Mastering Double Dipping Points & Miles To Maximize Earnings

Since immersing myself in this hobby, I’ve become obsessed with double dipping points, constantly strategizing how to maximize my earnings whenever I buy groceries, dine out, or pay for internet services. The quicker I accumulate enough points for a trip, the sooner I can embark on it. As a points enthusiast, mastering the art of double-dipping points or leveraging multiple earning opportunities simultaneously is crucial.

Fortunately, award travel aficionados have numerous methods for double- and even triple-dipping their points.

Shopping Portals

Online shopping portals are a wonderful way to earn more rewards than you would by making purchases directly with a merchant, effectively double dipping points with just a few extra clicks, significantly boosting your earnings.

There are a few types of shopping portals: travel miles/points, cashback, and bank rewards. Which one you use depends on which type of rewards you value most.

If you’re serious about earning extra points, miles or cash back, I recommend making CashBackMonitor one of your go-to websites. The site lists a plethora of stores that partner with online shopping portals and their respective earnings. Not all merchants partner with every shopping portal, which is why it’s a great tool to start looking for potential double-dipping.

Let’s use Sephora as an example. The store offers 8% back on purchases made through the Top Cashback portal, 5X Avios per dollar spent via British Airways Avios eStore or 4X points per dollar spent with the Chase Ultimate Rewards portal.

I’m not much of a cashback person and don’t intentionally collect Avios, so in this case, I prefer earning 4X Ultimate Rewards points on my purchase. Their flexibility and the many redemption options are why I choose to earn UR points, and a quadruple bonus is a good haul.

So, here’s how you double-dip. Log in to your Ultimate Rewards portal, make a Sephora purchase via the special link and reap rewards. On a $50 purchase, you’ll earn 50 points on whichever credit card you use to pay plus 200 UR points in your Chase account—all for taking one extra step and making a purchase via the portal.

Keep in mind that taxes and shipping costs don’t earn portal points. Also, make sure that your computer’s cookies are activated for tracking purposes.

The bonuses vary, but online shopping portals become extra generous around holidays, such as Memorial Day or Thanksgiving, and increase their payouts at many stores. If you shop during these promo periods, you can earn more by making purchases you plan on making anyway.

Double Dipping Points With Dining Rewards

Going out to eat is another great way to earn extra points or miles.

Many domestic airlines, such as Delta Air Lines and Southwest Airlines, to name a couple, partner with Rewards Network Dining Rewards and offer extra miles for dining at select restaurants. To earn bonus miles, you must register via an airline program of your choice, save a credit or a debit card number and pay for your meal with the registered card. If you’re enrolled in multiple dining rewards programs, you can’t register the same card twice so pick carefully.

In this example, we’ll go with SkyMiles Dining, a program that earns bonus Delta SkyMiles. The website makes it easy to search for participating restaurants by location. Simply enter the city name and look through the available dining options.

As a regular member, you earn 1X mile per dollar spent at one of the participating restaurants, and yes, tips are included, so don’t be stingy. However, if you sign up for the program’s emails, you earn 3X miles per dollar spent. If you dine at least 11 times per calendar year and become a VIP member, you earn 5X miles per dollar.

To double-dip, pay for your meal with a registered credit card, preferably one that earns multiple points on dining, such as the American Express Gold Card or the Chase Sapphire Reserve®, and then earn SkyMiles on top. So, a $50 meal will net you either 200 Membership Rewards points or 150 Ultimate Rewards points plus 150 Delta SkyMiles if you’re subscribed to emails.

Because not many restaurants in my area participate in the rewards program, I don’t go out of my way to earn additional points through the dining network, but it’s always a nice bonus to see miles appear in your account unexpectedly.

MileagePlus X App

If you’re not familiar with MileagePlus X App, I suggest you rectify the situation this very second. As far as I’m concerned, it’s a gold mine for those who enjoy a bonus or two. Doesn’t that include you, too?

MileagePlus X is an app for your phone that offers an opportunity to earn United miles. It’s similar to online shopping portals in a way that it awards bonus miles, except you purchase electronic gift cards instead of merchandise. These gift cards can be used online or at brick-and-mortar stores and restaurants.

Because the gift cards can be redeemed at a physical store, you can earn extra miles on the go. When I shop at any store that sells gift certificates via MileagePlus X, I quickly buy one while at the register once I know the final amount and use it to pay for merchandise in my hands. This way I earn miles on my credit card and in my United MileagePlus account.

You can earn even more miles by holding a co-branded United credit card. If you simply link your MileagePlus Explorer Card or the no-fee MileagePlus Card to the app, you earn a 25% bonus on the total miles earned, and you don’t even have to use it to pay for your purchase.

Can I Triple-Dip on My Purchases?

Now that you know of all the ways to earn bonus miles, I bet the wheels in your head have started turning.

By choosing to shop with a merchant that appears in both the MileagePlus X app and one of the online shopping portals, you can stack all kinds of rewards on a single purchase.

To triple-dip, buy a gift card via the app, then use it to make a purchase via a shopping portal of your choice and enjoy your United miles, portal miles, and credit card points. Having a linked MileagePlus credit card will result in quadruple-dipping as you earn yet another bonus on the same transaction.

Let me help you visualize this mess. Say, you want to make a $100 purchase at Guess. Go ahead and buy a gift card via the MileagePlus X app (4X points), then use it at guess.com via the American Airlines AAdvantage eShopping portal (2X points).

In this scenario, you’ll walk away with 100 points on the credit card used to buy the gift card, 400 United miles for buying it through the app, 100 miles for having a co-branded United card linked to the app plus 200 AAdvantage miles by making the actual purchase through the AA shopping portal. You take just a few extra steps for 800 points versus 100 points for making the purchase directly at a Guess store.

Final Thoughts

Depending on each portal’s payout, your results will vary store to store. As mentioned before, shopping around certain holidays yields all kinds of bonus earnings, and a few hundred extra miles here and there can’t hurt. The quicker you earn, the more points you have to burn. Please let us know what kind of stacking opportunities you’ve taken advantage of in the effort to earn more miles.