Originally Posted by
elilaw
For example, I'm flying to Rome this summer on vacation, and am wondering if I should 1) pay for two coach/business class seats with points 2) pay for one biz class ticket and get the other free [companion benefit] 3) pay for 2 coach/biz class seats and hope for an automatic upgrade to biz/first class.
Welcome to FlyerTalk!
As
mia points out, the "free upgrade" on your flight to Rome doesn't exist, so that isn't an option. There is such a thing as an operational upgrade, but chances of that coming through are incredibly low.
On top of that, there are two types of "pay with points" that could be used. One is the booking through AmEx's web page and using your MR points at 1 cent per point. That rate is pretty low. But if you're buying a pair of $5000 tickets you're still spending 1MM MR points. On the plus side, you'll earn miles on the trip, but that seems to not me much of an issue for you. The other option is transfering MR points to one of the airlines and redeeming that way. If you can find a "saver" seat you can get to Europe for ~100K points each on DL or CO. If you cannot find the "saver" seat you're going to have to pay 250K points each for a total of 500K points. While that is a lot, is is still fewer than the 1MM points you were looking at paying with MR points directly.
Depending on your timing requirements you may be able to find a pair of "discount" J seats to Rome, but if not the IAP might not be a terrible deal, though it usually is for US-Europe travel.