Looks like 4 hour pick up window went into effect on 11/17/17, or as @missoverexcited would say 17/11/17 
I certainly would!
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If getting home late will not make the next day horrid I would do that. Otherwise the midday. Definitely NOT the early. We did that once - and unless circumstances are really difficult to overcome, we will never do that again. 4am wakeup after a day in the parks til late is literally nauseating. Night shift hangover for non-nighshifters
I do like the idea of sending the ILs when they need to go. With DME there’s really not much thinking involved for them.
I am always in the midset of the latest flight home. Leaving is so heartbreaking I delay as much as possible.
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What do you usually do and does it work? On the trip we just did, we had a park day and an evening flight home (on a Friday so no work the next day anyway). After frantically packing our last night to be out of the room, we remembered similar on our DL trips and pledged to each other to remember not to do park days on the last day. Midday with time to finish packing in the morning is now our goal. I hope we remember next time!
Do what works best for your family
Is there a reason you have to fly Southwest? Check the other airlines, who’ll likely be price competitive anyway.
It used to be that the best fares required round trip, but that’s no longer the case. Usually you can mix and match; I’m flying to Washington in July on Delta and returning on American. Turned out to be $5 less than the best round trip fare on either airline. (Go figure.) Last year, we flew American to Orlando and returned on Southwest.
We were just there in May.
Magic Express pick up was 5:10 for an 8 o’clock return flight
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Our airport has very few nonstop flights to Orlando. There are only about 6 per day. Our choice is Southwest or Delta most days. Sometimes Frontier is an option.
6 is pretty good - presuming you’re flying out of Indy - granted it’s probably nothing compared to Chicago, but…I think Cleveland is down to 4, 1 each on SW, United, Spirit & Frontier. Back when CLE was a Continental hub it was more like 4 to 6 just on Continental - the good old days…
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I know that I am going to be crazed trying to pack my last night so I can check out and do the park the next day for an evening flight - especially because I am going to be doing the Halloween party my last night - but I am traveling alone, so I only have myself to make crazy LOL
Last time I did a mid-day flight, so didn’t do the park the last day - it really was perfect, but that was with my BF and I know he would have lost his mind if I told him we had to pack after the party or at 6AM so we could go to the park again LOL