Seven of my favorite travel hacks for people of all skill levels

I was impressed by Greg’s post at The Frequent Miler yesterday, although I was a bit worried since I’d been planning my own post about my favorite still-working travel hacking tips. Fortunately, his list didn’t end up overlapping with mine much at all. Still I thought I should get this post up before anybody else had the same idea.

The list below runs the gamut from “using the program as intended” to “highly illegal” so as always apply your own judgment and discretion when deciding which of these are right for you.

Nesting Alaska Airlines companion tickets

One of the posts I’m most often asked about gives some examples of the zany routes you can book with the companion tickets you get when signing up for Bank of America Alaska Airlines co-branded credit cards and on your account anniversary. It’s such a good deal (a $95 annual fee and a $99 fare (plus taxes!) for any Alaska-operated flight in any economy fare bucket) that almost anyone who lives in or near a city served by Alaska and flies with a companion once a year is virtually certain to come out ahead.

The example I gave in that post is booking a flight from Washington National Airport to Los Angeles, then a roundtrip between LAX and Maui, then a flight back from LAX to DCA. Since you can spend an unlimited amount of time in both Los Angeles and Maui, that’s functionally two itineraries: one between DCA and LAX, and one between LAX and OGG — and the second passenger gets to take both while paying for a single companion ticket (a little over $170 in that example).

If you’re able to “nest” companion tickets on routes you fly regularly you can get even more value from multiple companion tickets. To continue the example above, say you want to return home to DC from LA before your trip to Hawaii. You could of course find that another airline has better timing or prices, but if Alaska is the best carrier for you, you can also book a second companion ticket partially “nested” inside the first one by booking a flight from DCA to LAX that meets up with your existing LAX-OGG itinerary. That gets you to LAX, but remember you already have your return flight from LAX to DCA from the first companion ticket. That means you can use the “return” portion of your second companion ticket to book any “reasonable” routing (see the original post for additional details on routing rules). For example, it’s perfectly legal to use a companion ticket to fly from DCA to LAX, then from Portland, OR to Missoula, MT, then from MSO to DCA.

Thus from two companion tickets we’ve built 3.5 round trips: DCA-LAX, LAX-OGG, PDX-MSO, and then a one-way ticket PDX-DCA.

Using closed or drained debit cards to pay for in-flight food and drinks

This trick has been around since the invention of the inflight credit card reader, but still works almost everywhere. For whatever reason (presumably so the flight attendants don’t screw around on Twitter while they’re working) the handheld readers flight attendants use to charge for in-flight food and drinks aren’t connected to the internet, or at least aren’t connected to a payment server. They apparently dump all the card data when they land, or at the end of the day. That means in flight, you can order whatever you like for free, as long as you have a card that will decline the charge once you land.

Obviously this doesn’t work on cash-only carriers (mostly regional flights these days), and some international carriers verify card data in real time as well. This also does not work for in-flight internet charges in my experience.

Earning free night certificates at hotels you stay at

A lot of people are paid to inflate the value of the free night certificates that come with many credit cards. I’m not, so I take a much more skeptical approach to them. One heuristic I like to use is: “would I use this certificate to extend a stay I’m willing to pay for?” For example, I used a Hilton free night certificate for a sixth night at the Grand Wailea resort in Hawaii, after paying for 5 nights with points (and getting the fifth night free).

On the other hand, in most cities I visit, Marriott properties are either non-existent or not competitive on price with Hilton or Hyatt, so I would never use a free night certificate if it meant locking in a higher daily rate on the remaining paid nights.

Of course, for road warriors who pay for their own expenses, having a trove of free night certificates in case of bad weather or other travel emergencies can save a ton of money on last-minute expenses. I think that’s perfectly reasonable — but it’s also not very many people.

Using Fluz as intended

I wrote about my first experiments using Fluz as intended back in 2021, and while I wouldn’t say I use it often, it’s become a resource I check at least a few times a week. Most travel hackers use Fluz to manufacture spend, but they do also sell gift cards to a range of merchants with automatic cash back (redeemable for cash once you hit a pesky one-time $26 payment threshold).

The basic premise of Fluz is that you can buy exact-denomination gift cards to a surprising range of merchants. Presumably Fluz buys this credit in bulk, then splits the discount with its customers. The value-add of Fluz is that it passes along not just the merchant category but the actual merchant for every card I’ve ordered. For my sins I occasionally order Domino’s pizza from around the corner, and I often have Chase offers on my credit cards for some percentage rebate on Domino’s orders. Since Fluz passes through the merchant to Chase, I can stack my 10% rebate through Chase with my 4% rebate through Fluz (after clicking through shopping portals and applying coupons).

Obviously, this isn’t a great idea at merchants you rarely shop at or are trying for the first time, since if you’re disappointed your payment will be refunded to a gift card you’ll never use. But for picking up a pizza or a burger, or at a store you shop at regularly, it’s a no-brainer.

Registering for hotel promotions

While this may sound like table stakes, I doubt there’s a person in the game who hasn’t gotten home from a trip before realizing that they could have earned a few thousand or more points on their hotel stays if they’d registered for an ongoing promotion in advance. It’s a bad feeling, so avoid it whenever you can!

I try to keep my Hotel Promotions page up-to-date with all currently ongoing and announced promotions, but I’m not always on the ball, so if the chain you’re staying with doesn’t have a promotion listed there, it’s a good idea to search Frequent Miler or go to the hotel promo page at Loyalty Lobby. Note that Loyalty Lobby publishes every promotion, even targeted and regional ones, for every chain so their site is incredibly cluttered, albeit comprehensive.

Using Hotels.com at non-chain hotels (or chains you don’t value)

For the most part, you’re better off booking chain hotels directly if you value the chain’s rewards currency or elite status benefits, since you won’t earn points and may not get elite benefits if you book through a third party like Hotels.com (or Priceline, Expedia, etc).

On the other hand, if you don’t value a chain’s loyalty program, or for stays at non-chain hotels, you can use Hotels.com to “lump” those stays together into Hotels.com’s rewards program. Plus you don’t need their co-branded credit card to participate, although it may help.

Hotels.com also appears in most shopping portals and in Fluz, so you can save money on hotel stays 3 times: clicking through a shopping portal, selecting your stay details, then going to Fluz and buying an exact-denomination gift card for the total amount. Credit cards periodically offer rebates on gift card purchases as well (American Express, Citi).

Knowing the difference between calendar year and cardmember year benefits

This one’s essential to maximizing the value of your credit card benefits, and if you’re paying an annual fee for a credit card, losing out on a benefit you’ve paid for is the worst case scenario. Take the Chase World of Hyatt credit card for instance: it offers a Category 1-4 free night award on every cardmember anniversary, and a second free night award when you spend $15,000 in a calendar year. That means you can get 3 free night awards during your first cardmember year, depending on your anniversary date. If you get the card in July, then you have until December 31 to spend $15,000 on the card to earn the first award, and until June 30 to spend another $15,000 to earn the second, before you even have to decide whether to renew the card for a second year (personally I value the free award nights so highly I plan to keep the card forever, but that may change down the road if my taste in travel evolves).

Other examples of calendar year benefits include most Global Entry and Precheck reimbursements, most airline fee reimbursements, and bonuses for hitting high annual spend thresholds.

Conclusion

My posts normally focus on one topic at a time so it was fun exercise to take a 30,000-foot view of the techniques I actually use to save money on my travel. I manufacture spend to earn the points and miles I need to pay for the outstanding cost of my travel, which makes it even more important to make those outstanding costs as low as possible by double and triple dipping my credit card rewards, portal cashback, and any other discounts I’m able to scrape together, since it means I don’t have to work as hard manufacturing spend!

Hotels.com exemplifies the importance of redeemable intervals

Affiliate bloggers (and Secretaries of Transportation) love assigning a dollar value to miles and points, which makes it easy for them to compare the value of signup bonuses across currencies and manipulate their valuations when a particularly large referral bonus comes along.

There are naturally people for whom this approach makes sense, like mileage brokers who sell award tickets and hotel stays to folks who don’t know or care where they come from: selling a hotel stay that might cost $10,000 in cash for $5,000 can be a good deal for all involved if you only paid $1,000 for the points.

But this approach has never made any sense to me, since miles and points aren’t fungible. I can’t opportunistically earn 20,000 American miles, 20,000 Delta miles, and 20,000 Spirit miles and redeem them for a 60,000-mile United flight. If the United flight is the one I need to take, my other three currencies aren’t worth 2 cents each, or even one cent each: they’re worthless.

This is one reason I work to keep many of my balances as low as possible. I only have 797 Mileage Plus miles in my United account, and have no intention of earning more any time soon (despite having flown United last month and flying them again next week!). If any potential use does come up, I can transfer the precise number of United miles I need from Ultimate Rewards, and then draw my balance back down into the 3 digits, just where I want it to be.

There’s no better way to illustrate this than with the example of Hotels.com.

Stamps, rewards, and the importance of thinking in tens

To refresh readers’ memory, Hotels.com has an extremely simple rewards program: when you book a night through them, you receive a “reward stamp.” Collect 10 stamps, and you receive a “reward night.” You can then redeem reward nights at virtually all the properties on their platform for the average nightly rate you paid for your 10 reward stamps.

Importantly, however, if the stay you’re trying to book costs more than the value of your reward nights, you can simply pay the difference in cash to “top up” the value of the night. This makes the risk of breakage single-tailed: you can lose some of the value when booking a room cheaper than the value of your reward night, but you’re not penalized for booking a room that’s more expensive (although you won’t earn a stamp on those “top-up” nights).

There are therefore two ways of thinking about the value proposition of the Hotels.com rewards program:

• it offers a 10% rebate on each paid night you book through the platform;

• after the 10th night you book through the platform, you receive a voucher worth up to the average value of your last 10 nights.

Regardless of the approach, the value of the voucher doesn’t change. What changes is the value assigned to each night you book through Hotels.com. If you take the first approach, then when you book through Hotels.com you can mentally multiply the cost of your stay by 90% to reflect the 10% rebate the program offers. If you take the second approach, the first 9 nights you book through Hotels.com generate no value whatsoever — only the 10th night you stay generates any value at all.

I prefer the second approach, because focusing on redemption thresholds makes it easier to compare the relative value earned by booking through different channels, as a recent experience illustrates.

Last month we visited the Midwest for a week to see some friends and family, and the best price I found was, as usual, at a centrally located Hyatt Place downtown. The lowest rate I could find was $136.85 per night, plus tax, which is irrelevant regardless of the booking channel.

Where the booking channel comes in is that $958 spent on a paid Hyatt rate would earn me 4,790 base World of Hyatt points, and 958 bonus points as an Explorist member, for a total of 5,748 points.

Now look at this through the same two lenses as above. On the one hand, since I redeem World of Hyatt points I’ve transferred from Ultimate Rewards fairly regularly, the points I’d earn on this stay could be valued at a minimum of $71.85 — the value of the same Ultimate Rewards points when redeemed for paid airfare.

Through the second, redemption-focused perspective, 5,748 World of Hyatt points are essentially worthless, since 5,000 points is just barely enough to book a Category 1 property, and only during off-peak and standard pricing periods! That story would be completely different if I had an upcoming high-value Hyatt stay and insufficient points to book it. In fact, I have plenty of Hyatt points and free night certificates, so the additional points would simply sit in my account growing stale.

That may well have still been my best option. After all, 7 Hotels.com reward stamps are just as worthless as 5,000 World of Hyatt points. What changed the calculus is that I already had 4 Hotels.com reward stamps in my account that had been rolled over all the way from 2019! That meant “crediting” my Hyatt Place stay to Hotels.com would put me over the redemption threshold and earn me a reward night, in my case worth $141.88, which I promptly redeemed with a small top-up for a night on our upcoming trip to the UK.

Sharp-eyed readers will have noticed one small but potentially critical error I committed: I was sitting on 4 existing reward stamps and then credited another 7 nights to Hotels.com — leaving me with a worthless “leftover” reward stamp! It may have been strictly superior to credit 6 nights to Hotels.com (securing my reward night) and the cheapest of the 7 nights to World of Hyatt (to save future Ultimate Rewards points). I say “may” have been because I didn’t bother checking the rates for individual nights, and it may have turned out the one-night rate was substantially higher than the longer-term stay rate I ultimately booked, erasing the value of the additional World of Hyatt points.

Two additional considerations: cashback portals and the Hotels.com credit card

Just as I set aside taxes and fees above, since as far as I know they are not included in the earning calculation with any loyalty program, I also skipped over cashback portals, which typically offer 1-4% cashback on hotel bookings (including Hotels.com bookings), although with periodic outsized offers, like the current 9% cashback rate at IHG properties offered by TopCashBack. Since those offers are for cashback, and have relatively low cashout requirements, you should always check where your total rewards (loyalty program + cashback + credit card earnings) offer you the most redeemable value.

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Finally, it’s worth mentioning the no-annual-fee Hotels.com credit card. The card has a paltry signup bonus (three $125 reward nights after spending $5,000, which can’t be stacked but can be topped up), but the earning structure does offer one interesting opportunity: for every $500 spent on the card, you receive one Hotels.com reward stamp. As mentioned above, each reward stamp has an assigned value which is averaged into the value of your reward night. Hotels.com assigns these credit card reward stamps the value of $110, so if you put exactly $5,000 on the card (for example, to meet the signup bonus), you’d end up with a fourth reward night worth exactly $110.

If you squint at it just right, that means someone trying to sell you this card could in principle convince you the card has a $485 signup bonus and earns 2.2% on ongoing spend (a $110 reward night for every $5000 in purchases). But that’s not the interesting opportunity offered by the card. Instead, since you earn a $110 reward stamp every time you spend $500 on the card, it’s ideal for topping up your reward stamp balance when your existing stamps have a relatively high average value (and you don’t have upcoming Hotels.com stays booked).

To give a simple example, if you have 9 reward stamps with an average value of $250 each, manufacturing $500 in spend on the Hotels.com credit card doesn’t yield $11 in rewards (2.2%). Instead, it yields a reward night worth $236 ($2250 plus $110 divided by 10).

I wouldn’t say this “supercharges” the Hotels.com rewards program. What it does do is reduce the downside risk of orphaned reward stamps, so at the margin makes it more appealing to book hotels based on price through Hotels.com, knowing that every time you accumulate 6 or 7 reward stamps through stays you can easily calculate the final value of the resulting reward night you manufacture with the credit card.

And if, like me, you have no interest in active participation in loyalty programs like Marriott or IHG, but notice that their properties are occasionally attractive in terms of price, location, or amenities, especially outside of big cities, it may be worth taking a look.

Conclusion

I tailored this post to Hotels.com rewards but hopefully I’ve made clear the point is universal, and not just for people who keep their balances as low as possible like me. If you’re saving up points for a week-long stay at the Conrad Maldives Rangali Island you might well need 600,000 points and a free night certificate, for example. But you don’t need 610,000 points and a free night certificate — only the points you redeem have value, the 10,000 leftover points are just gonna sit there, getting stale.

Reminder: restrictions do differ between different shopping portals

Starting online purchases at a shopping portal is one of the simplest techniques travel hackers use, and it’s also one of the most reminiscent of extreme couponing: click through an online portal (be sure to clear your browser’s cookies first), make a purchase, and you’ll earn some miles, points, or cashback from the portal in addition to your credit card rewards.

While there are dozens, if not hundreds, of different online shopping portals, with a little bit of experience they can come to seem more or less interchangeable (they’re mostly operated by the same firm on the backend), which can be both a good and bad thing. It’s a good thing when it means the same technique will work on multiple portals, like the Wall Street Journal/Barron’s subscription deal; it’s a bad thing when the same restrictions are imposed on each portal, or even across portals.

It’s worth keeping an eye out for differences between portal restrictions

For my sins, I’ve had to book a couple upcoming hotel stays with cash, and decided to see what the current situation was on my online shopping portal accounts. The problem, in general, is that merchants got wise to people double-dipping through both shopping portals and their proprietary rewards programs, and so began to limit portal payouts when you log into your rewards account before completing a reservation. To give a simple example, if you click through to Hotels.com through TopCashBack, you’ll receive 8% cashback if you make your reservation without logging in, but only 2% cashback if you log in first:

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BeFrugal is slightly more competitive, at 10% and 2.5%, respectively:

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While this may seem like a cheap move for Hotels.com (because it is), the logic is obvious: they already operate a loyalty program offering a rebate of “about” 10% on hotel stays (every ten nights booked through the site earns a free night of equal or lesser average value). Giving people an additional discount just for knowing about it must give their director of marketing enough heartburn as it is.

This compromise at least makes shoppers stop and think: it’s true 12.5% (through BeFrugal) is higher than 10%(logged into Hotels.com), but a 10% cash payout might be more valuable than a 10% in-kind payout with a 2.5% cash bonus. In fact, I think under virtually all circumstances it would be.

But not all shopping portals have identical restrictions

Ideally, what you’d like is a shopping portal with a competitive payout rate that still works on rewards-earning transactions, and that’s why it’s worth checking the restrictions on each portal, instead of just assuming they’re all identical.

Lemoney, for example, offers 5.5% cashback at Hotels.com without restriction on whether you’re also collecting Hotels.com free night credits:

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To be clear: while my full cashback amount has already tracked properly, it won’t be payable for months so there’s no way of telling whether I’ll actually receive the full amount.

I found the same was true at Hilton, where BeFrugal offers 6% cashback to non-members and non-elite members, but just 1.5% to Silver, Gold, and Diamond elites:

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While Lemoney offers 4% cashback to everyone:

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Conclusion

Shopping portals have never played a particularly large role in my travel hacking game, simply because I’ve always been fortunate enough to have access to adequate manufactured spend to meet my travel needs, so this isn’t meant to be a comprehensive look into shopping portals, let alone a recommendation to use one over another (although feel free to find my own personal referral links on my Support the Site! page).

But it is meant as a reminder that while shopping portal terms are often similar, they aren’t always identical, and the differences between them can end up being more lucrative than you expect, particularly when you do end up needing to pay cash for travel expenses.

Starting from scratch: hotel stays

In yesterday's post I talked about how to develop a strategy for booking airline tickets that works for you. As I said then, "the options you have available today are restricted by the decisions you made in the past." For example, your ability to get approved for new American Express credit cards depends on the number of American Express credit cards you currently have (in general folks are restricted to 4 total American Express credit cards each).

Hotels are cheap, if you ignore loyalty

Yesterday I explained that airfares are cheap, if booked using cheaply acquired fixed-value points. The opposite is true of hotels: while you can redeem fixed-value points for hotels, you'll be redeeming them against the full retail price of the hotel room, which means you're virtually certain to overpay.

For example, it's possible to use a cashback portal like TopCashBack to click through to Hotels.com and earn 9% cash back from TopCashBack, plus 10% back in the form of a Hotels.com award night when you book and stay 10 nights through Hotels.com.

There are additional benefits to booking through an online travel agency: you'll be able to pay with the credit card of your choice, meaning you'll earn that credit card's reward points as well, while redeeming US Bank Flexpoints, Citi ThankYou Points, or Chase Ultimate Rewards points through their booking tools necessarily keeps you from earning credit card rewards on your reservations.

But the most important benefit of booking through an online travel agency, rather than a hotel chain's own website, is that it frees you to book the cheapest hotel available (that meets your other requirements like location and amenities)!

To see how this works, let's take the example of a weekend stay in Portland, OR, from May 20-22, 2016. Once I've filtered by 3-star hotels in the downtown neighborhood, I find that the cheapest Hilton property is $189 per night, the cheapest Marriott property is $213 per night, and the cheapest Starwood property is $269 per night, before taxes.

Now, clicking through TopCashBack and booking through Hotels.com will save you 19% off whichever property you choose. But being agnostic as to the chain you're staying with saves you even more: an additional 11.27% compared to being loyal to Marriott and an additional 29.7% compared to Starwood loyalty.

Loyalty programs: cheap, but loyal

Hotel loyalty programs can also bring down the cost of your stays from retail, but only under certain conditions.

The biggest problem with hotel loyalty programs is that if you're not saving money on every single stay (compared to the online travel agency method described above), then you're faced with the unpleasant choice of deciding between overpaying for a hotel stay within the loyalty program or saving money but earning online travel agency rewards too slowly to notice your savings, or, God forbid, even wind up seeing a message like this:

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Having said that, there are 3 principle ways to use hotel loyalty programs to consistently bring down the price of your stays:

• Wyndham Rewards. The Barclaycard Wyndham Rewards credit card earns 2 Wyndham Rewards points everywhere, and Wyndham has a huge global footprint. Since all Wyndham Rewards properties cost 15,000 Wyndham Rewards properties per night, if your hotel stays typically cost more than about $150 per night (or about $180 before accounting for cash back portal and online travel agency rewards), you'll save money manufacturing spend on the Wyndham Rewards credit card compared to a 2% cash back card.
• Hyatt Gold Passport. If your travel takes you primarily to the kinds of mid-size European cities or larger American cities served by Hyatt, then you can often save money by transferring Chase Ultimate Rewards points to Hyatt Gold Passport from a Sapphire Preferred or Ink Plus credit card, earned with a Chase Freedom Unlimited card. Compared to paying with cash back earned on a 2% cash back card, you need to get a consistent value of at least 1.59 cents per Hyatt Gold Passport point to break even, since cash back is worth roughly 19% more than face value when spent on hotels at Hotels.com.
• Hilton HHonors. The good thing about Hilton's program is that, like Wyndham, Hilton has a huge global footprint, so it's not unreasonable to expect you'll be able to find Hilton properties to accommodate you almost anywhere you travel. Since the Hilton HHonors Surpass American Express earns 6 HHonors points per dollar at supermarkets and gas stations, you'll need to consistently get about 0.4 cents per HHonors point in order to come out ahead compared to a 2% cash back card, with the cash back spent at an online travel agency like Hotels.com. The $189 room we found in Portland above would cost about $186 after discounts and taxes, or 50,000 HHonors points, giving a value of 0.37 cents per HHonors point — in other words, you'd be better off earning cash back and using it to make a Hotels.com reservation at the same hotel, which happens to be the cheapest option for the weekend I searched.

It's not unreasonable to suggest that the Club Carlson Premier Rewards credit card, which earns 5 Gold Points per dollar spent everywhere, might be a competitive option for manufacturing unbonused spend. But due to the heavy discount afforded when using cash to book stays through online travel agencies, you'd need to consistently get 0.48 cents per Gold Point on all your Club Carlson award stays to break even compared to cash. Club Carlson is simply not a program that affords that kind of value anymore: Hotel Hustle's average value found for Club Carlson is 0.41 cents per point, with a median value of 0.379 cents per point.

Conclusion

As you can see, just as I showed yesterday, the best approach to booking hotel stays as cheaply as possible will depend on your situation: the fixed cost of hotel award nights can be an argument in their favor if you typically travel to expensive cities during peak travel times, or it can be an argument against them if you're a flexible leisure traveler who travels when hotels are cheap in dollar terms, and can be made even cheaper using online travel agency rewards.

Tomorrow I'll conclude this series with a look at the prepaid and alternative banking products I would use differently if I were starting out from scratch.