servus

Hi Bombo,

Welcome to Hilton ^

First of all, my experiences is there's no consistency in getting an upgrade or any other VIP benefits you should be entitled to. To find reliable information I suggest you do a search about the specific hotel here on FT.

Your idea of booking the cheapest room and hoping for an upgrade is indeed the right way. Keep in mind, that lounge access is guaranteed for Diamond VIP's only if you've set your on-property VIP benefit to room-upgrade.

Since I became Diamond not one hotel gave me the story "sorry, no upgrade due to booked Executive Floor". While being Gold, it happened pretty often.

Checking right prior check-in might help, but keep in mind, that might become a huge hassle. Are you willing to argue whith some Front Desk Agent while on vacation?

Hope you have a great trip!