Transportation to Italy

Google Flights shows prices from lowest to highest while listing most airlines for September 2019
https://www.google.com/flights?hl=en

also this site
https://matrix.itasoftware.com/

once you see a price you like you book directly on the airline's platform;
You can also track if the price goes up and down

If you see something costing under $800 (I see a price at $719) from Seattle to Rome for example I would snag it.

I would start looking now for tickets. Most on this forum will recommend doing research on sites like Kayak or Google Flights, then buying on the airline site. Also, consider multi-city (aka open jaw) tickets whereby you fly into one city and home from another.

Recent anecdotal evidence suggests that travelers are getting better prices 8-10 months before the travel date. In September 2018 we purchased tickets for April/May Boston-Paris for $492 including checked bags and advance seat selection.

It's best to buy the tickets from the website of the airline you will be flying. I use Google Flights to research the options and then go to the appropriate airline website to make the purchase.

There is no magic time to buy tickets. What has worked well for me is monitoring fares for quite some time--ideally daily--to develop a feel for what the normal price range is. That puts me in a good position to spot a deal if one comes along. On some routes, fares bounce up and down a lot, and you can save considerable money buying on a dip rather than right after an upward bounce. I know nothing at all about airfares from the Pacific Northwest, but I would be nervous if I was within 60 days of my trip and still had no plane ticket. I prefer to buy farther out than that (recently it has been more like 6 months), but it depends on what I see as I track the fares.

If you have some date flexibility, that can be helpful. Similarly, if you are willing to change planes twice rather than just once, that gives you additional options that may save some money (though not always). The pickier you are, the more dangerous it is to wait to buy your ticket, because the options you consider acceptable may get snapped up by others.

Most travelers to Italy can make their vacation time go farther by flying into one airport and out of another (that's a "multi-city" ticket), but sometimes there are large savings from flying round-trip into Milan or Rome. In that situation, you have to balance the costs in time and in money. On a short trip, time can be a very valuable commodity.

It's best to buy your air tickets when the prices is below normal. That could be a year before your travel or it could be a day before your travel or anywhere in between. People who tell you they have a "good idea" of when the best purchase time is - they don't know anymore than you.

You have some good advice here. Look NOW. Find out the price for the dates you want. Then keep checking back. Use whatever flight software, online programs you like, but when the price goes down to a fare you find acceptable, book it then. And don't look back.

It's best to buy your air tickets when the price is below normal.

And what is 'normal'? Or how does one discern that?

One monitors fares for a good while; I do it for several weeks at least, and I'm in a fairly competitive market where I have reasonable chance of scoring a ticket at a decent price. I really don't think there is any substitute for looking at the current price pattern for the specific itinerary one is interested in and the specific routings one considers acceptable.

If you're budget minded, you can fly on Norwegian Air Shuttle to London Gatwick and switch over to EasyJet.com to many Italian airports. We have flown into Gatwick and connected to a flight into Italy..

After checking daily for a couple of weeks, my wife and I were able to book tickets on Jan. 20, Denver to Rome on British Airways round-trip, one stop each way, for $636 each, non-refundable of course. Traveling in September for Rick's South Italy tour. I hope you find a great deal too.