Windbag Miles is a blog about points, miles, credit cards, travel, and general windbaggery.

A couple Hilton updates, including a “trick” that’s either a great award booking hack or just me having good luck over the phone for once.

I’ve been pretty critical of Hilton in the past, mostly because things that are easy to do with other hotel loyalty programs are inexplicably difficult with them. Case in point is the free night certificates that you can earn through their co-branded Amex cards (either by having the card and/or by spending a certain amount in a year). You can read my earlier article on the matter, but the gist is that many of their phone agents don’t know how to handle them (and that’s assuming you get an agent that even knows what the free night certificate is in the first place).

For my previous redemptions, I’ve had to hang up and call back multiple times until I reached an agent that knew what they were doing. The worst instance was a few weeks ago when my wife called in using my phone, and due to the mismatched phone numbers, they insisted on creating an entirely new Hilton Honors account for her. She hung up right away, but we then had to deal with having the duplicate account combined with her main account.

However, I think there has been some improvement here recently. My wife tried again to book a reward night using the certificate, and the agent knew exactly what she was talking about and even said that Amex had attached it to her Hilton account automatically. I don’t know if this was just luck of the draw, given the wide disparity in Hilton agent knowledge I’ve encountered in the past, but it’s an encouraging sign that the certificates seem to be more visible to agents now — she didn’t even ask for the number, she just confirmed the last four digits to make sure it matched the email Hilton had sent out with the certificate ID. 

I’m looking for feedback here — is it true that Hilton/Amex are simplifying the process of redeeming the free weekend night certificates, or was this just luck of the draw? 

Speaking of luck of the draw, I found out something interesting when I tried to book two nights at the Waldorf Astoria Beverly Hills. As one of the nicer hotels in Hilton’s system, it’s predictably difficult to find award nights here. Sure the base rate for a standard room award is 95,000 points, but there are barely any of those in the hotel, and the next category up is a premium redemption that goes for over 200,000 points. So while it’s theoretically possible to get a room for 95k, it’s not going to be easy.

(As an aside, these 95k redemptions are the last pockets of outsize value in the HIlton program, since — thank god — Hilton hasn’t decided to add redemption levels for standard rooms above 95,000 points. Once they do (and this is most likely an inevitability), well, I hope they leave a good option to cash points out on Amazon. But if you can get a hotel that normally goes for $7-800 per night for 95,000 points, you’re doing significantly better than the normal 0.5 cent value people usually put on Hilton points. Of course this opens up the interminably irritating question of whether a room is really “worth” $800 when you wouldn’t pay that in cash. Regardless, some hotels cost lots of money and at those hotels, you can get a pretty good return on your Hilton points.) 

The problem I kept having yesterday when trying to book two nights at the WABH was that I could see standard awards available on the first page of search results, but when I clicked through to choose a room, my only option was premium awards. I finally called in to see if I was missing something, although I didn’t expect Hilton to be particularly helpful, since the norm is for them to deny standard room awards exist even when they’re easily bookable online. 

Much to my surprise, however, the agent I spoke to was very helpful, and she explained that some upper tier hotels kill two birds with one stone by making the ADA rooms the only ones that are normally available for standard redemptions. Since those rooms often don’t show up online, the system thinks the hotel has standard awards when it lists the hotel in the search results, but the rooms aren’t listed in the available room types when you try to book the award.  

Luckily I got a great Hilton rep on this call, and she went ahead and booked the ADA room for two nights and put a note on the reservation requesting that I be upgraded “although it’s at the discretion of the hotel” or translated into Beverly Hills-speak “not a chance in hell, you threadbare street urchin.” Still, the small design concessions an ADA room has to make in order to be accessible are immaterial in my opinion, and I’m still as excited for the Waldorf Astoria Beverly Hills as I’ve ever been for a hotel stay. 

Is this an award booking hack when Hilton won’t let you book standard awards that show up online? Maybe... It’s tough to tell with Hilton, since their reps often have wildly divergent stories when you call up with requests like this, and it probably also depends on how helpful the agent is feeling at that particular moment. If you’re running into the same issue at a hotel that limits available standard rooms, at least try calling in and requesting an ADA room — you may get lucky. 

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I spent way more time messing around in Photoshop on my jokey graphics than I did actually writing this post about Marriott Bonvoy.

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