I booked my flight down the other day from Chicago to Orlando. It went from what had been a steady 112 to 99 and said there were only 2 left at that price. checking to see what they were if I needed more, the price was up to 115 so I decided to not wait any longer. We go to wd Jan 2nd. But, the price has stayed at 99 for our trip back a week later and I just keep waiting, though I'm not really sure how long to wait.
Last year, for our Jan 2nd(again) trip I bought our down tickets on Aug 31, and then our return tickets on Sep 11. I got the down ones for 89, but I knew I'd seen it at 79 once so I kept waiting and suddenly on a Fri morning it dropped to 79 and I jumped on it! Hoping for something like that this year, though it may just as easily jump up unexpectedly the next time I go on, lol! I check several times a day, at all hours. I do remember though, that after I bought last year, the prices didn't change lower or even as low as I got, after that so I definitely hit it at exactly the right time!
ETA: Btw, I did just go to bing.com(never heard of it before) and for my dates, it says to buy, fares are steady or rising. Hmmm, hate being confused, lol! Then, I checked just the return trip on the 9th and it doesn't give predictors for one way trips. But, when I tried to click on the different choices it brought up for the lowest fair, which was through AT, which is the airline I'm using, when I clicked it took me to AT but it said there were no flights available? Confused, but doesn't matter I guess, though not sure what it means. Going directly through AT I don't have any problem, just still deciding how long to wait, lol!