Aeroplan Multi City Hack: Montreal to Vancouver via Colombia

Aeroplan multi-city bookings are something I try to use on any redemption outside of North America. With a bit of creativity and patience, it’s possible to turn a simple one-way flight into a full-blown adventure.

In 2025, I pushed the limits of Air Canada’s multi-city booking tool and added stops in Colombia and Mexico on my way home from Montreal to Vancouver — all while maximizing Aeroplan points.

Here’s how I did it, what worked, what didn’t, and some tips to help you take advantage of Aeroplan multi city rules.

Why Aeroplan Multi City?

With not much planned for 2025 besides another VIA Rail journey, I decided to get creative with my flight home between Montreal and Vancouver.

This routing came about because I was heading to the East Coast to take my mom on The Ocean train journey from Halifax to Montreal. With no rush to return west, I saw it as the perfect opportunity to stretch my Aeroplan points.

Over the years, I’ve had great success with complex Aeroplan bookings, including several incredible mini round-the-world trips. I’ve flown in Thai Airways First Class, Oman Air First Class, and Emirates A380 Business Class, the one with the bar in the sky, all part of complex Aeroplan multi city routings with stopovers along the way. So I knew it was possible to find outsized value with some effort and flexibility.

For some past examples of Aeroplan Mini-RTW tickets I have booked, check out this post.

Having previously detoured between Montreal and Vancouver with Air Canada’s Mexico City flight, I wondered if I could push it even further this time and tag on a few new countries in South America.

It wasn’t easy, but it turned into an amazing redemption that took me farther than I expected, and for fewer points than most Air Canada direct flights.

Aeroplan Multi City and Stopover Rules Refresher

Before diving into this itinerary, let’s review the Aeroplan stopover and multi-city rules. Aeroplan’s updated flight rewards system is more flexible than ever, especially when it comes to building complex itineraries with multiple stops.

With Aeroplan, you can now add a stopover of up to 45 days on a one-way flight for just 5,000 extra points (excluding flights within North America). This opens the door to creative multi-leg trips that let you explore multiple destinations without breaking the bank—or your points balance.

Some key rules and things to keep in mind:

✅ One stopover per direction of travel is allowed (i.e., one on the outbound or one on the return).

✅ Stopovers cannot be added on domestic or transborder flights within North America.

✅ You can mix and match airline partners, as long as they’re within the Star Alliance or part of the Aeroplan program.

✅ The trip must follow logical routing and remain within the maximum permitted mileage (MPM) rules, or Aeroplan may not validate the itinerary.

This flexibility is what allowed me to build the following route—stretching a simple flight from Montreal to Vancouver into a multi-country journey through South America and Mexico. Let’s take a closer look at how it worked.

Booking Challenges: Aeroplan Multi City Rules Are Confusing

Using Seats.Aero—an awesome tool for finding reward seat availability—I was able to find business class flights from Montreal and Toronto directly to Bogotá. But trying to go beyond that or return to Vancouver on the same ticket was a serious challenge.

Using the Aeroplan site, I found flights through Mexico City and either San Francisco or LA to Vancouver. The problem? I couldn’t book them online. When I called Aeroplan, I was quoted 125,000 Aeroplan points. The agent treated the trip as two separate awards rather than a single aeroplan stopover for 5,000 points.

I pushed back. I’ve done Aeroplan stopovers with Avianca business class before and had even seen someone post about doing two stopovers on Avianca earlier in the year. But this time, the agent said Avianca doesn’t allow stopovers at all.

Another call gave me a slightly different answer: Avianca does allow stopovers, just not in certain cities. None of it made sense.

I was hitting a wall and starting to believe it had to do with the 100% max rule — the requirement that the total distance can’t exceed 100% of the direct mileage between the origin and destination.

So I went to Great Circle Mapper. The direct distance from Montreal to Vancouver is 3,686km (2,291 miles). A routing through Bogotá blew past that. That’s likely why Aeroplan wouldn’t ticket it as one trip.

Success with Mexico City As Destination

After failing with Vancouver as the destination, I decided to flip the idea and book Mexico City as the destination with a stopover in Medellín. And it worked. Even better? The whole segment cost me just 40,000 Aeroplan points and didn’t even include the 5,000 extra for the stopover even though it is included in the final bill?

This was one of those rare moments where Aeroplan stopover rules (or the lack of clear ones) played in my favor. I took it.

From Mexico City, I booked a return home in business class to San Francisco, then economy to Vancouver — all for 24,800 Aeroplan points. The total came to 64,800 points. This also gets me back to the Air Canada Maple Leaf lounge at SFO, which I love.

That’s a killer deal, especially compared to the 40,000 points it would have taken just to fly Montreal to Vancouver in business class direct. That was a rarity too and on a day I didn’t want to fly. Also, it’s nearly half what I was quoted on the phone.

Couldn’t Add a 24-Hour Stopover? Work Around It

I really wanted to add one more stop — another new country — for a 24-hour layover. I have done this several times in the past as part of these Aeroplan multi city trips. This has included spending a day exploring the Panama Canal and taking an interesting day tour in Bahrain.

Sadly, I couldn’t make it work within the Aeroplan rules this time around. I tried adding destinations on the front end and backend of the trip but it wasn’t bookable, likley due to milage restrictions again. So instead, I looked into separate tickets.

From Medellín, there are direct flights to Quito, Ecuador for cheap. It’s just over an hour and a half flight. If it fits the schedule, it’s worth booking separately for a quick trip to the equator.

Tips for Booking Air Canada Multi City Awards

Booking a complex Aeroplan itinerary can be incredibly rewarding—but also frustrating if you don’t know how to navigate the system. Based on my experience building multi-country trips with Aeroplan points, here are a few practical tips to help you get the most value (and the least headache):

• Use Great Circle Mapper to understand your routing limitations and how the 100% distance rule might block your ideal itinerary.
• Be persistent with Aeroplan agents. Call back if you get an answer that doesn’t add up—you’ll likely get different responses from different agents.
• Book complex itineraries segment by segment and try plugging them in different ways (e.g., destination vs stopover).
• Factor in taxes. My total fees were high even though the points were low. Sometimes it’s better to pay a few more points to save on cash.

Aeroplan South America Flight Experience

Not all business class is created equal. Avianca business class from Montreal to Medellín is a redeye flight, and the seats aren’t lay-flat. Not ideal. But for 40,000 points and the added bonus of visiting country #82 (and maybe #83), I’ll take the discomfort.

If you want a better ride home, check out Air Canada 737 Max business class or United business class from Mexico City or Bogotá. Although not lay-flat seats, they tend to offer more comfort and provide a better overall experience than Avianca or Copa Airlines business class.

And if you need a place to freshen up or crash between flights, Mexico City business class lounge and Maple Leaf lounge options are solid.

My Aeroplan Stopover Final Routing

So, after all the searching and calling into the Aeroplan call center, what does this Aeroplan South America trip look like?

• Montreal to Medellín (stopover) via Bogotá > Mexico City (destination) via Panama City = 40,000 pts
• Mexico City to San Francisco to Vancouver = 24,800 pts
• Total: 64,800 Aeroplan points (bought down to 52,800 points) + $657.11 in taxes/fees

Not bad considering the alternative was a simple Montreal-Vancouver Air Canada business class flight for almost the same number of points.

If you have time and flexibility, Aeroplan multi city tickets are a great way to see more of the world for less. Just be ready to put in the work.

READ MORE: Check out the new Air Canada Cafe in Montreal!

Air Canada Multi City FAQs

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Cover Image by Andres Fernandez from Pixabay