I’m briefly in New York, and decided to check out the iconic Waldorf Astoria New York, which recently reopened after a massive renovation. While I’ll share some initial thoughts shortly, in this post I’d like to talk about an interesting occurrence at check-in, as I’m curious how others feel about this…
In this post:
Waldorf Astoria offers junior suite upgrade for $200
I redeemed a Hilton Honors free night award to stay at the Waldorf Astoria New York for one night. The hotel has 375 rooms and suites, and a vast majority of the accommodations at the hotel are suites (initially the plan was for the hotel to be all-suite, but they backtracked, and added a small number of non-suites, I guess).
For what it’s worth, standard room points bookings confirm into the “king room” category. Ahead of check-in, I noticed that I had been upgraded one category as a Hilton Honors Diamond member, to a “deluxe king room,” This retails for $92 more, so it’s better than nothing, but also certainly not a very exciting upgrade (which basically sums up my expectation of Diamond upgrades in the United States).
I was totally fine with that, and was happy to just be staying there with a free night award. At check-in, the front desk associated informed me that I had been upgraded to a deluxe king room. I didn’t ask about a further upgrade, but before being given keys, he shared what was supposed to sound like an enticing offer — he asked if I wanted to upgrade to a junior suite for just $200 more, and then he explained the features of the room.
For context, below is how much the three entry level king room categories were retailing for on the night I’m staying.


This was the first time I’ve been offered an upgrade like this
Hotels selling upgrades for cash is nothing new. However, as a fairly high tier elite member, I’ve never been offered what would be a pretty standard elite upgrade for cash at check-in. After all, an upgrade from what I booked to a junior suite would be “only” two categories, which hardly feels like an overly generous upgrade.
Now, I’d like to think that I have reasonable expectations with Hilton Honors Diamond upgrades. If you look at how Hilton’s upgrade benefit is published, it says the following, which sounds quite generous:
Space-available room upgrades
If we have a better room available, it’s yours – up to a 1-bedroom suite.
However, when you look at the terms, you’ll see the following:
Diamond Hilton Honors Members may receive upgrades to preferred rooms, based on availability at the time of arrival. Upgrades for Diamond Hilton Honors Members may include upgrades up to “junior”, “standard” or “one-bedroom” suites.
As I interpret it, hotels have have discretion as to what types of rooms they upgrade you to. So while some people will disagree with me, I don’t think the hotel was technically doing anything wrong by providing me with some sort of an upgrade, and then trying to sell me an additional upgrade. However, it definitely doesn’t make a great first impression. It’s one thing if the cash upgrade were to a speciality suite, but we’re talking about the most entry level suite here…
What most rubbed me the wrong way was the upgrade price. It was made to sound like it was some sort of a bargain, and in theory, getting a suite upgrade for $200 might not sound bad. However:
- The deluxe king rooms are 575 square feet, while the junior suites are 620 square feet, so we’re talking about a room that’s 7% bigger
- The $200 upgrade amount was actually greater than the price difference in the first place between the most basic room and a junior suite ($184)
- If you’re going to offer someone a paid upgrade, I think it should be (at most) the price difference between the room you’re blocked in and being promised vs. the room you’d be upgraded to; if they’re telling me I’m getting a deluxe king room ($1,077) and they offer me a junior suite ($1,169) for cash, I shouldn’t be on the hook for more than $92, in my opinion
Anyway, I rejected the upgrade, and was ultimately very happy with the room I got. Still, I found it to be an interesting interaction, as it’s the first time that I’ve been offered such a modest paid upgrade as an elite member, all while being asked to pay more than the rate difference between rooms.

Bottom line
While hotels frequently sell upgrades, I was a bit surprised to be offered a cash upgrade to two categories above what I booked while checking in at the Waldorf Astoria New York as a Hilton Honors Diamond member.
What surprised me most was the extent to which this wasn’t a deal — the upgrade price was more than the difference in rates between an entry level room and a junior suite, and way more than the price difference between what I was blocked in and what I was being offered.
What do you make of this upgrade “offer,” and how would you have handled it?
@Ben - please tell me the "entertainment" is still in the cocktail lounge. Watching the kabuki dance between client and "entertainer" was always a kick in the pants. Literally watched men some down in their smoking jacket and pajamas to meet the "entertainers."
@Jack any particular reason why you are so fixed on Ben's hotel choices? If you haven't been paying attention, this is a travel blog focused on a segment of the traveling audience...
@Ben - please tell me the "entertainment" is still in the cocktail lounge. Watching the kabuki dance between client and "entertainer" was always a kick in the pants. Literally watched men some down in their smoking jacket and pajamas to meet the "entertainers."
@Jack any particular reason why you are so fixed on Ben's hotel choices? If you haven't been paying attention, this is a travel blog focused on a segment of the traveling audience that generates revenue for its advertisers. My guess is Ben would profile Motel 6 in Moose Snout, MT if that's what generated clicks...but it doesn't because none of us beating a path to the internet to learn about chic lodging options in Parker, AZ.
Ben, I doubt you were perfectly happy about the room you got. You always show pictures of suites. Your a snob. Lets be honest. I still have not seen a review of the motel 6 in parker arizona.
@ Jack -- I'm sorry you have that impression of me. I was perfectly happy with the room, as I wrote here, as you'll see in my initial thoughts I publish about the hotel, and as you'll also read in the full review. I'm not so insecure that I need a room that's 7% bigger and technically called a suite in order to feel good about myself.
I'm not sure you get the point of the entire blog, Jack.
In the late-1990's I was staying there regularly and using my client's heavily discounted corporate rate, often in tiny rooms - but once VIP DIAMOND came out and its was like the magic gates opened. Managers would appear to escort you to a room. Those days many of the suites were the floor and a letter (eg, 25-M) & named, and I always seemed to score a great room. Funny enough, while more "exclusive", the...
In the late-1990's I was staying there regularly and using my client's heavily discounted corporate rate, often in tiny rooms - but once VIP DIAMOND came out and its was like the magic gates opened. Managers would appear to escort you to a room. Those days many of the suites were the floor and a letter (eg, 25-M) & named, and I always seemed to score a great room. Funny enough, while more "exclusive", the Towers upgrades seemed to wedge you into these tiny over-decorated rooms... but the Waldorf became my favorite hotel for years. Despite continuing to be DIA, I haven't had a great upgrade in two decades. Sad, sad, sad.
Was at this hotel just when un general assembly was going on using aspire free certificate and was upgraded free to this same junior suite! No way it's so special I'd pay extra $200 cash for
@Lucky: last November we stayed at the JW Marriott Cancun. I am Lifetime Titanium. I asked for an upgrade, they told me that the hotel is full (it wasn’t, 40% occupancy at best). Then the check in agent immediately offered to upgrade me to a junior suite for $750 for 5 nights. It was a paid stay, not using award nights.
I thought the photo on the intro page to this article was your upgraded suite. I'm like, Wow, that's worth $200 bucks!
Strange. We were just there a week ago on an FNC and was upgraded to a junior suite by the system a day ahead of check in. It was a weekend night FWIW.
By the way if you’re still there, check out the ballrooms on the fourth floor!
The Chinese state controls 98% of the company that owns the WA NY. Ownership matters. Please book with care.
And that means what exactly? As you probably typed that from your Iphone.
My phone is Korean, and what my comment means, "exactly", is that 98% of the hotel's net profits are repatriated back to Beijing for the benefit of the Chinese government. I thought that was plainly obvious.
A savvy traveler once said that —paraphrasing— "the guests are not the hotel brands' clients, The property owners are."
In this case, the brand served its client by feeing it another revenue opportunity.
*Ben, that savvy traveler was you. Some years ago.
Only acceptable if hotel states the upgrade policy: “We only upgrade Diamonds up to X room category”
The more interesting take, regarding the comment below, are Diamond upgrades now worse because of the new Diamond Reserve tier?
Ben I'm curious if you're going to be writing your impressions on the WA NYC soon? I'm debating using my free night award for an overnight on one of my two trips home, and if it's even worth the effort of traveling from and back to JFK.
@ Samar -- Give me like an hour. :p
Awesome thank you.
Many flyertalk posts about getting Junior suites on FNCs.
@ Beachfan -- Yeah, I had seen lots of reports of people being upgraded to junior suites, so that's why I was a bit surprised. You'd think the hotel would have a policy of upgrading Diamond members to X room category based on what's available, rather than it just being whatever the front desk person feels like.
I wonder if the $200 was going to go into the agent's pocket?
Ben, this story is just another data point of how inconsistent this hotel is. I stayed there last fall with a Hilton FNC and was upgraded to the junior suite a few days prior to arrival. However, I ran into service issues there including no welcome gift when others have reported getting them, staff losing a personalized card I had written to my fiancée and handed off to be delivered to our room (luckily they...
Ben, this story is just another data point of how inconsistent this hotel is. I stayed there last fall with a Hilton FNC and was upgraded to the junior suite a few days prior to arrival. However, I ran into service issues there including no welcome gift when others have reported getting them, staff losing a personalized card I had written to my fiancée and handed off to be delivered to our room (luckily they found it while we were checking out...), concierge unable to book the restaurant I wanted even though I was able to find a way to book it with my own persistence, and staff knocking on the door when we had the do not disturb sign on.
I guess The Greatest of Them All is not the greatest even for the biggest bloggers. Have you considered changing your name to Paris Hilton?
This practice is why I have chosen other hotel chains. Not because I get more upgrades but purely due to the insulting way they do this.
Ben, good use of free night award (because 150K points is absurd); may have to try a staycation here, soon. Glad it's finally reopened.
Quick question: If you use your Hilton Aspire Amex for room charges, spa, meals, etc., would the $200 semi-annual 'resort' credit work? I know it's not currently listed on the page as qualifying, but sometimes WA's apply, regardless.
@ 1990 -- Sadly I don't believe so since it's not a resort, though the charge hasn't yet hit my account, so I can't say for sure.
It is common. I've been offered paid upgrades as an elite member (not at Hilton though) to rooms or suites I had expected to be upgraded for free due to status. And the upgrade price was invariably much higher than the cash rate difference between the rooms.
There is also a new, unrelated phenomenon: early check in fee. Some hotels now charge a fee to check in earlier than a published time of 14:00 or...
It is common. I've been offered paid upgrades as an elite member (not at Hilton though) to rooms or suites I had expected to be upgraded for free due to status. And the upgrade price was invariably much higher than the cash rate difference between the rooms.
There is also a new, unrelated phenomenon: early check in fee. Some hotels now charge a fee to check in earlier than a published time of 14:00 or 16:00, even if the room is ready, even for elites. Early check in is not a status benefit, so some hotels now try monetizing it. Just like upgrades.