Let me set the record straight here … I absolutely hate paying for flights if I can help it but paying for flights is not outside the realm of possibility when it comes to my travel.  It’s just the last option but nevertheless, it’s an option.


We are headed on a Disney Cruise in May that departs out of San Juan, Puerto Rico and terminates in Port Canaveral, Florida (1 hour from Orlando) because of that, we need to find a somewhat unique open-jaw from Calgary to San Juan with the return flight from Orlando to Calgary.  As May is shoulder season, finding reward flight should be fairly simple, however because we are locked in on dates due to the cruise, it might be more difficult to find an easy routing to get to our destination in time to catch the cruise.

Award Routing

San Juan was my biggest concern because there is plenty of vacation traffic from and to Orlando from all around North America but San Juan isn’t as popular, meaning there are going to be fewer flights which means fewer reward booking options (or so I thought) …


Looking at the Star Alliance Route Map, I can see that there are direct flights to San Juan, PR from both Chicago and Houston, both of which have direct flights from Calgary on United.


So now that I have my outbound route possibilities, I can now search for award availability.  What I am looking for is YYC-ORD/IAH-SJU but I also need to arrive in San Juan (SJU) with enough time to board my cruise by 5PM on May 7th, 2017.  As you can start to see, the constraints on this award booking are mounting as we delve deeper and deeper.


Again, I am not as worried about my return flight from Orlando because we have a lot more flexibility and can always just take an extra day off work if need be whereas if we aren’t in San Juan in time, we throw away thousands of dollars worth of cruise.

Award Availability – Outbound

The first thing I did was to search for flights from Houston and Chicago to San Juan on May 7th.  The results were less than ideal.


Only one option for a direct flight.  IAH-SJU and it arrives in enough time to get on the cruise.  Ok.  Let’s look for the YYC-IAH leg then.  So we need to set the parameters to get us to IAH by May 6th at 11:54PM and I’m planning on flying economy.


Success … well … sort of.

We have a routing but we have a LONG layover at IAH but with the Centurion Lounge there, it’ll be less awful but still a long time to be in an airport.   What’s worse is that there is no availability from YYC-IAH on United .. just Air Canada, which means high fuel/carrier surcharges.

So let’s take a look for these flights.

YYC-IAH on Air Canada
Depart 5/6/16 @ 7:40AM
Arrive 5/6/16 @ 10:44AM

13:10 Layover

IAH-SJU on United
Depart 5/6/16 @ 11:54PM
Arrive 5/7/16 @ 5:29AM

aeroplan-yyc-sjuJust my luck.  The route we chose is not bookable online so I need to eat a $25 Call Centre Fee but let’s try to get an idea of what taxes would be.  I’ll price each segment on its own:





Total Taxes and Surcharges

If I were to book these flights, I would pay $427.82 in taxes and surcharges as well as a $25 CalL Centre Fee for the privilege of speaking to an Aeroplan agent.

Award Availability – Inbound

Now that we know that we can find availability and know the out of pocket expenses for the inbound flight, let’s take a look at the return to Calgary.


For Orlando direct flights on United, we know from the map above, we can find direct flights to Houston, Denver and Chicago, all of which have direct flights to Calgary.

We disembark the cruise on May 13th at 7AM so let’s take a look for availability for May 13th.  We have to keep in mind that we arrive in Port Canaveral but we have to account for 3 hours (to be safe) to get to the airport from the cruise port.  So anything after 10AM should theoretically work.


So now that we have these two options, we need to see if there are flights back to Calgary.


And BOOM!  There’s the bust.

No direct availability from either Houston or Chicago.

I know that I made you read a lot with no payoff, but that’s kinda the experience of finding award bookings if you have tight constraints and little flexibility.  I can already see that because most of these options include an Air Canada leg, taxes and fees will be high.

Let’s just say that we found direct availability on United.  We are still going to pay at a minimum about $100 a ticket in taxes and surcharges.

Let’s call it $730 in taxes and fees for all three tickets or $240 each (rounded numbers) for the entire trip.

Pretty pricey so let’s look at the alternative … gasp … paid flights.

As a side note … I did look for availability with other programs that I have points in but they didn’t result in any better of a result.

Revenue Tickets

I neglected to take screenshots when I found the flights and because they were the last 3 tickets in that particular fare bucket, I can’t recreate them but the itinerary is as follows:


YYC-JFK on Westjet
Depart 5/6/17 @ 10:25AM
Arrive 5/6/17 @ 5:08PM

Layover 2:22

JFK-SJU on Delta
Depart 5/6/17 @ 7:30PM
Arrive 5/6/17 @ 11:39PM


MCO-JFK on Delta
Depart 5/15/17 @ 11:35AM
Arrive 5/15/17 @ 2:16PM

Layover 3:44

JFK-YYC on Westjet
Depart 5/15/17 @ 6:00 PM
Arrive 5/15/17 @ 9:26PM


The cost of this ticket was incredibly inexpensive considering the distance flown.


$492.71 each including all taxes and fees.

Some of my more detailed oriented readers may ask why not depart on the last day of the cruise.  That’s simple … after thinking about it a bit more, we decided we wanted to have a day at Universal Studios in Orlando and some time to hang out in Florida but there was availability at the same fare to leave on the 13th if we wanted.

Why is the Revenue Ticket Better?

That’s simple.  Let’s compare the costs of each.

The Revenue Ticket cost $492.71 per ticket.

The Award Ticket costs $240 per ticket (rough numbers) but you also have to consider the points required for the redemption.  Because San Juan is not in North America, you have to pay one way cost for Canada to the Caribbean which is 20,000 Aeroplan miles per ticket.  You also have to pay the one way cost for North American Long Haul which is 12,500 miles per ticket.  So the total cost in points is 32,500 Aeroplan per ticket.

So if we look at the CPM calculation, we see very little return for our points:

= (Cost of the Ticket You Are Offsetting – Taxes) / Points Required x 100
= ($492.71 – $240) / 32,500 x 100
= 0.78¢ per point

This is WAY below my threshold for points redemption as I earn my points at about 0.8¢ per point so this equation is underwater.

The decision here is a very simple one but the legwork was required to definitively prove that paying for the ticket made much more sense.


You should never turn your back on paid revenue tickets because at times, they can provide you with much more flexibility and value than if you cashed in your points.  Make sure you explore all options or you might do yourself a great disservice.

Jayce is the founder of PointsNerd, and avid traveller and a teacher by nature. He prides himself on flattening the learning curve through step-by-step guides because everyone needs to start somewhere.


  1. I’m all about the points, but I am pretty flexible with destinations, so I often book revenue fares because I can usually find a great deal to somewhere interesting.


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