Slightly over a year ago I shared about why I thought Hilton Honors Gold was a solid mid-tier hotel status. I still think so, but even back then we had commenters asking why go the chain route instead of the cheaper OTA route. Similar sentiments arose more recently in response to Jon’s article comparing OTAs with direct hotel bookings.
The number one reason I’m currently concentrating on Hilton properties is really to maximise the use of my Diamond status obtained through the insanely generous but now-defunct status match offer.
Given that I’d admitted to going ‘full Hilton’ mainly because I’d managed to rather effortlessly launch myself to the top tier, I figured that I owed it to myself to do a stock take and evaluate if the perks I’d gained were actually worthwhile.

What I’ve done is to reflect on the benefits I’d enjoyed in 2017 as a Hilton Diamond member (also considering what a Gold member would receive, since that’s the tier that’s more easily accessible by the average mile hacker), attempt to quantify them somehow, and finally evaluate if I’m really okay foregoing the potential savings of booking via OTAs.
(Spoiler alert: Yes, I very much am.)
Methodology
I found it pretty difficult to meaningfully quantify all the benefits I’d received over the course of the year in a manner that would also mean something to a large audience, each of whom would have different spending behaviour on hotels. What I’ve endeavoured to do is to consider what I think I’ll be willing to pay out of pocket for each of them, expressing this as a percentage of the room price so that the value of this benefit can be applied to a wide range of room types.
There’ve been a number of assumptions and generalisations made in this article, and you may disagree (greatly) with the exact valuations I’ve assigned, but I’ve also attempted to show the reasoning behind all of this so you can swap in your own figures as well.
One figure I’d needed before embarking on this review – based on my records, the average price of my stays at Hilton properties was about S$280/night (including taxes).
The Perks
The Hilton website gives a nice lengthy list of benefits for each tier of elite membership. For simplicity, I’ll focus on the three I really value – complimentary breakfast, executive lounge access, and room upgrades.
Complimentary breakfast (7% value)
Depending on where you stay, complimentary breakfast might look something like this…

…but hopefully you get something more like this:

Now I know that hotel breakfasts are typically crazily overpriced (satisfying as it was, I highly doubt I’d cough up S$45 for a breakfast buffet even at Conrad Tokyo), but when made available to you for no additional cost they can truly be a delight to have.
I’d assign this the conservative value of $10/person (that’s a figure I can imagine paying out of pocket across the board). You get complimentary breakfast for up to two guests as a Gold/Diamond, so that represents an approximate 2x$10/280 -> 7% value to me.
Executive lounge access (5%/1% value)
This is another property-dependent benefit – the bulk of the Hilton properties don’t actually have a lounge, but most higher-end properties (e.g. Conrads and city Hiltons/DoubleTrees) will have an exclusive space that are accessible only to Diamond members and guests staying on executive floors.

Other than providing a separate (often beautiful) space for you to lounge at, these spaces usually serve afternoon tea and evening cocktails.

Depending on the property, the food served could sometimes even suffice for dinner (or at least supplement it). I think $20 per person is a fair price to pay for this benefit, so I’ll value this at approximately 2x$20/280 -> 14% for properties with a lounge. Only about 39% of my nights were spent at such a property, so that brings it down to about a 5% value.
This is probably the one perk of Diamond membership that I’ll miss when I finally lapse back to Gold status. Gold members usually only enjoy lounge access if upgraded to an executive room with lounge benefits. Since Gold members often receive only a one-class room upgrade, they usually will not enjoy lounge access if booking the cheapest available room at a property. This varies from property to property, though – some are more generous than others. I’ll estimate myself getting lounge access in about 10% of my stays previously, which would bring this benefit down to about a 1% value for Gold members.
Room upgrades (12% / 1% value)
Room upgrades can come in different forms. Sometimes, upgraded rooms come in the form of the exact same room type on a higher floor. Other times, you might be upgraded to a suite, an immensely larger room that typically comes with its own living room space.


This is an area where Hilton pales in comparison to other chains like SPG which offer a more consistent upgrade experience, sometimes even guaranteeing suite upgrades. For a Hilton member, it’s more usual to get upgraded to a deluxe room (higher floor, slightly larger space) or an executive room (with executive lounge access – I already consider this a win) than an actual suite.
In my experience I’ve been more successful netting suite upgrades by trying my luck and asking (nicely) during check in if a better room is available (you need a thick skin to maximise your benefits).
If asked to pay out of wallet for a suite, I might top up 50% of the basic room cost. I was upgraded to a suite at about 25% of my nights stayed in 2017; I don’t think I’ve ever received a suite upgrade as a Gold. That makes about 12% value for Diamonds and 1% for Golds (I’ve assigned a token value there in recognition of the nicer views and extra space I sometimes get).
The Points (18% / 12% value)
The points earning structure for Hilton members will soon be adjusted; in essence, starting Apr 2018 Diamond members get 20 points (and Gold 18) for every USD spent at a Hilton property (excluding taxes).
You can also buy points directly from Hilton at US 1¢ each, though you could sometimes buy them on discount at as low as US 0.5¢ each. The Points Guy currently values Hilton points at US 0.6¢ each, which would make it 0.8¢ in SGD, but I prefer to value them conservatively at SGD 0.6¢ as well.
I’d gained a rather substantial amount of Hilton Honors points this year – using the 0.6¢ valuation I’d managed to net about 18% returns in value. As a Gold member I estimate the gains would have been closer to 12%.
So what can you do with these points? They can be used to redeem award nights at hotels, typically at rates close to the 0.6¢ value. At certain properties like Conrad Maldives Rangali Island, seen as the crown jewel of the Hilton points redemption scene, redemption value can be considerably higher (in this case, 95,000 points for one night that might retail for upwards of US$1000).

I’d managed to accumulate a fair chunk of Hilton points in 2017, so I guess the Milelion’s going to be getting a Conrad Maldives review sometime later this year…
Promotions
The mathematically-minded among you might have noticed that 20 points per USD doesn’t quite add up to the 18% value I’d quoted earlier – it’s probably just half of that, actually. The reason for this is that throughout the whole of last year (also continuing this year), Hilton has been running promotions that allowed you to double/triple your point earn – a number of these were even able to be used simultaneously and stacked. I won’t go into too much detail of past promos here, but as you can imagine how that allowed points to have been accrued very much faster than the advertised rate.
This could also be chained with some other offers like using the Citi Prestige 4th night free feature, where the discount comes in the form of reimbursement and you still get the points earned for the 4th night, since the reimbursement is invisible to the property.
Peace of Mind (5%)
I have 2 issues with OTAs.
No walk policy and no upgrades.
That is not worth the savings.
One of friends had a booking at a hotel that went on strike, the OTA simply refunded the money and had my friend rebooked at another hotel, lower tier and at the higher prices.-Fred, 2016 comment
I won’t belabour this point too much since I’m sure that OTA screwups are statistically not that common, and that similar screwups do happen at chain hotels as well. That said, being an elite member of a chain would offer you some protection in that you can raise feedback directly to the chain’s help desk – I’ve found this to be rather helpful since many properties don’t seem to man their email addresses particularly religiously.
If paying even 5% more for a hotel booking acts as a sort of hotel insurance, I’ll take it.
The Verdict
Even just counting the less subjective benefits (namely breakfast and points), I gained 25% extra value as a Diamond member (I estimate 19% for Gold) in 2017.
After including the more subjective benefits such as lounge access, room upgrades and peace of mind as an elite member, I find that I gained 47% extra value as a Diamond (I estimate 26% for Gold). This is actually way more than I’d initially expected.
Sticking to a single chain is probably not going to get you the cheapest stays (Airbnb, OTAs and other avenues of finding discounted hotels exist), but for travel hackers who’re willing to endure other opportunity costs to enjoy flying in premium cabins, I’m surprised not more are exploring leveraging on hotel chain loyalty as well!