I am really am not sure what to do. Has anyone every booked through Southwest for hotel and flight with the jackpot savings? Our stay at POP in Feb will be a little under $2000 not including dining (hoping for free dining to come out soon). Then add on $1000 for our flight, and that is $3000 I was checking flights today and if I was to book a "package" through Southwest I could get flight and hotel (Best Western Buena Vista) for $1360 (flight alone is $998). If I buy tickets from undercover tourist, it is only about $2400 for all. That's a $600 savings. Free dining changes all that, but I don't know how long I can hold out for that. The rooms look bigger and nicer at the dtd hotel. Any suggestions? Has anyone every stayed there?