Airfare has.... uh... increased a tad since 2016

Now that my interest has been peaked on this I don't know if driving is really much worse than flying. Let's go with 17 hours drive. We would leave Friday after kids get off school (take afternoon off work) and drive for 6 or so hours from 3-10 (1 hour stop for dinner). Then on Saturday we'd get up at 8:00 and drive the last 11 hours from 9:00-10:00PM (1 hour for lunch and 1 hour for dinner).

Or for flying let's leave Saturday and keep the same 8:00 AM wake up time as the drive. So you get up at 8:00, leave the house at 9:00, get to JFK at 10:30 (via the LIRR), flight leaves at 12:30, arrive at MCO at 3:30, get to the Mickey Bus and check in 4:00, bus ride to WDW 5:00.

So with flying you'd really save about 5 hours on Saturday. In the flight scenario you could get to a park by 6:00 and have 4 hours at the park whereas driving you lose that 4 hours of park time.

And it would be a similar idea on the way home, you'd lose Friday evening at the parks and then some hours Saturday morning before leaving for your flight (assuming you have a flight that leaves at 5:00 and would get us back hime by 10:00).

If you have two drivers, seventeen hours is doable in a day. You want to start way early in the morning (like 3 or 4 am), and not stop for anything but quick potty breaks. Its no different that a flight to Asia - in fact its shorter. I've done 15 hour days - me and my daughter who was thirteen at the time (and therefore a non-driver). And as a kid we used to do sixteen hour days, five people in the car - "home" for Summer and Christmas every year.

The kids will snooze until 8 or so. Make sure you have ample charging. Or listen to books - Harry Potter is really good.

Saves two nights worth of hotel.
 
So here's the end of the tale:

I booked flights on Southwest and paid $15 per person for early bird check. in. It said with early bird check in you get an earlier boarding group but not A1-A15. The flight for 4 people was $2,362.40 after taxes and the early bird fee. So it was frankly cheaper than what I was seeing on Expedia or JetBlue.com

LGA - ATL - MCO 10:20 AM - 3:55 PM
MCO - MDW - LGA 12:05PM -7:20 PM

We're going through LGA so I can't take the train directly there but we'll just hire a taxi to take us or harass our neighbor or something.

Thanks for all the tips. I wouldn't have even looked at Southwest if you guys didn't mention it.
 
Glad you got a price you could live with! Hope you have a great trip! Our family flies southwest often and we often come out ahead with the price, free luggage etc even with EBCI.

With EBCI you should have no trouble getting seats together! We usually buy tickets the day they go on sale so I don’t have any info to add on where you would be in the boarding process, but A or Early B for sure. We are usually in top 30..
 



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