Google Flights - Booking 2 separate tickets for one return trip?

Ticket 1 is with American Airlines and ticket 2 is with Condor.

Odd, since Lufthansa partners with United and Air Canada, and occasionally with Condor. Why not try going to the Condor site and see what they offer. Looking at ITA-Matrix (also a Google product), I see a listing from Condor with a Lufthansa flight from Catania to Frankfurt followed by a direct Condor flight to Toronto. The flight to Halifax is actually a few EUR more than to Toronto.

If you book 2 completely separate tickets, you will not be protected if the Lufthansa flight is delayed, and you miss the Condor flight.

Two big problems with booking separate tickets:

1. If your first flight (American) is delayed and you miss your second flight, you need to buy new tickets for the second flight. The airline (Condor) is not obligated to get you to your final destination, as they would be if it was one ticket.
2. If you are checking bags, they will not be checked to your final destination. You will need to collect them at baggage claim, stand in line to check in with the next airline (Condor), and go through security again.
   

This scenario would cause me a lot of stress. I would want a long layover (maybe even overnight) in case the first flight is delayed. That would be awful on a return flight. By that point I just want to be home.

If “best arrangement” means “cheapest”, it would have to be waaaaaay cheaper to be worth that.

If you continue to be confused, seek help from a travel agent. I would hesitate to book flights as you are describing for the reasons posted above. Missing a flight gets real costly!

Len, Google Flights is not really a booking service. They are trying to find for you the cheapest flight options. In some cases, you might save a lot of money booking tickets separately like this. You can of course choose not to book those choices and just booked something else that's all on one ticket. (I am the kind of person who LIKES having this option to book separate tickets, as I've done that manually a few times!! But it does have pitfalls as others have described above.)

Looking at the flights from CTA on Lufthansa, the earliest arrival at FRA is 1250PM.

The Condor flight departs at 305PM

Is this what you are looking at?

If so, your odds of success are only marginally better than a snowball in Satan's domicile.

If you have checked bags, I see no way you could make it.

With carry-on only, you have a theoretical chance, akin to your becoming a starting pitcher for the Blue Jays.

If what I found is not what you are contemplating, then feel free to ignore my comments as irrelevant.

2 hours and 15 minutes not enough time? Really? Booked as one ticket from Condor, should be no problem.

2 hours and 15 minutes not enough time? Really? Booked as one ticket from Condor, should be no problem.

The 'problem' is that OP is looking to buy 2 tickets, CTA-FRA on Lufthansa and a separate Condor ticket FRA-YHZ-YYZ

Just picking random date in June shows no real advantage to buying separate tickets, thus one ticket from Condor is the way to go.

Hi Len,
I will add to make sure that you book all flights directly with the airlines, and not through any company such as Expedia, Orbitz, etc.
If anything goes wrong….delays, flight schedule changes, etc, the airlines are much much better at fixing a problem.
Third party resellers definitely are not.

Thank you to all.
You are all invaluable.

Price was not a factor -- minimum number of stopovers and shortest overall travel times were the greatest considerations.
This flight lasts 16 1/2 hours. The next shortest flights take 28 1/2 hours and 34 hours respectively.

Also, Frankfurt Airport: I try and avoid that connecting airport if possible even wirh one ticket unless I have a minimum 2.5 hrs but preferably 3+ hours,whuch I know sounds a bit overcautious. However I have had numerous experiences of a lot of stress making my connecting flight.
Many flights disembarked on the tarmac which requires transfer by bus to the terminal, either 1 way or both,thus consuming time and energy. Many times inbound flights are late thus cutting into your time. And finally, if you have to go through passport control there can be long lines. With separate tickes as others have said there is a whole other level of stress and expense if you miss your flight .

Google flights is not a booking service. Have you bought your outbound ticket to Italy separately and now you need to book your return trip? Is there any reason why you didn’t buy the roundtrip so you could have it on one itinerary? Or have I misunderstood something?

What is your proposed itinerary?
Then maybe we can help you a bit better.
You should be able to fly Toronto-Rome-Catania, and return.
Or Toronto-Germany somewhere-Catania.
Not sure why you would need to go to Halifax.