My good Delta companion certificate redemption proves how bad companion certificates are

I rarely pretend that my posts are supposed to be "timely," but since the new Bank of America Alaska Airlines Visa Signature credit card, with its $0 base fare companion ticket, instead of the $99 base fare companion ticket the card has traditionally offered, has occupied the blogosphere for the last few weeks, and since I just received and redeemed my American Express Delta Platinum Business credit card companion certificate, this seems as timely a moment as any to revisit the issue.

The problem with Delta companion certificates

There are two conflicting issues when redeeming the Delta companion certificates offered by the American Express personal and business Delta Platinum and Reserve credit cards:

• Certificates can only be redeemed for flights in fare classes L, U, T, X, and V. Those are, naturally, the cheapest 5 fare classes (plus E), which sell out first as people book their tickets and the departure date approaches.
• Flights in those fare classes are, as you'd expect, cheaper than flights in the more expensive fare buckets.

In other words, Delta and American Express have contrived to "cap" the cost of offering free companion tickets by allowing their redemption only on flights that are far enough in the future, and empty enough, that they're unlikely to cost very much.

To maximize the value of a Delta companion ticket redemption, therefore, you'd want to find a flight sufficiently far in the future that "cheap" fare buckets are still available, but to an expensive destination in the continental United States.

My Delta companion certificate redemption was close to ideal

Fortunately, I grew up in Montana and while my hometown is served by several airlines, including Delta, tickets there are unspeakably expensive. I've been watching tickets home for the Western Montana Fair for the last month or so, until my companion fare certificate finally posted last week to my Delta account (the last two years, my companion certificate has posted on May 4, while my anniversary statement closes on May 20; do with this information what you will).

On May 4 the two tickets I needed were retailing for $774, which meant I could redeem my companion certificate and get $1,548 in airfare for $824 (after taxes and fees are applied to the second ticket).

Of course, I'm also due to pay a $195 annual fee for the credit card, bringing my total out-of-pocket expense to $1,019, roughly a 34% discount off the retail price of both tickets.

Not bad! Unless you're a travel hacker.

I overpaid by $219

The key insight travel hacking provides is that two $774 tickets are not worth $1,548. They're worth $800. That's because I can redeem 40,000 US Bank Flexperks Travel Rewards Flexpoints for each ticket, or I can redeem those points for 1 cent each, i.e., $800 in total. In other words, I paid $1,019 for $800 in airfare.

What companion certificates are and aren't good for

I stand by my decision to redeem this particular companion certificate for this particular flight, primarily because Delta companion certificates are so difficult to use, given the fare class restrictions, that there's no certainty of being able to redeem them at all (I have tried, unsuccessfully, to pawn off my certificates to family members in the past).

There's a sort of core logic to redeeming your most restrictive travel instruments (free night certificates, companion certificates) where possible before redeeming more flexible instruments (miles, points, and fixed-value award currencies).

And indeed, by securing a "mere" 34% discount on this pair of flights, I'm left with the same 80,000 Flexpoints, worth up to $1,600 in airfare, that I would have otherwise redeemed. I haven't "lost" anything by redeeming the companion certificate instead.

However. This game of rolling forward "more valuable" points currencies while redeeming "less valuable" travel instruments is just another way of keeping large, unredeemed (and therefore worthless) points balances and reducing your total return on your travel hacking practice. Your travel hacking objective should not be to get the most value possible from your least valuable rewards, but to identify and get the most value possible from your most valuable rewards!

Conclusion

The point of this post isn't to say that "companion tickets are worthless." Companion tickets aren't worthless, but they're valuable only to the extent they can be integrated into a coherent travel hacking practice.

That means, for the most part, that they're best redeemed for cheaper, rather than more expensive flights. The logic should be obvious: more expensive flights are more target rich environments, where airline miles and fixed-value currencies like US Bank Flexpoints are likely to shine.

Cheaper flights pose a real problem: you can redeem fixed-value currencies like Chase Ultimate Rewards for 1.25 cents each, or Membership Rewards points for 2 cents each (for certain American Express Business Platinum customers), but those are also currencies with more potential upside on more expensive tickets and other kinds of travel redemptions.

Paying $200 for two $200 tickets won't save you much cash, because it's hard to save much cash on tickets that cheap. However, it's likely to be a better use of a companion certificate than a 34% discount on an $800 ticket, for the simple reason that on an $800 ticket you can do better.

Fun with Delta partner award space

Like anyone who does a fair amount of paid and award travel on Delta, I've been annoyed by their "flexible" award prices, which are generally calibrated to ensure you don't get too much value from your SkyMiles. On the other hand, if you keep a variety of points currencies around you always have the option of redeeming the one best suited for the flights you have in mind.

The real trouble comes about when trying to get value from one of Delta's partner award programs, like AeroMexico, Korean Air SKYPASS, or Air France/KLM Flying Blue. We used to say that airlines typically make "low-level" award space available to their partners. But with Delta's "what you see is what you get" pricing, that terminology doesn't make much sense. In fact, Delta awards at a variety of price points show in award searches as what used to be low-level "N" award seats.

What we'd really like to know is what kind of partner award space Delta makes available to their SkyTeam partners. Fortunately, Korean Air SKYPASS now shows Delta award availability online. I've been fiddling around with a variety of search terms and have a few preliminary observations.

Partner award space generally corresponds to "low-level" space

Drew at Travel is Free put together a sort of brute force Delta award chart based on an algorithm running award searches. If you can find flights at those prices then they'll typically be bookable as partner awards.

If you're using Korean Air SKYPASS you can only book roundtrip awards (although open jaws and stopovers are allowed), and I believe you can only search single-cabin awards online, but if you can find roundtrip award availability in the same cabin, there are good values on Delta. For example, a roundtrip on one of Delta's transcontinental Delta One flights costs 80,000 SkyMiles, but just 45,000 SKYPASS miles. Likewise roundtrip flights from the continental United States to Alaska and Hawaii cost just 25,000 SKYPASS miles in economy and 45,000 miles in first class.

I stumbled over a few tricks to keep in mind when booking Delta flights with SKYPASS miles. When searching for SkyTeam awards on the Korean Air website, you have to select "Economy Class," "Prestige Class," or "First Class." For flights in Delta's domestic first class cabins, you select "First Class," but flights in Delta One are coded as business class partner awards, which corresponds to "Prestige Class." There's no difference in cost for flights within North America including Hawaii and Alaska.

Sample booking: JFK-LAX, 6/1 - 7/17, Delta One: 80,000 SkyMiles, 65,000 Alaska Mileage Plan miles, 45,000 SKYPASS miles.

Partners generally have access to sub-low-level space

While Delta's flexible redemption rates generally punish SkyMiles members by charging them more for more expensive flights, they also sometimes show flights that are cheaper than the "low" award rate. In those instances I was able to find the same flights with Korean Air SKYPASS, although Korean Air naturally charged the higher, standard rate.

Sample booking: JFK-PDX, 6/2 - 6/8, Main Cabin: 24,000 SkyMiles, 25,000 Mileage Plan miles, 25,000 SKYPASS miles.

Partners have more creative routing rules

One big problem with "what you see is what you get" pricing is that even though you may have found Delta partner award space on an itinerary, Delta might not price it out at the low level through their multi-city pricing tool due to their own award routing rules. For example, this is a perfectly legal SKYPASS redemption for 25,000 miles:

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While there should be low-level SkyMiles award seats available for the entire route, Delta prices it out at 38,000 SkyMiles, instead:

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I presume this is because Delta treats the overnight stay in Las Angeles as a domestic stopover and so prices the itinerary out as 3 separate legs, but since "what you see is what you get," I can't say for sure.

What this means is that while you might start your search by looking for Delta low-level award space between your origin and destination, before giving up hope you should also experiment with Korean Air's search tool to identify routings that Delta won't show you by default or will charge more for. Unfortunately SKYPASS searches are both fairly cumbersome and will return an error message if there's no availability on any one of your search legs, which makes it difficult to diagnose exactly where the error is originating.

Now, naturally many of these irregular routings won't be especially convenient (like the overnight stay in LA above), but that's the point: more flexible routing rules increase the likelihood of finding some routing that will allow you to redeem miles instead of spending cash.

Sample booking: DCA-AMS, 8/29 - 9/5, Main Cabin. Outbound: 3 low-level SkyMiles routings found, 30 low-level SKYPASS routings found. Inbound: 20 low-level SkyMiles routings, 30 low-level SKYPASS routings found.

That sample booking has the added bonus of revealing that there is a ton of award space available between JFK and Glasgow and Edinburgh this summer and fall. It's enough to make you want to visit Scotland!

Conclusion

The ease of earning Delta SkyMiles through transfers from American Express Membership Rewards, Starwood Preferred Guest, or putting spend on an American Express Delta Platinum or Reserve card, and earning Korean Air SKYPASS miles through Chase Ultimate Rewards transfers, creates the following curious situation:

• where SkyTeam partner award space is available, it's best booked using Delta SkyMiles since (with a few exceptions) they don't pass along fuel surcharges;
• when Delta makes premium cabin award space available, it should be booked using SKYPASS miles, since Delta doesn't charge fuel surcharges for SKYPASS to pass along!

Blending earning and redemption rates

When an affiliate blogger is trying to sell you a credit card that allows you to redeem bank points against a travel purchase, they sometimes pull this fairly ingenious, if transparent, sleight of hand:

• When you earn airline miles for a purchase, then redeem those miles for travel, the value you get per dollar spent depends on the value you get per airline mile.
• When you earn bank points and redeem them against a paid flight purchase, you don't just get the value of your bank points, you also get the value of any airline miles earned for your paid flight.
• Therefore you should value a dollar spent with, for example, a BankAmericard Travel Rewards card not as the 1.5 cents in travel you get, but as 1.5 cents plus the airline miles those 1.5 cents in airfare will earn.

Did you catch the switch? All the work here is being done by the value of a dollar, a value which the blogger then assigns to whichever credit card has the highest signup bonus this week.

I thought of this yesterday because I'm in the process of booking a couple of spring and summer trips, and found myself in a somewhat related situation.

A Southwest Business Select fare buys a lot of Wanna Get Away fare

When I was booking my Southwest ticket to Montego Bay using US Bank Flexpoints, I booked a Business Select fare since Wanna Get Away fares weren't available and the difference in cost between Business Select and Anytime didn't move my fare into a higher Flexperks redemption band.

This creates the somewhat interesting situation wherein I redeemed 50,000 Flexpoints, worth $500 in cash, for a ticket worth $953.61, and earned 9,336 Rapid Rewards points, worth roughly $93 in Ultimate Rewards points I wouldn't have to transfer to Southwest in the future.

That future turned out to be yesterday, when I booked a ticket to Las Vegas for dates when Wanna Get Away fares are available. Since my ticket cost about 16,000 Rapid Rewards points, I only had to transfer 7,000 Ultimate Rewards points, worth $70, to Southwest to buy my ticket.

Now, it's worth saying that actual Southwest Airlines enthusiasts don't run into this situation: they book Wanna Get Away fares on every flight they're even remotely considering taking as soon as the schedule opens up, knowing they can cancel all their unwanted flights up to 10 minutes before departure.

But since I'm not a Southwest enthusiast, I was pleasantly surprised to see my best, cheapest choice for one flight earn over half the cost of my next flight on Southwest, which was also my best, cheapest option.

My first Delta Pay with Miles redemption

As long-time readers know, I earn 1.4 miles per dollar spent on my Platinum Delta SkyMiles American Express card by spending $50,000 each calendar year (or sometimes slightly more for technical reasons).

In order to break even against a 2.105% cash back credit card, my overall objective is to get about 1.5 cents per SkyMile on my award redemptions. If I can break even on my spend in that way, then I'll end up paying a $195 annual fee for 20,000 Medallion Qualification Miles and a domestic economy companion ticket.

Meanwhile, Delta-operated flights have a kind of "floor" on redemptions of 1 cent per SkyMile, since you can use Delta's Pay with Miles feature to reduce the price of revenue tickets by that amount: 10,000 SkyMiles reduces the cost of your ticket by $100, for example.

With all that said, today I made two Delta SkyMiles redemptions, both below my target threshold of 1.5 cents each!

I needed to book two one-way tickets, with a retail price of $362.80 and a SkyMiles award ticket price of 32,500 SkyMiles and $5.60 in fees. That produces a redemption rate of 1.1 cents per SkyMile for an award ticket, or just 1.54% cash back for purchases with my American Express card. Since I had the SkyMiles in my account, and I know my miles are worth nothing until they're redeemed, I booked my partner's ticket that way.

For my own ticket, I used the Pay with Miles option to redeem 35,000 SkyMiles against $350 of the fare, and pay $12.80 in cash for the remainder, getting exactly 1 cent per SkyMile in value. However, since Pay with Miles tickets now earn Medallion Qualification Miles, I'll also earn 2,663 Medallion Qualification Miles for the ticket. Compared to the award ticket redemption I booked for my partner, I'm paying 2,500 SkyMiles and $7.20 for 2,663 Medallion Qualification Miles.

From a pure imputed redemption value perspective, these two redemptions together leave me with a shortfall of $305.30, getting just $707.20 in cash value compared to the $1,012.50 I needed to break even on the prorated amount of spend (67,500 out of 70,000 SkyMiles).

What do these redemptions have in common?

I connected these redemptions in my mind because I happened to be making both of them on the same day. But they also both illustrate that, for me, there's no such thing as the perfect redemption: there's only the perfect redemption for the moment.

Instead of refusing to fly Southwest unless there were Wanna Get Away fares available, I redeemed fixed value points for the flights I actually wanted to take, and earned a boatload of Rapid Rewards points towards a future redemption. On the other hand, instead of redeeming SkyMiles at a low valuation, I redeemed them at an even lower valuation in order to accumulate a few thousand more Medallion Qualification Miles.

Finally, what all these redemptions have in common is that they let me pay as little as possible for the trips I want to take. And that, for me, is what travel hacking will always be about.

Conclusion

While the affiliate blogger version of this phenomenon is a barely-concealed attempt to sell credit cards, there's another element that rings perfectly true: earning a combination of fixed-value points, flexible points, and brand-specific currencies may give you the opportunity to leverage currencies against each other.

On the other hand, such a combination may cause you to orphan points in multiple programs without every getting sufficient value from any of them.

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.

Hotels

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.

Restaurants

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.

Conclusion

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.

I don't buy points, but maybe you should!

Every major loyalty program sells their points for cash, normally at a fixed rate through the industry-sponsored site Points.com.

For example, you can buy up to 60,000 Delta SkyMiles per calendar year for 3.76 cents each, up to 75,000 United MileagePlus miles for 3.76 cents each, up to 150,000 American AAdvantage miles for 3.19 cents each, and up to 60,000 Alaska Mileage Plan miles for 2.96 cents each.

Hotel programs likewise sell their points currencies for cash, with IHG Rewards Club selling up to 60,000 points for 1.15 cents each, Hilton HHonors selling 80,000 points for one cent each, Marriott Rewards selling up to 50,000 points for 1.25 cents each, Starwood Preferred Guest selling up to 30,000 points for 3.5 cents each, and Hyatt Gold Passport selling up to 55,000 points for 2.4 cents each.

Purchased points are too expensive for me

I don't personally buy miles or points because it's a more expensive way of acquiring miles and points than the other methods I have available.

United MileagePlus miles and Hyatt Gold Passport points cost just 1 cent each when purchased with Ultimate Rewards points transferred from a Chase Ink Plus account.

I happen to have a Citi AAdvantage Platinum Select MasterCard, so if I ever needed to stock up on AAdvantage miles, I can do so for 2.105 cents each — the cash back I'd earn manufacturing the same unbonused spend on my Barclaycard Arrival+ MasterCard.

And of course I earn 6 HHonors points per dollar spent with my American Express Hilton HHonors Surpass card at grocery stores, so even compared to an "optimal" redemption rate of 2 cents per US Bank Flexpoint, I'm already buying HHonors points at a mere 0.67 cents each, 33% less than the 1 cent per point Hilton wants to charge.

Purchased points may make sense for you

As the examples above make clear, the decision whether to purchase miles and points or manufacture them rightly depends upon your next best alternative: your opportunity cost.

If you're currently manufacturing the bulk of your otherwise-unbonused spend on a 5% cash back card like the Wells Fargo Rewards Visa during the introductory promotional period, then manufacturing spend on a one-mile-per-dollar card costs not 2.105 cents per mile, but 5 cents per mile, 57% more than, for example, American is willing to sell them!

Likewise, if you have $100,000 on deposit with Bank of America, you might be earning 2.625% cash back with a BankAmericard Travel Rewards card. That may make purchasing Hyatt Gold Passport points at 2.4 cents each worthwhile, compared to manufacturing spend on a Chase Hyatt credit card.

Purchase small numbers of points for high-value, upcoming redemptions

While you usually see affiliate bloggers advocate buying large numbers of points speculatively when loyalty programs offer the highest bonuses on purchased points (bringing down the cost per point), I have exactly the opposite view.

If you find yourself with an upcoming, high-value redemption, and don't have the time to manufacture the required points, then go ahead and buy them. Paying "too much" per point, if it drastically brings down your total out-of-pocket cost, makes perfect sense: the goal isn't to pay as little as possible per point, it's to spend as little money as possible on the trips you actually want to take!

But the money you spend speculatively buying miles for redemptions you don't actually have planned could almost invariably be better spent building a credit card and manufacturing spend strategy that generates the trips you want to take at far lower out-of-pocket expense.

Excited about Ultimate Rewards transfers to Flying Blue? Let's talk about it

In case you've been staying in a buddhist travel hacker monastery for the last week, the big news to come out of the loyalty world this week was the unannounced addition of Flying Blue, the loyalty program of Air France and KLM, as a transfer partner for "flexible" Chase Ultimate Rewards points.

This post is going to come across as a bit cynical, so in the hopes of heading off sniping in the comments, let me first explain why this is phenomenal news.

Korean Airlines is not a great Skyteam program

While it's true that Ultimate Rewards already had transfer partners in oneworld (British Airways), Star Alliance (United), and Skyteam (Korean Airlines), Korean Airlines SKYPASS is a notoriously complex program to work with, with the gaping drawback that you can only book award tickets for relatives — and if you take them at their word, that even excludes stepchildren!

By contrast, Flying Blue has an online award search engine that allows you to book award tickets for anyone you like (as long as you don't get caught in one of their fraud traps).

Ultimate Rewards is a vibrant and growing program

Any expansion of a loyalty program to include new ways to earn or redeem points is an objective positive. If I never book a Flying Blue award ticket, I'll still be glad to know that it's someone's job at Chase to hunt down loyalty programs, negotiate transfer agreements, and implement the technology required to expand our Ultimate Rewards redemption options. To me that's a sign that the program still has a degree of vibrancy and is not yet ready to stagnate, like American Express Membership Rewards.

With that out of the way, let's talk about Flying Blue redemptions.

Delta makes life as hard as possible for their partners

To understand how difficult it is to redeem Flying Blue miles on Delta, it's important to understand how Delta makes award space available to its own members and to partners.

Delta dynamically prices awards for its own members. It's no longer rare to find cases where the constituent flights on a connecting award ticket are more or less expensive than the complete itinerary. Here's an itinerary connecting in Minneapolis that's more expensive than either of the constituent flights on their own:

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The constituent flights price at 12,500 SkyMiles:

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And 11,500 SkyMiles:

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Unrelated to SkyMiles pricing for their own members, Delta makes some seats on some flights available to partners for awards.

Let's see those same three searches using Alaska Airlines Mileage Plan. Here's the first leg (it's 25,000 instead of 12,500 because I'm searching for one-way flights):

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Here's the second leg:

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Here's the catch: Delta doesn't make that complete itinerary available to partners, which we can only surmise is because it prices higher at the 15,500-mile level. Here are the only options Alaska shows when doing a one-way search between BWI and MSO on September 19:

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Fortunately, Alaska allows you to construct your own Delta routing as a "Multi-city" flight search. By feeding Alaska the flights I know have award space (because I checked earlier), I can easily produce my desired award:

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It's important to understand exactly what's happening here: Delta is making its cheapest award space available to its own members and to partners on individual segments, but charging its own members more on the complete itinerary and not making that complete itinerary available to partners. The reason the Alaska workaround works is that Alaska is willing to search for each leg individually in a multi-city search, and then price the entire itinerary according to its own routing rules, which make it a valid one-way itinerary.

Flying Blue does not allow multi-city awards to be booked online

This is what Flying Blue's multi-city search engine looks like:

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Flying Blue doesn't let you construct Delta itineraries online because your final destination must be your originating airport.

I assume you could construct this itinerary over the phone

Good luck with that.

Conclusion: how I'll be using Flying Blue

So Flying Blue isn't the key to unlimited cheap flights on Delta. That doesn't mean it's useless! On the contrary, it's going to be one of my first stops along with Alaska, British Airways, and United, each time I start planning a new trip. The search engine makes it easy to see at a glance whether there are award seats available, and if there are, they will usually be among the cheapest, not because of their great award chart or their low fuel surcharges (on the contrary, they have a fairly standard award chart and pass along fuel surcharges to customers), but because the miles themselves are so cheap when transferred from a Chase Ultimate Rewards account.

To make the same point another way, a redemption of 12,500 SkyMiles manufactured with a Delta Platinum American Express card costs $188 in opportunity cost ($8,929 manufactured on a 2.105% cash back card), while a 12,500-mile Flying Blue redemption costs just $125 in Ultimate Rewards points: a 33.5% discount.

I don't expect those redemption to be very frequent — but I do expect to make them each and every time the opportunity presents itself!

Starting from scratch: alternative banking products

This week I've been writing about some strategies, credit cards, and loyalty programs I would use differently if I were building a travel hacking practice from scratch. If I were ignoring my elite status and current stable of credit cards, I'd focus even more on fixed-value points for use in booking airline tickets, and I'd ignore hotel loyalty completely in order to maximize my cash discount booking hotel nights through online travel agencies.

Today's post is about the alternative banking products I've used, abused, and lost throughout the last five or six years.

High-interest prepaid savings accounts

Back when CVS allowed virtually-unlimited numbers of Vanilla Reload Network reload cards to be purchased with credit cards, the American Express "old" Blue Cash offered unlimited 5% cash back, and the Hilton HHonors Surpass American Express gave 6 HHonors points per dollar spent at drug stores, there was a constant search for new prepaid products that could be loaded and unloaded as quickly as possible through the Vanilla Reload Network. I burned through 3 MyVanilla accounts, 2 Netspend accounts, and a Momentum account all in order to liquidate as many Vanilla Reload Network cards as possible.

In hindsight, with Vanilla Reload Network cards today mostly unavailable to credit card users, that was a mistake: Netspend and Momentum offer savings accounts with higher FDIC-insured interest rates than those available anywhere else in the market today, and I'd prefer to still have working relationships with those companies.

American Express prepaid banking products

Like most aggressive users of American Express's Bluebird and Serve prepaid products, on January 8, 2016, my accounts were all closed. I had been using both accounts to liquidate PIN-enabled prepaid debit cards for free, and in the case of Serve, earn cash back by loading funds from my Fidelity Investment Rewards American Express card.

If I were starting over today, I wouldn't use American Express prepaid banking products to manufacture spend at all: I'd use them to manufacture transactions for high-interest savings, checking, and credit card accounts that require a certain number of transactions per month to unlock their highest reward levels.

Conclusion

I don't have any regrets about the path that my travel hacking practice has taken, even though I focus more on airline and hotel loyalty currencies than I would if I were starting from scratch today.

I probably slightly overpay for my checked bags by earning Delta Medallion elite status with a Delta Platinum American Express each year, and I earn only part of that value back with high-value SkyMiles redemptions.

Likewise, I tend to overpay for my hotel stays by earning Hilton HHonors points and Diamond elite status with my Hilton Surpass American Express, instead of booking through a cashback portal and online travel agency, and I've certainly overpaid by directing stays towards Hyatt during this year of my Diamond status match.

But building relationships with banks and merchants is a process that necessarily develops over time, and as things stand I'm more or less happy with the decisions I've made and the relationships I've built, even if I would have proceeded different in hindsight.

I'd sure kill for another shot at a Serve account, though.

Starting from scratch: airline tickets

Travel hacking is an iterative game: the options you have available today are restricted by the decisions you made in the past. That's one reason I avoid giving advice whenever possible: your situation is different from mine, not just depending on the merchants you have available geographically, but also depending on which banks you have relationships with, which products you've already had or lost, and the amount of time you have available to dedicate to the game.

Having said that, I do sometimes think about how I would design a travel hacking strategy from scratch: with a blank slate, what approach would I take to the loyalty ecosystem to get the most value for my travel hacking dollar?

Today's post is about how I would approach booking airline tickets if I were starting from scratch. Tomorrow's will be about hotel stays.

Revenue versus award

Starting from scratch, there's a basic decision you have to make about how to pay for the flights you're responsible for securing each year: will you book revenue tickets or award tickets? Once you're deeply involved in the game you may have large balances across a range of programs you can deploy for their optimal uses. But when you're just getting started, it's much easier to focus on this stark choice.

When booking revenue tickets, you'll usually get a fixed return on your travel hacking dollar, or one that falls in a relatively narrow band: US Bank Flexpoints are worth 1.33 to 2 cents each, Chase Ultimate Rewards points in a premium (Ink Plus or Sapphire Preferred) account are worth a fixed 1.25 cents each, and Citi ThankYou points are worth between 1.25 cents and 1.6 cents depending on whether you have a Premier or Prestige card, and the airline marketing the flight.

When booking award tickets, there's no such band of values: points can range in value from a fraction of a penny up to 10 cents or so depending both on the cash price of the flight and the number of miles required to book it.

Note that neither of these options is any more or less "free" than the other. Since you should be manufacturing spend furiously, you're paying acquisition and liquidation fees for whichever currency you happen to choose. The only question is which strategy will bring the cost of your travel down the most.

Revenue tickets are cheap

On the revenue side, there are lots of good options depending on your situation:

• Citi ThankYou Premier. A fixed 3.75 cents in airfare per dollar spent at gas stations. At $5.75 in "all-in" cost for $505 in spend, a 69.6% discount off retail.
• US Bank Flexperks Travel Rewards. Up to 4 cents in airfare per dollar spent at grocery stores or gas stations (wherever you spend more each month). At $6.30 in "all-in" cost for $506 in spend, an "up to" 68.9% discount off retail.
• BankAmericard Travel Rewards. For those with $100,000 on deposit with Bank of America, Merrill Lynch, and MerrillEdge, a fixed 2.625 cents in airfare per dollar spent everywhere. At $4.30 in "all-in" cost for $504 in spend, a 67.5% discount off retail.
• Chase Ink Plus. For small business owners, a fixed 6.25 cents in airfare per dollar spent at office supply stores (and 2.5 cents per dollar spent at gas stations). At $9.18 in "all-in" cost for $309 in office supply spend, a 52.5% discount off retail.

When I say "depending on your situation," I mean to draw attention to the fact that you when starting from scratch, you shouldn't pursue all four options! If you don't have access to gas station manufactured spend, the Citi ThankYou Premier won't work for you. If you don't have access to grocery store manufactured spend, the Flexperks Travel Rewards card isn't for you. If you don't have access to $100,000, the BankAmericard Travel Rewards card won't give you the same value it will someone who does. And if you don't own a small business, Chase probably won't give you an Ink Plus.

Award tickets are cheap and (can be) hedged

On the award side, the picture looks radically different. Three of the four major domestic airlines offer some form of "last-seat" availability on their own flights: Delta, American, and Alaska will sell almost any seat on almost any date for some number of miles, while United reserves last-seat "standard" availability to their co-branded Chase credit cardholders. Thus there are three pots airline rewards currencies fall into:

• Delta. When starting from scratch, there are two main ways into the Delta ecosystem: their own co-branded credit cards, and American Express Membership Rewards co-branded credit cards. Unfortunately, neither of them is cheap. The American Express Delta Platinum and Reserve credit cards offer 1.4 (Platinum) and 1.5 (Reserve) SkyMiles per dollar spent everywhere when you spend exactly $25,000 (Platinum) and $30,000 (Reserve) and $50,000 (Platinum) and $60,000 (Reserve) each calendar year. But the Delta Platinum card costs $195 per year and the Reserve $450 per year! Meanwhile, the American Express Premier Rewards Gold costs $175 per year and earns 2 Membership Rewards points per dollar spent at gas stations and supermarkets. Those points can then be transferred to Delta on a 1-to-1 basis. Moreover, Membership Rewards points let you hedge your downside risk: if a particular Delta award redemption gives you less than 1 cent per Membership Rewards point, you can book it as a revenue ticket. If it gives you more than 1 cent per point, you can book it as an award ticket.
• Alaska and American. Advanced travel hackers muck about with applying for Alaska and American co-branded credit cards over and over again at various intervals. But when starting from scratch, there's a simple way into both ecosystems at the same time: with the Starwood Preferred Guest American Express. When transferred to either Alaska or American, the card earns 1.25 miles per dollar spent everywhere, which is higher than the amount you can earn directly with either airline's co-branded credit card. Like Membership Rewards points, Starwood Preferred Guest also offers a hedged downside risk, since you can redeem their points for between 1 and 1.43 cents per point for revenue tickets using "SPG Flights."
• United. If you're able to make United your main airline, then you'll never do better than with a Chase Ink Plus small business credit card, because of its bonused earning rate at office supply stores and 1-to-1 transfer ratio to United MileagePlus. But if you can't get a small business credit card, then you have some hard decisions to make. You could get a Chase Freedom Unlimited, which earns 1.5 Ultimate Rewards points everywhere, and a Chase Sapphire Preferred, which enables the transfer of Ultimate Rewards points to United, but that combination comes with a $95 annual fee. Alternatively, a Chase United MileagePlus Club card earns 1.5 United miles on all purchases but has a $450 annual fee. That's the kind of up-front expense that's not precisely crazy, but needs to be well-justified before taking it on.

Your situation should drive your decision between revenue and award tickets

As I mentioned, I try not to give advice.

Your situation is different from mine: your award availability, typical revenue flight prices, and airline service have nothing to do with mine.

But in my experience, for many people, much of the time, a focus on revenue tickets will generate bigger savings than a focus on award tickets, and if I were starting from scratch, that's where I'd start.

Fortunately, you don't need to take my word for it: all the numbers are above. Look at your own travel needs and it should quickly become obvious whether revenue flights or award flights will generate more value for your travel hacking dollar.

Tomorrow, I'll take the same approach to hotels: starting from scratch, are award nights really cheaper than just paying for your hotel stays?

Anatomy of an Award Trip: Spring Break in San Francisco

If you follow me on Twitter (as you should!) you know I spent last week in San Francisco. It was only upon returning that I realized I hadn't posted an anatomy of the award trip. Better late then never!

Getting there: Amtrak's California Zephyr

This was my last long-haul Amtrak sleeper cabin redemption before the December 8, 2015, revenue-based Amtrak Guest Rewards devaluation. I transferred 40,000 Chase Ultimate Rewards points to Amtrak Guest Rewards points for a 2-zone bedroom reservation between Chicago and San Francisco on the California Zephyr.

Total cost: 40,000 Amtrak Guest Rewards points, transferred from Ultimate Rewards. Total value: $1,246. Value per point: 3.12 cents per Ultimate Rewards point.

Staying there: Hyatt Fisherman's Wharf

As a newly minted Hyatt Diamond, I was eager to see what all the fuss was about and booked a 5-night Points + Cash reservation at the Hyatt Fisherman's Wharf, and applied one of my 2015 Suite Upgrade Awards.

Total cost: 37,500 Hyatt Gold Passport points and $582.25. Total value: $1,769.96. Value per point: 3.17 cents per Ultimate Rewards point.

I then earned 3,250 of those points back, bringing my final value per point to 3.47 cents per Ultimate Rewards point. Note that this value is based on an ordinary room reservation, not a suite reservation, since I could have applied a Suite Upgrade Award to either type of reservation.

Getting back: Delta first class tickets

To get back, I employed a strategy I use increasingly often: I booked my partner on an award ticket and myself on a paid ticket using a Delta voluntary denied boarding voucher. My partner doesn't play the game at all (besides traveling with me) so I don't make any attempt to get her elite status or earn bonus miles in her accounts.

Total cost: 37,500 Delta SkyMiles and $5.60, plus $729.10 in voluntary denied boarding compensation. Total value: $1,458.20. Value per point: 1.93 cents per SkyMile.

Conclusion

From my point of view, this award trip was quite close to ideal: I redeemed points I earned extremely cheaply for relatively expensive reservations.

In the case of Ultimate Rewards points redeemed at 3 cents or more per point, I earned close to 15% back on spend I manufactured with Ultimate Rewards-earning credit cards in their 5-points-per-dollar bonus categories.

In the case of Delta SkyMiles earned at 1.4 SkyMiles per dollar spent with my American Express Delta SkyMiles Platinum credit card, I earned roughly 2.7% back when redeeming those miles for my partner's first class ticket, which is quite strong for unbonused manufactured spend.

And of course when redeeming Delta voluntary denied boarding vouchers for my own travel, I came out ahead simply by being able to redeem it at face value.

Tune in tomorrow for some reflections on the train ride, hotel stay, and my impressions of a 5-day visit to the bay area!

What revealed preferences have taught me about valuing miles and points

One fascination of the miles and points community is "valuing" their loyalty currencies. This should be, in principle, one of the most important aspects of an earning strategy: earn more valuable points before less valuable points is a mantra as obvious as it is useless.

But determining the value of points is vigorously disputed terrain.

Hotel Hustle can tell you the value other people are getting for their hotel points

I love Hotel Hustle, and write about it relatively often. It has two relevant features here: you can plug in your own points valuation and search by "Hustle Hotness:" what percentage of your assigned value you're getting at each property in your search destination.

But additionally, Hotel Hustle will show you the range of values other people using Hotel Hustle have found on their own, real-world searches.

For these purposes I've always like the median value, which has 50% of search results giving more value, and 50% of searches giving less value. So across all the tabulated Hotel Hustle search results, you can see that Hilton HHonors points are worth a median of 0.44 cents each.

That doesn't mean you'll get 0.44 cents per point, but it's a benchmark you can use to evaluate your earning and burning decisions, and it's based on real-world award search results.

Affiliate bloggers make up values depending on which way the wind is blowing

Bankrate.com employee Brian Kelly will tell you each month what cards have the biggest affiliate payouts.

Likewise Thought Leader from Behind Gary Leff will periodically post his updated points valuations.

And of course Rich Weirdo Ben Schlappig has a whole page devoted to valuing miles and points.

Here are the values revealed preferences show for the miles and points I earn

The concept of "revealed preferences" is a powerful one in behavioral economics. Rather than attempting to establish the value of goods in the abstract, or by measuring quanta of pleasure, revealed preferences allow you to determine a good's value to the consumer by the price they're actually willing to pay for it. Revolutionary, right?

So here are the values I actually put on my miles and points, determined strictly by what I do, in fact, pay for them each month:

• 1.4 SkyMiles are worth about 2 cents. When buying cheap, PIN-enabled prepaid debit cards at unbonused merchants, I split my purchases between my American Express Delta SkyMiles Platinum Business card and my 2% and 2.105% cash back cards. My indifference between earning 1.4 SkyMiles and 2% cash back means I value SkyMiles at about 1.43 cents each.
• 6 Hilton HHonors points are worth up to 4 cents in airfare. I only have a single local grocery store that sells PIN-enabled prepaid debit cards, and I can choose between using my American Express Hilton HHonors Surpass card or my US Bank Flexperks Travel Rewards card. I use my Surpass card, valuing each HHonors point at up to 0.67 cents in paid airfare.
• 2 Ultimate Rewards points are worth slightly less than up to 4 cents in airfare. As above, I have a single local merchant that codes as a gas station and sells PIN-enabled prepaid debit cards. I could use either my Chase Ink Plus or my US Bank Flexperks Travel Rewards card for purchases there, but lean towards the Flexperks card, valuing an Ultimate Rewards point at slightly less than up to 2 cents in paid airfare.

Conclusion: my values aren't yours

My situation is unique, as is yours. I travel all the time, and am dedicated to keeping my rewards balances as low as possible, meaning I'm not stockpiling millions of any one currency. Instead, I'm redeeming miles and points roughly as quickly as I redeem them, giving me lots of "gut-check" opportunities to see whether I'm getting enough value from my rewards currencies to justify earning more of them.

For example, in January I had decided to cancel my American Express Delta SkyMiles Business Platinum card, when a health emergency in the family caused me to redeem most of my SkyMiles balance at a value of over 5 cents per SkyMile. With an empty SkyMiles account, and the possibility of future urgent travel, I decided it made more sense to keep the card and pay 1.43 cents per SkyMile again this year.

Likewise, just this week I redeemed 20,000 US Bank Flexpoints for a first class flight that otherwise would have cost $343. Alternatively, I could have redeemed 27,440 Ultimate Rewards points (at 1.25 cents each), making me feel fantastic about earning 2 Flexpoints per dollar instead of 2 Ultimate Rewards points per dollar at my local gas station.