Plane Tickets

Does US citizens have to have one ticket for the flights?

Airlines do not care about your citizenship. You need a ticket for each and every flight.

Or did I miss the point of the question?

No you can fly to Canada Toronto or Montreal and take a flight from there to Italy.

Are you asking if can you buy a separate roundtrip ticket from NYC to Canada, then roundtrip Canada (assuming Toronto) to Italy? Sure. But if that first flight is late and you miss the overseas flight, you are out of luck. Seems doubtful that you'll come out ahead that way.

What are the "crazy expensive" numbers you are seeing?

Are you by chance looking at one-way tickets? Although there are a few budget airlines that price that way, in most cases you'll do much better by buying a round-trip. If you need to fly into and out of different cities in Europe, look for a multi-city flight.

Have a a look at AirTransat flights to Italy from Montreal. Or Air Canada ... NYC/Montreal/Rome

As a US citizen you can enter Canada pretty easily, by air or car, you just need a valid passport. They don’t care why you are coming in, as long as it’s legal. People in Buffalo regularly drive to Toronto for cheaper flights.

So yes, fly to Canada, then on a separate ticket fly to Italy if you want. The issue is practical- leave plenty of time because if you are delayed getting into Toronto/Montréal and miss your flight to Italy you are out of luck.

This is what I was told by a travel agent. I found cheaper prices than this but want to make sure it can be done.
I just called Air Canada and flying via Toronto and/or Montreal is pricing at $1839 round trip for those dates.
I know it's cheaper to fly r/t just from Canada and then buy a separate ticket from the U.S. to Canada, but U.S. citizens need the whole itinerary on one ticket.

A travel agent told you that?

Wow...

Find a different agent.

I’ve never hear US citizens need while ticket on one itinerary- who told you that !???

You can fly to Canada on whatever gets you here cheaper then grab a separate flight to Italy ( really do look at air transat they are cheap ) just be sure to allow a LOT of time in between flights in case your flight is late from US .

Yeah and don’t trust Travel agents - do your own bookings ! Haven’t used one in decades !

Not knowing your destination airport or exact dates, this may not help but I checked on Kayak using a midweek date near the end of May. The most expensive were one way flights from JFK to Rome. There was a banner showing Norwegian Airlines from Newark was cheaper. Going to the Norwegian website there were one way flights from Newark for $639, $779, or $1090 per person depending on the plan chosen. I did not look at what was, and wasn't, included. Also flying multi-city was less expensive than one way. Such as flying JFK to Heathrow, stay over one day, and then fly to Rome for $1,360 per person. This may be the reason for your plan on going thru Canada. As mentioned, booking your tickets yourself should not be that difficult. I prefer to book them through the airlines, though many people have good luck through a third party company.

Something is off, way off. Give us you exact travel dates and plans so we can respond on appropriately. Total unaware of any need for a US citizen or any other citizen for that matter, needing only one ticket. Not making much sense.

Hi tmc0298:
You should be able to book round trips from New York to Italy via Canana (or any other city) in one single ticket.
Have you try Google Flights, it's a really good tool to search for cheaper tickets. It will show you many months of all available flights for any airlines, times, cities etc. I recommend that you give it a try: www.google.com/flights
Once you find the flights/airlines you want, Google will give you the options to book directly with the airlines or through Google.
Also if you can give us your departure/destination cities, and dates we might be able to help you better.

Edit:
I create a 'scenario' to flying round trips from JFK to Rome FCO (Fiumicino Airport), departs on 5/27/19 and returns on 6/7/19.
According to Google Flights the cheapest non-stop round trips is $686 by American Airlines.
If you need a connecting flight from somewhere else, say Syracuse to JFK, then it will be significantly more expensive to book as one ticket ($1612 with 1-stop, or $1171 with 2-stop). In this case you might want to consider booking the domestic flight from Syracuse to JFK as a seperate ticket which is about $200. Total for the 2 tickets comes to $686+$200=$886 (Syracuse-JFK-FCO, just 1-stop).
The down side with two seperate tickets is that you are on your own if delay causes you to miss your flight at JFK. Whereas if you book both flights as single ticket (one single booking) the airlines will make sure (guarantee) to put you on the next available flight at no additional cost to you.
So you want to book your whole itinerary as two tickets to save money, you will want to give yourself plenty of layover time at JFK.

Thanks for all the information. We are looking for my daughter and her boyfriend going to Rome on 5/25 arriving 5/26. We would be going to Italy on 6/27 arriving 6/28 going on these dates there would be 6 of us. We all 8 of would like to come home on same flight leaving Rome 7/6 arrive in NY 7/7. Hope this makes sense. Thanks.

We all 8 of would like to come home on same flight leaving Rome 7/6 arrive in NY 7/7.

I suspect any flight from Rome to NY will arrive on the same day as it leaves

As you are going west, and assuming a non-stop, you will arrive in NY 4 hrs after you left.

Example-- a flight leaving Rome at 2:50 PM arrives at 6:45 PM NY time

Even if you have a flight that stops somewhere it is unlikely it would be the next day when you arrive.

tmc0298:
You will want to book two sets of tickets for:
A) Your daughter and her boyfriend (X2), depart 5/25 return 7/6, one single ticket for all flights for two
B) The rest of you (X6), depart 6/27 return 7/6, one single ticket for all fights for six

A) Scenario 1: depart 5/25 return 7/6 JFK-FCO: (non stop, $1330 per person), (1-stop Oslo, $951* pp)
A) Scenario 2: depart 5/22 return 7/4 JFK-FCO: (non stop, $860* per person), (1-stop Oslo, $597** pp)

B) Scenario 1: depart 6/27 return 7/6 JFK-FCO: (non stop, $1440* per person), (1-stop Oslo, $1134 pp Air Italy)
B) Scenario 2: depart 6/26 return 7/5 JFK-FCO: (non stop, $1160* per person), (1-stop Oslo, $849 pp 10H 10M)
B) Scenario 3: depart 6/26 return 7/4 JFK-FCO: (non stop, $990* per person), (1-stop Oslo, $842 pp)
* EWR airport Norwegian Airlines (Norwegian is a budget airlines so these prices will go up once you add the checkin luggage & seat selection etc)
** LGA airport

You can save by either traveling mid week, putting up with one stop or longer total travel time, departing from different airport, or flying different airlines.