If you are staying at Hiltons anyway, and are paying with your own card (as opposed to a corporate card), why wouldn't you get the Amex Surpass? You get 9 HH points per dollar spent at Hilton, on top of the bonuses you get as a Diamond.

Assuming your My Way selection is Points + Points:

$1 = 10 base + 5 P+P bonus + 9 Surpass bonus + 5 Diamond bonus = 29 HH

Even if you value HH at 0.5 cents each (I value them at twice that), that's 14.5 cents per dollar spent.

Pretty good return. ^

You can get into a lot of discussions about what chain to give your business to, what program has the best payback, etc. But if you are charging a lot at Hiltons, I don't think you'll find a card with a better payback that Amex Surpass.