Everyone wants to be a travel hacker but for a seasoned traveller, it’s not always entirely clear how the heck these travel hackers do their thing. If you’re like me, you’re tuned onto the fact that points are key and credit cards are a big way to build up your cache fast. Collecting points is only one side of it though. On the other side is the smart use of these points to maximize their value. That’s where things get a bit more fuzzy.
A question I get all the time is, how do you find those crazy cheap flights or pay only $100 for that Aeroplan flight to the other side of the world? The truth is that it is quite complicated and that’s why people pay for services like Book Your Award where experts help hunt down the best flight options. What if you don’t want to pay someone to do it? There’s got to be a way to do this yourself without needing to be a rocket scientist. There is, and my hope is to explain how to do it with a very specific example.
Before I do, I’ll preface this in saying that my technique is probably not the most thorough nor master-level in travel hacking. That being said, I’m pretty happy with the results and my intention is to give my Aeroplan friends another weapon to add to their hacking tool belt.
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Setting The Scenario
I started planning our honeymoon at the beginning of the year with nothing more than the idea that I wanted to use up my Hilton Honors and Aeroplan points. In a way, this is going to be my last chance to use my Hilton points on an aspirational property like what we did in the Maldives many years ago.
It came down to picking from one of these 3 properties:
- Conrad Maldives – some will argue it’s still the best property in the whole portfolio
- Hilton Seychelles Labriz Resort & Spa & Hilton Seychelles Northolme Resort & Spa
- Conrad Bora Bora Nui – Recently rebranded from Hilton
It was not an easy choice but in the end, the coin toss landed on Seychelles. A large reason for that was that we could pair it up with a trip to a region of the world we haven’t explored much at all – Africa.
Once this was decided, it anchored the rest of the trip but the rest was still flexible.
Knowing Your Alliance
When you’re with one program like Aeroplan, the focus then should be on Star Alliance partners. What makes the program so powerful is that you can mix and match with a variety of other airlines to get you to where you need to go.
Knowing Seychelles was a hard requirement, the next question to answer was “so what cities fly to Seychelles?” Since we wanted to include a safari component to our trip, I narrowed down the possibilities to the following countries:
- South Africa
Looking at all 3 countries, any flight to Seychelles required taking Ethiopian Airlines via Addis Ababa in order to get to Mahe Island Airport in Seychelles.
It wasn’t an easy choice at this point because it seemed like I could get something to work from all three but what I liked about South Africa was that South African Airways was part of Star Alliance and gave additional options. Tanzania and Kenya on the other hand had good flying options with Kenya Airways but the problem is that they’re with SkyTeam which is another alliance.
Final decision: South Africa! As much as this was a decision about flight availability, this was more of a choice around what we could see in the country and the variety that could be had between safari, wineries, surfing, and hiking. From this, it became clear that we’d be doing some combination of Kruger National Park from Johannesburg and Cape Town.
Tool used: Skyscanner – Nothing fancy here. I just wanted to see what routes were out there. Use the alliance filter and play around with a few dates to see the options since not all routes fly everyday.
The next key to finding good reward tickets is flexibility because if you are restricted to specific days, things become way harder to find.
With Johannesburg, Cape Town, and Seychelles and roughly a week +/- a few days in each spot, I had a rough idea of how it would all come together.
Before we can dive into that, let’s talk about some of the basics around reward rules that I didn’t even fully understand at the beginning.
Understanding Reward Rules
At this point in time, it probably makes sense to go into a small lesson about reward rules. There are a lot of rules but here are the ones that matter.
Rule 1: Routing cannot include the same city more than once in each direction
You wouldn’t think this would be an issue but in my specific scenario, because of the prevalence of Ethiopian Airlines in the region, this was a massive problem when all flights seem to fly through Addis Ababa.
For example, I was initially finding flights where Washington Dulles -> Addis Ababa -> Johannesburg -> Cape Town -> Addis Ababa -> Seychelles. While Air Canada’s multi-city tool will display these routes, they won’t let you go further in booking.
Rule 2: Two stopovers are permitted in addition to point of turnaround on intercontinental flights (travel between two continents)
This rule seems innocent enough but is crucial in finding creative ways to build your flight itinerary.
So what is a stopover exactly? A stopover is where you can essentially get off the plane and stay in the city for X number of days. It’s a stopover and not an open jaw because you have to get back on a plane from the same city. A stopover is also different from the term “layover” which is essentially connection at the airport where you don’t usually get out of the airport. The “point of turnaround” is the furthest point in from your destination city.
To truly maximize on your reward trip, you want to leverage stopovers to:
- See more places – In my case, this allows me to include Johannesburg and Cape Town as stopovers
- Allows you to open up flight options to potentially reduce taxes via other airlines
- Open up award availability again by going through different airports
- For travel within Canada and continental US (not including Hawaii/Puerto Rico), one stopover permitted.
- Between Canada/Cont. USA and Hawaii/Puerto Rico/Mexico/Central America/Caribbean, two stopovers permitted if all flights are with Air Canada. If any of the flights are with a partner airline, it’s only one stopover.
- Intracontinental travel (travel within the same content) not covered by the first two points, stopovers are not permitted.
- Stopovers are not permitted on one-way flight rewards.
Rule 3: Open Jaws Are Allowed
Open jaws are another creative way to get to where you need to go to but are straight up confusing so hopefully I can properly explain it.
Without making it too complicated, the gist of it is this. An open jaw is when you fly A to B and then fly from City C to A. Note that B is different from C so you get a disjointed itinerary in between where you’re supposed to find your own way there (i.e. drive, take a tour, etc.).
If you introduce stopovers into the picture, you could do something like fly from Washington to Johannesburg, take an open jaw where you drive to Cape Town, catch a flight from Cape Town to Seychelles and then complete the journey by flying Seychelles back to Washington.
Revisiting the stopover rules, here’s how they look with open jaw in the mix:
- For flights within Canada or between Canada and the Continental US: one stopover OR one open jaw
- For flights between Canada/Continental US and Hawaii/Puerto Rico/Mexico/Central America/Caribbean solely on Air Canada: Two stopovers OR one stopover and one open jaw
- For flights between Canada/Continental US and Hawaii/Puerto Rico/Mexico/Central America/Caribbean with at least one flight on a Star Alliance carrier besides Air Canada: One stopover and one open jaw
- For travel between two continents: Two stopovers OR one stopover and one open jaw
- For travel within the same continent (excluding North America): One open jaw
Other base rules:
- Ending city has to be the same as your starting city
- If you’re crossing an ocean on your way to your destination, you have to return crossing that same ocean
When you combine all of these together, all sorts of mayhem can happen. The bottom line is that you want to leverage this knowledge to help you build a creative itinerary to maximize on travel. When you realize that you can do all of this in ONE ticket, that’s when your jaw really opens.
The Available Tools
Aeroplan Multi-City Tool
This is naturally going to be the first place you go to. It’s free to use and you get instant results. This was my starting point as well.
Problem is that you’re limited to these 3 types of searches:
This means that if you want to do anything more complicated, you can’t. For instance, you’ll notice that you can’t even do a multi-city with an open jaw and you definitely can’t do flights with two stopovers because that would require 4 legs.
If that’s the case you’ll have to call Aeroplan to get an agent to book it which costs $30 CAD + tax per passenger.
Star Alliance Routing Tool (no longer available)
There used to be a pretty neat tool out there that can show you literally every route that is within the Star Alliance. It’s a great way to check to see if there is a direct flight from one city. Unfortunately the page is down now.
The only issue I have with it is that it doesn’t figure out connections for you. So for instance, if I put in Toronto -> Johannesburg, it doesn’t tell me I can take an Air Canada flight to Washington and then South African Airlines to Johannesburg.
Award Finder Chrome Extension
NOTE: This tool has been discontinued with the new Aeroplan program. This has now been replaced with another tool designed specifically for Air Canada called cowtool. Cowtool was designed by canadiancow on Flyertalk and is meant to be a Unofficial Advanced AC Reward Search Tool with Calendar
This is where the GOLD is at and ultimately what allowed me to piece together my version of a perfect flight itinerary. The tool isn’t pretty but it shows you reward availability for a specific route quickly without having to go through Aeroplan’s own tool which simply isn’t as comprehensive.
Award Finder is something you used to be able to find in the Chrome web store or on their official Awards.Flights page.
Starting With Aeroplan
Quick recap, so far at this point, I know that I want to hit the cities of Johannesburg, Cape Town, and Seychelles. I also know that I want to go October 23 or later. I also only have roughly 200,000 points which I knew was only good for economy between two people.
Fooled By Aeroplan
I started with Aeroplan’s multi-city tool and it was a great place to start but being the newbie I was, it really limited what I could do with my points since I didn’t have a full understanding of the rules laid out above.
With only 3 legs, I was able to try out various options such as this one:
At this point, I was looking all over the place. Could I get reward from Canada, Europe, or the US? The issue with Toronto was that Air Canada doesn’t fly to Africa so that ruled that out quickly. Europe had a lot of good options including Munich and Frankfurt. For the US, I tried a number of large east coast hubs.
The other fatal flaw I didn’t realize at this point was that I had not realized yet that Kruger National Park was outside of Johannesburg which is quite far away from Cape Town.
Even when I found something that seemed like it could work, the problem every time was Ethiopian Airlines. If you look at the above example, Munich to Cape Town requires a connection in Addis and so does the Cape Town to Seychelles flight. The sneaky thing is that Aeroplan shows you these routes as options but once you try to book, it denies you.
Building From Scratch
Realizing that Aeroplan’s multi-city tool just wasn’t going to give me what I wanted, my good friend from Wandering iPhone, gave me all the knowledge that I now have on Award Finder and building my own itinerary.
I’m not going to bore you with more details about trying more routing options but if I were to summarize it, here’s what went into it:
- Flying from the US made more sense in order to cut down additional flight costs (i.e. it’s easier and cheaper to find a flight from Toronto to Washington than Toronto to Frankfurt)
- Understanding that to get to Seychelles, it was more or less inevitable that this would involve Ethiopian Airlines and a stop in Addis Ababa.
- In order to circumvent the problem of going through Addis Ababa twice, realizing that I had to look for a route to South Africa that didn’t include Ethiopian Airlines.
- Identifying that the best flight from North America was the direct flight from Washington (IAD) or New York (JFK) to Johannesburg (JNB). I knew this by checking South Africa Airway’s route map page.
The final routing I decided on without having dates locked in looked like this:
Using Award Finder To Find What’s Available
If you can’t use Aeroplan’s multi-city tool, what the heck are you supposed to do?
That’s where Award Finder comes into play. It’s going to be tedious in some ways but it’ll also make your life so much easier compared to using Aeroplan to search leg by leg.
What makes it easier is in the fact that it is so basic and ugly. You’ll see why by following my footsteps below.
Step 1: Download
Okay I get it, kind of weird that this couldn’t just be a website but with how good this is, you really don’t question it.
Go to the Chrome web store and install the extension on your Chrome browser.
Step 2: Launch Award Finder
This part is a little less intuitive because despite this being an extension, it doesn’t exactly show up as a shortcut in your Chrome navigation like other tools. The easiest way is to just go back to the extension page on the web store and click on “Launch App”.
Step 3: Set up your Aeroplan account
Enter your Aeroplan number and password.
Step 4: Search Your First Leg
Enter your departure and arrival destinations and date. To open the search results, add a few days if you’re flexible. I’d recommend up to 3.
Set your carrier to AC and Cabins to Economy (check off Business and First if that applies to you).
For example, let’s say I’m doing that search from IAD to JNB for October 25 in Economy for 2:
Step 5: Interpret Results
Immediately you’ll see a list of all the flights. These are all the flights based on your parameters. There are 4 columns for the cabins: F (first class), J (business), W (premium economy), and Y (economy). If you only care about economy, look for the check mark under the Y column.
Step 6: Filter
In my case, I knew that I had to look for routes that didn’t include any legs with Ethiopian Airlines. Open up the filter section and remove ET from the list of carriers and ADD connection cities.
Looking at this, it looks like there is no direct flight to Johannesburg that have economy availability and all the connections are pretty nasty or only have partial economy availability (first one).
Step 7: Try Again
With no availability, you keep trying until you find something that works. In this example’s case, I changed the departure date to October 30th and while I couldn’t get the direct flight with South African Airways, there was an interesting option through Istanbul with Turkish Airlines.
Step 8: Start Building Your Spreadsheet
At this point, this is where you start a spreadsheet to keep track of this and all the scenarios you’ll build out based on start and end dates, and everything else in between. I felt that this was very helpful to help visualize the trip and all the flight options in one place.
In my experience, I learned that you’ll arrive at an optimal flight itinerary pretty quickly because you should ideally know how many days you should allot for each destination.
Step 9: Figuring How Much It’ll Cost
While not 100% accurate, if you want to have an idea of how much an itinerary will cost in taxes, go back into Aeroplan and do a search leg by leg and add all the tax costs together.
In terms of Aeroplan points, refer to the reward chart. In my case since I was putting together a trip from North America to Africa, I knew my point cost was going to be 100,00 points per person.
Step 10: Call Aeroplan
Once you’re all set, the last step is to call Aeroplan at 1-800-361-5373. Since you have every single leg mapped out at this point, this should be a very easy and smooth process.
I’ve been told that if you’re lucky, some agents will waive the $30 CAD + tax per ticket fee for booking since the argument is that they didn’t have to do any work. I was not one of the lucky ones.
The Final Result
After all was said and done, I was able to get the itinerary I wanted. The beauty of it all was that the whole thing was under one ticket which meant no need to purchase additional airfare other than the one we’ll need to get to Washington (IAD).
- Washington to Johannesburg
- Johannesburg to Cape Town
- Cape Town to Mahe, Seychelles via Addis Ababa
- Mahe, Sechelles to Washington via Istanbul
- 100,000 Aeroplan points
- $169.70 surcharges/taxes/fees
- $33.90 booking fee per person
It still blows my mind that all of these flights only cost $203.60 CAD per person.
Not Enough Aeroplan Points?
Don’t worry, make sure you read my latest post about the BEST Canadian credit cards to get which will help you top up your points to reach your goals. The best one I recommend right now is the American Express Platinum Business card where you get 75,000 welcome points for signing up through me. The beauty is that you can transfer these points 1 to 1 to Aeroplan.
As much as I wish there is a specific formula for you to follow, it really does depend on your scenario.
The key takeaway you should be able to take from this is:
- Understanding of reward rules with Aeroplan
- How to use Award Finder
- Steps to a ton of trial error and narrowing down your choices eventually to get you what you want
I am sure you have questions so fire away!
What you should read next
Travel Resources For Your Next Trip
If you’re in the process of planning your trip and putting together your itinerary, these are genuinely the best resources that the Going Awesome Places team stands by 100%.
Airport Parking: You’ll need a spot to leave your car at the airport so why not book a spot at a discount. Use code AWESOME7 to get at least $5 off at Airport Parking Reservations or Park Sleep Fly packages.
Hotels: Our go-to is Booking.com because they have the best inventory of properties including hotels and B&Bs. The exception is Asia where Agoda always has the best prices. TripAdvisor is also useful for reviews and bookings.
Vacation Rentals: Airbnb is the market leader but you’d be surprised how you can find cheaper deals on the lesser-known VRBO.
Travel Insurance: Learn how to buy the best travel insurance for you. This isn’t something you want to travel without.
- Insured Nomads – Popular insurance provider for frequent travelers and comes with great coverage and special perks.
- RATESDOTCA – Search engine Canadians looking for the cheapest insurance including multi-trip annual policies.
- SafetyWing – A perfect fit for long-term nomads.
- Medjet – Global air medical transportation.
- InsureMyTrip – Best for seniors, families, and those with pre-existing conditions.
If you need more help planning your trip, make sure to check out our Travel Toolbox where we highlight all of the gear, resources, and tools we use when traveling.