Would you spend $277 More for nonstop flight?

OP, I feel your pain. In order to get a non-stop flight to MCO, DH and I travel to a major hub a day early and fly from there.
 
I would jump on changing the flights to non stop! $277 is not that bad for all your flights and it will save some of the "are we there yet?" questions from the kids. 5 hours is a huge difference and traveling can be very taxing on children.
 
It is also cheaper to park at Green than at Logan. I know in the past we have printed off a coupon to park at TF Green in the B garage and with the coupon you save about $5 a day. Have a fun trip!
 
Absolutely! Even forgetting about the benefit of extra time at the parks, let alone trying to haul a whole family from gate to gate, connections definitely increase the likelihood of flight delays. Now somehow I have been VERY lucky to have never missed a connecting flight due to my first leg being delayed, though DH has a few times on business trips. But for some reason we seem to quite often have a delay on our connecting flight -- anywhere from 30 minutes to many hours. On top of decreasing my amount of time at WDW, it is stressful and throws off my plans.

Your only concern will be if your family will have a problem with likely not having a room to check into right away with such an early arrival. I know my DH is not a hit the ground running kind of guy (i.e. reach the hotel room at Disney, he just want to lie down for at least 30 minutes to unwind from the travel). Though, at least on this board, he's definitely in the minority! ;)
 

I would do it with Southwest. Southwest almost never changes a scheduled flight, obviously excluding weather and mechanical issues. I'm not sure I would do it with another airline, months in advance. A schedule change could leave you with a connecting flight, but at the higher fare.
 
We are already booked with Southwest out of Logan. We got an amazing fare for all four of us in May. The total was 707.00 We have layovers and are not getting to MCO until 7:35pm and then our flight home leaves MCO at 7:35am on our departure day.
I have been checking flights and realized that SW flies out of Providence and just checked their flights (wish I had checked when we got the great deal out of Logan). I can get a non stop flight out of Prov. and getting into MCO at 9:50am instead of at night but its an additional $277.00 (Total) for the one way change.
Do you think its worth it?

Yes.
 
We are already booked with Southwest out of Logan. We got an amazing fare for all four of us in May. The total was 707.00 We have layovers and are not getting to MCO until 7:35pm and then our flight home leaves MCO at 7:35am on our departure day.

I have been checking flights and realized that SW flies out of Providence and just checked their flights (wish I had checked when we got the great deal out of Logan). I can get a non stop flight out of Prov. and getting into MCO at 9:50am instead of at night but its an additional $277.00 (Total) for the one way change.

Do you think its worth it?

:thumbsup2 worth it!
 














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