Flights to Italy in 2027: When to Go, Where to Land, & What to Pay

Timing. That's the biggest thing standing between you and a cheaper flight to Italy.

If you pick the right month, book at the right time and land in the right city, the same trip can cost a lot less. Get it wrong, though, and your flights could eat a big chunk of your budget.

We dug into RatePunk's fare data to help you nail all three, so your money goes into the trip of a lifetime, not the plane ticket.

In this guide:

• What a Good Fare Looks Like
• The Cheapest Months to Fly
• What Holidays Do to Fares
• Flying in Summer
• When to Book
• Choosing an Arrival City
• One-Way Tickets vs Round Trip
• Choosing a Departure Airport
• Nonstop or Connecting Flights
• Frequently Asked Questions

What a Good Fare Looks Like

Before you open a dozen browser tabs, it helps to know what a good price looks like. That way you'll know a deal when you see it, and won't panic-book the first fare that pops up.

So what counts as a good fare? One that's cheaper than nine out of ten fares we saw for the same trip. Fares like that don't pop up every day, so when you spot one, it's worth grabbing.

Here's roughly what a good round trip to Rome looked like from some of the busiest U.S. airports. If your city isn't on the list, use the closest big airport as a rough guide.

• New York: $340
• Boston: $425
• Los Angeles: $435
• Miami: $470
• Washington, D.C.: $475
• Chicago: $480

When you fly changes the picture just as much as where you fly from. A good fare in November looks very different from a good fare in July, so here's what one looks like for every month of the year.

The Cheapest Months to Fly

The cheapest time to fly to Italy from the U.S. is October to February. Every one of those months came in under the usual fare for the year, meaning the middle price of all the fares we saw. If your dates are flexible, this is where the deals live.

Here's how much less each of those months cost:

• February: 15% less
• November: 14% less
• January: 9.6% less
• October: 9.1% less
• December: 5.5% less

March and April hover right around the usual fare, and then prices take off. By July, fares were 83% higher than the usual fare for the year.

So if you remember one thing from this guide, make it this: pick your month first. The month moves the price more than anything else we looked at.

Round-trip fares from the U.S. to Italy by departure month, compared with the usual fare for the year. February was 15% below usual, followed by November at 14% below, January at 10%, October at 9%, and December at 6%. March and April were 1% above usual, September 8%, August 9%, May 36%, and June 75%. July was highest at 83% above usual.

What Holidays Do to Fares

Holidays can make flights to Italy a lot pricier, and Christmas is the big one. Flying over Christmas and New Year cost 103% more than other December and January dates, so you're basically paying double. Easter week is gentler, at just 16% more than other March and April dates.

Both holidays are big weeks in Italy itself. At Christmas, markets like the one in Bolzano, one of the largest in Italy, draw visitors from around the world. At Easter, Holy Week brings pilgrims to Rome for the Pope's Easter Mass at the Vatican.

The holiday rush isn't only in Italy. Back home, the Transportation Security Administration expected one of its busiest stretches of the year from just before Christmas into early January. So on top of paying more, you'll be elbowing through packed airports on your way out.

U.S. holidays can move fares to Italy too, though not always up. Here's how the bigger ones compared with the week before and the week after:

• Presidents' Day weekend: 12% to 49% more
• Memorial Day weekend: 5.7% to 26% more
• Thanksgiving week: 1.1% to 5.9% more
• Fourth of July: 12% less than the week before and 2.9% more than the week after

Good news! If you get Thanksgiving off, fares barely budge that week, so it's a good time to sneak away.

For the other holidays, if your dates can move, fly a week before or after and save the difference for a meal with a nice view.

Flying in Summer

If summer is the only time you can go, aim for August or September. Both cost far less than June and July. Here's how the summer months stacked up against the usual fare for the year:

• May: 36% more
• June: 75% more
• July: 83% more
• August: 8.7% more
• September: 7.8% more

July is the priciest month of the year to fly to Italy, so it's the one to dodge if you can. Push your trip to late August or September and your wallet will thank you.

When to Book

The best time to book flights to Italy is one to three months before you fly. Wait until the last minute and you'll pay for it. Book way too early and, weirdly, you might pay for that too.

Here's how each booking window compared with the usual fare on the same route:

• Last week before you fly: 7.6% to 14% more
• 1 to 3 weeks out: 3.8% to 4.3% more
• 3 to 4 weeks out: 0.3% more
• 1 to 3 months out: 1.4% to 2.2% less, the best window
• 3 to 4 months out: 0.8% less
• 4 to 6 months out: 2.3% more
• 6 to 10 months out: 36% more, on fewer routes

Honestly, the gaps between one and four months out are small, so don't waste a lot of energy hunting for the perfect day. Pick your month, then book somewhere in that window.

Booking in that window also gives you a safety net. Under U.S. Department of Transportation rules, tickets you buy at least seven days before departure come with a 24-hour grace period. The airline must let you cancel for a full refund within 24 hours, or hold the fare for 24 hours without paying. So if you spot a better deal the next morning, you can change your tickets.

Round-trip fares to Italy by how far ahead they were seen, compared with the usual fare for the same route and month. Fares seen one to one and a half months out were cheapest at 2.2% below usual, followed by one and a half to two months at 1.9% below, two to three months at 1.4%, and three to four months at 0.8%. Fares seen three to four weeks out were 0.3% above usual, four to six months 2.3%, two to three weeks 3.8%, one to two weeks 4.3%, four to seven days 7.6%, and zero to three days 14.1%. Fares seen six to ten months out were highest at 36% above usual.

Choosing an Arrival City

Milan and Rome are the cheapest places to land in Italy from the U.S. Compared with the usual fare to Italy, fares to Milan were 8% lower and fares to Rome were 3.9% lower.

Dreaming of Naples, Venice, or Florence? Flying straight there costs more than the usual fare to Italy:

• Naples: 16% more
• Venice: 20% more
• Florence: 21% more

Here's the trick: if Florence or Venice is the goal, price flights into Milan or Rome first. Then, take the train or a short flight from there.

One-Way Tickets vs Round Trip

Two one-way tickets cost a lot more than one round trip. On every pair of Italian cities we checked, two one-way tickets cost 40% to 55% more than a round trip.

Say you want to fly into Milan and home from Rome. Doing that on two one-way tickets cost 55% more than a round trip to Milan and back.

Still want to see the north and the south without backtracking? Look at multi-city tickets, which airlines sell on one booking.

Choosing a Departure Airport

Live near New York or Boston? Good news: those are the cheapest big U.S. cities to fly to Italy from. Compared with the usual fare to Italy, fares from New York and Boston were 33% and 21% lower, respectively.

Chicago and Atlanta landed right around the usual fare, so nothing special, but nothing scary either.

If you're flying from New York, Rome is the sweet spot. New York to Rome was the cheapest of the busiest city pairs we tracked, at 41% below the usual fare, with New York to Milan and Boston to Rome close behind.

Rome isn't always the cheaper place to land, though. From Washington, D.C., flights to Milan cost 15% less than flights to Rome, and from Dallas they cost 4.4% less. So check both cities before you book.

Usual round-trip fares on the 10 cheapest of the 30 busiest U.S.-to-Italy city pairs. New York to Rome was about $425, New York to Milan about $495, Boston to Rome about $555, Miami to Rome about $590, Miami to Milan about $605, Los Angeles to Rome about $620, Los Angeles to Milan about $630, Chicago to Rome about $650, Washington, D.C. to Milan about $665, and Fort Lauderdale to Rome about $670.

Nonstop or Connecting Flights

Connecting flights are the cheaper way to fly to Italy most of the time. On the same route and dates, nonstop flights usually cost about $135 more.

Nonstop flights were the cheaper pick only 14% of the time. With that said, where you land can make a difference in how much extra you pay.

• Rome: about $95 more for nonstop flights
• Milan: about $155 more for nonstop flights

If you'd rather skip the layover and land ready for your first espresso, Rome is where that splurge hurts less.

Frequently Asked Questions

What is the cheapest month to fly to Italy?

February is the cheapest month to fly to Italy from the U.S. February fares were 15% below the usual fare for the year, and November fares were close behind at 14% below it.

January and October are solid picks too, with fares 9.6% and 9.1% below the usual fare. Skip July if you can. It was the most expensive month, at 83% above the usual fare.

What day of the week is cheapest to fly to Italy?

Tuesday and Wednesday are the cheapest days to fly to Italy. Fares on those days were 2% and 1.5% below the usual fare on the same route.

Friday and Saturday cost the most, at 4.4% and 3.3% above the usual fare. But the gaps are small, so don't plan your whole trip around the day. The month you travel matters more.

Which airlines have the cheapest flights to Italy?

No single airline is always the cheapest to Italy, but United showed up among the cheapest fares more than expected. United was on 18% of the cheapest fares.

Budget airlines weren't the bargain. Frontier was only 5.4% of the cheapest fares.

Does the length of your trip change the price of a flight to Italy?

No, the length of your trip barely changes the price. From five nights to three weeks, fares matched the usual fare for the same route and month. So stay as long as you like.

What do U.S. citizens need to fly to Italy?

U.S. citizens don't need a visa for trips to Italy for less than 90 days, according to the U.S. State Department. Your passport must be valid for at least three months after you plan to leave the Schengen area, but six months is safer.

Your passport also needs two blank pages for the entry stamp, so flip through it before you pack.

How We Got These Numbers

We used round-trip economy fares between U.S. airports and Italy that RatePunk saw in flight searches, mostly three weeks to four months before departure. The usual fare is the median, so half the fares were cheaper and half cost more. Entry rules come from the U.S. State Department. These are prices shown in searches, not prices anyone paid.

About RatePunk

Reading fares and understanding what makes them move is our area of expertise, and the prices in this article come from our own flight data. RatePunk Flights is a flight-deal service that watches prices from your home airport and alerts you when a flight costs less than usual. You can then book it wherever you like, with the airline itself or a travel site you already use.

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• How to Find Cheap Flights in 2027: 10 Tips Tested With Real Fares
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