Originally Posted by roknroll

I think we could be of more help if you gave a list of airports you'd be willing to fly to, the dates you want to travel, and if those dates are flexible (if so, give a date range). AA has great options for flying to the Caribbean, so that will probably be your best option. Also what mileage balances are you working with? Sounds like you have some Chase UR points, AMEX MR points, and some miles in various airline programs.

When you say UR points, is that using the UR points to just pay for the travel, and not transfer to an airline FF program? Since you'd have to pay $300 in taxes/fees with BA miles to book on AA, you're nearly at a breakeven compared to spending 80k UR points to get to your preferred airport. Plus those should earn miles, compared to the award earning you nothing.

Southwest is now a redemption partner of Chase UR, and their aquisition of AirTran provides new international routes to the Caribbean. I don't think the two airlines are integrated to the point yet where you can use your Rapid Rewards points to book travel on AirTran, but keep an eye on it. Others would know more than me, and the WN forum would be a good place to snoop around.

Expertflyer will let you set up up to 30 flight alerts that will check for award availability on your selected flights and email you when something pops up. That would save you a lot of time every day from searching the various combinations.