The concept of miles and points is simple. Earn miles and points through a variety of methods, and redeem these points for flights, hotels, and other travel-related expenses. However, anyone who has booked award travel knows that this is a gross oversimplification compared to the realities of this hobby. Therein lies the necessity of having additional strategies to make your miles and points work for you.
Working backward when making redemptions is one of those strategies that I think everyone should be aware of. While not the only approach you can take when redeeming, learning how others approach challenges can help improve and re-frame the way you approach the challenges you face, even if you only take away bits and pieces of a strategy.
Let’s take a look at the concept of working backward and how you can use this strategy to plan for your next award travel redemption.
What Does Working Backwards Look Like With Award Travel Redemptions?
Working backward when planning and making an award travel redemption goes hand-in-hand with some of the award travel best practices we’ve written about previously.
This means you want to implement the strategy opposite of what many people do. Instead of wildly earning miles and points and then figuring out a redemption, working backward takes into account a more pointed and precise approach where you figure out where you want to go, how you want to get there, and then earn and redeem (with a few caveats).

While there is merit to always earning as many miles and points as you can, the working backward approach cuts down a few of the risks that can be prevalent if you are spamming credit card applications with no real plan for future redemption.
The Risk of Not Working Backwards When Redeeming Miles & Points
When you get started with miles and points, it can be tempting to sign up for any and all credit cards with a welcome bonus that looks good. This opportunistic approach and mindset may never go away for many, myself included, as I literally can’t turn down a good deal when I know the value is outsized (mainly why I currently have far too many American Express Business Platinum (US) cards).
However, depending on the currency you are earning, the opportunistic approach is usually not the most efficient approach when compared to working backward toward your next redemption.
The main reason is that you run the risk of accruing large amounts of points in various currencies that you might not have an immediate use for. Miles and points are subject to devaluation over time, and the larger the unused balances you have, the more devaluation of your points you will experience.

Recklessly signing up for credit cards and earning a ton of points becomes less of a problem if you earn a flexible or transferable currency such as American Express Membership Rewards, instead of a program-specific currency like Flying Blue Miles. At least if you are earning flexible currencies you won’t have to worry about orphaned miles and points or having your points balances expire, as you can transfer when a redemption opportunity is readily available.
Either way, planning your redemption ahead of time and working backward is always a promising approach. That being said, it never hurts to earn transferable miles and points currencies along the way, or a currency you consistently have a need for, such as Marriott Bonvoy points or Air Canada Aeroplan points.
How to Work Backwards to Book Your Next Redemption
Decide Where You Want to Travel To
The first step in working backward to book your next redemption can sometimes be quite challenging: picking where you want to travel to.
Once you realize the value of miles and points, there quite literally isn’t anywhere you can’t go to, even on a budget. This freedom, while awesome, can be overwhelming and is still something that I struggle with when deciding on my next vacation.

Ultimately, it is a personal question and will vary based on your travel desires. If you have a young family, maybe you aren’t interested in traveling around the world and would prefer to travel within North America. On the flip side, maybe you do want to pack your kids up for a month-long journey around the world. There really isn’t a right or wrong answer.
You could even choose a general destination, like Europe, especially because it is easier to get around once you are over there. This would also make the next steps much easier as you only need to worry about finding flights to a specific continent, and not a specific airport.
Determine Which Airlines Fly There
Now that you have a destination in mind, you need to determine what airlines fly there before you can determine which brand of miles or points you will require. The best tool to find this out is FlightConnections.

With FlightConnections, you can enter two city pairings and see which airlines fly between those two airports and on what days. This makes it easy to narrow down which airlines fly to a specific destination, which opens up the next step of determining which frequent flyer program you need to earn points with.
Note that you don’t need to just look at flights from your home airport, as you might want to utilize a positioning flight to open up your options when it comes to finding award flights. For example, as someone who lives in Edmonton, my go-to searches include flights departing from Toronto (YYZ), Montreal (YUL), Vancouver (YVR), Seattle (SEA), San Francisco (SFO), and Los Angeles (LAX).
Determine Which Frequent Flyer Program You Will Use & How Much The Redemption Will Cost
Once you find a few flight routings that work for your desired destination, you need to determine which frequent flyer program you will use for your redemption. If you are interested in flying on Air Canada, it makes sense to earn Air Canada Aeroplan points. But Air Canada Aeroplan points, and other frequent flyer currencies, can be used to book partner award space on other airlines.
For example, if you are interested in booking Japan Airlines business class, it doesn’t mean that you can only do so with JAL Mileage Bank miles. In fact, you can book Japan Airlines business class with British Airways Avios, Cathay Pacific Asia Miles, Alaska Miles, and American Airlines AAdvantage Miles. Many of these options are far easier to earn than JAL Mileage Bank miles, making it a much easier redemption overall.

Partner awards are usually the way to go when making a flight redemption where possible, as you can typically fly on better airlines with more consistent award pricing. That being said, finding partner award space can be difficult, so be prepared to put some work in.
When it comes to determining pricing, you will need to do some dummy searches. Whether you use a tool like Seats.aero or search within the frequent flyer programs search engine, you should be able to find some availability that will give you an indication of the expected points price and any applicable taxes and fees you will need to pay.
I would recommend having a few flight options in mind and pricing those out, as sometimes you simply won’t be able to find the award availability you desire. Also, depending on the frequent flyer program, flight awards can be dynamically priced meaning that pricing can fluctuate on the same route for different dates.
Determine Where You Want to Stay & With What Hotel Loyalty Program
I believe that looking into and finding where you want to stay is the easiest piece of the puzzle with award redemptions. This is usually because there are many options for accommodations in popular destinations, and oftentimes many options within each main hotel loyalty program.
When I travel, I’m looking for the best cross-section of value vs desired amenities in a hotel. For example, if I’m staying in a city, I’m most interested in whether the hotel is in a good location plus do the accommodations meet my needs. I also try to plan my stays to take advantage of the fifth night free benefit for those loyalty programs that offer it to effectively save even more.
You may also have an affinity towards an existing hotel loyalty program if you already hold elite status. For example, if you are a Marriott Bonvoy Platinum or Titanium Elite member, it would be hard to pass up free breakfast at Marriott properties plus the ability to use nightly upgrade awards, take advantage of late checkout, and even more perks. If so, it would make sense for you to stay at a Marriott Bonvoy hotel so you can benefit from your hard-earned status.

You typically want to look for your desired hotels while you are looking at flight redemptions, so you can have a rough plan on where you are going, where you want to stay, and how much the total cost will be. Flights are the most important part of the entire package though, as they are the hardest to find availability on and to actually get booked. On the flip side, securing hotel bookings is much easier, unless you have a niche or in-demand resort or hotel redemption in mind.
You should now have an estimated amount of points as to what your desired hotel stay will cost, so onto the next step.
Determine How to Earn Points in Required Loyalty Programs & Start Earning
At this point, you will have an idea of the flights you want to book and the hotels you want to stay at. As a result, you should have the total expected points cost, recognizing that redemptions can sometimes be dynamically priced (depending on the loyalty program), so build in some flexibility for the total cost.
When it comes to earning frequent flyer program miles, there are a few different approaches you can take. If you need to earn miles in a program that many points programs transfer into, such as if you want to earn British Airways Avios, you could consider earning American Express Membership Rewards points or RBC Avion Rewards which both transfer at a rate of 1:1.

If you want to learn more about transferable points and how they can be used, look into our miles & points transfer partner tool to see what options (and bonuses) are available. There are quite a few transfer opportunities like the above in Canada, so it’s worth exploring transferable currencies for the ultimate flexibility, plus you can also take advantage of valuable transfer bonuses from time to time.
On the flip side, if you want to earn points in a frequent flyer program that already offers co-branded credit cards in Canada, such as Air Canada Aeroplan, the best approach can be to sign up for one of these credit cards, such as the TD Aeroplan Visa Infinite card and start earning via a hefty welcome bonus.
The TD® Aeroplan® Visa Infinite* card earns Aeroplan points and offers cardholders various benefits including a free first checked bag on Air Canada and a $100 NEXUS membership credit.
40,000 Aeroplan
$12,000
$840+
$139 (FYF)
Yes
–
As for hotel points, options are much more limited for Canadians. Marriott Bonvoy is the most accessible and easily earned hotel loyalty program currency in Canada since there are two co-branded credit cards: the American Express Marriott Bonvoy card and the American Express Marriott Bonvoy Business card.
The American Express Marriott Bonvoy card earns Bonvoy points and offers cardholders benefits including an annual free night and 15 qualifying nights towards elite status.
Check out our American Express Marriott Bonvoy card review for more details.
50,000 Marriott Bonvoy
$1,500
$330+
$120
Yes
–
Miles and points enthusiasts may also look to Hilton Honors and World of Hyatt as potential opportunities as well, but you will need to be more involved in the US credit card game to make those loyalty programs truly worth it.
Don’t just get stuck on only using points either, as there are also valuable free night certificates earned within many of the hotel loyalty programs, often from credit card benefits and perks:
- Marriott Bonvoy Free Night Awards
- Hilton Honors Free Night Certificates
- World of Hyatt Free Night Awards
Search for Availability & Book Your Flights
Full stop, the biggest challenge most people face is finding flight availability. While this becomes less challenging with the more time you spend on this hobby, it is still an annoying aspect of redeeming miles and points, and it becomes even more difficult if you are looking to book more than one seat.
However, don’t be discouraged, as searching for flight availability has never been easier thanks to a number of tools we now have at our disposal:
- Seats.aero: A Simple & Effective Flight Award Search Tool
- A Comparison of Popular Flight Award Search Tools
Seats.aero is the best flight award search tool for most, and we recommend paying for a pro membership so you can search up to a year in advance. Pro members can receive availability alert notifications via SMS or email, making it easy to complete your booking once availability pops up.

If you are looking to book far out, Frugal Flyer has a guide to flight award release dates, allowing you to be prepared to book your desired seats as soon as they become available. For many travelers who don’t have a lot of flexibility, this is often the best approach worth implementing.
Keep in mind the change and cancellation policies for frequent flyer programs as well, since flights can be much more difficult and costly to change or cancel compared to hotels.
Book Your Hotels
Booking the hotels for my vacation is usually the step I leave for last, as availability is often wide open for many of the hotels I choose to stay at. For many of my reservations it is as simple as searching on their website or within their app, and making my booking. Closer to my stay, I do reach out to the hotel to ask for the upgrade I want if I hold status with that chain.

For those hotels where award availability is more hotly contested, such as the Waldorf Astoria Los Cabos Pedregal, I usually end up searching daily for availability to open up. Alternatively, depending on where I am looking to travel, I might even book the hotel first and then figure out flights afterward just to ensure I can secure the booking for the resort I am interested in.
Conclusion
Thinking about how you can work backward when redeeming miles and points will better prepare you for making your next booking, and at a bare minimum, will give you a plan to follow. After all, the last thing you want is to have a pile of miles and points with no plan to use them while devaluations are always looming!

Josh Bandura

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