Best Ways To Solve The Multi-Leg Dilemma

Are you saying that you're pricing flights for each of the combinations you list - eg a flight from Bari to Chicago? (I wasn't clear on your reference to train travel mixed in).

If that's the case, then I wouldn't be shocked if you were finding some high prices. Booking flights between city pairs like Bari/Chicago, and even Palermo/Chicago might yield high prices (is there really much competition for flights from Bari to Chicago?).

You may find more reasonable results if you just book separate tickets for at least some of these legs (those that include smaller cities like Bari, Palermo and even Naples). The bigger cities, which are hubs, should not be a problem.

Not sure I understand why you're going through Amsterdam. Is it because of cost? Why not look at flying into Rome, Milan or even Marseilles? British Airways has relatively cheap flights to all of those locations. And if you're headed into Italy those are a heck of a lot closer to your destination.

What about Chicago to Rome R/T.

Then travel from Rome to Venice via high -speed train, and travel Venice to Palermo via something like EasyJet or RyanAir or Vueling. Check Sky Scanner to see what's available. And Palermo to Rome again via EasyJet or other low-cost airline.

For the Venice to Palermo leg, you will probably find a lot cheaper options if you take the train first to Milan instead - so check rail for Venice to Milan, and then SkyScanner for flights from Milan to Palermo.

Are you visiting Amsterdam before moving on? If so, look at booking the multi-city option to cover only the two trans-Atlantic flights and book a separate budget airline in the middle (try www.skyscanner.com).

If you're not visiting Amsterdam, then you just request your search from Chicago to Italy and prices should not be unusual.

Check flying to Europe through Madrid. Since you weren't clear where you are going it is hard to determine any assistance on returns. However, I did Chicago/Madrid and Paris/Chicago and it was quite reasonable. Make your life easy if you are only talking a few hundred dollars.

There are some things with fare buckets, code shares, and intra-Europe flights that can screw up pricing. (Example- BA often holds the cheap fare bucket seats for its own use rather than letting American have access to sell them as code shares)

So I's tend to book the transatlantic legs as an open jaw/multicity into Amsterdam and out of Italy and then buy the Amsterdam-Italy ticket as a one way standalone.

Are you visiting Amsterdam before moving on? If so, look at booking
the multi-city option to cover only the two trans-Atlantic flights and
book a separate budget airline in the middle.

Yes, Laura, we're spending 3 nights in Amsterdam. And thanks for the tip of Skyscanner, I was able to find a $699 nonstop R/T Chicago/Amsterdam, through KLM. Also on KLM, a nonstop to Venice for $137. Finally an Alitalia flight Bari/Milan/Amsterdam for $114. Tight connection in Amsterdam on the return (90 minutes), but at least I know it can be done for a reasonable price, under $1000. Thanks!

. Finally an Alitalia flight Bari/Milan/Amsterdam for $114. Tight connection in Amsterdam on the return (90 minutes)

Two flights have to be on time and you have just 90 minutes to go through exit protocol ( retrieve and recheck luggage?) to get your US bound flight. You may spend an 'extra' day in Amsterdam( and spend a bunch of $$$) if you try that.

I would look at ORD-VCE, AMS-ORD as an open-jaw/multi city booking, and fill in the Euro flights and spend your time in Amsterdam at the end of the trip and not have the heart attack 90 minute connection you are now looking at.

Your airport choices are a couple of the more expensive ones in Italy (Bari and Palermo) since neither are serviced well for international flights, so that may be playing into the price issue.

Your options....

Do a straight ORD-AMS round-trip and then fly within Europe getting back to AMS for return. This may actually be your cheapest option since within-Europe flights are often cheap on their own, but the price is higher if they're attached to an international ticket.

Do your ORD-AMS-VCE going, then return with FCO or CIA (Rome), or PSA (Pisa) or VCE (Venice) or MXP/LIN (Milan) for less expensive return to ORD...and train to your return airport within Italy since the cost of the train will likely be less than it costs to fly back from a more expensive airport in Italy.

Last option to look at, and one I actually am doing myself in September since ORD was way more expensive than NY flights.....see if getting to a starting US airport is less expensive (ie. JFK, LGA, ERW, BOS and MIA are often less expensive - significantly so - than ORD)....then route from that airport to where you're going and returning with your return in the US at least 6-8 hours later than you land, if not the next day, since clearing customs in the big east coast airports takes more time.

It's worth repeating how to research multi-destination itineraries trans-Atlantic. Fly into Amsterdam, fly home from Palermo, for instance. You may save money, including the cost of returning to Amsterdam, and will certainly save time. But it must be arranged by a multi-destination search function, found on many agency sites. These are not a set of one-way tickets.

Last option to look at, and one I actually am doing myself in
September since ORD was way more expensive than NY flights.....see if
getting to a starting US airport is less expensive (ie. JFK, LGA, ERW,
BOS and MIA are often less expensive - significantly so - than
ORD)....then route from that airport to where you're going and
returning with your return in the US at least 6-8 hours later than you
land, if not the next day, since clearing customs in the big east
coast airports takes more time.

You know, Regina, when it comes time to fire away & book I'll probably investigate that, but I'm of a mind that when I get on my initial flight at O'Hare, next time I get off the plane I want to be across the pond. And this is especially true if I'm traveling in possible inclement months, which we've done last two trips, end of February. Both times, it was colder than you-know-what here but a lot of snow in the East. Had we not been flying direct into Paris (2015) and to Frankfurt (2017), no doubt we'd have gotten bolloxed up.

This is a great discussion--I appreciate the help!

Since Amsterdam is actually a stop on your trip, I'd modify my earlier advice to seek multi-city "big" ticket:

O'Hare-Amsterdam
return
Rome - O'Hare

and then buy your internal tix after a Skyscanner search.

• Amsterdam-Venice

• (train Venice to Milan to get more options?) Venice or Milan to Palermo

• Palermo- Rome

You do NOT need to be back in AMS to get back to the States, so don't put yourself through the hassle of getting back up there. Get back to the States from somewhere closer to your last actual destination (as I understand it, Palermo).

I agree with what Kim said above. I think the Palermo to Chicago leg is driving the cost up. Hop a intra European flight from Palermo to another gateway city (Rome, Milan, London, etc.). And then to Chicago from that gateway city. Be sure to allow yourself plenty of time for this unprotected connection. I generally allow myself an overnight.