Having been to both the Cancun Jamaica properties, if it comes down to these two - go Cancun!
Originally Posted by
dukerau
You mention Hyatt and Fairmont - I imagine you have 2 or 4 free nights at each that expire within a year, so it would be best to try to use those. One obvious choice is Hawaii, but you can't use Southwest to get there (yet). For Hyatt, perhaps the Zilara in Cancun or Jamaica? Southwest flies to both.