Always Hilton for us. After 100% travel for 17 straight years as a consultant, DH has Diamond (Plus) status with Hilton. No other hotel chain treats him the way Hilton does (too many stories to list*), so it’s never a question for us. Same with Hertz and American Airlines.
*Well, one story. DS and DIL just happened to choose a Hilton boutique property for their wedding. When DH realized it (we weren’t paying for the wedding), he called the hotel and was able to get them the Presidential Suite for the entire weekend free, and the hotel comped our room as well. Also, the events manager used DH’s status to apply a discount to the catering bill. The hotel also spontaneously closed their rooftop bar to the wedding party/family/friends the night before when DH approached the manager and offered to open an unlimited tab until closing time. (I don’t think the hotel made out on that deal.)