I bood the resort first. For us, a trip to WDW is a BIG thing, and we tend to book as soon as the next year's prices come out. So I contacted our
travel agent last June about our upcoming trip for July.
Airline tickets won't be available that far out. And, as others have stated, you can always change your resort to accomodate a good price on flights. And, to be honest, the best deal on a resort won't be available until pretty close to your vacation; we got a HUGE savings on our trip when the Summer deal came out a few weeks ago-- our travel agent had it applied to our reservation.
For airfare, I check just about every day. Again, using our upcoming trip as an example-- I started looking in about November. I know that we like to fly Jetblue-- we like their prices. And, in addition, the first bag flies free. And each of us has our own TV, and they serve a free snack, all of which makes my family happy. I checked every day for about 2 months, and the total price for flights we wanted was the same every day: $1474 for 5 tickets. Then, one day in January (the 3rd I think) it dropped by about $200. That day I bought, and the next day the same tickets were back up to $1474.
They say it's cheaper to fly midweek. I'm not sure about that, but I figure the airports are probably less crowded. And, as teachers in July, we have the luxury of being able to do that, so we do.
We also have the luxury of having a choice of airports. (For us, JFK, LaGuardia and Islip MacArthur are all very close.) If you have a choice, don't forget to check all of them. As it turns out, this trip we'll be leaving from LaGuardia and returning to JFK.
I love using a travel agent-- I can reccommend ours if you want. I love the freedom of emailing her with our request, then checking my email when I get to work to find out it's been done. She handles our booking, makes any changes when discounts come out, calls in our ADRs (Advanced Dining Reservations) and answers all my questions-- she's a delight to work with, all at no cost to us!
OK, on to Disney basics: do you know where you'll want to stay? Onsite or off? if you're on, do you have an idea of the resort? If not, then take a look at
www.allears.net -- they do a great fact sheet on each resort, complete with slide shows.