Best time and place to book airfare?

What is the best time (how far in advance), and place (website/carrier) to grab a great deal? We booked with All Inclusive Outlet early booking for 2013 and it was so far in advance that airfare was not yet available. I checked today and it is now showing up for availability but it doesn't look like a good price to me ($768 p/p from Chicago to MBJ). We want to arrive early, depart late afternoon with no layovers. What is a good price? When is the best time and place to nab the deals? We could also fly from Des Moines, IA or Cedar Rapids, IA or Moline, IL. We are open to other alternatives. Dates already set for July 3(wed) - July 13(Sat).

Airline prices are up right now it seems. We used the same agency as you to book our vacation and had to move our travel date by one day to be able to book rooms and airfare at the same time. We did save a couple hundred dollars by booking together. That early booking deadline and the 330 days ahead on airfare pricing really do create a headache though. Also the air prices are up at least $100 pp since we booked.

Very good question my wife and I are going to book our 4th trip to couples before the end of the month most likely thru All Inclusive Outlet as well for the savings (Nov. 30--Dec. 7 2013) Our first choice would be Omaha Ne but are open to any suggestion on saving some $$$ on airfare. We have even considered flying to Chicago Friday night so we can catch the earliest possible flight to MBJ.

You have plenty of time to book the flights, and I would just watch the prices. I did that for our trip in 5 weeks. I think I finally booked it for 508 per person out of CWA (Wausau/Mosinee WI). However I booked over night layovers for personal reasons. But, I just watched flights on Kayak.com and when they looked reasonable, I booked. I believe it was July before I booked. They had been higher before that, and then they came down, and now they are way up again. I think when I checked now they were over 800 pp for a similar flight. Although we are on AA, and they have changed our flights a couple of times. Our arrival time is still the same, and our departure time is still the same, it is the connecting flights that have changed.

Airfare is so high. We found we got the best prices when booking packages (air and hotel)with online companies.

I used this site to keep an eye on flights. ITA Software by Google

I like this site because it shows several different airlines and flights so I was able to figure out the earliest flight in and leave fairly late in the day.

We always book our hotel way ahead of time to get the best prices at Couples.

We then book our flights from OHare to Montego Bay anywhere from six to nine months before the trip. We use kayak.com to compare prices. I almost continuously watch for pricing for flights and the 6-9 months is the best pricing and usually doesn't get any less (and I'm too afraid to wait much longer). We have never paid more than $450 for per person -- this price has been pretty consistent for 5 or 6 years.

We have flown American lately, which has direct flights on Saturdays and Wednesdays (at least for Dec 2012), and baggage is included. We have also flown US Air and Delta, connecting through Charolette and Atlanta those times (worked ok, but prefer the American Airlines direct flight).

As for flight times, the AA flights are the best -- arrive early afternoon in MBJ and don't depart until mid-afternoon. The US Air left a bit early and gets there about the same time (we live in southern WI, so stay near O'Hare with a park/fly special, which works great!).

If your flight is later in 2013, I would wait a bit longer before booking. Oh, and the AA direct flights didn't open up early either -- I think these are added in the 6-9 month timeframe (probably closer to 6 months).

I think I got everything. Let me know if you have any questions, and have a nice trip.

Thanks TallMan2nd for the info

I booked our trip today for Nov 30th-Dec 7th 2013 now to put it out of my mind which isn't going to be easy:)

My plan is just as you mention to keep a close eye on Kayak.com over the next several months. We live in South East South Dakota and I am thinking of flying in to Chicago Friday night with hopes of catching the earliest flight out Saturday.