We found good prices at the end of July/ beginning of August but my husband kept making me wait to book so those lower fares sold out and I had to get a flight that was not as good to keep from spending an arm and a leg.
We go every year in November and generally book in June or sometimes the first part of July...most often June. Last year we went in October and booked in March because our travel agent felt air fare might be going to rise but that's the first time we've ever done it that early. It's always just a gamble so when you do decide to book don't look at prices again, they may rise or they may fall but you are locked in so no point in torturing yourself.
I checked on flights constantly for our last Oct trip to CSA. I have to say that the lowest rate was about 2 months before leaving. I booked at 3 months out because the rate had dropped and then the next month it was even lower. Check on Wednesday's throughout the day. There are some deals out there, but have a price you are comfortable with and then when you see it, book it. Good luck.
We book through Orbitz, they have a price assurance guarantee that if someone books the same flight and gets a lower price, they will refund you the difference! For our late April trip, we just booked a few days ago. Tues/Wed seem to be a good day to book online (pricewise) and it worked out for us! Our airfare went from $500pp to $390 by the time I clicked "buy".
Don't forget to check on BAGGAGE FEES! Just because an airline offers a lower price doesn't mean the end total will be cheaper than if another airline offers a slightly higher price but NO baggage fees. If you fly Delta (we do) there are NO baggage fees when flying to Jamaica, up to 2 bags per person!
soon as possible seeing as fuel prices are going to sky rocket this summer! we go in feb i book about 10mo. out seeing as that is when the airlines release the prices. i checked prices recently and our flights have gone up almost $700...happy we booked when we did
Having heard the talk of $5+ gas coming this summer, I opted to book now and (sort of) hope gas prices do go up. At least that way I'll be happier when airfare goes up. I booked through Orbitz for the same reason Melvin76 did, so if someone books the same flights for less, I'll eventually get a refund of the price difference.
I've never been to Jamaica, so I can't say who might be the better airline, so I went with who was cheapest on Orbitz, and will be flying US Airways. Baggage fees don't seem to outrageous to me ($25 for the first, $35 for the second) as I doubt the wife and I will be checking more than 2 bags. If we check in separately, we only pay $25/ea, so that saves a couple bucks...