Quick Announcement before we jump into the meat of today’s post:

Super short notice but on Thursday, December 9th at 11:00 am MT / 1:00 pm ET (yea, like right meow!) we will be taking place in a live Q&A webinar with TD Direct Investing regarding financial independence!

You can register for this free event using this link.  Hope to see some familiar faces over there!

While I do not personally use TD Direct Investing for my investment accounts, I love to see that a large “big box” bank is covering the topic of Financial Independence in their investing webinar series.

For those who are unable to make it, once I have the link to the recording I’ll share it in a future post so stay tuned for that 🙂

Ok back to our scheduled programming!


Some people may find travel rewards points useless, mostly because of certain headaches, limitations, and restrictions such as blackout dates, navigating rewards points charts, fuel surcharges, and difficulty finding availability with partner airlines.

Let’s review some tips to keep in mind so that making an award booking will be a less frustrating experience.

1) Know Your Airport

Be sure to know which flights are available near your local airport.  You need to know what options you have. The options that you have near your local airport will affect the next factor.

For example, thanks to simple search using Flight Connections, I know that year-round I can get to Europe on a non-stop flight from Calgary by the following options (with some season options sprinkled in as well):

  • WestJet: London Gatwick (LGW) and Paris (CDG).
  • Air Canada (Star Alliance): London Heathrow (LHR) and Frankfurt (FRA).
  • KLM (SkyTeam): Amsterdam (AMS).

With this ammo on hand, I know that I’ll be looking for deals that have to do with WestJet (rarely any), Air Canada, or KLM… or their partners.

2) Consider Airline Alliances

Though it may seem obvious to many of us, and as we mentioned in our previous Travel Hacking 101 post in this series, keep in mind that many airlines belong to an airline alliance. This means that you can use your points to fly on other member airlines. This is especially useful because different airlines have lower tax and fuel surcharges.

Keeping with our European theme, a prime example of taxes and fuel surcharges to be aware of is American Airlines.  American is part of the One World alliance, as is British Airways.  This means, if you have American Airlines Aadvantage points, you could use those to book a flight with either American or British.  Unfortunately American tacks on huge taxes and surcharges when travelling from North America to Europe when using one of their carries for the leg going across the pond – to the tune of hundreds of dollars which basically wipes out the benefits of using points.  Whereas if you log in to your American Aadvantage account and instead find a flight from North America to Europe using a British Airways carrier for the flight across the pond, poof those taxes and surcharges are gone or significantly lower.  And no British Airways Avios points needed.  The only (major) problem is there are way fewer options to get to and from Europe with British vs American.

Another example, looking at the section above, if I knew I wanted to go to Europe but did not have any Air Canada Aeroplan points, instead I could target points within their alliance (Star Alliance) and book an Air Canada flight that way.  For example, if instead I had United Mileage Plus points (which is also a member of Star Alliance and thus a partner with Air Canada), when I log into my United account I can see all Star Alliance flight options and book an Air Canada flight using my United Mileage Plus points. No Aeroplan points needed.

3) Break Your Trip Down In Segments

Some websites allow you to use the multi-city option. What this means is that you would break your flight down manually into various segments. This will be more time-consuming, but it may help you figure out a decent route.

Going back to our original example, let’s say I’m starting out in Calgary and want to go to Europe but instead of returning back to Calgary, I need to go to New York on the way home for a wedding – yes we’ve done trips like this before!

You have a few options on how to go about searching for the best routes.  You can do multiple one way searches or you can do a multi city search starting at A, going to B, and then to C.  (If you use Google Flights, look for the word “round trip”, next to it you should see a drop down arrow, after selecting that, you should see “one way” and “multi-city” as your other search options. You can then add as many additional segments that you’d like once you’ve selected “multi-city”.)

When I entered random dates, the first date showed no non-stop flight options from Calgary to Frankfurt.  But thanks to step one above, I knew there should be a non-stop flight with Air Canada.  I simply adjusted the departure date back a day and poof the non-stop flight appeared.

For the return from Frankfurt to JFK, I can see that there are non-stop options from Lufthansa (Star Alliance), Delta (Sky Team), and Singapore (Star Alliance).

If I only had United (Star Alliance) points available, I’d then dig into Lufthansa’s award chart as well Singapore to see which carrier has better flight options and rewards requirements.  For example, thanks to Googling “Lufthtansa award chart“, I can see that Luftansa requires 60,000 points one-way for an economy flight from Europe to North America.  Similarly, a Google search of “Singapore awards chart” shows that Europe (zone 11) to East US (zone 13) is 40,000 points for a one-way economy seat.  You bet I’d be leading towards using my Star Alliance points with a Singapore flight then.

4) Call The Agent

Use this option when you feel that you are unable to plan your trip through the website. The agent generally has the same access to information as you do, but they may be a little more familiar with breaking down your trip into segments. However, you may need to pay an award booking fee for using the phone service. I would politely ask if the fee can be waived. Or jot down the segment that they came up with and determine whether you can duplicate their work on the website.

Sometimes, you may see a flight available on an airlines website (or a flight search engine) but when you go over to a partner airline (where you have points available) to book, suddenly that flight is nowhere to be found.  In this case, you’d have to call with the partner flight info on hand to feed it to an agent to book a partner alliance reward flight instead of doing it yourself on the computer.  You can ask for the phone reservation fee to be waived since the online option was not available to you.  Sometimes the airlines will waive this other times they won’t.

5) Be Flexible With Your Dates

This is part of the beauty of FI.  We are no longer tied to the same national holidays that everyone else is trying to vacation around.  We can fly based off off-peak dates which tend to provide the same flights but at lower required points.  Or we can fly on a random Tuesday and return back on a random Wednesday and not worry about how many vacation days we have left for the year.

The example in step 3 above is a prime example of why having flexible dates are so important.  Many long haul flights do not operate daily.  Sometimes they are every other day, sometimes weekly, etc – it really depends on the demand of that particular route.  By shifting the dates around in that search, I was able to eliminate an unnecessary stop which could add delays and/or lost baggage to the mix.

This is the factor that helps me alleviate the most stress. Generally the award flight that you want will be available, but on specific dates. If you are not restricted to your travel dates, you should generally be able to find a reward flight. If this option is not available to you, then the next factor will be important.

6) Plan In Advance

I know that this is easier said than done as often times we cannot pinpoint the exact dates that we can travel. But if this option is available to you, then I would book a reward flight earlier rather than later. It will save you a lot of trouble.

Sometimes, when booking using points, the airlines allot a certain amount of reward flight redemptions per flight. So for example, maybe the flight you’ve been eyeing has 15 spots available to be booked via points.  If you sit on the sidelines or look to make a last minute trip, there’s a higher probability that either A. you can no longer book that flight with points or B. it may cost you more points to book as economy is no longer available.

7) Flight Changes

After you book your reward flight, often times the airline may change the itinerary on you. This actually creates a new opportunity for you. When they change the schedule of the flight, you have an opportunity to rebook your flight to an even more desirable time, generally with no charge. Just keep in mind that the time-frame on when you can rebook your flight after a scheduling change may be limited, so stay on top of this (most of the time any changes must be made within 24 or 48 hours of the notification). If you already selected email notifications for scheduling changes, you should receive the notice within the required timeline but you’ll have to act quick to do some research to see if a better alternative exists that you could switch over to.

8) Diversify Your Portfolio

This factor is for those of you who are able to earn a lot of points (I’m looking at you US readers!) and are willing to invest more time to keep track of your points.  I would study the airlines that you frequently use to determine which airlines are available in your local airport to determine which points to stock up on.  But don’t stop there.  Also become familiar with the alliances so you know when to transfer points for maximum value.

If you live in a larger city, you likely have many airlines flying to different regions.  This basically means you have a cornucopia of options as you have those multiple airlines plus all the partner airlines that are a part of their alliance.

Study the charts of the airlines that make the most sense to you and your flying preference to see where the sweet spots are to be found.

There we have it!  This wraps up part 7 of our Travel Hacking 101 Series and we are almost done with this series. We haven’t travelled internationally in years (thanks ‘Rona!) so all of this writing is giving me the itch to travel again! …. Although the thought of international travel with two kiddos under 3 sounds awful.  So we shall keep collecting and hoarding our points for now! Nic and I have around 1,200,000 airline points and another 400,000 hotel points combined so yea I’d say we’re pretty well versed in this topic, ha!

I’ve been trying to break this series up into digestible posts so hopefully I haven’t gone too far into the weeds!  If you’d like to check out the other posts from this series, please check out our Travel Hacking 101 page. Hope today’s post cleared up any additional questions you may have.  Let us know in the comments below if you have any additional questions from today’s post.

I’ll be taking off from here now through the new year so I hope you all have a lovely holiday season!

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4 thoughts on “Travel Hacking 101: Award Booking Tips”

  1. I, too, dream of traveling again.
    I am glad I signed up for your emails.
    I will check out the rest of the Travel 101 series.

  2. I understand the principles of nuclear fusion, but travel points and travel hacking, that’s on another level. Court, your explanations are the best. I’m going to have to read this series again, again! Cash back credit cards, no problem; ‘points’ – zero mental connection. I’m going to have to put in more effort.

    Another excellent post, and BTW, great discussion on the TD Direct Investing webinar.

    1. Hahah thanks Bob! I’m trying to explain this series in as easy to digest pieces as possible as it can get very very detailed and intricate depending on how deep you go into this topic.

      And thanks for tuning into the TD webinar! It meant a lot to see some familiar names firing questions out during the Q&A 🙂

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