Quintuple Dipping: Maximizing Your Earning When Purchasing Travel

Key Links:

• Chase Sapphire Preferred
  
• Chase Ink Bold Charge Card and Ink Plus
  
• American Express Premier Rewards Gold

In writing about changes at Frontier Airlines, I explained some benefits of booking through an online travel agency like Expedia, Orbitz, and Travelocity.

• You can compare prices across several airlines in one place (though personally I use ITA Software’s Matrix website for this purpose).

• Combine more than one airline on a single ticket much more effectively than when booking through most individual airline websites.
• Use a foreign-issued credit card on the US website, not have to show the credit card at check-in (which some airlines still require when booking directly through them), and even choose which country your ticket is issued in (I can book through Expedia’s German, Spanish, Canadian or New Zealand websites for instance).
• Rebates in the form of cash back or points, you can check EV Reward to see which website will offer you the best return for the booking you plan to make.

In most cases the best part really is this last point. While Travelocity offers 2 points per dollar through the Chase Ultimate Rewards Mall (for users of Chase Sapphire Preferred as well as Ink Bold Charge Card and Ink Plus small business cards), I personally prefer Expedia. I like the interface better and I seem to be able to get the exact flights I want much more easily.

The nice thing about using Expedia, which offers 1 point per dollar through the Ultimate Rewards Mall, is that you can double dip with Expedia Rewards points as well.

In fact, you can double, triple, quadruple, and even quintiple dip when booking airline tickets. Which is why I love booking other peoples’ airline tickets so much, when they’re paying me back.

• Online shopping portal, such as the Chase Ultimate Rewards Mall (and other programs offer rebates as well, which you can look up at EV Reward).
  
• Online agency’s own rewards program, such as Expedia Rewards
  
• Earning miles from the credit card spend, which is often bonused — double points on all travel spend with Sapphire Preferred, triple points on airfare with American Express Premier Rewards Gold (I use the Amex Premier Rewards Gold for airfare spend, I do it enough that I’ll spend $30,000 on the card and earn 15,000 bonus points for it as well, and I do this going through the Chase Ultimate Rewards mall to Expedia.). You can also get up to 10% cash back on Travelocity purchases with the Travelocity American Express from Barclays.
  
• Small business rewards program, like American’s Business ExtrAA program, Delta offers Skybonus too.

I want to expand a little bit on this fourth point. Booking primarily my own travel with American I have a balance of 6000 Business ExtrAA points. That’s enough for a business class award ticket to Hawaii, or an Admiral’s Club membership and gifting someone Gold status.

I used to think you had to book at AA.com in order to be eligible for BusinessExtrAA points, but commenter al613 corrected me:

After I book @ XP I call AA business line and ask to add Xtra #. I have never heard from AA any negative feedback. reg. this. Also, they provide travel agency instructions to add Xtra number as the Tour code (doubt XP will do it for you) If it does not post I go to “request ticket credit”. Always posts then (couple month later). Just keep good records. Theoretically you can do it to any ticket number you get your hands on. No need to book it yourself

That’s great for an additional dip for air, but something similar now exists for hotels as well.

Expedia has just launched Business Rewards exclusively for Chase Ink cardmembers, where every 10 eligible ‘Expedia Special Rate’ hotel nights booked through Expedia from accounts linked to a business rewards profile will earn a $100 hotel discount.

The nice thing is that you can still go to Expedia through a shopping portal, can still earn points as you would otherwise (to the extent the hotel you book through Expedia is eligible), and still earn Expedia Rewards points as an individual even as a Business Rewards account also gets credit.

I don’t buy Expedia Special Rate hotels often, since I don’t earn elite status credit for them and in Starwood’s and Hilton’s program am not even entitled to elite recognition (although on those occasions I’ve booked a Starwood property through these sorts of channels I’ve actually had benefits honored, though it’s certainly at the discretion of the hotel to do so).

But it’s a good option, and when booking infrequent stayers — many of the folks whose travel I do book — the program is a nice option for an additional reward.

I’ve always thought there was a real opportunity in these business programs to reward the actual decision-maker as opposed to the traveler. Southwest Airlines was a pioneer in this with their secretaries program (and also in the late 70s they offered customers traveling on a company dime the ability to get rewarded with alcohol to take home if they bought up to a higher fare).

Regardless of who is being rewarded, these business programs offer a fourth way to earn when buying travel.

You earn points for your credit card spend, generally the Sapphire Preferred and American Express Premier Rewards Gold are the best card for buying airline tickets.

You earn points by going through a shopping portal to purchase those tickets, such as the Ultimate Rewards Mall to Orbitz, Expedia, or Travelocity.

You can earn points from the shopping portal itself.

And you can earn points by crediting travel to a business program in addition to a frequent flyer account.

Booking travel through Travelocity and paying with Chase Sapphire Preferred, you earn 4.14 points per dollar spent on travel.

Booking that same travel with an American Express Premier Rewards Gold (through the Chase portal you’ll still generally earn, though it can be a challenge if the points don’t post automatically to get Chase to post them for you) earns 5 points per dollar.

I give up one of those points booking through Expedia, but I also earn Expedia Rewards and earn free travel, and then get American’s Business ExtrAA to credit flights to their small business program earning flights or status or lounge access.

And that’s all in addition to earning standard loyalty program points so you can quintuple dip on your travel purchases.

So a reminder not to leave points or other credits on the table when booking travel for yourself and others!

(Note that the applications for credit cards mentioned in this post do earn me a referral credit, they’re also the best available offers I’m aware of, and I truly appreciate it.)