Our successes that easily come to mind are trips to Vegas.
Once we got upgraded to a suite at after arriving late and they had run out of the category of room we booked.
The other times we were just nice to the clerk and chatty and asked if we could get a complimentary upgrade to a high floor overlooking the strip which was like a $20-50/night upgrade IIRC. Once, they even threw in line passes to the buffet. We did tip them after they were able to secure us the upgrade though.
The guidance I would give is (similar to Aerides):
Be nice to the front desk clerk.
Try to be specific on the upgrade that you are looking for (try to know the room types).
Book off the hotel site vs Expedia, Booking, Hotels, Agoda, etc.
Be part of their loyalty program
Once we got upgraded to a suite at after arriving late and they had run out of the category of room we booked.
A Hampton Inn I stayed at last year let me choose my room a day in advance, as an HHonors member. Maybe this is standard now. I hope so. It was very nice for me because I was staying 2 nights, before a marathon, and planning on hanging out in the hotel and resting the day before the race, watching college football. I looked at the room map and oriented it to a google satellite view and picked a room at the end of a hall away from an elevator (less noise), not looking into the sun (so I could have the curtains open during the day), and the end further from the interstate (less noise). It worked out well.
Reading TripAdvisor's room tips is another way to ask for what are probably better rooms.
I haven't tried asking for an upgrade.
A Hampton Inn I stayed at last year let me choose my room a day in advance, as an HHonors member. Maybe this is standard now. .
I've been doing that for a long time. I think most Hiltons let you do that through their app on your phone. I also like getting the digital key that way so I don't even have to go near the front desk - just go straight to my room and unlock it with my phone.
I believe Marriott is starting to follow suit with this as well.
I’ve been told that smaller hotels may save upgrades for people who book direct and not through a service like Expedia. The services take a big chunk of cash.
No, not at all. I think it may require making the reservation through Hilton (online or through the app).
The small family owned hotel we like on the beach in Mexico mentioned in passing once that Expedia clipped them for almost 30% of the nightly rental.
Oh I always reserved directly with Hilton , but never discovered these perks.
Ouch!
I usually reserve directly because it avoids a middle man which can create more hassle if things aren’t right. “I’m sorry, we don’t have that reservation.......” And in case of overbooking, direct reservations often get priority.