The patterns change depending on the prevailing winds and where your flight is coming from or going to.
If flights are landing from north to south, its highly unlikely you could see WDW at all. If flights are taking off from south to north its also highly unlikely you could see WDW.
If flights are landing from south to north and you are coming from the west then you might get a chance to see WDW on the left side of the aircraft. OTOH, if you are coming in from the Northeast Coast, you won't see it at all.
If flights are departing from north to south and your destination is more to the west there is a good chance you would see WDW if you are on the right side of the aircraft. Again, if you're heading up the Atlantic coast you probably won't see it.
I live just a couple of miles from the castle and fly pretty regularly (well, in the pre-shutdown days) and have been able to occasionally spot my house from the plane. But that doesn't happen often.