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.

Can Hyatt promo codes override seasonal cancellation policies?

Over the New Year holiday I braved the madness that is flying Southwest Airlines and took a weeklong trip down to Playa Del Carmen, Mexico. While putting the trip together, I noticed something curious as I sifted through the hundreds of hotels lining Quintana Roo’s coast: using a Hyatt promo code seemed to remove the restrictive cancellation policy at the hotel I ultimately chose. Since I didn’t need to cancel the stay, I’m not certain this is replicable or even useful, but I wanted to put the possibility on readers’ radars.

Planning my stay

Sparing the details of how I narrowed down the options, I finally settled on the Thompson Playa Del Carmen Main House, which had a nice combination of being both “in town” as opposed to the isolated beachfront resort hotels and a Hyatt property which at 15,000 points per night was an order of magnitude cheaper than any other hotel I was seriously considering.

The plan was complicated, in a good way, by the fact that I had two stackable American Express Offers, one for $60 off $300 spent at any Thompson in the world, and the second for $100 off $400 spent at any Hyatt property in Latin America. I also had over $1,000 in Hotels.com gift cards I got from Cardcash in an earlier gift card exchange.

This meant I wanted to break my weeklong stay into three pieces: paying for the most expensive nights with Hyatt points and a free night award certificate, paying for the cheapest night with my American Express card in order to trigger $160 off $400 (I used room charges to “top up” my bill to $400, since the cheapest of the 7 nights was only $379.90 after tax), and paying for the remaining nights using my Hotels.com gift card.

Cancellation policies, promo codes, and “Pay Your Way”

Since I was looking for the cheapest night to pay with my American Express card, I started on my irregularly-updated Hotel Promotions page and saw that the promo code “GOJALIN15” was offering up to 15% off paid stays. When I plugged that code into Hyatt’s “Special Offer Code” field, the rate popped right up.

This Thompson property, at least between Christmas and Epiphany (apparently a big deal in Quintana Roo), had a 30-day cancellation policy on award reservations and on all the normal paid rates I found. Inside of that 30-day window, no changes or cancellations were permitted without forfeiting the entire price of the stay.

The GOJALIN15 rate did not have that restriction. Instead, it had the standard 3-day cancellation policy you’ll find on stays if you go searching right now. This wasn’t particularly interesting on its own: I only wanted to book one night with cash, and the 30-day cancellation rate was much cheaper than the GOJALIN15 rate.

What got my attention was that when I clicked through the GOJALIN15 rate, I was offered the ability to “PAY MY WAY,” Hyatt’s booking feature that allows you to combine paid nights and award nights on a single stay. And using that option, the favorable cancellation policy passed through to the PAY MY WAY booking page.

Two observations follow from this, one actionable, the other merely interesting. The interesting point is that some (or all!) coupon codes generate PAY MY WAY-eligible rates; typically only "standard” and “member” rates are eligible for PAY MY WAY, so it’s nice to be able to identify potential future exceptions.

The more practical consideration is that if you plan to redeem points for a stay with unfavorable cancellation conditions, but can use a coupon code that applies more generous terms to the whole stay, then you might be able to “buy” a more flexible cancellation policy by paying for one night of the stay with cash.

Additional considerations

That’s the potential play, as far as it goes, but there are two more wrinkles.

First, it seems that even if you use PAY MY WAY on a coupon code with favorable cancellation terms, if you pay entirely with points or award certificates, then the stay is treated entirely as an award stay and the cancellation terms revert to the standard ones after making the reservation. In other words, you can’t change the cancellation policy on an award reservation merely by clicking the PAY MY WAY button.

I say “after” making the reservation because all through the booking process the more generous coupon code terms were shown. It was only after making my reservation and receiving the confirmation e-mail that I saw the 30-day cancellation policy on my reservation. I think this gives you a pretty airtight case for having the more favorable terms manually applied, as long as you are sure to take plenty of screenshots during the booking process.

Second, because I didn’t ultimately make a “mixed” PAY MY WAY reservation, I don’t know if the same thing would have happened in that case. If so, I still think the case for invoking the “original” more generous terms would be ironclad, but it’s never ideal to get into a position where the score is up to the ref.

Conclusion

I’m aware that what I’m describing is a fairly advanced corner case. You need to have a working coupon code that is set up with favorable cancellation terms (GOJALIN15 expires February 28, 2024), a property with unfavorable cancellation terms during your stay, and a stay with at least one paid night cheap enough to justify paying in cash to swap the cancellation policies — plus the willingness to fight for your points back if you do need to cancel the reservation in the window between the favorable and unfavorable policies.

And if you don’t ultimately cancel the reservation, then you’ll never know whether it “worked” or not!

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.

My successful experience replacing an Incomm Visa prepaid card

There is, by all accounts, an epidemic of fraud striking prepaid debit card retailers across the Western United States. I’ve had the remarkable good fortune of never encountering a tampered prepaid debit card in the wild. So when I needed an Incomm prepaid debit card replaced this month, I jumped at the opportunity to find out how the process works in practice.

Fraud has become a huge problem, but not my problem

If you visit manufactured spend forums you quickly find an ocean of complaints about gift card fraud. Not the “elder abuse” fraud that newspapers love to write about, but genuine larceny: card packaging is opened, the details of the card are swiped, then the card is repackaged so that when an unsuspecting customer activates the card, the balance is quickly drained by the fraudsters. I don’t have a representative sample but it sounds like there are at least some stores on the West Coast where almost every card seems to have been tampered with.

This was not my problem. My problem was that I messed up the magnetic stripe on a card. In other words, user error. Since the balance was still there and I had the card details, I could have liquidated the card online for a tax payment, or to reload my Amazon balance, but instead I called up Incomm to see what the process was to replace the card.

Incomm prepaid card Replacement process

When I realized my error, I first called the number on the back of my Visa prepaid card (833-322-6760). During that call, which according to my phone lasted 17 minutes, I provided the usual card information, as well as the prepaid card’s “serial number,” which is located on the bottom right quadrant of the back of the card, as well as on the card packaging. The phone representative also asked for my name and address. Finally, he asked me to send “copies” of the receipt, the front and back of the prepaid card, as well as my government ID, to “consumed@incomm.com”. I took photos of the documents using my phone on my dining room table.

I first sent the documents on Friday, December 1, 2023, and on Monday, December 4, I received an e-mail from the same address asking for copies of the front of the card and the receipt again. I immediately submitted new pictures.

On Monday, December 11, I received a new card via USPS first class mail. That card had to be activated over the phone, which according to my phone records took 1 minute. I had the option to set a PIN over the phone or use any 4 digits on the new card’s first use, like a normal Incomm prepaid debit card. The card could be and was immediately liquidated through one of my usual in-person channels.

Conclusion

Obviously I wasn’t going to freak out over holding a card for 10 days instead of my usual 90 minutes, but despite my story being anti-climactic there are some obvious lessons you may need a refresher on if you’ve gotten lazy in your manufactured spend routine:

1. Keep your cards, receipts and packaging together. You can use filing cabinets, ziplock bags (guilty) or anything else you like, but if you get a fradulent or defective card you will want to be able to pull everything out at once without having to triple check card numbers and your purchase dates and times. Any unforced errors you make are going to slow down the replacement process.

2. Act quickly. In the case of tampered cards this is more important, but even if you mess up your own card, Incomm isn’t going to replace it until you contact them. Set aside 20 minutes and pick up the phone.

3. Don’t float more than you can afford to. I got stuck with $500 in the ether for 10 days, which didn’t bother me because it was a short period and a reasonable amount. If I’d just bought $10,000 worth of cards and needed them all replaced before my next credit card bill was due, I’d have been sweating a lot harder!

Leaving money on the table: you can use Railcards for Heathrow Express, too

I was playing around doing some research for my recent posts on my trip to the United Kingdom and made a discovery that left me equally pleased (that I get to share it with you) and frustrated (that I didn’t realize it at the time): you can and should use Railcards on the nonstop Heathrow Express service between London’s Paddington Station and Heathrow airport. It’s not exactly “tricky,” but you do need to know what to look out for.

As a brief refresher, Railcards offer savings on all National Rail services in Scotland, England, and Wales. They can be purchased online in advance, are typically valid for between one and three years, and they are virtually never checked by conductors on-board (although supposedly if you get caught without the applicable Railcard you have to pay a “penalty fare” or buy a full-price ticket).

My error was simple, although hopefully readers will find it excusable: Heathrow Rail, despite only operating a single 15-minute route between two stations, still belongs to National Rail, and consequently Railcard savings do apply to these tickets — and the savings can be substantial.

Add your Railcard on the Heathrow Express search results page

Unlike the other National Rail booking engines I looked at, which allow you select your Railcard up front, Heathrow Express’s own booking page only allows you to add a Railcard after searching for tickets. You’ll find the option on the right-hand column of the search results page:

View fullsize

Adding a Two Together Railcard to a £50 one-way itinerary reduced the price by £17 — over half the price of the Railcard itself, meaning the Railcard would pay for itself with a single round-trip ticket for two at that price.

Since Railcards offer a percentage discount, the savings are naturally lower on cheaper tickets booked further in advance, but the point is the same: if you’re traveling by rail in Great Britain, it’s simply irresponsible to do it without a Railcard!

Heathrow Express tickets can be booked through some (but not all) National Rail companies

In my previous post I highlighted how each National Rail booking engine differs in subtle ways, including how accurately they code the precise requirements for each Railcard. The example I used was that Greater Anglia correctly requires a child ticket to be added to a reservation in order to apply the Family & Friends Railcard, while Avanti West Coast would price out the discount with an itinerary consisting solely of adults (violating the requirements for that Railcard).

Once I realized Heathrow Express participated in National Rail, I naturally wondered if tickets could be booked through those other booking engines. The answer, it turns out, is “sometimes.” Greater Anglia and Northern Railway (which seem to share a backend, with only a modestly different branding), will not apply a Family & Friends Railcard to Heathrow Rail booking at all, but will apply a Two Together Railcard (I have a theory for this I’ll explain in a moment). Avanti West Coast will show schedules, but will not allow you to book Heathrow Express tickets at all.

When you can (and can’t) book Family & Friends Railcard tickets on Heathrow Express

It’s going to sound obvious once I say it, but it took me a few minutes to figure out so I hope you’ll indulge me: children under the age of 16 ride free on Heathrow Express (although they seemingly must be accompanied by an adult). That means when the third-party National Rail engines try to validate the conditions for the Family & Friends Railcard on Heathrow Express, it fails the requirement to purchase a children’s ticket!

Fortunately, when booking through Heathrow Express directly, they seem to have identified and fixed this issue. To test this, pick a date and search for 4 adults without a Railcard, 4 adults with a Family & Friends Railcard, and 4 adults plus one child with a Family & Friends Railcard.

In the first two cases the price is the same (because the Railcard’s conditions aren’t met), and in the third case the base price won’t increase (because children ride free) but the conditions of the Railcard are now met and the price drops by the expected 34%.

Conclusion

It would be tiresome to say that this illustrates the importance of interrogating systems by looking under the hood and examining how they really work instead of relying on the nonsense put out by their public-facing organs.

Instead, I’ll simply conclude that entry and exit from the Heathrow Express is automated, and no one is there to check whether you actually have a child, or a Railcard.

View fullsize

Double booking into the same Delta award space

So-called “fare buckets” are a curious feature of the airline ecosystem. For the overwhelming majority of flyers, even frequent travelers, the wide-ranging alphabet of letters, usually shown in parentheses after the class of carriage, is simply irrelevant: most people book on some combination of convenience and price, or have little or no choice if they’re required to fly on tickets booked by their corporate travel office.

So fare buckets don’t matter at all — until they’re the only thing that matters. For example, American Express Delta Platinum companion tickets can only be used to book into the L, U, T, X, and V fare classes. If those fare classes aren’t available for the flight you want, you simply cannot use the companion ticket on that flight.

The other important use of fare buckets is for finding award space on foreign carriers, especially ones that won’t show you availability unless you have sufficient miles in your account. Expert Flyer has a paid service that allows you to see the inventory available in each fare bucket for hundreds of airlines.

It’s important to note that there’s nothing magical about fare buckets. There’s not a “fixed” inventory in each fare bucket that never changes. While I assume most if not all airlines assign inventory to fare buckets algorithmically, the algorithms were still written by humans. An algorithm might say, “if there are 6 or more seats available in First Class, make one available for awards.” If that award seat is then booked, the algorithm might run again and make another single award seat available. One of the Japanese airlines is famous for doing exactly this.

Double booking the last available seat on Delta

As I wrote last month, although I’d finally booked my outbound tickets to England with SkyMiles, the price in Mileage Plus miles had ticked back down to 30,000, and I hoped to cancel the Delta award ticket and rebook using worthless-to-me United miles.

Having successfully completed that switcheroo, and with my Delta award ticket instantly refunded, I turned to booking flights to Wisconsin for a June wedding. There’s a single nonstop flight per day, and I found a ticket available for 26,000 SkyMiles. Almost like the good old days! But when I confirmed the dates with my partner and started booking seats for two, the price had jumped to 28,000 SkyMiles each! A 4,000-mile penalty just for waiting a day to book?

You probably see where this is going: the lower-priced ticket was still available, but there was just one seat available in that fare bucket. When I searched for two tickets on a single search, I was shown the lowest fare bucket with two seats in it.

What to do? Well, as Derek Trotter would say, “he who dares, wins!” So I had my partner fire up her laptop and log into her own Delta account. With both of us searching for a single seat, we both saw the 26,000-mile award available.

We each selected a seat, plugged in our payment information, and gave it a dramatic countdown: 3, 2, 1, click!

And we both got the last 26,000-mile seat.

This is obviously, in one sense, an almost trivial anecdote. We both had 28,000 SkyMiles in our accounts so if either of our purchases had errored out with “this fare is no longer available” whoever lost would have restarted the search and forked over the extra 2,000 SkyMiles.

But upon a moment’s reflection, the opportunities begin to come into view.

First, there are lots of tickets that cost more than 26,000 SkyMiles! For example, a one-way flight to Maui from Los Angeles in First Class costs 66,000 SkyMiles on December 3, 9, and 10. But on December 9, only one seat is available for 66,000 SkyMiles — try to book two, and the price jumps to 85,000 SkyMiles each. More realistically for a travel hacker, that means 66,000 SkyMiles for the first and 85,000 SkyMiles for the second, still a difference of 19,000 SkyMiles.

View fullsize

Second, lots of people travel in groups of more than two passengers. If scalable, for groups of 3 or more the savings start to look astronomical. A family of four might save 57,000 SkyMiles flying in First Class to Hawaii; almost the cost of the first ticket!

I think this is a pretty neat trick, but to bring down the temperature let me state the obvious caveats.

First, to simultaneously book awards you need multiple accounts with sufficient miles in each. For a lot of people in “two-player” mode that’s not a big deal, but if you’re trying to book your kids or parents who don’t play the game, you will quickly struggle to find enough miles in enough separate accounts. If you have friends or colleagues in the travel hacking community that’s a good option, although it will likely involve at least some Zooming and screen-sharing to make sure all the booking details are right for each passenger, plus getting the timing exactly right.

Second, I don’t know how scalable this is: maybe it works for two passengers but not three, maybe for three but not four. Presumably at some point when the cabin is actually full Delta will reject issuing the ticket, so it’s essential to select your seats (different seats!) during the checkout process to make sure there’s room in the cabin for everyone.

Finally, I have no idea if this works on partner or international awards. I was booking nonstop, Delta-operated domestic flights. Would connections break it? Would partner award availability break it? I simply don’t know.

Conclusion

Like everything in the travel hacking game, your mileage will vary. If anything comes from this post, let it be the recommendation to search for individual seats before you search for seats for your whole family, since whether or not this trick works for you, securing one or two low-level seats before paying more for more expensive seats is an easy way of saving miles anyone can enjoy.

While this trick almost won’t certainly work for everyone, on every flight, in every class of service, I wanted to pass it along because it worked for me.

Monitoring prices and rebooking can be one of the highest-return plays

For experienced travel hackers, the game can sometimes feel a bit mechanical: you earn the most valuable points you can at the lowest cost you can, and periodically re-evaluate which points are the most valuable, and how to earn them at the lowest cost. This doesn’t necessarily make it easy (electrical engineering is also “mechanical” — but it’s still hard!), since earning and redemption opportunities are constantly changing, but when you have a framework in mind it makes it relatively simple to calculate which miles and points are worth earning and when.

But travel hacking isn’t just about earning miles and points efficiently; it’s about paying as little as possible for the trips you want to take. When business class awards are available, or hotel rooms during peak demand periods like the Kentucky Derby are bookable with points, that can often mean saving hundreds or thousands of dollars booking awards. But the cheapest way to book a room, flight, or rental car may well be with cash, and monitoring those prices can save you with a few clicks hundreds of dollars that would take hours of manufactured spend to earn.

The bad old days: Southwest, hotels, and car rentals

These are the three buckets I put the best-behaved companies from the pre-pandemic days into.

• Southwest Airlines would allow you to change or refund Rapid Rewards points into your account up until your flight’s departure, so monitoring the price of your flights from the time you book up until your flight time would allow you to shave down the price a few hundred or thousand points at a time. Paid flights were slightly more restrictive, since any price difference would be deposited in an eventually-expiring travel bank account that could only be used by the original ticketed passenger, which created some urgency to plug more money into the Southwest Airlines ecosystem.

• Hotels have long had flexible rates which require no upfront payment and cancellation policies between 1 and 5 days before arrival. This creates an obvious incentive to immediately book every hotel you’re even considering staying at. If prices fall, rebook at the lower price, and if prices rise, cancel the more expensive reservations and keep the cheapest. If you have high-level status in multiple hotel loyalty programs, this also allows you to monitor for upgrades as you approach your travel date: at the same price point, you might prefer a Globalist suite upgrade at the Park Hyatt Vienna over a standard room at the Hilton Vienna Park, but access to the Hilton executive lounge over a standard room at the Park Hyatt. Booking both in advance lets you pick the one you end up wanting more. And no, I’m not comparing the two hotels in terms of price or quality, but if a family of 4 is deciding whether to book one room at the Park Hyatt (hoping for a suite upgrade that accommodates them all) or two rooms at the Hilton, the prices can sometimes end up fairly close.

• Rental cars are even better, since they don’t even require billing information to book most rates, and Autoslash exists to both find the cheapest rates and monitor existing reservations to alert you when rates fall and you should rebook. Purely as a courtesy to the overworked rental car company staff I usually cancel my prior reservations when I rebook, but it’s not strictly necessary.

Other than those obvious examples, before the pandemic opportunities to rebook and save money were fairly limited. Mid-level airline elite status usually allowed you to redeposit awards tickets for a full refund, so if flights were expensive enough to meet whatever your threshold is to book using airline miles (and everyone’s threshold is different!), but subsequently dropped below that threshold, you could cancel your award tickets and rebook using cash.

Likewise, schedule changes that move your departure or arrival by more than an hour could be refunded to the original form of payment, so if you booked your flights far enough in advance you had a good chance of having an opportunity to request a penalty-free refund, as I did in May, 2020.

The opportunity set has greatly expanded

All of the tools I described above still exist, but the new “permanent” (where I have I heard that before?) policies adopted by US airlines have increased the number of opportunities to save money by booking early and continuing to monitor prices afterwards. However, while they sound similar and were announced around the same time frame, to take advantage of them you need to understand the key differences between airline policies.

1. Which fares are eligible? United, American, and Delta exempt Basic Economy fares from their no-change-fee policy, as Alaska does with its Saver fares and JetBlue with its Blue Basic fares. If you’re trying to play fares against each other, be sure not to book a fare that’s non-changeable and non-refundable! Note that these non-changeable fares are still eligible for refund under Department of Transportation rules if there’s a significant schedule change.

2. What happens when you cancel? For paid fares, unless you’re eligible for a refund due to a schedule change, or booked into a refundable fare class, you’ll usually be given a “flight credit” (United), “travel credit” (American, JetBlue), “eCredit” (Delta) or “Wallet” (Alaska). These funds expire, so it’s important to keep a close eye on them.

3. Who can use the ticket value? I believe (but correct me in the comments if I’m wrong) Alaska is the only airline that allows you to deposit “Wallet” funds into your own Wallet or, by requesting a voucher be e-mailed to you, any other Mileage Plan account. This is notably a way to share Companion Fares without sharing the cardholder’s credit card information, since Companion Fares can be paid for in full using Wallet funds, even if the person booking the ticket is not an Alaska Airlines credit cardholder (if Wallet funds don’t cover the full cost, any residual must be paid for with an Alaska Airlines credit card).

4. What are your expected flight needs? This is a highly individualized calculation. For example, my partner and I fly to the Pacific Northwest on Alaska and the Midwest on American and Delta at least once or twice per year, so any travel credit, eCredit, or Wallet funds I receive by cancelling a flight on those airlines is absolutely certain to be used. Conversely, it appears I have not flown on United since October, 2017 (although I may be breaking that streak this summer!), so I would never book a paid United flight as a “backup” since there’s virtually no chance I would ever use the flight credit.

Conclusion: use flexibility to your advantage, but don’t get too clever

Especially with respect to hotels and rental cars, making multiple reservations as far in advance as possible and then monitoring prices for opportunities to rebook has always made sense. But the added flexibility of pandemic airline policies makes this is a meaningful way to save money on all the main components of travel planning.

Still, as the voice of caution, I have to remind my beloved readers not to bite off more than they can chew. While rental cars don’t typically charge no-show fees, airlines and hotels absolutely do, so if you don’t trust yourself to keep a close eye on all your reservations as your travel date approaches, don’t bother, since a single no-show penalty is going to wipe out any savings you may have been counting on in advance.

Combining Ultimate Rewards points, transferring Hyatt points, and Hyatt booking follies

Today’s post is a bit of an information dump, but it combines a number of issues I’ve been working through to get my trips booked for this spring and summer and that I haven’t seen covered clearly anywhere else online.

Combining Chase Ultimate Rewards points

For those of us with multiple Ultimate Rewards-earning credit cards, combining points between our own accounts is routine: earn 5 points per dollar in a quarterly bonus category, like this quarter’s grocery store bonus category on the Chase Freedom, then transfer those points to a card that allows for transfer to Chase’s travel partners or higher-value Ultimate Rewards travel portal redemptions.

But what about combining points between new household members or employees? It’s possible, but there are a few important things you need to know.

First, combining points is always done from the “sender’s” side. There’s no way to “request” points, or “pool” points held in multiple card accounts. Each sender Ultimate Rewards account has to initiate a non-reversible transfer to a “receiver” account.

Second, adding a new receiver account can no longer be done online; you’ll need to call the number on the back of your Ultimate Rewards-earning credit card and provide the recipient’s credit card number. Since my flexible Ultimate Rewards card is a business card, in my case I chose to have my sender add one of my non-flexible Freedom cards as the receiver card. I was then able to instantly convert those non-flexible points into flexible Ultimate Rewards in my legacy Ink Plus account.

Finally, senders are only allowed to add “one member of your household or owner of the company, as applicable” as recipients.

There’s a lot to unpack here. Most importantly, it means that you should not set up you and your partner as mutual recipients, since this would use up the recipient slots of each household member. Instead, it would be ideal to keep the receiver’s recipient slot open to add an additional recipient. In this way, points could be moved and consolidated in larger and larger numbers across multiple Ultimate Rewards accounts before being transferred to a single travel partner account.

Additionally, it suggests the possible value of keeping your flexible Ultimate Rewards accounts attached to separate Chase online accounts. The logic here is that while you want to preserve the flexibility of your own Ultimate Rewards points, you also may want to have more than one household transfer target, so if you have, for example, a Chase Sapphire Preferred or Reserve and a flexible Chase Ink product, you could attach separate recipient targets to each online account.

I have not experimented with this extensively, but wanted to alert readers to some interesting possibilities they can explore further for themselves.

Chase World of Hyatt point transfers are no longer instant

Transfers from Ultimate Rewards to World of Hyatt used to be immediate: log out and log back in and your balance was already updated. Regrettably, no more. I submitted a transfer on the evening of Thursday, February 17, and my points didn’t land in my World of Hyatt account until the morning of Saturday, February 19. It wasn’t the end of the world, but since I wasn’t aware of the new delay, it certainly kept me awake for a couple nights frantically refreshing my Hyatt account.

On the one hand, if you’re planning a trip weeks or months in advance, you have nothing to worry about; your points will probably arrive in plenty of time. On the other hand, if you’re frantically booking a last minute stay, don’t count on immediate Chase transfers for your Hyatt redemptions.

Member-to-member Hyatt points transfer timing

World of Hyatt, like Hilton Honors, allows members to transfer points between each other for free using the Point combining request form. For an upcoming stay, I submitted the form on Saturday, February 19. I received an immediate automated response, and the transfer was finally completed on the following Friday, February 25.

So if you’re planning to combine points in order to book an award, give yourself plenty of time to allow the transfer to go through.

Hyatt award booking chaos

Of course, combining Ultimate Rewards points, transferring them to World of Hyatt, then combining them in another member’s account aren’t done for fun. They’re done to book Hyatt awards, and this is where I ran into the truly stupefying and genuinely serious consequences of Hyatt’s new award charts and booking system.

It’s worth reminding readers of two facts:

1. World of Hyatt properties are still defined by category;

2. Within each category, award nights are charged at either an “off-peak,” “standard,” or “peak” rate.

This has the key corollary that a Category 1-4 free night certificate is worth 50% more on a Category 4 “peak” day than on a Category 4 “off-peak” day, saving 18,000 points instead of 12,000 points.

Now let’s get to the chaos. When booking a multi-night stay, World of Hyatt will only show you the rate available on the first night of the stay, even if the property moves from “standard” to “peak” during the stay.

To find out the nightly award rate, you have to view the property’s “Points Calendar.” Here’s the calendar for the Hyatt Place New York City / Times Square:

View fullsize

In this case, trying to search for a 2-night award stay will show that standard nights are available “from” 17,000 points per night.

View fullsize

But unless you have enough points in your World of Hyatt account to book the reservation, it will not show you the final price of 37,000 World of Hyatt points, which might lead you to transfer 34,000 Ultimate Rewards points instead, and then find out to your horror you’d run out of time to book the award.

View fullsize

Finally, and most egregiously, in order for award availability to appear online, the exact same room type has to be available for every night of your stay.

Putting it all together

You’ve made it this far so I don’t want to make you do any more homework and I’ll put the pieces together for you. When planning a Hyatt award and transferring Ultimate Rewards points, take the following steps in this order:

1. Find the property you want to stay at and click the “Points Calendar” button

View fullsize

This will allow you to see the award rate for every night of your planned stay. Add those rates together and you will get the total cost of your stay.

2. Check standard award availability for your entire stay. Plug your hotel and dates into Hyatt and it will show you whether there is standard award availability in a single room type for your entire stay (although it will miscalculate the total cost of your stay if award rates vary by night). If so: congratulations! Transfer the required number of Ultimate Rewards points you calculated in Step 1 to Hyatt and hope the space is still available when the transfer is completed.

3. If standard award availability isn’t available for your entire stay, don’t despair. It may be the available room types simply shift during your stay. Now comes the boring part: check each day of your stay individually for standard award availability, and book “clusters” of nights in each room type. For example, standard award availability might be available in a two queen room for 2 nights, a one king room for 2 nights, and an accessible king room for 1 night. Book them each separately.

4. If necessary, call the hotel and ask to stay in the same room for your entire stay across all your reservations. They might not accommodate you, depending on the circumstances, but moving your crap around a single hotel is a lot easier than moving between hotels, which I’m not too proud to confess I’ve done more than once over the years.

On the Justice of Squeaking Wheels: made whole by filling out an automated survey

Anybody who knows me knows, the only thing I hate more than driving is renting cars. It combines all the worst features of the travel experience: you’re charged a constantly fluctuating price (thanks Autoslash!), with ambiguous requirements (do I qualify for a USAA rate as a member, or is that for employees of USAA?), face unlimited liability for anything that happens on the road in an unfamiliar car, and are upsold at every single step of the transaction. It’s a terrible experience for customers, and I imagine an even more terrible experience for the cashiers who have to deal with a stream of furious customers all day every day.

I’ve tried to eliminate as many of these variables as possible over the years. In 2020, I bought non-owner car insurance from USAA for the first time to cover personal liability while driving a rented car. I naturally pay for my rentals with a credit card that includes insurance for the value of the car itself. And I fuel rental cars before returning them to avoid paying their extortionate fuel charges.

But that leaves one pain point: picking up and returning the car itself. Different rental car companies have tried to address this in a variety of ways: elite check-in desks, “choose your own car” gimmicks (National’s “Emerald Aisle,” Budget’s “Fastbreak,” etc). But I’m not actually that annoyed by waiting in line for a rental car. After all, I just waited in line to check my bags, waited in line to board, waited to get off the plane, waited to collect my checked bags, and waited to take a shuttle to the rental car lot. What do I care if I have to wait another 15 minutes to get the car keys?

No, what drives me nuts is how car rentals are so completely unlike any other element of the travel experience, and no lesson you learn anywhere else can be applied to understanding how rental car companies operate:

• an airline schedules a set of flights, some of which take off late and some of which land early. But one flight landing early (besides giving the pilots and flight attendants a little more time to use the bathroom or get a bite to eat) doesn’t make any other flight take off any earlier, and in fact realistically is more likely to clutter up the taxiways and gates.

• a hotel sets a check-in time and check-out time, which they’re typically willing to be flexible about if your room is ready early or you want to keep it a bit longer, assuming there isn’t another guest about to check in.

Car rental companies operate more like private jet services or love hotels. You can show up early, or check-out late, but you’re definitely paying for every minute you have possession of the car.

Getting charged for showing up early

Over the New Years holiday my partner and I flew to Hawaii where we met up with my mother-in-law (yes, I know this is also the plot of the Netflix limited series “White Lotus”). Our flight was scheduled to land around 1 pm and hers around 3, so I booked a weekly car rental at the only-slightly-off-airport Budget Car Rental site, with a pickup and dropoff both scheduled for 1 pm on Wednesdays, a week apart.

Then our flight got in early — very early. We were scheduled to arrive at 12:50 pm but were already at the Budget office at 11:30 am. We didn’t have anything else to do (the Kona airport is kind of in the middle of nowhere) so we decided to pick up the car and drive into town to explore for a couple hours.

I popped in to see if the car was ready yet, and after a few minutes in line, was asked “when are you returning the car?” I naturally replied, “I have it reserved until 1 pm,” and the cashier responded, “but you’re picking it up early. That means you need to return it early.”

And she was right!

After stressing about it for 7 full days, I managed to get the car back at 12:20 pm the following Wednesday — 40 minutes before the end of my original reservation, but 50 minutes after my 7-day “week” expired.

They stuck me with a fee that was, for one hour, a full 14% of the cost of the week-long rental.

But then they gave me my money back

On January 5, in what must have been just a few minutes after returning the car to the lot in Kona, I received one of those thousands of automated e-mails asking for feedback on my experience renting from Budget. Like any normal person, I never complete these surveys unless something is obviously amiss or an employee goes above and beyond. But since I was still steaming about this stupid “late” return charge, I went ahead and filled out the survey.

Shockingly, 5 days later, I received another message from the same generic survey provider:

Thank you for taking the time to tell us about your recent experience. We appreciate your feedback since it helps us improve our service and your rental experience.

I deeply regret that we were not able to meet your expectations regarding your previous rental. We will send in an adjustment for the extra hour charge. Please allow 7-14 business days for this to reflect on your end.

I wasn’t exactly convinced this would actually happen (the e-mail address’s domain was “app.medallia.com”), but was willing to watchfully wait. Then, as much to my surprise as yours, on January 26, 21 full days after I returned the car, Budget refunded me almost $100, which seems to actually be slightly more than they charged me for the extra hour, even accounting for taxes and fees.

Conclusion

I know this was a long way to go to complain about how terrible rental car companies are, which is why I’m trying to make a slightly different point: sometimes, somebody actually reads those surveys you submit after flying, staying at a hotel, or renting a car, and if they do, then making as specific, particularized complaints (or praise!) as possible seems likeliest to get the most favorable results.

Quick hit: easily adding all available Amex Offers (if you're an idiot, like me)

Yesterday I was excited to see Danny the Deal Guru’s post about a simple technique to quickly add all your available Amex Offers to your cards with a simple click. It worked for him and some other people who commented, but it didn’t work for me. Since I’m computer illiterate, I assumed it had something to do with my ad blocker or privacy settings, or the fact that I use Apple hardware, or any one of a hundred other things.

This morning I caught my second wind and decided to try again. Upon closer inspection of the error message, I saw a string that looked familiar: “U+201C.” That looks like a unicode character. Some light googling revealed that it was, indeed, a unicode character, specifically the “left double quotation mark” character, like the ones on the left side of those quotes.

Turns out, JavaScript doesn’t like left (or right) double quotation marks. JavaScript likes upright double quotation marks, and after replacing the former with the later, the code sailed through.

It turns out, in the original Reddit thread, user blamsonyo had used upright quotation marks, and if I had bothered to click through and copy the original code I wouldn’t have had a problem. Lesson reinforced: when possible, go to the original source! Save the games of telephone for summer camp.