Grocery store spend and the possibilities of loyalty-agnostic travel

I'm a big proponent of the US Bank Flexperks Travel Rewards card, since I think it provides the straightest path for most people to pay as little as possible for their airline tickets. With the recent return of PIN-enabled prepaid debit cards to many grocery stores, that view has been confirmed and even strengthened.

But it's also true that another favorite card of mine, the American Express Hilton HHonors Surpass card, also earns bonus points at grocery stores. And of course unbonused spend can earn between 2% and 2.625% cash back, and at lower cost than grocery store manufactured spend.

So I thought it would be useful to revisit some break-even points, or what I call imputed redemption values, for spend on a variety of cards, to help readers think through the best way to book their flights and hotel stays.

Three opportunities, three costs

The simplest way of approaching the tradeoffs between bonused grocery store spend and unbonused spend is to look at the cost per point. Using only the most widely available methods of manufacturing spend, you'd arrive at these simple calculations:

  • US Bank Flexperks Travel Rewards, 2 Flexpoints per dollar spent at grocery stores: 0.62 cents per Flexpoint;
  • Hilton HHonors Surpass American Express, 6 HHonors points per dollar spent at grocery stores: 0.21 cents per HHonors point;
  • 2% cash back credit card at unbonused merchants: 0.43 cents per cent in cash back.

That final line allows us to have an anchor for the kind of value we should expect to get from Flexpoints and HHonors points that would make them competitive with unbonused cash back. For example, if you redeem Flexpoints for cash back you'll never come out ahead compared to a 2% cash back card, since you're paying 44% more for each Flexpoint, which are, like pennies, worth just a penny each.

The flip side of that calculus is that all Flexpoint airfare redemptions above 1.44 cents each are cheaper than paying cash for the same trip. For example, a $288 plane ticket would cost 20,000 Flexpoints, and $124 in out-of-pocket grocery store fees, while the same $288 plane ticket paid for with cash earned on unbonused spend with a 2% cash back credit card would cost $123 in fees. That means for all airline tickets between $289 and $399 (or any other price point that falls between a multiple of 10,000, 0.0144, and 0.2), the Flexpoint redemption is cheaper than the cash ticket.

Now let's do the same math with Hilton HHonors points earned at grocery stores with a Surpass card. Due to the difference in total price per point, compared to a 2% cash back card, Hilton HHonors points have to be redeemed not at 0.33 cents each, but rather at 0.49 cents each. For example, a 5,000 HHonors-point stay would cost $10.50 in fees, while $10.50 in fees would earn $24.42 in cash back — 0.49 cents per point. This is a purely mechanical calculation: a 95,000-point HHonors redemption would cost $199.50 in fees, while $199.50 in fees would earn $463.95 in cash back — 0.49 cents per point. That produces the simple maxim that stays which offer more than 0.49 cents per HHonors point are cheaper if paid for with HHonors points than with cash.

Flexpoints can also be used for hotel stays

There's one additional wrinkle worth mentioning here: Flexpoints can provide value on hotel stays that are too cheap for HHonors redemptions. I'll be the first to admit that this doesn't happen very often, but it's something to keep an eye out for: when Flexperks redemptions fall in the 1.44 to 1.5 cent per point band on hotel redemptions, they still entail a lower out-of-pocket cost than manufacturing the needed cash with unbonused spend on a 2% cash back card.

For example, a $144 stay (including taxes) would cost 10,000 Flexpoints ($62 in fees), and paying in cash earned with a 2% cash back card would require $62 in fees. Of course, it might be cheaper yet depending on the HHonors point rate available, if any.

This makes Flexpoints one of my favorite currencies to earn speculatively: if good flight opportunities present themselves, they can be redeemed for valuable flights; if middling hotel opportunities present themselves, they can be redeemed for middling hotels; and if no opportunities present themselves, they can be redeemed for cash.

While it's easy to posit a general principle that Flexpoints should be spent where they're most valuable — on paid airline redemptions — it's also true that they're more valuable redeemed for hotel stays than for cash, so if you find yourself in the situation of having to choose between spending precious cash or spending down a constantly growing balance of Flexpoints, you'll probably thank yourself later if you save the cash today.

Wyndham Rewards is a pretty good program. But is it necessary?

The "news hook" for this post is the launch of a new landing page for Barclaycard's Wyndham Rewards Visa cards, raising the annual fee on the Visa Signature card from $69 to $75 and cutting the earning rate on purchases to 1 Wyndham Rewards point per dollar except on gas, utilities, and grocery purchases.

Meanwhile, the landing page for the old offer is still live, showing a $69 annual fee, a signup bonus of 45,000 Wyndham Rewards points after spending $1,000, and an earning rate of 2 Wyndham Rewards points everywhere.

Barclaycard has, in the past, been pretty good about preserving benefits for existing customers after a product has undergone significant changes. For example, Barclaycard US Airways customers who signed up under a 10,000-anniversary-mile offer continue to receive those anniversary miles, to the best of my knowledge (I cancelled my anniversary-mile card when I wasn't offered a retention bonus).

That means that in all likelihood there's a narrow and narrowing window to sign up for the current, superior offer, and retain its superior earning rate on otherwise-unbonused spend.

So, should you?

Wyndham Rewards is a pretty good program

I'm on record from all the way back in April, 2015, saying that the new fixed-rate Wyndham Rewards program would be great.

I think that prediction has been borne out by events. Wyndham hasn't gone to aggressive lengths to exclude properties or dates from their 15,000-point fixed-rate awards, and the program doesn't seem to have experienced mass defections from properties unwilling to accept however much Wyndham is compensating them for these fixed-rate awards.

Compared with a 2% cash back card, the imputed redemption value of Wyndham Rewards award nights is $150, since the same $7,500 in unbonused spend can earn you either $150 in cash back (which can be spent on paid hotel stays or anything else) or a free night at any Wyndham Rewards property in the world.

Comparing Wyndham Rewards

Whether Wyndham Rewards makes sense for your own travel hacking strategy depends on both your goals and your alternatives. First, here's a quick glance at the imputed redemption value of Wyndham Rewards award nights compared to the imputed redemption value of award nights with Hilton HHonors (earned at 6 points per dollar), Hyatt Gold Passport (purchased for one cent each in Ultimate Rewards transfers), Starwood Preferred Guest (earned at 1 point per dollar), and Club Carlson (earned at 5 points per dollar):

What you see, as you'd expect, is that fixed-rate Wyndham Rewards stays cost less in foregone manufactured spend than higher-tier properties with the other chains, but cost more in foregone cash back than lower-tier properties with the other chains.

In other words, you can save money staying at the Wyndham Grand Chicago Riverfront instead of the Waldorf Astoria Chicago (Hilton), staying at the Wyndham Midtown 45 instead of the Park Hyatt New York (Hyatt), the Wyndham Garden Manhattan Chelsea West instead of the Gramercy Park Hotel (Starwood), and at the Days Inn London Hyde Park instead of the Radisson Blu Edwardian, Sussex (Club Carlson).

Meanwhile, the other programs shown above offer award tiers with imputed redemption values below $150 (highlighted in red) and, of course, some hotel nights simply cost less than $150 in cash, especially when combined with cashback portals and online travel agency rewards programs.

That means that by combining Wyndham Rewards with one or two other programs, as well as a cash back card, you could theoretically limit your downside (since the most you'd ever pay is $150 in foregone cash back) while having almost unlimited upside as you take advantage of cheaper room rates and lower-tier properties in other loyalty programs.

But is Wyndham Rewards necessary to a travel hacker?

All the foregoing is meant to say that I commend Wyndham Rewards for trying something new and fun.

The trouble is that it's difficult to come up with an actual travel hacking strategy that incorporates Wyndham Rewards.

Let me put it this way: I'm totally indifferent between road trips with your kids and luxury vacations with your romantic partner. You do you!

But if you're taking road trips with your kids, you should be able to take advantage of the dirt cheap low-category properties with the chains highlighted in red above.

And if you're taking luxury vacations with your partners, the difference in imputed redemption value between the most luxurious Hilton and Hyatt properties and the most luxurious Wyndham properties just isn't that big.

Conclusion: the right way to use Wyndham Rewards is to plan Wyndham Rewards trips

The $69 Wyndham Rewards Visa credit card has a good signup bonus (3 nights at any Wyndham Rewards property in the world) and a good earning rate ($150 per night in foregone cash back for a night at any Wyndham Rewards property in the world).

But if you have a developed travel hacking strategy already involving Hilton, Hyatt, and Starwood or Club Carlson points, you're unlikely to accidentally get a good value from a Wyndham Rewards credit card.

That means the right way to pay as little as possible for the trips you want to take is to proactively look for the Wyndham Rewards properties that are going to get you outsized value, earn the points necessary for your stays, and then redeem them. Speculatively signing up for Wyndham Rewards credit cards and speculatively manufacturing spend is unlikely to yield savings any greater than those you can earn much more consistently with other programs.

In which the new Walmart POS software briefly messes with my game

I don't keep track, but if I had to guess, I'd say I swipe cards through point-of-sale terminals around 50-100 times at Walmart store locations every month. That doesn't make me an expert, by any means, but it does give me a lot of individual datapoints to work with. And last week, I found that my swipes were being rejected more or less consistently.

At the same time, I noticed that the point-of-sale software on the customer-facing terminal had been slightly updated, with a different arrangement of the icons and slightly different background color.

I have no idea if the two were connected, but I figured out the solution my problem, so if any readers are running into the same roadblock, I hope this helps.

My old swipe: slow and deliberate

When you deal with a lot of different point-of-sale systems, you develop a certain habit of swiping cards. Mine was not too fast, not too slow, but just the right speed while making sure the card was flush against the swiping surface.

But last week, my old swipe started failing over and over again, with a customer-facing message of "card read error."

My new swipe: greased lighting

After running into this problem at multiple store locations running the new point-of-sale software, I tried something completely different: I tried swiping a card through as fast as I could. Uncomfortably fast. Dangerously fast.

And it worked. The same machines that were rejected my careful, deliberate swipes started eating up my lightning-fast swipes.


If you haven't run into this "card read error" problem, then you're in luck: you don't have to change anything. But if you have been experiencing this problem and been frustrated, or even scared that you got a batch of bad cards or ran into a sudden change in policy, hopefully this will set your mind at ease and get you up and running again.

Why I manufacture cash

I was chatting with a blog subscriber the other day who expressed surprise when I told him I was manufacturing spend on a 2% cash back card, rather than a mile- or point-earning credit card.

That exchange made me think I should present my argument for why travel hackers as a general rule either should manufacture cash back, or at least should be willing to manufacture cash back. The simple reason is that doing so keeps you honest.

Bonused spend is capped or limited

There are cards that are straightforwardly superior to cashback-earning credit cards, or may be under certain circumstances. For example, if you have access to grocery store manufactured spend, a US Bank Flexperks Travel Rewards card (2x), Hilton HHonors Surpass American Express (6x), Amex EveryDay Preferred (4.5x), or American Express Premier Rewards Gold (2x) card are either clearly or convincingly worth more than manufacturing spend on a simple 2% cash back card.

But manufacturing spend at grocery stores faces all sorts of obstacles, from daily limits on purchases to annual caps on bonused spend. Whether the limits you face are imposed by the stores you visit, the cards you carry, or the inconvenience of visiting bonused retailers, they leave you with a simple choice: restrict your manufactured spend to bonused retailers, or manufacture unbonused spend as well?

Unbonused spend should present hard choices between rewards currencies

I loosely consider the 3 most lucrative travel rewards-earning credit cards for unbonused spend to be:

  • Chase Freedom Unlimited. 1.5 Ultimate Rewards points per dollar spent, flexible if transferred to Chase Sapphire Preferred, Ink Plus, or Sapphire Reserve.
  • Amex EveryDay Preferred. 1.5 flexible Membership Rewards points per dollar spent.
  • Starwood Preferred Guest American Express. 1 Starpoint (1.25 airline miles) per dollar spent.

You would need to get 1.33 cents per Ultimate Rewards or Membership Rewards point in value, or 2 cents per Starpoint (1.6 cents per mile when transferred in 20,000-Starpoint increments), to break even compared to a 2% cashback-earning credit card.

Those thresholds are, on the one hand, trivially easy to meet. Getting 1.33 cents per Hyatt Gold Passport point or United Mileage Plus mile is considered a poor redemption of those currencies since it's so easy to get so much more value from them. Even 1.6 cents per transferred Starpoint is relatively easy to achieve on long-haul flights, especially in premium cabins.

On the other hand, those thresholds are only easy to meet when the points are redeemed for travel. When you earn rewards currencies other than cash because of their possible future value, then fail to redeem them, you are ultimately paying a premium for an inferior product.

Consider two travel hackers, each of whom manufactures $10,000 in unbonused spend each month for a year. The first uses a Chase Freedom Unlimited and earns 15,000 Ultimate Rewards points. The second uses a 2% cash back card, and earns $200 in cash back. Both pay the same purchase and liquidation fees. At the end of the year (in the 13th month), the first travel hacker will have 180,000 Ultimate Rewards points, and the second will have $2,400 in cash.

To make up the $600 in cash value, the first could redeem all 180,000 Ultimate Rewards points for 1.33 cents each — an easy lift, as described above.

But what if the first travel hacker redeems just 120,000 of their Ultimate Rewards points for travel, leaving them with a 60,000-point balance? Now she needs to get 1.5 cents per Ultimate Rewards point — still not too difficult, on long-haul United award redemptions or at mid-tier Hyatt properties. After all, Hotel Hustle pegs the median Hyatt Gold Passport point value at 1.862 cents.

Finally, consider if the first travel hacker redeems just 60,000 of their 180,000 Ultimate Rewards point haul for the year. They still have $1,200 in cash value, but that means they'll need to get 2 cents per Ultimate Rewards point to break even with the 2%-cashback travel hacker. Now we've found ourselves, rather than being safely below the median Hyatt point value, 7.5% above it. Rather than merely looking for a decent United redemption, we need an excellent one. All to break even with the person who's been taking their rewards to the bank in the form of cash each and every month!

This has nothing to with devaluations

When I point out the folly of hoarding miles and points, people often think I'm talking about the risk of devaluations. But as I wrote in the linked post, 

"For all the wailing and gnashing of teeth whenever an airline or hotel devalues its miles, that process is relatively gradual and relatively predictable.

After all these years, despite everything that's happened in the airline loyalty industry, the 25,000 domestic saver award ticket still exists."

If there is never another devaluation of any loyalty program under the sun; if every loyalty program opened up every seat, in every cabin, on every flight, for award redemptions, unredeemed points will still be worth nothing, while cashback earned can still be put to work paying for the expense of your choice, from groceries to retirement savings.


Past performance is no guarantee of future results. But it's as good a place as any to start!

When deciding between a cashback-earning credit card or putting the same unbonused spend on a travel rewards-earning credit card, take a look at your existing balances and your account history. Do you redeem the points you earn? Are you consistently getting the value you need to break even compared to a 2% or higher cashback card, taking into account the orphaned points you don't redeem?

If so, terrific — keep doing what you're doing. If not, then it's time to ask further questions about your manufactured spend strategy.

And those questions are how cashback credit cards keep travel hackers honest.

Thinking about Hyatt Diamond requalification

I took advantage of the Hyatt Diamond status match late last year and have been enjoying my suite upgrades, free breakfast, lounge access, and check-in amenities for over half a year now. With just under 5 months left to requalify, I've been giving some thought to whether and how to do so.

Whether to requalify

I have a high baseline level of skepticism that elite status benefits are worth paying anything for.

For example, I manufacture elite status on Delta with a Business Platinum American Express card, but I also earn 1.4 SkyMiles per dollar spent when I meet the $25,000 and $50,000 annual spend thresholds. Since SkyMiles are the airline currency I use most frequently and to greatest effect, I manufacture spend on the card with the SkyMiles in mind, and appreciate the bonus Medallion Qualifying Miles merely as an ancillary benefit.

Requalifying for Hyatt Diamond status has a related logic: since Hyatt Gold Passport points are some of the most useful points, thanks to how easy they are to earn through Ultimate Rewards transfers, qualifying for Diamond status means getting more value from points I'll redeem anyway. I'm not going to try to quantify that additional value — I'm pointing out the difference between elite status in programs you already use aggressively and elite status in programs you use infrequently or never, like the periodic elite status challenges you see offered by airlines.

How to requalify

Hyatt Diamond status requires 25 paid or Points + Cash stays, or 50 paid or Points + Cash nights during the calendar year. There are three important things to consider when deciding on a path to requalification: the Chase Hyatt credit card; requalifying on stays; and requalifying on nights.

Chase Hyatt Credit Card elite-qualifying stays and nights

The Chase Hyatt credit card gives 2 elite-qualifying stays and 5 elite-qualifying nights after spending $20,000, and 3 additional elite-qualifying stays and 5 additional elite-qualifying nights after spending a total of $40,000 during the calendar year. If you spend $40,000 on the card, and value Hyatt Gold Passport points at the 1 cent each you can buy them for with a transfer from Ultimate Rewards, you'll pay $400 in foregone cash back for 5 stays and 10 nights, compared to a 2% cashback card.

Whether that's cheap or expensive depends both on your alternatives and on whether you decide to requalify on stays or nights.

Requalifying on stays

Qualifying with elite-qualifying stays is the option that gets the most attention from travel hackers for three reasons.

First, it's much cheaper to mattress run for additional stays than additional nights. If you are requalifying on stays and get 80% of the way to Diamond status (20 stays), you only need to book 5 more one-night stays. If you are requalifying on nights and get 80% of the way to Diamond status (40 nights), you need to book twice as many more nights, at double the cost.

Second, requalifying on stays allows you to mix and match your booking options. Since Hyatt guarantees standard room award availability, you can book just one night of each stay with cash or Points + Cash, and the remaining nights using only points. This is, in fact, the strategy I've been following this year.

Finally, requalifying on stays allows you to rapidly earn stay credits on longer trips by moving between multiple Hyatt properties in the same city. For example, the Andaz 5th Avenue is just 2 street blocks from the Grand Hyatt New York. It would get old fast, but if you travel alone or have understanding travel companions, on a 5-night stay in New York City you could earn 5 stay credits alternating between the two hotels each night.

As indicated above, if you choose to requalify on stays, then the Chase Hyatt credit card will earn you 5 stays for $400, or $80 each. Is that cheap or expensive? In general, it is cheaper than mattress running with Points + Cash stays unless you have access to Category 1 properties. Those Category 1 Hyatt properties cost 2,500 Hyatt Gold Passport points and $50 per night, plus taxes. If you're able to mattress run at one of the 12 Category 1 Hyatt Regency properties in the Americas (there are many more in the Asia/Pacific region), you'll be able to select a 1,000-point Diamond amenity and earn 325 Hyatt Gold Passport points per stay, bringing your total cost down to $61.75, plus taxes, cheaper than the $80 you'd pay manufacturing spend with the Chase Hyatt credit card.

Using the same logic, even a Category 2 Hyatt Regency Points + Cash stay would cost $81.42, plus taxes (the proof of this is left as an exercise for the reader).

Requalifying on nights

While the case for requalifying for Diamond status on stays is strong, it's not airtight.

Looking at my own stay history this year, I have 7 elite-qualifying stays and 15 elite-qualifying nights. But I have also redeemed 7 free nights. If I had booked those nights as elite-qualifying Points + Cash nights, I'd be at 22 total nights, or 44% of the way to Diamond status, whereas by trying to requalify on stays, I'm only 28% of the way there.

Of course, I had reasons for booking those nights as free awards: 4 of them were redemptions of Chase Hyatt credit card certificates, for example, which can't be booked as elite-qualifying nights!

There are three key questions when deciding whether to requalify on stays or nights: the average length of your stay, the availability of Points + Cash award availability, and the category of property you typically stay in.

If your average length of stay is less than 2 nights, you're strictly better off requalifying on stays, because twice as many nights than stays are required to requalify. This is true even if you have more than 25 stays or more than 50 nights! That's because the more easily you can qualify, the more flexibility you have in selecting between free nights, Points + Cash, and paid stays, and flexibility in this game is worth a lot.

If your average length of stay is 2 nights or longer, then you have to consider the category of property you typically stay in and the availability of Points + Cash award availability. Two extreme examples illustrate this point: if you stay exclusively at Category 7 properties, each night you book with Points + Cash instead of just points costs $150 in extra Hyatt Gold Passport points — that's an expensive elite-qualifying night! If you stay exclusively at Category 1 properties, each night you book with Points + Cash costs just $25 per elite-qualifying night, plus taxes. However, if the properties you stay at don't regularly make Points + Cash awards available, you're out of luck: back to requalifying on stays.

Manufacturing spend on the Chase Hyatt credit card, at $40 in foregone cash back per night, is far superior to mattress running for nights, which even with Points + Cash awards starts at $61.75, as shown above. However, if you already stay 50 nights per year at Hyatt properties, the Chase Hyatt credit card elite-qualifying nights are inferior to simply swapping your award nights for Points + Cash nights, which only requires a "top-up" of $15-25 in Hyatt Gold Passport points (until you get to Category 7 properties).


I already have 2 additional elite-qualifying stays booked, with another 2 planned. Together with the Chase Hyatt credit card elite-qualifying stays, those trips will get me to 16 of the required 25 stays. To mattress run for the 9 remaining elite-qualifying stays at a Category 1 Hyatt Regency property would cost $555.75, plus taxes, which is out of the question.

On the other hand, I haven't planned my fall and winter travel yet, so it's still possible that enough real trips will come along to either get me over the finish line naturally, or get me close enough to mattress run for the final few stays.

Some bonus categories I never think about

I belong to the noisy-but-unpopular school that believes everyday spending should properly be a rounding error in the typical travel hacker's overall miles and points strategy. That's because more miles can be earned in an afternoon of light manufactured spending than will be earned in a month or year of trying to earn as many points as possible on actual purchases.

The flip side of that is a blind spot when it comes to the bonused categories of spend on cards that I already carry, either for purposes of manufactured spend or recurring annual bonuses. In the interests of keeping my blind spots few and far between, I decided to take a closer look at a few of those categories.


With increasingly limited access to gas station manufactured spend, you may find that you're not able to manufacture $50,000 in spend in a Chase Ink Plus's double point category of "gas stations and hotel accommodations when purchased directly with the hotel."

Since Ultimate Rewards points are worth 1.25 cents each when redeemed for paid airfare, or more when transferred to Hyatt Gold Passport, Southwest Rapid Rewards, and (usually) United MileagePlus, you're strictly better off paying for your hotel stays with a Chase Ink Plus than with the 2% cash back card you use for your other everyday purchases. One possible exception is if you are having trouble finding eligible expenses to redeem your Barclaycard Arrival Plus, Capital One Venture, or BankAmericard Travel Rewards miles against, although you can always consider refundable reservations in that case.

I'm fond of paying the revenue component of my Hyatt stays with Hyatt gift cards purchased at a discount using cashback rewards, but if you pay for Hyatt stays directly, the 3 Hyatt Gold Passport points earned per dollar with the Chase Hyatt credit card are superior to the 2 Ultimate Rewards points earned by both the Chase Ink Plus and Chase Sapphire Preferred — assuming you plan to transfer your Ultimate Rewards points to Hyatt Gold Passport at any point in the future.

The math is somewhat less favorable when paying for Hilton stays with the American Express Hilton HHonors Surpass card, which earns 12 HHonors points per dollar spent at Hilton properties. According to the Wandering Aramean visualization tool, 12 HHonors points are worth a median 5.376 cents, while 2 Ultimate Rewards points, transferred to Hyatt Gold Passport, are worth a median 3.724 cents. That's an edge, but it's an edge that's highly dependent on your actual redemption pattern.

Finally, the Chase Marriott Rewards Premier credit card is by and large not worth holding for either its recurring benefit (one free category 1-5 night each account anniversary) nor for manufactured spending (one elite night credit for each $3,000 spent). But if you do have it for one reason, the other, or both, you are still unlikely to get more value from the 5 Marriott Rewards points earned per dollar spent at Marriott properties than you would from 2 Ultimate Rewards points earned on the same spend — unless, of course, you are already planning to transfer Ultimate Rewards points to Marriott for some reason, like booking a 7-night Hotel + Air package.


As I've written before, most of the time one or more rotating cashback bonus card is offering 5% cash back at restaurants, so the idea of needing a particular card "dedicated" to restaurant spend is misleading: you should use your most lucrative card, which will, at least 6 months of this year, be a Discover it or Chase Freedom card. But that leaves the other half of the year, which makes it a legitimate question whether there are better cards than a straight 2% cashback card for use at restaurants.

Using the same median Hilton HHonors point value as above, the 6 HHonors points earned per dollar with the Hilton HHonors Surpass American Express at restaurants slightly edges out a 2% cash back card, earning the equivalent 2.688 cents per dollar spent, while the Chase Hyatt credit card earns 2 Hyatt Gold Passport points per dollar spent, or a median 3.724 cents per dollar.

This matters because the Chase Sapphire Preferred, often promoted by affiliate bloggers for its high affiliate payout and earning rate on travel and dining, earns 2 Ultimate Rewards points per dollar. In other words, for just $75, rather than $95, you can earn 2 Hyatt Gold Passport points at restaurants with a card that also offers a free night at Category 1-4 Hyatt properties worldwide. That's a fact that's helpful to keep in mind the next time someone tells you the Chase Sapphire Preferred is the best card to carry for restaurant spend.

Airline tickets

Finally, I very rarely find myself booking air travel directly through an airline (preferring to use miles, Ultimate Rewards points, or Flexpoints earned with a US Bank Flexperks Travel Rewards card), but if you do book air travel directly, or need to pay the taxes and fees attached to award tickets, you can do better than a 2% cashback card with cards you may already carry.

If you periodically sign up for a "spare" US Bank Flexperks Travel Rewards card, for example during the current Olympics promotion, you can use that extra card to pay for airfare, earning 2 Flexpoints per dollar spent, and transfer the resulting bonus Flexpoints to your primary account for future redemptions.

If you use an American Express Premier Rewards Gold card to manufacture grocery store spend on an ongoing basis, you may as well use it to pay for airfare, earning 3 Membership Rewards points for your airline tickets as well, which can be transferred to potentially lucrative travel partners like Delta SkyMiles. The same goes for a Citi Prestige card you may carry to raise the value of your existing Citi ThankYou points.

And the Chase Hyatt credit card earns 2 Hyatt Gold Passport points per dollar spent on airfare, giving it an edge over a straight 2% cashback card, depending as always on your actual planned redemptions.


I don't think it's useful, let alone necessary, for a travel hacker to stress over every possible bonus point at every possible merchant. But for the kind of purchases that you know you make frequently, it's at least worth considering finding additional value by keeping in mind the bonus categories offered by cards that you already use to manufacture spend, or hold for their recurring annual benefits.

As I indicated above, I don't usually pay for airline tickets or hotel stays with credit cards. But digging into my existing cards' bonus categories, I realized I could replicate the majority of the Chase Sapphire Preferred's "travel and dining" bonus categories with cards I already had: the Chase Ink Plus and Chase Hyatt credit cards. Between the two, they cover hotels, airlines, restaurants, and rental cars.

Obviously that leaves out things like cruises, travel agency bookings, local transportation, and so on. But they do include the bulk of reimbursable business travel, so if you do spend a large amount in those categories each year, you may find yourself coming out ahead by examining the bonus categories on your existing card card portfolio.

When deals don't stack

One of the most popular approaches to travel hacking is finding deals that "stack:" when you can apply multiple techniques to a single transaction, you can bring your out of pocket expenses even lower than you would applying any one of them individually.

Some deals stack

Since stacking deals can amplify total savings, deals that stack tend to get a lot of attention. For a simple example, you might click through a cash back portal to, apply a coupon, and pay for your stay with an Arrival Plus card. The cash back portal and coupon lower the amount you're charged, and then your final out-of-pocket cost is reduced further by redeeming against the transaction Arrival Plus miles you've manufactured as cheaply as possible.

Stacked deals can get much, much more complicated that that: Frequent Miler has painstakingly shown how portal cashback, coupons, credit cards, and even the tax code can be stacked to earn a Southwest Companion Pass with as little out-of-pocket expense as possible.

Most deals don't stack

What's usually glossed over by credit card salesmen is that most deals don't stack, which is important to both understand and take into account when developing a travel hacking strategy.

To take an example from last Thursday's post, the 4th-night-free benefit of the Citi Prestige card gives a roughly 25% discount off paid stays of exactly 4 nights. Ideally, you'd like to stack that with something like the Barclaycard Arrival Plus or BankAmericard Travel Rewards credit card, to redeem cheap points against your final bill. But because the stay has to be paid for with the Citi Prestige, your discount is limited to 25% — less than you'd save simply paying for a 4-night stay with one of those credit cards.

Another example is the American Express Delta Platinum and Reserve credit cards, which offer an annual companion ticket in economy (Platinum) or first class (Reserve). Such tickets offer a discount of almost 50% off 2 domestic tickets (though only the primary ticket earns redeemable and Medallion Qualifying miles). But manufacturing spend at grocery stores with a US Bank Flexperks Travel Rewards card offers a discount of, for example, between 53.2% and 68.9% on paid airfare! Buy two tickets with Flexpoints and not only are you unconstrained by fare class, but both tickets will earn miles and be upgrade-eligible, as well.

That doesn't mean the Delta American Express cards are bad cards (I personally have a Delta Platinum small business card). It does mean you need to think critically about the value of the companion ticket, perhaps using it to book travel for friends or relatives who will reimburse you (maybe) rather than using it for your own travel.


The question, "can I stack this deal?" should be one of the first ones you ask whenever you see a pitch for a new credit card or discount on purchased points, but also as you proceed through your everyday routine. If the answer is yes, you can amplify your savings by applying as many angles as possible to each transaction.

If the answer is no, that doesn't render a deal instantly worthless. But it is an invitation to examine the deal more closely, to ask whether and how you'll incorporate it into your overall travel hacking strategy. It may turn out to be superior to your other techniques, and it's those other strategies that should yield to the new, cheaper method of paying for your travel.

But if it offers a smaller discount (like the Prestige 4th-night-free), less-flexible booking options (like the Delta companion tickets), or interferes with your other goals, like elite status requalification, then you should take seriously the possibility that you will get less value, or have greater out-of-pocket expense, then you would pursuing a different strategy that incorporates more, better, and stackable deals.

Is the Citi Prestige a good deal? Compared to what?

This isn't my favorite kind of blog post to write, but I do consider it essential service journalism in the context of a travel hacking blogosphere whose default mode is "breathlessly excited."

The Citi Prestige credit card is often pitched as an essential tool for the sophisticated travel hacker. In this post I want to make the argument that, on the contrary, the benefits of the Citi Prestige are valuable almost exclusively to the least-sophisticated travel hackers, who don't have a well-designed portfolio of credit cards, or to travelers who don't have access to even the most mundane techniques for manufacturing spend.

Let's take each of the benefits of the Citi Prestige card in turn.

Price compression makes airfare cheap

The first thing you hear about the Citi Prestige card is how it multiplies the value of your ThankYou points: with the card, ThankYou points are worth 1.33 cents each towards airfare, or 1.6 cents each towards airfare on American Airlines-marketed flights.

That creates a theoretical cash value of the current 50,000 ThankYou-point signup bonus of $665-$800 in paid airfare.

But $800 in paid airfare manufactured with a Chase Ink Plus card at office supply stores costs $380 in purchase and liquidation fees ($665 in paid airfare costs just $316).

So don't tell me a 50,000 ThankYou-point signup bonus is worth $800; it's worth between $316 and $380, the money you'd spend manufacturing the same airfare with a much more versatile (and, obviously, much cheaper) Chase Ink Plus.

If you have access to manufactured spend at grocery stores, then you'll find a card like the US Bank Flexperks Travel Rewards Visa runs around the world before the Citi Prestige has even got its boots on.

Compare a 25% discount on paid hotel stays to real travel hacking

The "killer app" of the Citi Prestige is supposed to be its "4th-night-free" benefit, whereby reservations made through Citi's contract travel agency, and paid for with the Citi Prestige, earn a statement credit equal to the amount of the stay's fourth night, including taxes.

In other words, when used for stays of exactly 4 nights, the Citi Prestige offers a discount of 25% on average (the actual discount will vary depending on the distribution of room rates over the four nights; Frequent Miler provides some extreme examples here).

By contrast, using only the most commonly available manufactured spending techniques, the Barclaycard Arrival Plus produces $21.05 in hotel stays for just $11.50 — a 45.4% discount.

A Chase Freedom Unlimited, earning 1.5 Ultimate Rewards points per dollar spent (or 1,515 Ultimate Rewards points for the same $11.50 above), paired with a $95 Chase Sapphire Preferred or Chase Ink Plus, requires just 1.01 cents in value per Ultimate Rewards point transferred to Hyatt Gold Passport point to match the 25% discount offered by the Citi Prestige. You have to look pretty hard to get that little value from a Hyatt Gold Passport point.

Finally, using an American Express Hilton Surpass card, you'll earn 6 HHonors points per dollar spent at grocery stores. Given only the most widely available cost of $6.30 for 3,036 HHonors points, you'll need to get just 0.28 cents per HHonors points to beat the Citi Prestige's 25% average discount on four-night stays. And that doesn't account for the value of 5th-night-free award reservations for Hilton elites.

Which brings me to the most important drawback of the Citi Prestige's "killer app:" it's only useful on stays of 4 nights or more! While all the cards and techniques I described above are useful on stays as short as 1 night, to get even a 25% discount on your paid stays, you'll have to stay for exactly 4 nights: any less, and your stay isn't eligible; any more, and your discount shrinks as a percentage of your total stay.

How does the the Citi Prestige 4th-night-free differ from the Club Carlson last-night-free?

When the US Bank Club Carlson co-branded credit cards offered the last night free on award stays, I was one of their biggest enthusiasts. That's because the last-night-free benefit allowed you to leverage the already generous 5 Gold Points earned per dollar spent on all purchases. In other words, it made valuable manufactured spend more valuable.

The Citi Prestige 4th-night-free benefit is exactly the opposite: it requires you to pay cash out of pocket for your room, which violates one of the most important principles underlying a successful travel hacking strategy: spend cash last.

Value all the other Citi Prestige card benefits at what you're willing to pay for them: nothing

You can check out the remaining benefits of the Citi Prestige over at Miles to Memories. They include:

  • airline fee credits (worth much less than cash);
  • lounge access (you're not paying for it now, are you?);
  • Global Entry fee credit ($100 every 5 years, so, $20 per year);
  • and 3 rounds of golf (not 3 foursomes, just 3 rounds: your friends will have to pay their own way).

Reimbursed business travelers should ignore everything I've said

Travelers who are reimbursed for their out-of-pocket expenses have opportunities that are, from a normal person's perspective, stratospherically lucrative. If you're able to book Monday-Friday hotel reservations for a product launch, investment banking intervention, or Republican Party platform committee meeting with your own credit card for later reimbursement, you have no excuse not to earn thousands or tens of thousands of dollars per year in 4th-night-free reimbursements from a Citi Prestige card.

But when a rich weirdo like Ben Schlappig tells you how much money he's saved with the Citi Prestige 4th-night-free benefit, remember that you don't have to pay cash for your hotels, and when you do, you can get a much better discount than 25% by developing a credit card portfolio and manufactured spend strategy that meets your actual travel needs.

Ways you could (but shouldn't) manufacture spend

In addition to the garden variety manufactured spend I do day in and day out, I also enjoy keeping my eyes open for new avenues that might prove easier or more lucrative. Naturally, most of those either don't work or do work, but cost too much to be worth pursuing. Here are a few examples in the latter category.

Reselling Marriott gift cards

There's a whole cottage industry devoted to gift card arbitrage, which consists of buying discounted gift cards and reselling them at a higher price or theoretically even the same price while pocketing any rewards earned on the initial purchase.

Remembering an Amex Offer from back in 2014, it occurred to me that you could manufacture unlimited spend by buying Marriott gift cards and earning bonus points on a card like the Chase Ink Plus, then reselling the cards below their face value.

And it would work! Except at the rate offered by Cardpool (currently the highest payout), a Marriott gift card receives just 88 cents on the dollar, meaning you'd need to get 6 cents per Ultimate Rewards point just to break even, or 4 cents per ThankYou point earned with a Citi ThankYou Premier or Citi Prestige card.

That's certainly possible with a premium cabin redemption on a partner like Singapore Airlines, but it's not even close to worth doing unless you're desperate to top up an account and don't have the liquidation bandwidth (or free time) to manufacture your points more cheaply.

Returning merchandise to a different form of payment

What if you could make a purchase with a rewards-earning credit card, preferably at a bonused merchant, then return it and send the refund to a different form of payment, like a non-rewards earning debit card or even a check?

That would be great, except for obvious and non-obvious reasons banks are extremely sensitive to returns or refunds from merchants where purchases weren't originally made. The obvious reasons have to do with interchange fees and the costs of processing transactions, and the non-obvious reasons might include concerns about money-laundering: a refund to a debit card would be a great way to deposit money in someone's checking account without attracting attention — which is why it attracts attention!

All sorts of stuff is plainly illegal

I've been living in my current apartment for 2 years, and an Oster-brand toaster has been living here with me just as long. I'm moving soon, and don't particularly care to haul a 2-year-old toaster across the country with me. If I were a thief, instead of a travel hacker, I could just order up a new one from Amazon, take it out of the box, send the old one back in the same back, and sell the new one on eBay.

But again, that would be illegal, so don't do that either.


I find that keeping my eyes open and walking through potential techniques step-by-step is worth doing, even when I find that a deal isn't ultimately worth pursuing. It usually isn't! But it's the rare deal indeed that's discovered by someone blindly following only the most-travelled paths.

Earn valuable points, or expensive points?

I've been messing around with shopping portals for the past few days, which is always a good opportunity to reflect on deeper questions about the miles and points lifestyle.

Manufactured spend gives one vision of cost

As a manufactured spend enthusiast, I spend a lot of time comparing different credit cards, merchants, and earning rates to make sure I'm getting the most value for each of my manufactured dollars in spend. Using that perspective, every mile or point I manufacture costs precisely the dollar value of the cash rewards I would otherwise earn on the same spend. That's my opportunity cost: the value I need from a non-cash currency to justify earning it instead of cash.

Portal spend can turn things sideways

What I started thinking about while mucking about on shopping portals was this question: should you earn the most valuable points (usually the points you'll actually redeem), or the most expensive points when clicking through a shopping portal?

Here's a simple example: according to Cashback Monitor, you can earn 5% cash back when clicking through the Discover Deals portal to purchase Apple merchandise. Alternatively, you can earn 1 United MileagePlus mile per dollar spent at the Apple store.

Paying 5 cents per MileagePlus mile is a preposterously bad deal, since United miles can be purchased for 3.76 cents each any day of the week directly from United.

Now take a look at a merchant like eBay, where we can earn either 1.3% cash back or 0.5 United miles per dollar spent. At 2.6 cents each that's a little below the retail price of United miles, so you might consider using the United portal instead of earning cash back.

How opportunity cost differs from price and value

At this point you should be asking yourself, "why would I pay 2.6 cents per Mileage Plus mile when I can pay 1 cent per mile by transferring flexible Ultimate Rewards points into my United account?"

And that's exactly right — if you would, in fact, redeem your Ultimate Rewards points for cash, then the price you would pay for United miles would be 1 cent. But if you would otherwise redeem your Ultimate Rewards points by transferring them to another travel partner, like Southwest or Hyatt, then your opportunity cost isn't 1 cent — it's one Rapid Rewards point or one Hyatt Gold Passport point.

This matters because you may get more value from a Rapid Rewards point (for example, if you have a Southwest Companion Pass) or a Hyatt Gold Passport point (by redeeming at expensive properties or taking advantage of Points + Cash redemptions) than you do from a United Mileage Plus mile. Using the example above, the opportunity cost (2.6 cents) of earning United miles rather than cash back may be lower than the opportunity cost (1 Rapid Rewards point or 1 Hyatt Gold Passport point) of transferring Ultimate Rewards points to United.

United miles aren't valuable, but they are expensive

I don't like United Airlines. I find them consistently rude and unreliable, so I don't fly them if I can help it. But even I admit that their miles can be useful for redemptions on their Star Alliance partners, like my upcoming Turkish Airlines flight to Europe. The problem is that United miles transferred from Ultimate Rewards are expensive, because I place a lot of value on the ability to transfer Ultimate Rewards points to Hyatt Gold Passport, and each point I transfer to Mileage Plus is one I can't transfer to Hyatt.

This creates the kind of situation I've described, where it may be worthwhile to pay a high price for each United mile, since doing so preserves the ability to transfer Ultimate Rewards points to Hyatt, where I'll get more value, instead.

For the sake of completeness (and to silence quibblers), I do want to mention that Hyatt also sells points (up to 55,000 per year before bonuses are added) for 2.4 cents each. So it's not strictly speaking worthwhile to pay 2.6 cents per United mile just to "save" your Ultimate Rewards points since your total cost will be lower simply earning cash back, transferring Ultimate Rewards points to United, and using the cash to buy Hyatt Gold Passport points. Using other merchants and portal payout levels, and accounting for bonuses on purchased miles and points, the numbers will naturally be different.