I can tell you what I've experience lately. We're going to WDW in April, Easter break. I knew with the holiday to expect prices to be higher. When I started looking at 11 months out, prices were in the mid $400's. From California to MCO with one stop. I thought since I was looking so early, at some point prices would go down. They never did. Another problem I had were the times and connections. They all changed! I went from one stop to minimum of two and most cases three stops. Stopped looking at that airline all together (United). Finally got airfare in December. Paid more, in the low $600's but the times are great and so are the connections. I don't know when you're flying in October, but I think for the most part kids are in school. It sounds like many fly Southwest, I don't know if that's an option for you. I never had but it sounds like their prices are good and if fares go down they give you the difference towards your next SW flight. I really think the days of a bargain are behind us. It's harder and harder to score that great deal. That's just my opinion. I think instead of finding the best time to buy, buy when you're most confortable with the price and of course what you can afford.