Maximize Monday: Getting The Most Points Out of Double and Triple Dipping When Booking Travel

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Update: Some offers mentioned below are no longer available. View the current offers here – The Enhanced Business Gold Rewards Card from American Express OPENThe Platinum Card from American Express

When I checked my Delta SkyMiles and Starwood Preferred Guest accounts the other day, I noticed that my SPG/Delta Crossover Rewards had kicked in and I had started earning Delta miles on my Starwood stays and Starwood points for my Delta flights.

The Delta miles I earned from my Starwood stays.
The Delta miles I earned from my Starwood stays.

At first I was happy to note that I was double dipping in a sensible manner and had ended up with nearly 1,000 bonus Starpoints. But the more I thought about it, the more I realized that even though I was earning both points and miles on my stays and flights with these two particular brands, when it comes to booking travel – and even general spending – I don’t always maximize the way I spend my money so that I earn the most points from my purchases. And I’m not alone.

And I got SPG points for the flights I took.
And I got SPG points for the flights I took.

Although there are obvious ways to maximize the points and miles you earn on purchases, such as using an airline or hotel co-branded credit card to earn bonus points on purchases with a particular airline or hotel, or using the Sapphire Preferred to earn 2X points per $1 on travel and restaurant spending, this is only just scratching the surface of earning the most points per dollar, and there are several other factors to consider, like going through an online travel agency (like Travelocity), using shopping portals, and even purchasing gift cards to earn even more points per dollar.

So I thought I’d put together a Maximize Monday post on making the most of your travel purchases as well as your everyday spend.


Although it might seem like booking airfare through an airline’s website using a co-branded card that earns 2-3 miles per dollar you spend might be your best option, it actually pays to look at what other bonuses are available through shopping portals as well – especially because unlike hotel points programs, even if you buy airfare through an aggregator like Expedia or Orbitz, you still earn the miles and elite credit for the flights you fly.

Most of these online travel agencies offer the same airfares as booking directly through airline websites and some are even better at displaying your options, especially if you’re trying to compare prices among airlines.

Not only that, but several of them regularly offer online shopping portal bonuses and you don’t even have to use your associated credit card. For example the Chase Sapphire Preferred Ultimate Rewards shopping portal is currently offering 2 extra points per $1 when you navigate through it to Travelocity for a total of 4 Ultimate Rewards points per $1 you spend there using your Sapphire Preferred. That’s the equivalent of 4 miles or points with the program’s several travel partners (which include United, Southwest, British Airways, Korean Air, Virgin Atlantic, Hyatt, Marriott, Ritz-Carlton, Priority Club and Amtrak) per $1 – a great value bonus.

You can earn even more bonus points by going through a shopping portal first. These are the current Ultimate Rewards bonuses.
You can earn even more bonus points by going through a shopping portal first. These are the current Ultimate Rewards bonuses.

The downside is that if you do this, you won’t be earning a purchase bonus by using a particular co-branded credit card to buy tickets on that airline, but I’d take 4X Ultimate Rewards points over 2X miles any day.

Just as a note, Ultimate Rewards is currently only offering 1 extra point per $1 at Expedia, Hotwire, Priceline and Orbitz, though these bonuses often change.

Then remember, that many of these sites have their own rewards programs allowing you to double dip. For example, Expedia offers  1 point for every $2 spent on flights. You can then redeem those points for flights at a ratio of 1 cent apiece (up to 2 cents apiece when redeeming for hotels). So you are getting an extra 0.5% return on your spending.

It’s not just Chase, either. American Express Travel offers an additional Membership Rewards point for all flights booked through them. There is sometimes a small fee of about $5 tacked onto flights you book through Amex travel, but sometimes the extra Membership Rewards point per dollar spent will be more valuable than the fee paid. If you use the Premier Rewards Gold or Business Rewards Gold cards to purchase airfare, you earn a base of 3x points when you book directly with airlines, so the additional Amex Travel point brings the total points per dollar for airfare to 4X, another great value. If you have one of Amex’s other Membership Rewards-earning cards like the personal or business Platinum cards, you will still be earning 2X points per $1.

Top Credit Cards for Airfare

When it comes to purchasing airfare, it pays to know the bonuses your individual cards offer – apart from those of an airline co-branded card. Here are some of the top non-airline credit cards to consider using to buy your tickets.

Amex Premier Rewards Gold and Business Gold Rewards Card from American Express OPEN: You earn 3x points on flights booked directly with airlines, and then you can transfer those American Express Membership Rewards points to any of 17 airline partners. When you hit $30,000 in spend per calendar year, you also get a 15,000-point bonus on the Premier Rewards Gold – making up to a 50% bonus on your earning.

Chase Sapphire Preferred: This card earns 2 points per $1 spent on travel, including airfare – and that actually ends up being 2.14 points per dollar once you factor in the 7% annual points dividend.

Barclaycard Arrival: Both the card with an $89 annual fee (waived the first year) and the no-fee version offer 2X miles on travel purchases including airfare, which you can then redeem at a rate of 1 cent apiece and get a 10% miles refund after each redemption for a total 2.2% return on your spending.

US Bank FlexPerks Visa Signature: Both the personal and the business versions have the potential to earn 2 FlexPoints for every $1 spent on airline purchases if it’s the category you spend the most on that month.

Citi ThankYou Premier: This card earns 2 ThankYou points for every dollar spent on dining and travel in the first 12 months, and subsequently 1 ThankYou point for every dollar spent on purchases. However, it also earns 1 Flight Point for any airline flown that you use this card to purchase a ticket on. In addition to the ThankYou points you earn for the dollar amount spent on airfare, an equivalent amount of Flight Points will also be credited to you as ThankYou points, so essentially you’re getting double ThankYou points on this spending (quadruple in the first year). If you have the ThankYou Premier, you can then redeem those points for airfare at the rate of 1.33 cents each, so in the first year you have the card, you’re earning 5.32% back on airfare purchases, and 2.66% back after the first year.

Citi Hilton HHonors Reserve: Although it’s a hotel card, this one earns 5 Hilton HHonors points per $1 spent on airline purchases while the Hilton Visa earns 2 HHonors points per dollar on all purchases including airfare and both the Hilton Amex and the Hilton Surpass card each earn 3 points per $1 on purchases.

Starwood Amex: Though neither the personal nor business versions of this card have an airline category spending bonuses, you can convert those points at a rate of 1.25 miles each when you transfer points to your airline program of choice thanks to the 5,000-mile bonus on transfers of 20,000 points.


Just like with airfare, sometimes it can make more sense to book hotel stays through an online shopping portal like Ultimate Rewards or an online travel agency instead of directly through a hotel – especially if it’s not a chain or a brand you normally have points activity with.

With hotel points, it’s usually the case that you only earn points and/or elite credit if you book directly through the hotel, so if you go through an online travel agency, you might not be earning points or getting your elite benefits. However, many people report that they still do even when booking through an aggregator. It’s taking a chance, though.

The good thing about going through a shopping portal is that you are booking directly with the hotel, so you’re still earning the points you would otherwise, plus bonus points or miles.

Like with airfare, Ultimate Rewards usually offers plenty of bonus earning opportunities on hotel purchases. Right now, the Sapphire Preferred UR portal is offering 3 extra points per $1 at Holiday Inn and Express, Intercontinental, Best Western and Choice Hotels, and 2 extra points per $1 at plenty of others including Marriott and Westin. That’s all in addition to the 2X points per $1 you earn by booking hotels with the Sapphire Preferred, Ink Bold and Ink Plus cards.

Current Ultimate Rewards hotel bonuses.
Current Ultimate Rewards hotel bonuses.

Amex Travel offers cardholders one extra point for eligible travel purchases made on the American Express Travel website.

The other great thing is that in the case of hotels, many airline shopping portals offer bonuses as well. For example, American Airlines is offering 3 miles per $1 at Crowne Plaza and Candlewood Suites right now, and 2 miles per $1 at Choice Hotels, Country Inn and Suites and Best Western. But you can also earn bonus points at sites like and now as well if there are no hotels in your choice programs offering bonuses at the moment.

Then remember, if you go through a portal to an online travel agency, even though you might not earn hotel points, you can still earn points with that agency’s loyalty program if it offers one. For example, Expedia Rewards allows customers to earn one reward point for each dollar spent on hotels. Likewise, offers a 10% rebate off your hotel stays through its loyalty program.

If you are not planning to stay at a brand with which you want to earn points, you also have some other options where you can earn airline miles instead. New sites like Rocketmiles partner with hotels in various US cities to offer miles with travelers’ choice of American, Delta, United or Hawaiian Airlines (one-night stays usually generate between 3,000-5,000 miles). Pointshound is another such site that gives travelers an average of about 3-4 miles per dollar spent at hotels with United, Delta, Hawaiian and Aeromexico – and it recently added American Airlines and Virgin America as partners as well. Even if you are staying with one of your usual brands, you might choose this option from time to time if you’ve already hit your elite level goals or if you need to top up a mileage account more than you need the hotel points.

Top Credit Cards For Booking Hotels Of Any Brand

American Express Blue Sky Preferred (Update: This offer is no longer available.) offers double points for hotel stays booked directly with hotels. Points are worth 1.33 cents each, so hotel stays return 2.66 cents in value.

Chase offers a variety of cards that earn bonus points on hotel bookings. Both the Sapphire Preferred and J.P. Morgan Palladium earn double points on all travel, including hotels booked either directly or through online travel agents. But the Sapphire Preferred features a 7% annual points dividend for a total of 2.14 Ultimate Rewards points per dollar spent on hotels. Chase’s Ink Bold, Ink Plus, Ink Classic (but not Ink Cash) earn double points on hotel stays booked directly with hotels.

Capital One’s Venture card features double miles on all purchases, and each mile is worth one cent towards a statement credit against any travel expense, so you’re earning 2% back on your spend, including on hotels.

Barclaycard has recently gotten into the game as well. Like the Capital One Venture Rewards, the Barclaycard Arrival (the version with an $89 annual fee waived the first year) earns double miles per dollar spent, but with a 10% miles refund. Therefore, cardholders receive about 2.22 cents back in value per dollar spent as statement credits towards any travel expense.


This is probably the biggest factor that many of us overlook when trying to maximize our points earning. The fact of the matter is, though, that a little strategic spending can equate to tons of bonus points if you can take advantage of gift cards.

That’s because gift cards are sold at many merchants at which certain credit cards offer lucrative category spending bonuses such as office supply stores, gas stations and drugstores. So instead of simply going to a restaurant an using your Sapphire Preferred card, let’s say, for 2X points per $1, you could instead buy gift cards to a restaurant at Staples or Office Depot using your Ink Bold or Ink Plus cards and earn 5X Ultimate Rewards points per $1 instead.

Among the gift cards on display at stores that offer category spending bonuses for certain gift cards, you’ll often find restaurant and hotel gift cards in varying denominations as well as to other merchants like Petco, Nike, Regal Cinemas and even Southwest.

Specifically in terms of hotels, if you know you’ll be spending money at a certain hotel chain, you could purchase a gift card for that chain at a merchant with a big category spending bonus and earn a per-dollar points bonus while still being able to earn the usual hotel points for booking directly with a hotel.

For example, Marriott gift cards are sold at Staples, where Ink Bold and Ink Plus cardholders earn 5 Ultimate Rewards points per dollar spent. There are also Marriott gift cards at Lowes, which is eligible for 5x rewards with Chase Freedom during Q2 of 2013.

To take this even one step further, you can triple dip by going through an online shopping portal and seeing what bonuses these retailers is offering and click through the links to earn even more bonus points.

Earn even more points beyond category bonuses by going through a portal first.
Earn even more points beyond category bonuses by going through a portal first.

So for instance, right now, the Ultimate Rewards portal is offering 3X points at Office Depot and Office Max and 2X points at Staples. If you clicked through to Staples, then, and bought a Marriott gift card using your Ink Bold or Ink Plus, you’d earn 3X points per $1 plus the usual 5X points per $1 at office supply stores with those cards for 8X points per $1.

Then you could go back to the Ultimate Rewards travel portal, which is offering a bonus of 2X extra Ultimate Rewards points per dollar when you click through to Marriott and make a reservation. You would pay for your stay with the gift card, and still earn a total of 10 Ultimate Rewards points per $1 you spend! Normally you earn 10 Marriott Rewards points per $1 you spend, which I would value at about 0.5 cents apiece for a 5% return on your spending. But those 10 Ultimate Rewards points are much more valuable in my opinion – worth about 2 cents apiece – so I’d prefer them any day.

Now you see why sometimes people don’t take advantage of all these possibilities – there are a lot of steps involved!

Best Credit Cards For Gift Card Purchases

American Express: The Premier Rewards Gold offers 2X points at gas stations and supermarkets, where gift cards are often sold, and the Business Gold Rewards card offers 2X points at gas stations. The Hilton HHonors Surpass and Hilton Amex cards both earn 6X points at gas stations.

Chase: The Ink Bold and Ink Plus both offer 5X points at office supply stores and 2X points at gas stations.

US Bank: The US Bank Flexperks Travel Visa offers 2X points at gas stations or grocery stores (or airlines) depending on which is your highest expense per statement period.

Although it can mean extra work (and calculations!) doing a little bit of math, plotting our your spending and choosing the most lucrative strategy for your needs can reap potentially huge points bonuses for you, getting you to your travel goals even faster.

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