Best way (cheapest) to book a flight to Italy?

Patience and daily checking Google, plus other sites

As said, set a flight tracker through kayak, google flights, etc. They will email you when the price changes.

Its also worth looking at the carriers that fly to where you are going, and sign up to be on their email list. FOr Italy, consider signing up for Air Italia though I don't know who they partner with? It may be better to plan on a domestic carrier.

Outside of big specials, most airlines don't give deals until 75-90 days out. So there really is no hurry at all to book, almost no one books a great deal a year in advance. For example, most airlines are running their fall specials right now. Then in a month or two, they'll start their winter deals.

As said, anything under $1000 a flight is a good price. Anything under $800 RT is a gotta book great price, and under say $600 with a connecting flight in the USA say baton rouge to Atlanta or NYC, is very rare and a fantastic price. So if you see any of those pop up, know to pull the trigger.

For next june, hold off a few months. They haven't even posted thanksgiving or christmas deals yet so you've got a long ways to wait. My best guess would be during the winter (November/January) you'll see one deal then a few more during early spring pop up for about $700 ish

Delta Sky Miles

Are you flying out of BR or Nola? If so, you'll be hard pressed to find any cheaper flights than what you saw.

But if you do a little work and due diligence, you can fly out of any number of large airports in other cities (mainly east coast) for super cheap comparatively.

I routinely see flights out of Boston and NYC to Italy in the $300-400's.

Sign up for an airline point system (SW, Delta, United, whatever), maybe get a credit card with a sign up bonus, and try to accumulate points in the next 6 months that that will let you fly to one of those larger airports for free.

Flying out of Nola or BR is always expensive.

Eta: even if you don't do the above strategy, it may still be considerably cheaper to pay for the domestic flight to a larger airport. Just don't rush. You have plenty of time. Check prices almost daily.

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Flying out of Nola or BR is always expensive.

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Not really, unless you mean direct flights only.
As others said, patience and keep checking. I've found some great flight prices out of MSY, but of course they include a US connection.

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I meant internationally

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Of course. I'm just saying there are deals to be had out of MSY. It certainly takes a little more patience than when looking out of larger cities.

We had RT multi city (to PRG, out of BUD) from MSY for $450 on United/Lufthansa in the Spring. Of course, that was an absolute steal and I booked within 2-3min of seeing it.

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next June

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Wait to book your flights. They'll be cheapest at around 3-4 months prior to your departure. Set a price alert on Kayak and check skyskanner periodically to get an idea of when the prices are best.

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am planning on doing AirBnB

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Smart. But stay openminded about Hostels. A lot of them are really nice and they're safe.

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travel agents

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Don't call anymore. They're expensive and they'll upcharge you for the "convenience" of their service.

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can I switch them to skymiles and get points right then?

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Gonna want to talk to your bank about that one.
I'm not sure about that deal in particular. But sign up for Groupon and TravelZoo. They have deals periodically that are really good. They're often not during peak travel times (like June) but it's worth a look.


A bit of advice, keep your dates/times/origins flexible. The more flexible you are, the cheaper your flights will be. If you're willing to go through the extra step, flying into another location (like Barcelona, London, Paris, etc.) then booking a trip to your final destination via budget airlines (like Ryanair), you can save a bit of money.

Sometimes flight aggregators like Kayak will do this for you. But often times they'll miss some cheaper options.

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Not impossible, but you're risking a delayed return should terrible weather/mechanical failure/other weirdness cause you to miss your return flight due to a delayed connection.

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After all of my flights, I still have never done a connection switching airlines (not talking about skyteam/oneworld alliance partners, but rather budget to popular airline) in an international destination. My personal safety net would be about 4-6 hours for connecting time just to save room for delays. In that case, you can at least find a lounge to relax in or a good restaurant. Same thing with connections in the US. If spirit flies to los angeles from nola and there's a connecting flight to tokyo on american or delta, I would give myself about 5 hours.