Please advise on airline ticket purchase

This fall, we flew American to Rome from Denver, with the option of connecting thru either Dallas/Fort Worth or Philadelphia. DFW (not my favorite airport!) had a much shorter layover time, so we went with that. Does American or United offer better flight times?

As for when to buy, I’m not sure what I’d do. Maybe wait a couple weeks, but not too much more than that.

It is hard to tell without knowing which airport in Italy you are flying to and what exact dates, and whether you are flexible enough to. I’ve your departure/arrival dates a bit, however using www.Kayak.com for some random dates in late May from RDU to FCO round trip I see a lot of options at about $1300-1350 with one stopover.

You have not given specifics of which Italian airport you're flying into or the dates of departure and return.

Putting in FCO-Rome for 14 days, I'm seeing some $1164 flights for various days. It's non-stop to CDG on Delta and switching to their partner Air France into FCO. But the return flight is to Boston with a 7 hour layover.

All the other flights are more expensive--more like $1344. And they have medium time layovers.

What I find interesting is that European flights out of Charlotte are not as cheap as going out of Raleigh-Durham.

If you were flying to Milan Malpensa, flights are around $1200 with United's connections being the best--in Montreal going and Newark return.

Cheapest price is not the best value. A don't want to sprint from gate to gate making connections, but there again I don't mind sitting around 2 hours if I'm for sure going to make my destination.

Sorry, I forgot to mention the flight cities and dates. I’m flying into Venice May 8 and the return flight is Rome to Raleigh on May 27. I have Global entry, so how much of a layoff do I need on the flight home? I do have my iPad on private browsing.

Regarding the practice of using incognito searches for tickets, there are sources that say this is not a factor in the prices you see.

Thrifty Traveler

Scott’s Cheap Flights

I searched my Rome flights earlier this year both regular and incognito and got the same prices on both.
I’d keep watching prices for just a couple more weeks, then go for it. I don’t think it matters much whether you go through Philly or Newark. I’d concentrate on the flight that is the best price for you.

I generally search everywhere (ticket sights and directly through the airlines). I search multiple possibilities too (e.g. what if I start in Atlanta? Am I willing to drive to save hundreds?). I set up trackers for anything that is a possibility. After a few weeks, you will have a good idea what a fair price would be. From there, I'll only purchase right away for a great price. Otherwise I wait until a couple months out and buy at a fair price. Typically you will see ups and downs. I avoid Google because they seem to have a formula for making you jump and pay too much. A VPN is also a good idea so you appear to be a new inquiry each time you check prices.

Here is the thing about layovers on return to the US. In general, 1.5-2 hours should be plenty. However, flights get delayed, technical issues come up, baggage claim is slow (if checking bags), or 3 large flights arrive at the same time. Go with the 1.5-2 hours, but realize that your plans may have to be adjusted as the travel day proceeds.

Also, what happens to the ticket price if you fly out of a different airport? Are there others within a 2-3 hour drive that might work?

We are going in June. I have been tracking prices throughout the year. From my location, I have a target range of $900-$1000 per person. I am expecting to buy by March whether prices hit target or not. I continue to watch prices after purchase because I have been able to get the difference, if price drops, in flight credits.

Without really stalking any flights, and with flexibile dates for August, I just booked Iceland Air from ORD - KEF - FCO and back for mid-late August. While I generally prefer non-stop, from Chicago, the cheapest was $1500+/person, of which I needed to book for three people. Earlier in August, the Iceland Air route was $1066/person. The dates I booked were $596/person; I did book Economy Standard (Economy Light would have been even less $)
I know some people say not to buy this far out, but I have a very hard time believing I will get anything in summer, with reasonable times (many times were atrocious, or 30 hour journeys) for any cheaper than that.

It looks like Iceland Air does doe Raleigh-Durham, and depending on your dates mght be better pricing as well.

-Buy now, at 5 months out you won't get much better.
-Buy directly from the airline, you gain nothing except a useless intermediary from OTA sites.
-Research multiple dates as events like a convention at a destination can distort prices.
-Don't look at prices after you buy..

I’m also looking and $1400 was my best price for an unreliable return airline. Next best was $1700. My trip starts when yours ends and seats in flight are 1/2 ton 3/4 full. I suggest buying now. And getting travel insurance. Save you money skipping something else.

You can save more than $100 by traveling Friday, May 7 rather than Saturday, May 8. I’ve had good luck flying into Milan and taking the train to my first city. In your case www.Skyscanner.com shows an 11-hour flight from Raleigh to Milan on May 8 with a return from Rome on May 27 for $1338. A fast train ticket from Milan for $35 will get you to Venice in 2.5 hours. Both flights connect at Paris CDG. You can sign up for fare bulletins at Skyscanner and also at www.GoogleFlights.com.
You can check for train schedules and best fares at www.TheTrainline.com
May of 2023 shows most European fares rising from April much more quickly than in the past. I would give the fare bulletins two or three weeks but not much longer.

I can’t leave until May 8 because my son graduates on the weekend of May 6. To those of you who recommend buying now, I’m beginning to think you are right. I noticed the flights I’m interested in are indeed filling up, so that you for sharing that info. Mike, you are right…buy and don’t look again! I found that the prices on Hopper are for basic economy and the economy price is a few hundred dollars more, totaling what the actual airline price is. Flying into Milan or Rome doesn’t save much at all, plus having to train into Venice. Question: if a seat has an x does that mean it’s filled or that the airline is holding it? And if so, why?

@kathyw, the 'x' can mean various things. It usually means it's unassigned but taken. For example, the first row behind the bulkhead is usually xx-ed out because that row is reserved for people with infants that need the bassinet. In premium cabins the x means that someone purchased a seat in that cabin but hasn't yet made a seat selection. Or an x might be to save a seat for a pilot or flight attendant who is catching a ride back to another airport.

I heartily second (or third) most of the advice given above. The incognito searching thing has been debunked. Book only through the airline, not a third party. Have you considered a positioning flight? It might be worth it if it saves you a lot of money:
https://scottscheapflights.com/glossary/positioning-flight

Seeing all these fares makes me feel good about buying tickets in September for next June/July going from San Francisco to Rome and returning from Milan. It seemed like it was early to buy but apparently it wasn’t. We are flying on Air Canada via Montreal. Our layover is 4 hours each way which isn’t great. We paid $1737 for two. Feeling good now