Does anyone know the best way, or timing, to get the best airfare, for a simple yet slightly complicated trip?
I have to travel to the East Coast this summer to pick up a child, bring him back, and then return him at the end of the summer.
So this involves two round trips for me, from here to the East Coast and back, and one round trip for the child from the East Coast to here and back.
So the second leg of my first round trip needs to correspond with the child’s first leg of his round trip. And then the first leg of my second round trip has to correspond to the second leg of his round trip.
Does that make sense?
I would like to book and purchase this all at once, and am finding it impossible to do online (where, of course, the best airfares are 
)
The first part of the trip is end of June/beginning of July, and the second part is at the end of August.
Of course, I am asked, how many passengers? Complicated, because its one and then two, and two and then one.
If I book them separately, the June/July ones are cheaper than the August ones. I thought about just buying the first part first, and then buying August later when its closer to the time and thus cheaper.
But that part is my second round trip, and what if my first leg of that trip (here to the East Coast) ends up being on a different flight than the child’s second half of his round trip, because maybe there are no more seats on his flight?
Of course that can’t happen because the whole point of this crazy charade is that he is too young to travel alone.
Does anyone have any knowledge or expertise in this, or know the best way to accomplish this?
