Hilton Honors is irritating (AKA Schrödinger’s hotel room paradox (AKA if Delta ran a hotel loyalty program))

In the past few weeks, I’ve been focusing much more heavily on the “burn” side of the “earn and burn” mantra. Part of that involved cashing out the remainder of my Hilton Honors balance on a couple nights at Hilton’s new Curio property in Rome, which looks really nice. It isn’t cheap (76,000 – 80,000 points per night), but I think between the nights I booked on points plus a free weekend night from Amex’s forthcoming Aspire card and a gift card I have laying around, I can cobble together a four night stay.

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The problem is that I ended up moving the trip back a week for various reasons, so I needed to change my Hilton award booking. Anyone who has tried to do this before will probably know where I’m going with this, because it seems to be a recurring problem: Despite verifying that the new dates I wanted to book had standard rooms available, the calendar showed only premium rooms when I went in to change my reservation.

This isn’t the first time I’ve run into Hilton playing games with availability – I dealt with the same thing when I booked an award stay at the Waldorf Astoria Amsterdam, and the dates I wanted suddenly had no more standard rooms available right at the exact moment I tried to book. It’s the award booking equivalent of Schrödinger’s cat paradox, in which availability both exists or doesn’t exist at the same time, depending on whether you’re trying to book that particular day. Just as Schrödinger was trying to find the exact moment when a superposition of two states becomes one state or the other, booking a Hilton award stay can become a maddening exercise in determining exactly when the availability that you found ceases to exist.

(I also get annoyed by Hilton’s hybrid revenue/chart-based award structure, which makes it impossible to predict the cost of an award stay until you try to book it. Hilton must have seen how much people hated Delta’s “enhancements” to Sky Miles and realized that they should do the same thing.)

Anyway, not being able to change the reservation, I just went ahead and canceled it, figuring I’d be able to re-book it later. However, when I went in to rebook, the hotel didn’t have any availability over the three-week period I was trying to book… and keep in mind that just hours earlier, it showed availability on every day.

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It’s as if me canceling an award stay at this hotel shut off availability on every other day in order to prevent me from rebooking. I tried different browsers and everything, but every time I logged into my account and searched that hotel, I found the same thing. Then it occurred to me that I should try going into incognito mode first and searching again before logging in. Lo and behold, standard availability gushed forth, and I was even able to see it after logging in to book the dates I wanted.

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I even found the room for cheaper than it was originally (76k per night instead of 80k). That brings me to another point: it’s usually a good idea to keep an eye on your Hilton award stays to see if the cost has come down as you get closer to the actual dates. However, if you do go to cancel and rebook, there’s a good chance your account will be locked out of rebooking at that hotel again, so definitely keep the incognito trick in mind. I don’t know if it’s just a quirk of how Hilton’s booking engine searches inventory, or if it’s something Hilton does on purpose to discourage people from monkeying around with their existing reservations. Either way, it’s annoying.

Oh well. At least I was able to figure out a workaround in the end, so I could book the dates I wanted… although there’s probably a 0% chance that there will be any additional availability around the days I booked when I get around to redeeming my free weekend night next month when I get the Aspire card.

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