Problems with Connecting Flights?

I would fly into New York the day before otherwise it is a gamble. I actually did this my last trip to Europe in August 2021. Go to a Broadway show or something.

Otherwise, you don't have any recourse if Southwest is delayed since the Air Canada flight would be on a separate ticket. You would be out of luck.

Only if you buy a ticket with Air Canada that is fully refundable and allows you to change your flight for free no matter what at the last minute then you have more flexibility; however these tickets always cost the most by several hundred dollars. I've never bought or wanted to try to afford a ticket like that in 20 years flying to Europe. Though I have gambled many times and flown in to another city to catch another flight on separate tickets and have not been burned usually giving myself between 3 hours minimum to a whole day to make the flight.

A question of pure curiosity on my part: I've heard Denver is expensive to fly to Europe from, but how much are you saving by positioning to NY to get to Europe?

Depending on what flight we buy, it could save two to three hundred dollars per person. And we can get to NY on our Southwest points, so that part of the journey is essentially free.

This better save you a TON of money, because this plan will cost you in time and stress. To answer your last question first: when you buy two separate tickets on two different airlines, neither airline will help you out. If the Southwest flight is significantly delayed, rescheduled or cancelled, you may have to buy new tickets on Air Canada or pay a lot to reschedule, and vice versa going home. Also, if you don’t actually fly on the first leg of a trip on an airline (for instance, the Air Canada flight to Lisbon) the airline might cancel your whole trip (I.e. the flight back from Lisbon). That would cost you even more.

I am assuming that you would do this through LaGuardia, since it appears that is the only NYC airport that both airlines serve. I looked at flights on Air Canada to/from Lisbon/Barcelona and they all make at least one stop after LGA for a layover - even more time and more opportunity for a delay or change or who knows what kind of problem. If you are planning a 5-7 layover at LGA (not a great place to spend a lot of time, by the way), you will have a very long and exhausting trip. I tried some random dates for your destinations on Google Flights and found some flights on Lufthansa that go non-stop Denver to Frankfurt (gets you over the pond and closer to your final destination) then non-stop to Lisbon at a pretty reasonable price and taking much less time. This would be my preference.

If you still feel that this plan is best for you, you might want to consider flying to NYC one day early, spend the night in an airport hotel, and then take the second flight the next day. This might wipe out some of your savings, but would be less risky and stressful, and less uncomfortable and exhausting.

Oh yeah I used points to fly to New York and points to stay in the hotel the day before flying to Europe.

+1 for what Renee said.

I often pay more for fewer connections, and that's even traveling on just one ticket. I'm not sure the savings here would be worth it for me. (But I certainly understand that's subjective.)

And to answer another part of your question: If you don't have top price refundable tickets, and Southwest made you miss your Air Canada flight, AC would say "tough luck". You might not even be able to use the value of the original ticket toward the very expensive last-minute replacement.

I don't recall any experience with schedules like the OP's, but in NY wouldn't they have to leave the secure area, retrieve bags, then recheck them with Air Canada? If so, more delay potential. Which NY airport will this be?

It would be LaGuardia.

I have used American Airline points to get to an airline hub for cheaper tickets but it has always been a substantial saving and then I have always flown in the night before.

There are so many chances of a flight getting rescheduled these days and with Southwest, there are typically no additional flights to quickly get you re-routed like there is with AA, Delta, or united. New York would also not be my ideal place for a stop-over as prices for hotels, meals, etc are higher taking away from any savings. I know the temptations of getting a cheap flight from an East coast airport but know your risks. You could potentially miss your main flight and have no recourse except to buy another flight at a walk-up ticket price.

Any advice would be welcome.

If you choose to do the '2 part' scheme, flying the day before to NY is the only sane thing to do.

If you miss the outbound Air Canada flight they cancel the return, unless you contact them before the outbound flight departs and reschedule it.. Probably a change fee and fare difference to pay.

The downside is huge for a few hundred bucks.

What if your Southwest flight to LGA is cancelled? You will have to buy all new round-trip tickets between Denver and Lisbon. I would never have two separate itineraries because you’re not protected. What if the flight to LGA is hours delayed? Do you have to change terminals at LGA and go through security all over again for your Air Canada flight? If you miss that flight to YYZ (Toronto), you’re going to be buying new round-trip tickets to LIS.

What if your LGA flight to YYZ is delayed several hours? LGA in the afternoon is not known for on time departures. Are there later flights to LIS if your LGA flight arrives too late? If not, you’re spending the night in YYZ.

My advice is don’t do this.

Separate tickets put you at a distinct disadvantage when you need to count on everything falling into place to make connections and eventually reach your destination. You may see your savings evaporate if you have to rebook a missed flight. Planning for a night in NYC can be costly as well but would certainly be advisable if you chose separate tickets.

If you could guarantee the on time arrival of your first flight into LGA then you wouldn’t need 5 to 7 hours but rather only 3 hours. That being said I would still avoid this scenario.

Why not book Air Canada, DEN-LIS, BCN-DEN? ( multi-city aka open jaw)

Looking at random dates in May, the cost difference of that vs NYC-LIS, BCN-NYC. was negligible.

Removes all the danger and drama of a risky connection in NYC or the expense of an overnight in NYC

Okay, you've all convinced me that it's a dumb idea to try to use two airlines and go through another city. Thanks for all your advice. I'm really glad I asked! We're going to go ahead and simplify and just fly from Denver to Lisbon and then directly back to Denver from Barcelona. We can save our Southwest points for another, separate trip! Thanks again, folks! :-)

Good decision. If you haven't traveled much, its an added level of stress that you dont want to deal with on either end of the trip.

aweingarten154 - Not a dumb idea! Maybe just not workable in this scenario. It's always good to consider options.