These Are the Cheapest Times to Fly to Italy

Ready to have a sultry seaside vacation along the Amalfi Coast? A Roman holiday? Perhaps a shopping getaway to Milan? Then you better book a flight ASAP.

According to the World Bank, in 2019, just shy of 100 million people traveled to Italy for a vacation. Though that number declined significantly due to the pandemic, tourism made a major comeback in 2022, with an estimated 56 million arrivals. And if you’re looking to be among the pack to visit in 2023 — and stay on a budget — Scott Keyes, founder and chief flight expert of Going.com, says you should book your flight right now.

“The two months with by far the highest number of cheap flights to Italy are January and February,” Keyes shared with Travel + Leisure. According to Keyes, these are “the slowest two months of tourism in the U.S. and Western Europe, and thus a time when airlines are forced to drop fares in order to fill planes. Sub-$400 round-trip flights to Italy have been commonplace, popping up every few weeks for the past five months.”

If you’re not particularly concerned with the flight cost but would like to avoid the crowds, Keyes suggested plotting out a shoulder-season getaway to just about anywhere in the European nation. “Aside from winter travel, shoulder season (March through May and September through November) is known for cheap Italy deals,” he shared.

If you can hold out until the end of the spring shoulder season, you’ll be rewarded with pleasant temperatures in the mid to high 70s across the country, according to WeatherSpark. The same can be said for the early part of the fall shoulder season, with temperatures in Italy going from the low 80s in September to the high 60s in October.

Keyes mentioned a few recent round-trip fares to Italy his team at Going found for its members, including flights departing New York City for $360, Miami for $380, Chicago for $489, Washington, D.C. for $455, Charlotte for $434, Dallas for $562, and San Francisco for $430. He added, they “even [found flights at] smaller airports like Cleveland for $581.”

There was one more time Keyes said could be the cheapest time to fly to Italy: Thanksgiving.

“I'd argue that the hidden best week of the entire year for cheap flights to Italy is Thanksgiving,” he said. “That's because while domestic fares get severely inflated that week, few Americans are traveling internationally then, and Thanksgiving is certainly not a holiday in Italy. Over Thanksgiving week, it usually costs more to fly to Minneapolis than Milan. Plus, by late November, the wonderful Christmas markets may already be in full swing in some parts of Italy.”

And really, who wouldn’t want to carve a turkey in Milan? You can pair your bird with a local truffle; as Eataly explained, white and burgundy truffles are at their peak between September and December, while winter black truffles are at their prime from December to early March. But luckily for you, there really is no bad time to visit Italy. Find the flight and the time that fits your budget, then start planning the Italian getaway of your dreams.