Behind the Scenes of a Complex Award

It can be tempting to think that once you’ve used your hard-earned miles to book an award ticket, you can just kick back, relax, and wait patiently for your travel date to arrive.

But that’s not exactly the case – there’s a reason why people say that redeeming points is the more challenging side of the game (compared to earning points) and a lot of that boils down to the process of continuously checking in on your travel arrangements and seeing if you can do things in a better way.

As I mentioned last week when discussing my upcoming trip to Bali, tweaking and optimizing your award travel is more art than science. I’ll walk you through the changes I made over the months as they relate to the Bali trip to demonstrate exactly which factors played into my judgment and how I approached each decision.

March 2017 – 9 months out

Planning for the holiday trip in late 2017 began as early as March. I really wanted to use my stack of Alaska Airlines miles to fly in First Class on either Cathay Pacific or Japan Airlines. Both are world-class airlines with spectacular premium cabins, so I wasn’t too fussed about which one exactly.

Award space on Cathay Pacific was pretty sparse for the holiday period, but I was able to quite easily locate two seats on JAL First Class, from Tokyo to Chicago. And since Bali was the focus of the trip, I booked the JAL ticket departing from Jakarta, Indonesia, with a 5-day stopover in Tokyo for New Year’s Eve – all for 75,000 miles per person.

After securing the return portion of the trip, I had to find something for the outbound. Luckily, EVA Air space from Toronto to Taipei popped up on just a few days before Christmas, so I was able to nail that down as well for 77,500 Aeroplan miles per person.

Thus finished the initial stages of the booking – what I’d call the “bones” of the trip.


What’s the big idea? First things first when it comes to booking a complex award ticket is to secure the longest flights with the most competitive award space.

May 2017 – 7 months out

When booking a complex itinerary and when dealing with rewards programs in general, it’s important to stay abreast on the change and cancellation policies. In particular:

  • Aeroplan charges $100 per person per direction to change a ticket and $150 to cancel a ticket; these fees are reduced to $75 and $30 respectively if you’re an Aeroplan Diamond member
  • Alaska Mileage Plan does not charge anything to change or cancel a ticket more than 60 days before departure, whereas the fee within 60 days is US$125; this close-in fee is waived if you are an Alaska MVP Gold or MVP 75K member

As you can see, Alaska’s policy is a lot more generous than Aeroplan’s, which means that you can feel comfortable changing Alaska award tickets for much more trivial reasons than an Aeroplan ticket (for example, if you really wanted to fly a certain aircraft type or business class seat).

This played into my thinking when booking the Jakarta–Tokyo–Chicago award on JAL. I knew I was able to change the point of departure within Asia to any other city with award availability up until late October, which was a very nice luxury to have.

And indeed, by summertime, it had become apparent that Jessica and I had had a change of mind – we’d rather spend New Year’s Eve somewhere else in South East Asia than in Tokyo. So I got to work on looking at changing the Alaska flight.

I had a friend I could visit in Thailand, but the only Bangkok–Tokyo flight that had business class space available featured JAL’s Sky Suite III seats rather than their Sky Suite, which I really wanted to try. So I booked a nearby option – the Hanoi–Tokyo overnight flight, connecting on to my First Class flight in the morning – surmising that I could easily “bridge the gap” with a cheap economy class ticketor an Avios reward flight. And thanks to Alaska’s fantastic program, I didn’t have to pay a dime in change fees to make this change.


What’s the big idea? Leverage the change and cancellation policies of your points program to continuously optimize your flights for any factors you consider important.

August 2017 – 4 months out

Okay, so now I had to book flights from Bali to Bangkok, and then from Bangkok to Hanoi. This should be easy enough. But looking at the first one, I discover that cash fares are in the range of $150 to $200 per person, which was surprisingly steep.

This was on Thai Lion Mentari as well, a low-cost carrier, meaning I couldn’t use my TD Points or my CIBC Business Aventura travel credit to offset the cost, since the flight doesn’t show up in major flight search engines.

There was only one solution. I signed up for two Scotia Gold Amex cards – one for myself, one for Jessica – and waited patiently for the cards to arrive, before charging the flights to my shiny new cards with the intention of “paying with points” later on. Looking back, I didn’t even need to wait for the cards to arrive, since one can always leverage the refundable hotel trick to “cash out” Scotia points.

Meanwhile, in studying the Bangkok to Hanoi leg, I noticed that Qatar Airways operates a fifth-freedom flight here. How cool would it be to redeem Avios for business class on this flight? Unfortunately, there was no award availability showing, until…


What’s the big idea? Always look for opportunities to use credit cards with fixed points currencies, like the Scotia Gold Amex, to offset the out-of-pocket costs of your travel.

October 2017 – 2 months out

…suddenly there was!

Award availability is a fickle beast by nature, and that’s especially apparent when you’re trying to piece together a complex trip involving different airline partners in different points programs.

One day there was zero seats available on Qatar’s Bangkok–Hanoi when I checked the British Airways website, and the next day, there was wide-open availability through the end of schedule! Needless to say I snagged two business class seats for the low low cost of 9,000 Avios per person.

The same was true for the last flight of the trip: the Chicago–Toronto segment. Now, on this date I needed to get back into Toronto for work by mid-afternoon, and our flight was getting into Chicago early in the morning. That meant there was ONE Air Canada flight I needed to catch: AC504, departing at 10am and arriving at 12:36pm.

A couple of weeks went by with no space showing up on this flight, and I considered booking a revenue ticket and calling it a day. But lo and behold, two business class seats opened up some time in mid-October! While I wasn’t exactly thrilled at the idea of dropping 15,000 miles per person on a two-hour business class flight, the alternative was paying $150 for economy… and I realized that the transition from JAL First Class to Air Canada economy class on an Embraer E190 might well be too much of a shock 😉

That just left the small matter of getting between Bangkok and Ko Samui, where the New Year’s Eve celebrations were taking place. A nifty little airline called Bangkok Airways is the primary operator on this route, and their flights were easily discovered on Expedia, meaning that I could use my stash of TD and CIBC travel credits to cover the cost.


What’s the big idea? Always check for availability often, or use alert services like ExpertFlyer whenever you can. Award availability can open up at any second, for any reason – perhaps the airline decided to release more inventory, or perhaps someone else cancelled their reservation. As long as you check back regularly, you have a good chance of snagging the space if and when it becomes available.


Getting all your ducks in a row when it comes to creating the “ideal” itinerary is one of the biggest challenges in Miles & Points. As you can see, it’s a process that takes place over an extended period, and a significant amount of energy went into making our holiday trip to Bali, Thailand, and Vietnam a reality. Luckily, like most of us who play this game, I find the entire process a lot of fun, and I can’t wait to start enjoying the fruits of my labour in a few days’ time.

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