Originally Posted by
PhillyPhlyer40
Ok, now I am more confused. (BTW, unusual routing, but I REFUSE to step on US...and IAD times didnt work out due to sold out flight). Back to my confusion.
It's not your fault that you're confused. There's a fair amount of misinformation in the replies to your question.
Here's the answer. Disregard everything else.
If your upgrades both clear before you check in for the flight, then only 1 e500 will be pulled.
But if they both clear at the gate, or one clears in advance and one clears at the gate, then you will be charged 3 e500s (one for PIT-ORD, one for ORD-LGA).
Flight numbers are irrelevant. Legal routing is irrelevant. Connection time is also irrelevant, as long as you're making a connection (and not, for example, flying back to your origin).
If you do a search on the UA forum, you'll find that most of the posts confirm what I've written above. Or you can just trust me on this.
I've upgraded IAD-LAX-PHL on one e500 before, based on the point-to-point distance from IAD to PHL.