The AMEX Premier Rewards Gold gives 3x MR points on flight purchases so that is a good one for purchasing your flights as long as MR points are useful for you. Chase Sapphire Preferred has 2x on travel spend and I think the Ultimate Reward Points are more valuable than AMEX MR points but it depends on what you want to use them for. I'm not a fan of Hilton anymore since Hilton points have been devalued a lot this year. Do you have a choice of hotels? You might want to look at Hyatt, Starwood, and Club Carlson programs and compare them with the Hilton program. Take a look at the awards charts and see what your Hilton points will get you. You might be surprised at how many points you will need. Ask yourself what is one trip you would like to take at some point in the future. Then plan that trip looking at what hotels are at that location and how many points you would need in each program. Then look at the airlines that could take you there. That's a good way to get a feel for what points in different programs are worth and will help you decide which cards to get.