Looking to fly May 18-28. Boston to Rome, Naples to Boston. Saw flight on Air Italia for $944 a few weeks back. The layover Milan-Rome was 3 hours. Now that flight is $1087. They do have a cheaper flight ($974) but the layover in Milan is 8 hours. Any advice? Should I wait it out? I'm becoming addicted to Kayak! Thanks!!

This may sound strange, but throw in another destination, different date, different carrier. That way you don't have to worry about losing your ticket.

We did Orlando-Rome, then Rome-Palermo, then Palermo-Milan and Milan-Orlando. We did not use the Palermo portions. This ended up being over $200 cheaper than a R/T Orlando to Rome or Orlando-Rome/Milan to Orlando.

Makes no sense, but it worked.

Would you consider flying into Milan and training to Rome?

Try Farecompare.com. I find it very helpful in determining the best fares. Also if you are willing to connect in different European cities, you might find a better fare/ sale on LUFTHANSA or AIR FRANCE, for example. Good luck!

Thanks for your feedback. I looked into taking the train from Milan, but the airfare was still $1000+ and the train take 4 1/2 hours - I don't think it's worth it. I guess I'll keep checking daily and pull the trigger soon!

What's available out of JFK? I know that there have been some sales advertised w/ both Delta and US Airways out of Boston, so it might be worth checking.

You can also check out EUROFLY. I think it only flies out of JFK, but it has been running a sale lately.

Good luck!

I'm heading to Rome in March and we got our best deal using AA to London Heathrow and then Alitalia to Rome. We saved about $150 a ticket with nearly the same layover. I checked back on Alitalia about a week later and the prices had dropped another $50.