Maximize Your Miles and Points by ‘Double Dipping’ on Purchases

If you take points and miles as seriously as we do here at Frugal Flyer, the goal should be to always optimize every dollar spent. Achieving this involves various strategies, including consistently utilizing your top-earning credit card for each merchant type, leveraging shopping portals, taking advantage of credit card offers, and participating in secondary loyalty programs. Yet, the real game-changer lies in combining multiple points-earning avenues into a single purchase, significantly supercharging your points accumulation.

Let’s delve into the concept of double-dipping and explore the plethora of opportunities available for points and miles enthusiasts who want to take their earning potential to the next level.

What is Double Dipping in Miles and Points?

Double dipping in the context of points and miles refers to the idea of earning points, miles, or a rebate from two or more sources on a single transaction. This can involve taking advantage of credit card rewards and offers, shopping portals, or loyalty programs, and stacking these rewards for greater earning potential. 

For example, let’s consider a scenario where a Marriott Bonvoy member utilizes their co-branded Marriott Bonvoy card to pay for a hotel accommodation. In doing this, they would stand to accrue Bonvoy points not only from their credit card but also from Marriott’s loyalty program, effectively earning rewards twice for the same transaction. This is double dipping in its most basic form; however, this strategy can be expanded upon and applied to our everyday and travel spending.

Shopping Portals

We’ve covered shopping portals extensively here on Frugal Flyer, as they are one of the most common and easiest ways to earn additional rewards on your online shopping activities. These websites partner with a wide range of retailers, offering members points, miles, or cash back when making purchases through its platforms. By making purchases through a shopping portal, you’ll earn rewards from both your credit card and the shopping portal.

This is made possible through affiliate marketing, whereby the shopping portal earns a commission for directing you to the retailer, and in turn, shares a portion of this commission with you as cash back, miles, or points, while keeping the rest for themselves.

If you’re unsure which shopping portal to use, a shopping portal aggregator such as Cashback Monitor is a good place to start. It allows you to compare earning rates across many shopping portals for each specific retailer. While Cashback Monitor is mostly tailored to US-based retailers, it does also include some Canadian retailers. 

Cashback Shopping Portals

There are numerous cash back portals available to Canadians, with the two most popular being Rakuten.ca and Great Canadian Rebates. These portals work with many popular Canadian retailer websites and payout a percentage of the purchase in the form of cash back. However, my personal favorite is actually the US-based Rakuten.com, which operates in the same manner, where members can earn cash back payouts via PayPal. 

Instead of just opting for cash back, the US-based Rakuten.com offers a much more enticing form of rewards for points and miles enthusiasts. Canadians who have access to US-issued American Express cards can choose to earn Membership Rewards points instead of regular cash back on Rakuten.com.

I primarily utilize Rakuten.com for booking travel-related expenses outside of flights and hotels. This can include booking cruises, car rentals, and tours through platforms like Booking.com and Viator. For example, on our recent trip to Vietnam we booked a 2-night Ha Long Bay cruise on Booking.com via the Rakuten.com shopping portal. This transaction earned us over 4,500 Membership Rewards on just $750 USD in spend. This is in addition to the rewards I would earn on my travel credit card.

Despite Rakuten.com being catered to those living in the US, Canadians can easily take advantage of the Membership Rewards earning opportunity that is offered here. The only prerequisite is holding at least one US-issued Membership Rewards-earning American Express card.  

Related: Guide to US Credit Cards for Canadians

If you haven’t acquired a US-issued American Express card, you can obtain your first one through Nova Credit or Amex Global Transfer. Moreover, if you haven’t acquired an Individual Taxpayer Identification Number (ITIN) yet, our ITIN service can help accelerate the process towards obtaining additional US credit cards, including Chase business cards.

Airline Shopping Portals

The alternative to cash back portals are airline shopping portals. Most of the major North American carriers operate their own shopping portal, offering members an additional avenue to earn frequent flyer miles. In addition to this, several of the financial institutions in Canada and the US operate a shopping portal where members can earn transferable currencies or cash back through online purchases. 

The most popular airline shopping portal in Canada is the Aeroplan eStore, which features over 250 Canadian retailers, making it a prime source for maximizing rewards on online purchases.

If you’re looking to expand your stash of points beyond just Aeroplan points, there are several US-based shopping portals that should warrant some interest. Several of the loyalty programs that are more challenging for Canadians to engage with, like American Airlines AAdvantage and Alaska Mileage Plan, run their own shopping portals. Moreover, Chase maintains a shopping portal, allowing members to leverage Chase Ultimate Rewards, one of the most powerful transferable currencies.

Another favorite of mine is British Airways Avios partnership with Airbnb. By simply routing your Airbnb bookings through the Avios Airbnb booking portal you can earn 2 Avios per £1/€1/$1 spent with Airbnb.

Finally, one of the best methods to maximize shopping portals involves buying gift cards at a grocery store using a 5x earning credit card such as the American Express Cobalt card or MBNA Rewards World Elite Mastercard. These gift cards can then be utilized alongside a shopping portal to further bolster the rewards you earn. However, it’s important to remember that you won’t have access to purchase protection typically offered by most credit cards, including extended warranties and theft protection. Therefore, this approach isn’t advisable for items where warranty coverage is important.

Linking Rewards Accounts

Ride Sharing Apps

Numerous loyalty programs accessible to Canadians have formed partnerships with others, enabling members to link their accounts and receive mutual rewards when utilizing any of the participating programs. Here in Canada, Aeroplan allows members to link their loyalty accounts with both Uber and Starbucks. 

Once your accounts are linked, you’ll automatically earn Aeroplan points when using these partner loyalty programs. Although the rewards through these affiliations are often quite modest, Aeroplan’s partnership with Starbucks does result in achieving the coveted triple-dip. This allows members to simultaneously accumulate three separate rewards currencies: credit card rewards, Aeroplan points, and Starbucks Stars while indulging in their coffee fix. Triple-dipping opportunities are few and far between, but I’ll cover some more examples later on. 

Lyft, the other major rideshare platform, also allows members to link their accounts with loyalty programs such as Hilton Honors and Alaska Mileage Plan. Moreover, Lyft and Chase have a partnership where Chase cardmembers can earn up to 10x Ultimate Rewards on Lyft rides. 

Gas Stations

Most of Canada’s prominent gas station chains run their own loyalty programs, while others opt to collaborate with other prominent programs in the country, enabling the linking of loyalty programs, similar to ride-sharing apps.

For example, Journie Rewards has partnered with Air Canada Aeroplan. This provides a straightforward path for members to double their rewards on their fuel spending. Simply use your preferred credit card to make purchases on gas or snacks, then scan your Journie Rewards card at any participating location. By doing this, you can earn rewards on your credit card while also accruing Journie Rewards, which can later be converted into Aeroplan points.

Similarly, ExxonMobil, which includes brands like Esso and Mobil have teamed up with PC Optimum, allowing members to double-up on their earnings at the pump. 

Further reading: Gas Station Rewards – Save Money & Earn Points at the Pump

These are only a handful of the numerous loyalty programs that can be linked. Others, such as World of Hyatt and American Airlines, exist as well, so there is no shortage of loyalty program linking opportunities to take advantage of.

Although none of the earnings from these kinds of partnerships are likely to be earth-shattering, they all play a role in maximizing every dollar you spend. So, while earning 300 Aeroplan points every now and then may not seem worthwhile initially, consistently capitalizing on promotions such as these over several years can make a meaningful difference to your points balances.

Retail Loyalty Programs

It seems like just about every merchant wants to have its own “in-house” loyalty program or app nowadays. These programs can be found across various sectors, including restaurants, clothing retailers, pet supplies, gas stations, and grocery stores. I recognize that a lot of people are experiencing “loyalty fatigue” due to the constant barrage of invitations to join new loyalty programs every time they make a purchase. Nevertheless, for those who regularly shop at a specific retailer, it’s usually beneficial to participate in their loyalty program.

While we always recommend trying to utilize as many retail loyalty programs as possible, if you prefer a simpler approach, just aim to focus on the retailers where you regularly spend. This will usually fall into categories such as groceries, gas, and pet supplies for many people. Although I no doubt enjoy a free McMuffin from McDonald’s as much as anyone, I try to focus on more lofty pursuits, such as offsetting purchases like car rentals, and airfares. 

This is where grocery store spending comes into play. Pairing what is most households’ largest expense every month, groceries, with a card that offers a high return on grocery spend can yield consistently lucrative double-dipping earning rates.

Loyalty programs like More Rewards, Scene+ Rewards, and PC Optimum all provide a reasonable return on grocery spend provided you’re able to maximize these programs. While you can redeem for free items from the grocery store, I’ve always found the best value lies in redeeming for travel with these programs.

For example, More Rewards points only offer a redemption rate of 0.15 cents per point when redeeming for free groceries, which works out to 10,000 More Rewards points for $15 off your grocery bill. However, when redeeming for travel, those same 10,000 More Rewards points are worth nearly triple the value, totaling $43.

Using our More Rewards points, we managed to completely wipe out the cost of our car rental during our trip to Ireland last spring. Moreover, earlier this year, we booked a positioning flight to Los Angeles ahead of our Starlux business class flight using exclusively More Rewards points. This same approach can also be applied at any major grocery chain in Canada to mitigate some of the costs that are typically more difficult to cover using airline miles and hotel points.

Credit Card-Linked Offers

Credit Card Offers

Many of the major card issuers in Canada and the US provide offer-based programs allowing you to earn cash-back as a statement credit or earn bonus points when making purchases with specific retailers. American Express, RBC Rewards, and Brim Financial are some of the institutions in Canada that provide offers linked to their respective credit cards. 

Most credit card offers are generally structured as “spend $X, earn $Y” at a specific retailer. To access offers related to your card, simply log into your online account to see what offers are available on your card. Select any offer you’re interested in to enroll in and then proceed to make a purchase using the enrolled card. Following your eligible purchase, you should see the cash back or bonus points reflected on your account.

Individuals with US-issued credit cards can take advantage of offers provided by American Express (US), Chase, Citibank, and CapitalOne. These programs operate much the same as American Express (CA) offers and allow cardholders to register their cards for specific retailers and receive rebates on their spending with those merchants when using their registered cards.

Welcome Bonuses

While welcome bonuses on credit cards may not fit the classic definition of double dipping, I think it’s reasonable to view them as such. Essentially, welcome bonuses are rewarding card holders twice for the same spend. Throughout the typical three-month welcome bonus period on most cards, you’ll accrue points from your regular spending alongside the eventual welcome bonus. By aligning the strategies outlined above, and concentrating the majority of your expenses towards securing a new welcome bonus, you can establish a consistent flow of points and miles.

Choosing the ideal credit card welcome bonus offer can frequently involve navigating through complex language and terminology. We’ve written a complete guide outlining the key factors to consider when evaluating a card’s welcome offer.

Also, remember that when applying for a new credit card through the FlyerFunds Rebates Program you can receive cash back after you are approved, which can help offset any annual fees.

Double and Triple Dipping on Annual Credits

Many credit cards, especially some premium cards issued in the US, provide credits that reset every calendar year. An example of this would be the US-issued American Express Platinum card (US) and American Express Business Platinum card (US), both of which have yearly $200 airline fee credits. If you can time your application appropriately, it’s possible to extract two (or more) uses of these yearly credits from a single annual fee.

An example workflow would look something like this:

• Open a new card that offers annual credits in early to mid-December. This should give you enough time to use the credit before the end of the current year.
• Once the new year rolls around, the yearly credit will reset. This gives you another credit to use. 
• Once your second annual fee is posted you’ll have 30 days from that date to close your account and have the annual fee refunded, which should now be mid-January of the following year. 
• Once the yearly calendar rolls over to a new year, the credit will reset again once more. This should allow just enough time to use the yearly credit for a 3rd time before closing the account.

If done correctly, you will end up utilizing 3 yearly credits and recouping at least $600 in your first cardmember year. You can apply the sequence outlined above to most credits that reset based on the calendar year. However, some credits are more challenging to liquidate than others, requiring some creative thinking to fully optimize their benefits.

Dining Rewards Programs

For individuals who spend time in the USA with any frequency, dining rewards programs offer another easy way to double dip when dining out. Many of the major US airlines like American Airlines AAdvantage, Delta SkyMiles, and Alaska Airlines Mileage Plan participate in a dining rewards program, allowing members to earn up to 5 miles per dollar spent at restaurants. Similarly, hotel loyalty programs, such as Marriott Bonvoy, Hilton Honors, and IHG Rewards also offer members an easy double dip on top of their preferred dining credit card. 

Earning rewards through any of these dining programs is extremely simple. Just link your credit card to your preferred dining rewards program and use that card for payment. No enrollments or online portals are necessary to start earning rewards.

Do note that these dining rewards programs are only applicable at dining establishments in the United States. Additionally, you can only link your credit card to one program at a time. Lastly, while hotel dining programs offer higher earning rates, airline miles generally hold greater value. Thus, opting for an airline loyalty program to earn rewards through dining is often more advantageous for the majority of people in most circumstances.

Miscellaneous Promotions

Occasional promotions like Edmonton’s Best Hotels and Stay Richmond offer an opportunity to earn extra rewards such as prepaid gift cards, gas cards, or dining cards. This presents another chance for double or triple dipping on a weekend getaway or a mattress run.

I like to view these promotions as an opportunity to acquire Marriott Elite Nights at a reduced cost. Additionally, even if reservations are not made directly through Marriott’s channels, you can still link your Marriott Bonvoy number to your booking to accumulate Bonvoy points, qualify for elite nights, and enjoy the privileges associated with your status.

Triple Dipping on Your Purchases

While double dipping is fairly commonplace and achieved with relative ease, triple dipping usually involves some more critical thinking and experimentation. Triple dipping usually requires utilizing multiple shopping portals in conjunction with rebates or discounted gift cards. I’ll provide a few examples of what to look for when seeking out opportunities such as these.

A typical workflow involving the use of gift cards could follow these steps: First, use a credit card to buy a gift card for a specific retailer via a shopping portal. Then, utilize the purchased gift card at the same retailer after accessing it through a shopping portal again.

If done correctly, you should earn rewards twice from the shopping portal in addition to the spend on your credit card. While this is a valid strategy, it can be quite inconsistent and unreliable. Some retailers view purchasing gift cards as an ineligible purchase, and furthermore, shopping portals can be finicky, as purchases are sometimes not accurately recorded. It’s often necessary to follow up on your purchase through a help ticket.

If you’re like me and prefer a more straightforward approach, here is a real-life example of triple dipping that I put to use fairly often.

This entails leveraging a shopping portal link to a specific retailer where a current Amex Offer is available. As illustrated below, I made an online purchase at Lululemon through the Aeroplan eStore and took advantage of an Amex offer: spend $100 and receive a $20 statement credit.

This combination earned me 154 Amex Membership Rewards, 352 Aeroplan points, and a statement credit for $20. This is my preferred method of triple dipping and I’ve found it to be more reliable and easily repeatable. 

There are of course other ways to triple dip, so hopefully, these examples will get you thinking on the right track.

Conclusion

Optimizing your everyday spending can significantly enhance your points and miles accumulation. By leveraging multiple loyalty programs to maximize everyday spending on groceries, gas, and travel, you can greatly improve your points and miles balance over the long term.

While welcome bonuses will always be the primary avenue for earning large chunks of points, integrating the habit of strategically optimizing your spending through double or triple-dipping will serve you well for many years to come.