I will be traveling with two others from Sicily (near Messina) to Rome to catch a flight back to Boston on August 30. Each of us has one checked bag. I first tried to get a single air ticket with Delta using ITA for a flight from CTA to FCO, but Delta wanted about $1500 more for that multi-city ticket so I stuck with the r/t BOS-FCO and thought I would find a way to get to FCO for the 10:30 AM departure to BOS. Nothing looks very easy, though. The earliest flight from CTA is ITA AZ 1722 leaving at 6 AM and getting in to FCO at 7:25 AM. That leaves 3 hours to collect the checked bags, get through lines at FCO, check in to the Delta flight and go through more lines to the gate. Is that enough time or should I just bite the bullet and take the train the day before and spend the night near the airport. I also worry the flight from CTA will be late, the bags will be lost, or who knows what - I have experienced every possible problem with air travel in Italy. What would you do?
. What would you do?
Go to Rome the day before
Absolutely go to Rome the day before. Too much risk that you cannot control. Personally would stay in Rome, have a nice final meal and catch a taxi in the AM. Is the 10.30 a direct flight to Boston?
PS -- An hour later ---- I am a huge fan of multi-city flights both as a time and money saver. Almost all of our trips are open-jaw and never pay more than standard round trip and often cheaper (+ - $100). When you said Delta was $1500 extra I didn't believe it. You must have price two single one way tickets but even that is high for single tickets. I did a quick check for BOS to Rome mid August and a return from CTA on Aug 30. Found many, many tickets in economy class on that route in the range - total - $1100-$1200. You may want to reconsider if you haven't purchased other tickets.
Go the day before. Too risky. I also often by multi city tickets and it doesn't usually cost me any more money.