We found a great deal out of ORD(Chicago) for $575 for both my wife and I on Air Jamaica. Leaves at 6:30am which is really early for us since we need to drive 2 1/2 hour to ORD, but we can sleep on the plane. We were going to fly non-rev on a buddy pass with USAir, but couldn't pass up a direct flight, more time at resort and a reserved seat.
By the way, watch out for the "discount fares". Many times they are just listed with the taxes excluded. The taxes can add up to almost the same as the roundtrip cost.
It's also a 2-3 hour ride for us to ORD and our flight leaves @ 5:40a. We booked thru Couples and I thought they'd put us on AJ for a non stop but didn't. We're on Delta. I was a little disappointedcuz I'd like a non stop too!