First try and look up or come up with your own value per point. Remember that restaurants/travel get double points on sapphire, so that will most likely get those spends. Then Hilton gives 9X on hilton spends. So make sure to use that card. And Hilton gives 6X on supermarkets, drug stores, stand- alone gas stations, and home telephone, wireless, cable, satellite TV and internet service providers, so probably use that card. I think 1 for 1 spends should probably go to sapphire assuming it's pref, which you didn't mention so it may not be, maybe time to upgrade if so?