How does Hilton price 5th-night-free awards?

/

I manufacture a lot of Hilton Honors points with the American Express Surpass co-branded credit card, and I redeem almost as many. The Surpass earns a free night certificate that can be used worldwide after spending $15,000 per year and Diamond status after $40,000 in spend, but I am perfectly happy earning 6 points per dollar spent at grocery stores all year.

I try to redeem points for at least 0.5 cents each, and do not have any difficulty finding opportunities to do so, although as always you have to be careful that you’re comparing redemptions against the money you would spend instead, not the cash value of the room you redeem points for.

For example, I stayed at the Conrad Hilton Midtown last weekend for 95,000 points per night (plus two of those free night certificates), which translates to something like 0.7 cents in value, but of course I wouldn’t spend $675 to spend the night in New York City, so it would be absurd to say I earned 4.2% in value on my grocery store spend.

One way to maximize the value of that spend is by using the fifth-night-free benefit on award stays whenever possible. Fourth- and fifth-night-free offers are pretty common across the industry, and Hilton’s is one of the most straightforward: to trigger the benefit, all you have to do is book a standard room for 5 or more nights entirely with points.

That’s how the benefit is triggered. Understanding how it’s calculated is trickier.

There are lots of ways to calculate the value of a night

I mention that other programs have free-night benefits for stays of a certain length because they illustrate how a simple-sounding benefit can have both opportunities and perils. Most importantly, how does the value of a fifth-night-free benefit change when the nightly rate varies over the course of the stay?

Chase IHG Rewards credit cardholders get a “true” fourth-night-free: the point cost of the specific night which happens to be fourth is zeroed out. This creates opportunities to stage your reservations so that the most expensive nights of your stay are the fourth ones and increasing the potential value of the boost to your points’ value over 33%, and the risk of “wasting” the benefit on a cheap fourth night..

The Citi Prestige card offered what they called a fourth-night-free benefit, but it was calculated as just 25% off the (apparently-inflated) prepaid cash rates offered through their travel portal. This meant the maximum value of the benefit was capped at 33%, with higher portal rates grinding down the value of the benefit from that theoretical cap.

Marriott Rewards’ version stretches the concept to the breaking point: on 5-night stays, the lowest-priced night is deemed to be the “fifth,” so on stays with varying rates you will never capture the full 25% boost boost in value; only on five-night stays where each night is priced equally do you get the maximum value from the benefit.

Hilton seems to use a “trimmed” fifth-night-free calculation

Since I have a fair amount of experience redeeming Hilton points, I’ve had the chance to observe how Hilton handles this inevitable question: how many points should you expect to save when using a fifth-night-free benefit?

First, to trigger the benefit, the same room type has to be available for the entirety of your stay. That means you need to go further than the Hilton award calendar, since you might see lower rates for one-night stay in a room type that isn’t available for all five nights.

Second, if the room type you’re booking has no change in price over your stay, then it’s as irrelevant as you’d expect: you save 20%, getting a 25% boost to the value of your points.

When the points rate varies over the course of your stay, then things get interesting. On the checkout screen, you’ll see a rate listed for each of the first four nights and “5th Night Free” listed next to the last night. But those first four rates are not necessarily the rates you’d pay if you were booking each night individually. Instead, Hilton sometimes “trims” those, slightly increasing or decreasing the price of each night.

Usually, but not always, this is done in Hilton’s favor: the first four nights will cost more as part of a five-night reservation than as four one-night reservations.

At this point, I would like to be able to pull off the napkin and reveal that I’ve reverse-engineered the precise formula Hilton uses to make these trims, but that’s not true. I spent the morning poking around the website and running experiments, and concluded that sometimes Hilton does this, sometimes it doesn’t, and when they do it’s usually against the customer’s interests.

Here’s a screenshot of the basic principle at work:


To walk through what you’re seeing there, a five-night stay starting on May 4 costs 199,000 Honors points, while the same five nights priced individually cost 248,000 points. In this case, the night of the 6th is “trimmed down” to 48,000 points, so the reservation costs 1,000 points less than it would if Hilton offered a true fifth-night-free, like IHG.

Meanwhile, a five-night stay starting on the 5th costs 196,0000 Honors points, while the same five nights would cost 253,000 points on their own. In this case, the nights of the 5th, 7th, and 8th are “trimmed up” to 49,000 points each, so the stay costs 3,000 points more than it would if the nightly rates were used. But because the night of the 9th costs so much more, the total cost of the stay is still less than the previous example.

Why does Hilton use this hybrid model?

The truth is, I’m not sure why Hilton has adopted this pricing model. And in fact, I’m not even certain that they did it deliberately. It’s perfectly believable that they price five-night reservations this way for reasons totally unrelated to the fifth-night-free benefit. Perhaps another day I’ll try searching for five-night stays in a new account without elite status to see if the pricing change is function of stay length and not trying to nickle and dime points redemptions after all.

If I did have to guess (we’ve now entered the reckless speculation portion of the post) I’d say that this was probably not actually designed to rob a few thousand points from their most loyal customers here and there, but rather to “simplify” the pricing page. The main visual effect of Hilton’s “trims” is to bring each of the four remaining nights closer together in price.

Here’s another set of examples where rates are trimmed up (against the customer):

And here are some dates and room types where rates are left as is, giving the customer the “full” 60,000-point credit for the last night:

In other words, what looks to us like a pricing decision engineered to get one over on us may have been as simple as a developer trying to think of a kludge that would make all the numbers look more or less the same.

Why it matters

While I’m sure there are folks as interested in the minutiae of pricing decisions as I am, the concrete reason this practice matters is that Hilton frequently sells points for “a bit less” than 0.5 cents if you first click through an online shopping portal to Points.com.

This isn’t usually an especially good deal, since Hilton points are also worth about 0.5 cents, and it doesn’t make any sense to buy anything for what it’s worth; keep your money.

Buying points for an immediate fifth-night-free redemption is an obvious exception. If you can buy $1.25 for a dollar, then the proposition becomes a lot more interesting, but only if you know how many points to buy.

And this is, sure enough, exactly how I got interested: I bought points for a five-night reservation, and once the points had hit my account discovered I didn’t have enough, because the Hilton website will not show you the total cost of an award stay unless you have enough points to book it (the iPhone app will if you click on “rate details”). Hilton had “trimmed up” the cost of my stay, and I had to buy a few thousand more points at a penny each to get over the top.

Hilton gift cards trigger American Express Surpass statement credits

/

In October, 2023, American Expressed announced changes to the Hilton Aspire and Surpass co-branded credit cards. American Express has acquired a well-deserved reputation as a “coupon book,” and these changes were no exception. Alongside an increase in the annual fee from $95 to $150, American Express added “up to $50 in statement credits each quarter for purchases made directly with a property in the Hilton portfolio.” The only question was, how easy would it be to trigger those statement credits?

Hilton gift cards trigger Surpass statement credits

Back in December I tweeted that I’d received the $50 statement credit for the fourth quarter for purchasing a $50 Hilton gift card. Since the first quarter of 2024 was just around the corner, I decided to wait to write a blog post until I’d replicated that experience. This is that blog post.

Interestingly, the gift card purchase also triggered the Surpass’s 12 points per dollar spent on “eligible purchases made directly with hotels and resorts within the Hilton portfolio.”

Timing

I purchased my first $50 gift card on November 23, 2023, and my first statement credit posted on December 2, 9 days later. I purchased my second $50 gift card on January 1, 2024, and the second statement credit posted January 10, again 9 days later.

Having established that pattern, do not worry if your statement credit still has not posted 8 or fewer days after making your gift card purchase!

Why does it work?

All I can do here is speculate, but there are two obvious explanations.

First, it’s possible that when Hilton set up their gift card provider, they explicitly coded it as a Hilton property. If gift cards were coded as regular spend, earning just 3 Honors points per dollar, there would be a real tradeoff between putting your hotel spend directly on your card versus paying with a gift card. Coding gift cards as Hilton purchases eliminates that tradeoff.

The second possibility is that when American Express coded the $50 statement credit, they used a simple filter for the word “HILTON” in transaction descriptions. Since gift card purchases post as “HILTON GC [STRING OF NUMBERS]” they trigger the credit. This raises the interesting possibility that, for example, purchases made in Hilton Head Island, South Carolina, would trigger the credit if the merchant included the town name in their credit card description!

The cards themselves

Perhaps fittingly given the relationship between American Express and Hilton, the gift cards take the form of American Express cards, in the sense that they have 15-digit card numbers starting with 3, and can be used at any Hilton property that accepts American Express.

Whether the cards can be used at non-Hilton merchants that accept American Express is an exercise left to the reader.

Conclusion

Each $50 Hilton gift card has a $1.95 shipping and handling fee, so purchasing $200 in gift cards per year raises the total annual cost of the card (including the annual fee) to $157.80. In order to break even, you therefore need to value Hilton gift cards at about 79 cents on the dollar. Whether that’s a high value or a low value depends on how you plan on using the cards.

From my perspective, 79 cents is “a bit high” for spending the cards on food and drink at Hilton properties, since hotel prices are typically marked up by more than 25% off street prices, so I rarely spend money at hotel restaurants.

On the other hand, 79 cents is quite low if you plan on using the gift cards to “pay down” your hotel room charges, whether for your room rate on paid stays or, for example, for resort or other ancillary fees that you’d otherwise have to pay with cash. While resort fees should be waived on award stays, some resorts (like the Maldives resorts that have launched a thousand blog posts) charge hundreds of dollars in transfer fees that should be eligible for payment with Hilton gift cards. A 21% discount on those fees is likely better than anything your credit card offers, unless you’re spending towards a particularly lucrative signup bonus and have limited manufactured spend opportunities at home.

Comparing IHG's 4th-night-free with Marriott and Hilton's 5th-night-free

/

I was reading Danny the Deal Guru’s write-up of the latest Chase IHG Rewards signup offers and something jumped out at me: the 4th-night-free benefit offered to cardholders, including those who hold the no-annual-fee IHG Rewards Traveler card. To be clear, this isn’t a new benefit, it’s just one I haven’t had a chance to think about in depth.

Generally speaking, I don’t rate IHG or their rewards program very highly, because while they have an enormous global footprint, they’re rarely competitive compared with the main hotel programs I rely on, Hilton and Hyatt. For example, I regularly visit Portland, OR, which on a sample search turned up two downtown Hyatt properties priced at 12,000 World of Hyatt points, a Hilton priced at 37,000 Hilton Honors points, a Marriott priced at 30,000 Bonvoy points, and a Kimpton priced at 25,000 IHG Rewards Club points (plus a nightly “amenity fee”). For a one-night stay, it would be ridiculous to choose the IHG property unless you’d built up a large orphaned balance through various shenanigans.

Since my framework is manufactured spend, not signup bonuses, it’s easy to make a direct comparison between the options:

  • 12,000 World of Hyatt points transferred from Chase Ultimate Rewards is worth $120 in cash.

  • 37,000 Hilton Honors points earned at 6 points per dollar with the American Express Surpass co-branded card is between $123 (if the same $6,200 in spend had been put on a 2% cashback card) and $185 if the points were purchased for 0.5 cents each, an offer which is regularly available, including now through March 7, 2023.

  • 30,000 Marriott Bonvoy points are worth between $240 (if you bought the points during one of their periodic promotions) and $300 (if you transferred the points from Chase Ultimate Rewards.

  • 25,000 IHG Rewards points are worth between $150 and $175 if you buy them using the “points and cash” trick (purchasing points while making an award reservation, then cancelling the reservation and having the points refunded to your account).

This makes comparing the four sample reservation options, and indeed comparing all reservation options at the four chains, easy, if on average:

  • World of Hyatt points cost 1 cent each;

  • Hilton Honors points cost 0.42 cents each;

  • Marriott Bonvoy points cost 0.9 cents each;

  • and IHG Rewards points cost 0.65 cents each;

then on a one-night stay you can convert the points cost of any property into the cash cost of manufacturing, transferring, or purchasing the required points. In the concrete example above, we saw that Hyatt and Hilton were quite competitive, while Marriott and IHG Rewards were significantly more expensive options.

On four-night stays, the equation changes, but only for IHG Rewards points. On four-night stays at the other three chains, the cost per point remains the same, while the 4th-night-free benefit offered by the IHG Rewards credit cards increases their value by 33% or decreases their cost by 25% to 0.49 cents each — same difference. The four-night IHG Rewards stay now costs just $122 per night, putting it squarely in the middle of the “competitive” pack of Hyatt and Hilton, or even on the cheaper end (ignoring that pesky Kimpton amenity fee, which you obviously shouldn’t in practice).

Moving to a five-night stay, the equation shifts again, but this time against IHG Rewards, since Hilton and Marriott both offer the fifth night free on award stays. The cost per night on the sample five-night stays with Hilton is $123 per night, with Marriott is $216, and with IHG $130. Hyatt doesn’t offer free nights on longer stays so their cost per night remains flat at $120.

Reference Card

I wanted to use a specific example to explain why I personally don’t care for IHG Rewards, but in case you want to bookmark this post or paste the values into your notes app, here are the shortcuts when calculating the cost of stays of various lengths.

Stays of 1-3 nights:

  • World of Hyatt: 1 cent per point

  • Hilton Honors: 0.42 cents per point

  • Marriott Bonvoy: 0.9 cents per point

  • IHG Rewards: 0.65 cents per point

Stays of exactly 4 nights:

  • IHG Rewards: 0.49 cents per point

Stays of exactly 5 nights:

  • World of Haytt: 1 cent per point

  • IHG Rewards: 0.52 cents per point

  • Hilton Honors: 0.34 cents per point

  • Marriott Rewards: 0.72 cents per point

Now you can easily calculate the cost of reward stays of up to 5 nights in length in every city in the world — not just in Portland, Oregon!

Don't sleep on Hilton's (extremely) variable award pricing

/

For some time now Hilton has employed variable award pricing to maintain a rough value of 0.5 cents per Honors point. That isn’t set in stone, and it’s not uncommon to see values as low as 0.4 or as high as 0.6 cents per point, but it’s clearly the benchmark redemption value they aim for across the entire Hilton portfolio. Outsized value of course is available when prices are unusually high and when booking stays in multiples of 5 nights, since the 5th night is free for all Hilton elites (when means just about everybody).

As my tone suggests, variable award pricing is usually treated as a defect in the program, but it has a silver lining: award prices also vary downward, as I found to my advantage during my recent stay at the Hampton by Hilton Glasgow Central.

I was redeeming US Bank Flexpoints at 1.5 cents each for the first night of my stay, and a topped-up Hotels.com award for the second night, which left me with two nights I planned to book using points. Here’s my booking history:

  • 7/8/22: booked night 3 for 35,000 points

  • 7/11/22: canceled night 3, rebooked for 33,000 points

  • 7/13/22: canceled night 3, rebooked for 32,000 points

  • 7/21/22: canceled night 3, rebooked for 31,000 points

  • 7/22/22: booked night 4 for 34,000 points

  • 8/6/22: rebooked night 4 for 32,000 points

That final reservation was just 2 days before night 4 — I had already checked into the hotel, but was still able to rebook that night and was instantly refunded 2,000 points! In total, these shenanigans saved me a total of 6,000 points, which you might reasonably consider to be kind of insignificant in the grand scheme of things. On the other hand, saving those points was a matter of clicking a few buttons on my phone, something we do for far less reward all the time!

Further considerations

In the list above I attempted to draw a subtle distinction: for night 3 of my stay, I was canceling and rebooking my stay, while for night 4, I rebooked my stay without canceling. This is because of a quirk in the Hilton reservation system: when editing an existing award stay, you must have enough points in your account to cover the full price of the updated reservation. When I was tinkering with night 3, I didn’t have the 31-33,000 points in my account, so I had to cancel the existing reservation before using the refunded points to rebook that night.

By the time August 6 came around, enough additional points had posted to my account that I was able to edit my existing night 4 reservation without canceling it first. I simply selected the same dates, the same room type, and 2,000 points were immediately redeposited into my account. This was ideal since I had already checked into the hotel at that point and all four of my reservations had been linked. If I had canceled the 4th night, I would have had to check back in and have the keys remade. A minor inconvenience, but one I was happy to avoid.

That brings me to a final consideration: if you’re not taking advantage of the 5th-night-free benefit, you may find it best to book each night of a 2-4 night stay separately, for the simple reason that when one night goes down in price, another might go up. If one night falls by 1,000 points, there’s no opportunity to rebook if the price of another rises by 1,000 points or more: separate reservations make it easier to capture intrastay price shifts.

Quick hits: what's on my mind in June 2022

/

It’s been a pretty slow month in the travel hacking world, and nothing’s jumped out at me so far in terms of killer deals that needed to be passed along immediately, but I’ve been taking notes about a range of opportunities and situations that I thought it would be useful to dump into a single reference post for folks who may have missed them.

Summer hotel promotions

I try to keep my Hotel Promotions page mostly up-to-date, but even if I miss a promotion, it’s always essential if you’re staying at a chain hotel to do a little light Googling to make sure you’re registered for any promotions you’re eligible for. All the chains but Marriott are currently offering universal promotions, so be sure to register for them before you stay.

Hotels.com for non-chain and secondary chains

I recently made two reservations through Hotels.com, one for a 7-night Hyatt stay, and another for a 3-night stay at an independent hotel in England.

There are two important things to keep in mind about Hotels.com. First, stays do not earn elite night or stay credit with Hyatt. Second, they earn rewards through two separate mechanisms: through the portal you click through to Hotels.com, and through Hotels.com “stamps” and “reward nights.”

For non-chain hotels this is usually a no-brainer: a portal rebate (currently 4% cash back through TopCashBack) and a 10% rebate through Hotels.com each time you earn 10 stamps and a “reward night” equal to the weighted average of your Hotels.com rates.

For chain hotels the calculation is somewhat more complicated, since you need to take into account the value of any points and elite status you might earn, especially during particularly lucrative promotions or when chasing particularly valuable elite status.

Hilton 5th Night Free math

Hilton Honors points are almost mechanically worth between 0.4 and 0.5 cents each, although with the caveat of massive upside value at particularly expensive properties, and when using them for 5-night-free redemptions on particularly expensive nights.

There are two important things to keep in mind. Just as Hyatt conceals the total price of an award reservation unless you have sufficient points in your account, Hilton will not reveal the total price of a 5th-night-free reservation unless you have enough points to book the first 4 nights. Instead, Hilton will only show you the price of the first night of the reservation.

This raises the obvious question: is the 5th night “free” in the sense that the average price per night is reduced by 20%, or is the precise 5th night of the reservation free? The answer is that the 5th night is free, which means during periods of dynamic pricing, it’s ideal to time the 5th night of your stay to be the one charging the most points, in order to maximize the value of the benefit.

How to buy Hilton points: Points.com or Hilton reservation?

I needed about 9,000 Hilton Honors points to lock in one of our hotels in London, so my natural first instinct was to click through the TopCashBack portal to Points.com to check out how much those 9,000 points would cost me. The answer: $50, which minus the 2.5% cashback comes to $48.75.

I then checked out the price of simply “topping up” my existing Hilton balance during the reservation process, and was quoted 34.65 GBP, or just $42.52 USD.

In other words, it’s cheaper to top up a Hilton reservation through Hilton than through Points.com — even during a promotion, and even when clicking through a cashback portal. It’s a story as boring as it is true: if you don’t shop around, you won’t get the best price.

American Express Hilton Honors Surpass lounge access

This is a bit of a silly one since most obsessive travel hackers have at least one ultra-premium credit card that offers unlimited Priority Pass lounge access, but since I’ve returned to traveling in 2021 and 2022, I’ve really enjoyed the 10 free Priority Pass lounge visits provided by the American Express Hilton Honors Surpass card. The overwhelming majority of our trips are non-stop, but the occasional long layover or delay in Seattle and New Orleans in 2022 has been a terrific and genuinely valuable benefit at times when air travel can be stressful and overwhelming.

Bilt Rewards

Finally, earlier this year a slew of bloggers started promoting Bilt Rewards when they offered 500 supposedly-transferable points when you linked your World of Hyatt account to your Bilt account. I, like a lot of suckers, linked up all my loyalty accounts, and ended up with just 1,400 Bilt points, 600 points short of the amount they require to actually transfer your points to loyalty programs (it would have been 1,500 but I’ve never been able to successfully create a Turkish Miles&Smiles account, for whatever reason).

I’m not here to say whether Bilt is an “ethical” or “unethical,” “profitable” or “unprofitable” company. I’m only here to say that while it exists, you have to hammer it as hard as possible, and one piece of that is only linking your loyalty accounts during promotions. When Hyatt is offering 500 points, link away. When they offer 100 points per account, you will never earn enough points to get any value from the Bilt program; make them come to you.

How I think about hotel free night certificates

/

I gather from my RSS feed reader that American Express has launched an aggressive campaign to move more Hilton co-branded credit cards in the new year, with the highest bounties naturally being paid to those who sell the most of their ultra-premium Aspire cards. And if you’re selling Aspire cards, you naturally need to play up the value of the annual free weekend night certificate. I like free nights, I like free flights, I like free car rentals, I like free groceries: I like everything free. But that doesn’t mean everything free is created equal, and free night certificates are one of the easiest, and most expensive, traps to fall into.

A free night certificate is worth its opportunity cost…

This is the commonsense idea that you should not value any award based on the retail price of its paid equivalent, but rather the amount you yourself would actually pay under the same circumstances. This is best illustrated in cities where multiple “reasonable” booking options exist.

Take, at the high end, New York City, where the Conrad New York Midtown, a Hilton property, is located about a third of a mile from the Park Hyatt New York. On a random day in mid-June, the Conrad is charging 95,000 Honors points per night, while the Park Hyatt charges 30,000 World of Hyatt points. The equivalent flexible paid rates are $945.30 and $1,202.63, respectively.

First, let’s state the obvious: these are great redemptions! If you became a travel hacker to get a taste of luxury you could never otherwise afford, then manufacturing about $15,000 in grocery store spend on a Hilton Surpass card, or $6,000 in office supply store spend on a Chase Ink Business Cash card, for a night in the lap of luxury in the heart of the metropole is just what you’re after.

…properly understood

But that’s not a strategy, because a strategy needs to take into account your overall travel preferences and needs. Even though it’s precisely what I was looking for, I admit I was still a bit surprised when I realized that 5 nights at the “DoubleTree by Hilton New York Times Square South,” about a mile from the Conrad, is going for just 40,000 Honors points per night, or 160,000 points for 5 nights after the 5th-night-free is applied for Hilton Honors elites. A flexible paid reservation in the same period runs about $1,658 (another great Honors redemption!).

Adding a 6th night to your stay at the DoubleTree using a free weekend night certificate will only save you $332, or 40,000 additional points, a much worse value than redeeming it at the Conrad. However, the redemption allows you to avoid changing properties 1 or 5 nights into a 6-night stay. In other words, maximizing the value of your free night certificate may cost you more in wasted vacation time and family disharmony than any cash savings your mental accounting conjures up.

Free night certificates have different value as different parts of a strategy

The key to integrating free night certificates into your travel hacking strategy is to ask yourself, “where do I stay, for how long, and why?”

Over the New Year holiday, my partner and I flew to Hawaii and stayed at the Grand Naniloa Hotel Hilo, where award nights cost 50,000 Honors points. Our initial plan was to spend 7 nights there: 6 nights for the price of 5 thanks to the 5th-night-free benefit, and the seventh night using my Hilton Honors Surpass free night certificate from spending $15,000 on the card in 2021. I don’t have the cash cost in front of me, but I remember it worked out to “roughly” a 1 cent-per-point redemption.

About halfway through our stay, we decided to spend the last night closer to our departure airport, Ellison Onizuka Kona International Airport at Keahole, so I cancelled our 7th night in Hilo and made a reservation with the same certificate at the 65,000-point Hilton Waikoloa Village.

The essential thing I want to highlight is that this did not save me any money! Moving our last night from a 50,000-point property to a 65,000-point property was an absolute wash, and did not increase the value of the certificate in any way. I even got an identical $30 daily food and beverage credit at both properties.

And this is the case more often than you would imagine. Since most experienced travel hackers have lots of booking options all the time, you should not expect any one booking instrument to consistently provide outsized value. Rather, having multiple instruments available allows you to select the one that serves your needs the best in any given situation.

Are Hyatt free nights more valuable than Hilton free nights?

I’m an unapologetic defender of the Hilton Honors program and especially the American Express Surpass card. Earning 6 Honors points per dollar on grocery store manufactured spend, combined with the 5th night free on award redemptions, makes it an outstanding play for my particular travel hacking strategy.

But I’m also not an idiot: transferring Ultimate Rewards points to Hyatt is a fantastic way to get 3 or more cents per point in value from the Ultimate Rewards points I manufacture at office supply stores, and on Freedom cards during this quarter’s 5-point-per-dollar grocery store bonus category.

While World of Hyatt free night certificates can only be redeemed at category 1-4 properties, World of Hyatt also doesn’t offer the 5th-night-free benefit Hilton Honors (and Marriott Bonvoy) does, meaning I’m never “wasting” points by redeeming a Hyatt free night certificate: each free night corresponds to the exact number of points I would have had to spend on that exact night.

A Category 1-4 Hyatt free night certificate can be swapped in at any place in a trip at its exact points value, without jeopardizing the value of the overall redemption. On the other hand, a 4-night Hilton points redemption can always be extended for a fifth night, either at the beginning or end of the reservation, without incurring any additional cost.

Hilton free night certificates are therefore most valuable if you find yourself consistently making short term, expensive stays, or extending award reservations beyond 5 nights. Under those conditions, the sweetest spots will always be one-night stays and adding 6th nights to stays you’ve already redeemed points for at the most valuable properties in the system.

Conclusion: Surpass earning versus Aspire certificates

For folks with multiple players in their household, this circle is easily squared, by combining one partner’s earning ability with the Surpass and the other partner’s annual statement credits and free night certificates with the Aspire. That’s a great way to play the game. But if you’re playing solo or with a reluctant (or bored) partner, the flexibility of the Surpass’s earning ability and the value of the World of Hyatt credit card’s free night certificates far outstrip the one-off gimmicks of the ludicrously expensive Aspire.

Don't sleep on the American Express Hilton Surpass $5,000 threshold bonuses through June 30, 2021

/

For obvious reasons since early last year I’ve been focusing my manufactured spend on cards earning cash back or rewards easily converted to cash or paid travel, and slacking off on the few remaining co-branded credit cards I carry. That allowed it to completely slip my mind that the American Express Hilton Honors Surpass card has been running a fairly compelling deal, for 10,000 bonus Honors points each time you spend $5,000 on the card, up to 100,000 points when you spend $50,000. If all of your Surpass spend is in the card’s 6-points-per-dollar categories, that works out to 8 Honors points per dollar each time your cumulative spend reaches a $5,000 threshold.

The offer ends June 30, 2021, but it’s well worth checking how close you are to the next threshold and seeing if any additional local gas station or grocery store bonuses make it worth closing the gap. Speaking from personal experience, I received a “Thanks for using your Amex Offer” e-mail as soon as a purchase put me over the $5,000 threshold, so you shouldn’t need to wait or worry about whether your purchase has triggered the threshold bonus.

In my experience Hilton Honors points are consistently worth about half a cent each, which makes this a 4% rebate at gas stations and grocery stores, with the potential for outsized return at specific properties and when using the 5th-night-free benefit on award stays.

Finally, if you plan on meeting the $15,000 annual spend threshold to receive a free weekend night certificate (and if you aren’t planning on meeting the spend threshold you shouldn’t be carrying the card and paying its annual fee), then it’s obviously better to meet that spend threshold while the same spend also counts towards the extra bonus point threshold. Free night certificates and bonus points: two great tastes that taste great together.

Two great, one good, and one marginal grocery store earning boost

/

By now you may have heard that starting May 1, 2020, Chase and American Express have enhanced the rate that several of their cards earn miles and points at grocery stores. I was notified by American Express by e-mail on May 1 (subject line “FQF, your Amex Card Member benefits just got better”), but I still haven’t actually received any official communication from Chase.

Here are the four most attractive offers I see, from the no-brainers to the tough call.

12 Hilton Honors points with Surpass and Aspire, plus a lifetime status angle

The American Express Surpass card usually earns 6 Hilton Honors points per dollar spent at grocery stores, and the Aspire card just an unbonused 3 points. Through July, both cards will earn 12 Honors points per dollar spent, with no maximum.

Hilton Honors points are worth about half a cent each, and normally cost about half a cent each when manufactured at grocery stores (since the same spend could be put on a card that earns 3% rewards). During this period, the card earns the equivalent of 6% cash back, which is essentially unheard of for an offer with no limit on the bonused amount.

Additionally, if your travel hacking strategy includes hitting the $15,000 spend threshold for a free weekend night with the Surpass card, or the $60,000 threshold for a second free weekend night with the Aspire, you obviously want to earn as many points as possible along the way, and the next 3 months are going to be a great opportunity to do so. American Express is also extending the expiration date of all certificates earned after May 1 and allowing them to be redeemed any night of the week.

Finally, I want to mention — without putting too much emphasis on it — that there’s a lifetime status angle here as well: all points earned with the Surpass and Aspire cards through December 31, 2020, will be treated as “base points.” Base points are a legacy feature of the Hilton Honors program from when it was a hotel loyalty scheme instead of a credit card loyalty scheme, and are (normally) earned only on your room rate and room charges. If you receive Diamond status by holding the Aspire card or by spending $40,000 on the Surpass, then you have probably never had any reason to think about base points.

The reason you might care about base points now is that Hilton has a “lifetime” elite status program: if you earn 2,000,000 base points, and maintain Diamond status for a total of 10 years (they don’t have to be consecutive), you are awarded “lifetime” Diamond elite status. For those with access to especially plentiful and socially-distanced grocery store spend, this is an opportunity to earn a phenomenal number of base points towards that 2-million-point goal.

If, like me, you believe every deal dies eventually, then you can treat lifetime Diamond status as a kind of long-term insurance policy: American Express can fire you as a customer, grocery stores can refuse to serve you, but Hilton will be stuck honoring your status for years to come.

If you do decide to pursue this angle, contact Hilton and ask them what your current lifetime base point total is and the number of years of Diamond status they’ve credited you with. I don’t know of any way to look up this information online (leave a comment if you do!).

3 and 5 Ultimate Rewards points with Chase Sapphire Preferred and Reserve

Over time every travel hacker should be diligently accumulating as many Chase Freedom cards as possible, which in the second quarter of 2020 are already earning 5 Ultimate Rewards points per dollar spent at grocery stores, on up to $1,500 per card in spend. I personally only have 2, but I know others have many more.

In May and June, 2020, Chase has increased the earning rate on their premium Sapphire Preferred and Reserve cards to 3 and 5 Ultimate Rewards points, respectively, on up to $1,500 per month in grocery store spend. That means after you’ve exhausted your quarterly Freedom bonus categories, you have another $3,000 in bonused grocery store spend to go.

Points earned with the Sapphire Reserve are worth a minimum of 1.5 cents each (when redeemed for paid travel), which makes the spend a no-brainer, but even if you only have the Sapphire Preferred I think the flexibility of Ultimate Rewards points, compared to the relative restrictiveness of Hilton points, suggests you should knock out your capped spend on these cards before going all-in on the Surpass or Aspire cards.

3 World of Hyatt points with Chase Hyatt cards

The two offers above are great, in the sense that my recommendation is: if you have the cards, take advantage of them. The Chase World of Hyatt earning boost is attractive, but doesn’t quite fall into that category: in May and June, 2020, you’ll earn 3 World of Hyatt points per dollar spent at grocery stores, on up to $1,500 per month in grocery store spend.

My perspective here is that if you plan to transfer 9,000 Ultimate Rewards points to Hyatt any time in the near future, these 9,000 World of Hyatt points should be valued the same as Ultimate Rewards points: every point you earn in World of Hyatt is a point you don’t have to transfer from Ultimate Rewards.

But whatever your plans and your level of confidence in those plans, you should almost certainly value World of Hyatt points “somewhat” less than Ultimate Rewards points, which is to say, maximize your Ultimate Rewards earnings first before turning to World of Hyatt.

4 Delta SkyMiles with American Express consumer credit cards

I no longer have an American Express Delta co-branded consumer credit card, having swapped my personal Delta Platinum card out for the business version several years ago (a card I’m planning to cancel, if the increased $250 annual fee ever hits). That means I’m not personally affected by American Express raising the earning rate on consumer cards to 4 Delta SkyMiles per dollar spent at grocery stores through July, 2020.

Let me get the obvious out of the way first: if you value and chase elite status with Delta through the Medallion Qualification Dollar waiver (spending $25,000 per calendar year) and Status Boost (bonus Medallion Qualification Miles when spending $25,000 or $30,000 on the Platinum and Reserve cards, respectively), then you should certainly try to earn as many redeemable miles as possible while doing so! A high, uncapped earning rate at grocery stores makes the next few months a great opportunity to sprint towards those goals.

Likewise, if Delta American Express consumer cards are the only cards you have featuring enhanced earning at grocery stores, they’re the only ones you can use: play the hand you’ve dealt yourself.

But as much as I enjoy the experience of flying on Delta, there’s no escaping the fact that SkyMiles are simply hard to use for high-value redemptions, and I hesitate to value them at more than 1 cent each (their value when used on “Pay with Miles” redemptions). The risk of unredeemed balances, or low-value redemptions, is much higher even than with a program like Hilton, where even break-even redemptions come with a 5th night free, for instance.

That’s what makes this earning boost a “marginal” play: a 4% earning rate in normal circumstances would be great, especially with the potential of accelerated elite status with a good airline. But given the other possibilities available, I would turn to Delta only after meeting Chase’s earning caps and satisfying my need for Hilton points.

Bonus tip: free manufactured spend at Safeway & Co.

I’d been noodling this post for a day or two when I saw Doctor of Credit share a new Safeway deal for $10 off $100 in MasterCard gift cards. The discount reduces the cost of each card below face value, making it a great opportunity to score some early wins this month.

The offer runs through May 16, 2020, but in my experience these offers must be added to your Safeway accounts during the week they launch (after which they remain linked until expiry).

So, get cracking!

How I did on the American Express Hilton Aspire card

/

I wrote previously about using the American Express Hilton Aspire card to cover most of the cost of my honeymoon in Hawaii at the Grand Wailea, A Waldorf Astoria Resort. Since I cancelled the card as planned earlier this year, I thought I’d give a rundown of the total value proposition I ultimately got from it.

Signup bonus

For signing up for the card using my referral link, my partner received 150,000 Hilton Honors points and I received another 20,000 (we also got another 12,000 from meeting the minimum spend requirement for the card, but that’s less than I’d earn putting the spend on my own Hilton Surpass card, so we can set that aside). Hilton now allows you to easily and (relatively) quickly combine points from multiple accounts, so we pooled those points to pay for about 45% of our five-night stay, which I value at $1,900 (half a cent per point).

Total value: $855

Free night certificate

The Hilton Aspire card also comes with a free weekend night certificate on approval. To be honest, we did so much traveling in 2019 that I don’t remember which specific night we redeemed this award for, but since we typically stay in 40,000-point-per-night properties, I’ll assume we redeemed the certificate for “about” 40,000 points.

Total value: $200

Resort credit

If you’re a travel hacking junkie you may have recently read that American Express was issuing $250 resort credits to folks who had not completed eligible resort stays in 2020. There seems to be some confusion over exactly what’s going on, but this wasn’t news to me: after completing our stay in early January, 2019, our $250 resort credit posted automatically a week or two later. Then, in roughly April of 2019, a second $250 credit posted without explanation.

The most obvious explanation to me is that since the card was launched so recently, there were some early coding errors which kept some resort credits from posting automatically. When they discovered the error, American Express then manually applied an additional $250 credit to all accounts that had eligible resort activity, whether or not they had received an automatic credit.

I value the first, correct $250 resort credit at about $125 (we wouldn’t have run up the charges we did if they weren’t going to be reimbursed), and the second, incorrect credit at full value.

Total value: $375

Airline fee credits

If all the above makes it sound like I’m bragging, here’s the part where I prove that’s not true: I blew it on maximizing the card’s airline fee credits. The plan was to receive 3 years’ worth of airline fee credits while paying a single annual fee: in late 2018, in 2019, and in early 2019 before cancelling the card.

2018 went according to plan: we received the card in late 2018, quickly designated American Airlines as our airline, and bought 2 $100 electronic gift cards. The credits posted quickly, but we forfeited the remaining $50 in credits. Fortunately, the cards were used for flights my partner would have otherwise paid cash for, so I assign them the full $200 in value.

The right move in 2019 would have been to immediately buy another $200 in cards. But with our January travel, it just didn’t happen, and then I saw reports that gift cards had stopped triggering credits. Other options (JetBlue pet fees, etc.) still worked, but that would have involved switching the designated airline, learning the new technique, and monitoring the account all over again. So I did…nothing. We used the card for a few American Airlines checked bag fees in 2019, but I believe we received a total of $40 in 2019 credits.

For much the same reason, 2020 was a complete write-off, before we cancelled the card in late January.

Total value: $240

Unlimited Priority Pass membership

This is definitely the benefit that I was most surprised by: it turns out there are a lot of Priority Pass lounges! One issue when you have free lounge passes, whether through elite status, SkyBonus redemptions, or the 10 annual visits through the American Express Hilton Surpass card is that you constantly have to weigh whether you’re going to be laid over in an airport long enough to justify burning one of your lounge passes.

But with an unlimited membership, you can just pop in for some celery sticks or cheese cubes; it’s kind of an awesome feeling. It’s hard to put a value on something you would never pay for, but in a heavy travel year like 2019, an unlimited Priority Pass membership was very conservatively worth $100 to me.

Total value: $100

Diamond status

Worthless, I already have it and can book reservations for my partner when she’s traveling without me.

Total value: $0

Conclusion

The basic math here looks pretty good: I paid a $450 annual fee for what I have tried to conservatively calculate as $1,770 in value. Of course, part of that was a fluke: it would have been $250 less if American Express hadn’t awarded us two resort credits. Likewise, part of that was human error: it would have been $510 more if I had been able to trigger all 3 airline fee credits.

If you’re wondering whether the card is worth getting, the obvious answer is yes, if you can:

  • get it at the end of the year;

  • through a referral;

  • with a plan to use your points for a high-value stay;

  • and a plan to use your weekend night;

  • and a plan to use your resort credit;

  • and a plan to use your airline fee credit.

If you meet all those requirements, you can easily get several thousand dollars in value for a single $450 annual fee.

But this is the first card I had my partner sign up for in what Frequent Miler calls “two-player mode,” and let me tell you, it is absolutely exhausting. We ended up doing ok this time, but I’m not planning to try it again any time soon. You probably already know whether your partner has any interest in travel hacking, and if they don’t, you’re not going to convince them with some free cheese cubes in an Alaska Airlines lounge.