting to fly with this airline when traveling to Italy. Keep in mind that there are 21 different airlines that fly to Italy on a routine basis, so you have a few additional options to choose from.

Historically, on average around 12% of flights between Boston and Italy have experienced a delay on any given week. The average delay length over the past 12 months has been 130 minutes.

Generally, flights departing in the evening tend to experience fewer delays. Flights at night have, in the past, seen delays more frequently in comparison.

Tuesday is statistically the day of the week which experiences the fewest number of delays on this flight route. Monday has historically seen more delays on average compared to the rest of the week.

According to our data, Delta have had the least number of delays on this route over the last 12 months; with about 8% of their flights experiencing any sort of delay.

5 flights are operational daily from Boston to Italy as of May 2026. The most popular departure time for this route is 5:00PM, with 100% of flights per day taking off in the afternoon.

As of May 2026, 40 flights take off from Boston and land in Italy each week. The most common flight departure day for this route is Mon, with 15% of weekly flights taking off on this day.