So we've already booked Club O in November and today arranged our flights. We're blessed (cursed?) with an American Air hub so we get to fly non-stop from Charlotte. $738 plus tax. The fare from JFK to SXM in November is $403, one stop (that stop being Charlotte). Six hundred fewer flying miles = $335 more dollars for the privilege of flying out of Charlotte. We used 70,000 points instead, but that's another story in itself.