In the past I have always booked my package first because I book early so I can make payments on it and have it paid for before time to book the flight, usually I fly with SW and they don't publish airfare further out then 6 months, that may have changed now, but that's how they used to do it, maybe a little longer now. But this trip, I am going solo and am very flexible in my dates, so I am actually going Wednesday to Wednesday, never done that before. Anyway, I had an idea of when I wanted to go, but hadn't booked yet and came across a super deal with SW, like $69 each way, and I had some points to use, so I grabbed it, of course to get those rates you have to fly mid week, so I will, round trip cost me $75 with my points. Anyway I actually did it backwards this time to what I normally do. Of course now I'm waiting on a pin code or a % off, but if I don't get it I will just stay at AoA, Little Mermaid room, I haven't stayed there yet so, it really won't bother me if I don't get a discount. I have also booked my rooms before and then waited on an airline sale.