Airline Secrets: What Are Nested Trips?

In this installment of Airline Secrets, we’ll continue looking at out-of-the-box ways to book travel whether using cash or miles. In particular I wanted to talk about nested trips, which is a technique with limitless possibilities that can help frequent travellers come out ahead.

Most people think that booking travel involves choosing between Round Trip, One-Way, and Multi-City, but the reality is that there’s a much wider range of options available to you, especially if you happen to be planning more than one trip at a time. The term “nested trips” encompasses all the possibilities beyond a single Multi-City booking, and it can be well worth your time to experiment with the possibilities in order to extract significant value.

Fair warning – this is a pretty advanced article with lots of juicy trip-planning talk!

In This Post

How Does It Work?

A nested trip is simply any occasion when you book two or more itineraries such that they overlap in some way; that is, one booking is nested within the other.

You can think of the classic “side-trip” as an example. Travellers who frequently visit Europe know that it’s a common practice to book a roundtrip to some European city and then secure cheap flights to other places on low-cost carriers like Ryanair or EasyJet. Doing so is usually much cheaper than trying to string together all your desired European destinations on a single multi-stop ticket.

North America to Europe round-trip:

Cheap tickets on budget airlines:


However, nested trips can get a lot more interesting and ingenious than that. One example is “back-to-back ticketing”, which is a booking practice that airlines don’t particularly like, akin to hidden city ticketing.

For any given route, airlines typically file dozens of different fares, with more restrictive fares priced lower than less restrictive fares. One of the restrictions you’ll commonly see on cheaper fares is a minimum stay requirement of, say, three nights (i.e., you must stay at your destination for at least three nights before taking the return flight home).

That makes sense, since the cheaper fare with the minimum stay would most likely be booked by price-sensitive leisure travellers who are looking to go on a vacation; in comparison, business travellers would likely require a shorter stay, and would be willing to pay a higher price for said shorter stay because their work is paying for it.

By leveraging back-to-back ticketing, though, some creative folks (whose travel patterns happen to involve the same destination more than once) are able to skirt around the minimum stay requirements and book their shorter trips for the lower price.

Here’s how this works. Let’s imagine a price-sensitive business traveller (perhaps she’s self-employed or unusually altruistic to her employer) needs to make two very quick trips from Ottawa to London, spaced two weeks apart.

If she booked this as two simple round-trips, she’d have to pay the relatively higher fare – the one with no three-night minimum stay requirement – for both bookings.

Ticket 1 (2 nights, $$$):

Oct 1: YOW – LHR
Oct 3: LHR – YOW

Ticket 2 (2 nights, $$$):
Oct 14: YOW – LHR
Oct 16: LHR – YOW

On the other hand, if she booked one round-trip from Ottawa to London (with the return leg two weeks later), and nested a second round-trip from London to Ottawa in-between, she’d be able to pay the relatively lower fare – the one with a three-night minimum stay requirement – on both bookings!

Ticket 1 (15 nights, $):
Oct 1: YOW – LHR

Ticket 2 (11 nights, $):
Oct 3: LHR – YOW
Oct 14: YOW – LHR

Oct 16: LHR – YOW

Airlines frown upon this sort of behaviour, since your back-to-back ticketing is costing them the revenue they’d otherwise earn if you had booked the tickets the normal way and had paid for the less restrictive fare. They’ve been known to suspend frequent flyer accounts of passengers who routinely employ this practice.

Indeed, if we look at Air Canada’s conditions of carriage, for example, we see the following:

Air Canada specifically prohibits the practices commonly known as:

“Back To Back Ticketing” – the combination of two or more round-trip fares end to end for the
purpose of circumventing minimum stay requirements;

If your circumstances are such that you would benefit from back-to-back ticketing, then, it’s often recommended to book your two tickets on different carriers (say, Air Canada and British Airways), in order to avoid detection.

The Award Angle

Unlike hidden city ticketing, where the tricks are primarily found when booking with cash but can also be applied to award bookings, it may well be the case that the true power of nested trips is unlocked when combining multiple award chart sweet spots in order to craft some truly incredible trips.

One example is the trip I described in Exploring Atlantic Canada with Aeroplan. Aeroplan lets you fly all over the Atlantic provinces for just 15,000 miles round-trip (including a stopover), so by nesting one (or more) of these trips within the round-trip that’s bringing you to the region, you can visit quite a number of destinations in this beautiful part of our country that would otherwise be quite expensive to get to.

The same lesson actually applies to the remote northern communities of Canada as well. Aeroplan partners with First Air and Canadian North, two airlines with extensive route networks all over the Northern Territories and Nunavut. A significant chunk of these territories falls within the “short-haul” definition, so you could again nest 15,000-mile round-trips with a stopover within a separate trip that brings you to and from the region.

(A separate post on the finer workings of such a trip – and indeed a potential trip itself – is in the works.)

Go swimming in the Arctic Ocean in Tuktoyaktuk, NT!

Go swimming in the Arctic Ocean in Tuktoyaktuk, NT!

But you can apply the same lessons to intercontinental travel as well – the more individual sweet spots you can take advantage of, the more outstanding value you can squeeze out of your miles.

Here’s one example. You have a stash of Aeroplan miles and want to embark on a round-the-world trip hitting up Europe, Australia, South East Asia, and Japan. Hold on a second, that’s four stops in total, and you’re only allowed three!

Before you start agonizing over which destination to sacrifice, think about whether there might be a smart way to incorporate a nested trip into your overall itinerary.

Indeed, if you were to designate Paris, Melbourne, and Singapore as your three stops, you’d then be able to nest a “pseudo one-way” award to Japan using just 25,000 Alaska miles for business class (read #7 in this article). The overall routing would look as follows:

Aeroplan Mini-RTW:

YYZ – CDG (stopover)
CDG – MEL (destination)
MEL – SIN (stopover)

Alaska one-way w/ stopover:

SIN – TYO (stopover)

Cheap AirAsia cash flight:


By nesting what’s effectively a round-trip that can be booked for one-way prices (an Alaska Mileage Plan sweet spot) inside a three-stop journey around the world (an Aeroplan sweet spot), you’re combining the power of two programs in order to attain some seriously impressive value for your points – and one hell of a trip.

An Illustrated Example

For the serious travellers out there who take off multiple times a year (and are therefore busy planning several trips at once), a little bit of careful planning might pay off tremendously.

The general principle here is that you tend to get the best value out of a certain program’s miles when you maximize that program’s stopover and routing policies. With Aeroplan, that means two stopovers in addition to the destination, with the ability to substitute one stopover for an open-jaw.

So if, for whatever reason, you’re not maximizing the stopover rules on a certain trip, you might be able to “use” that stopover allowance towards a future trip if you can plan ahead and the circumstances allow for it. Let’s look at a few examples in detail.

5+ stops in one trip…?

5+ stops in one trip…?

Let’s imagine you’re planning to bring the family to Europe twice this year – once during the summer holidays when kids are out of school, and once later on during Thanksgiving just to visit some in-laws in London.

You have a much looser schedule during summertime, meaning that you’d like to hop around Europe and see a few more places. On the other hand, you only have a week during Thanksgiving and so are looking for a simple round-trip.

Ordinarily, two round-trip bookings would give you the ability to stop in three places each, but that allowance would be “wasted” on the second trip. So what can you do?

That’s right – nested trips can help you “transfer” the stopover allowance from the second trip to the first!

North America to Europe round-trip:

YVR – CPH (stop)
CPH – MUC (stop)
MUC – LHR (stop)

Europe to North America round-trip:

LHR – GVA (stop)
GVA – LIS (stop)
LIS – YVR (stop)
[end of trip 1]

[beginning of trip 2]


Summer Trip

Thanksgiving Trip

You’re making two bookings – one from Vancouver to London with stopovers in Copenhagen and Munich, and another from London to Vancouver with stopovers in Geneva and Lisbon. However, you schedule these stops such that you’re essentially enjoying five stops in Europe during summertime (which makes for an amazing trip with the family) and a simple round-trip for Thanksgiving (which is all you need). Maximizing indeed!

We can get even more elaborate. If you haven’t read about “The One-and-a-Half Trick” yet, brush up on that one and then come back, since we’ll be building on it here.

Imagine your travel plans for the year involve a South American getaway (let’s say Buenos Aires) sandwiched by two trips to Europe (let’s say Vienna and Madrid). You’re looking for simple round-trips rather than stopovers, but you’d still like to use miles if possible and avoid paying cash.

According to the Aeroplan Reward Chart, round-trips to both Southern South America and Europe 1 would cost 60,000 miles in economy class. So if you booked ordinary round-trips for all three, you’d be paying 180,000 miles in total.

But what if you booked the following?

North America to Europe round-trip:

YUL – VIE (stop)

Europe to South America round-trip:

VIE – YUL (stop)
[end of trip 1]

[trip 2]
YUL – EZE (stop)
EZE – YUL (stop)
[end of trip 2]

[trip 3]

VIE – MAD (stop)

North America to Europe round-trip:

Europe to South America Round-Trip (nested):

Instead of three round-trips all originating from Montreal, you book one round-trip between Montreal and Europe and another one between Europe and South America, with Montreal as your stopovers. Now, you still get to travel on the same flights as before, except you only have to pay a total of 140,000 miles, netting a savings of 40,000 miles!

The savings are potentially even bigger in business class, and while this example is geared towards East Coast residents who travel to Europe, a similar principle applies for West Coast travellers heading to Asia.

These techniques are most useful for travellers who 1) can plan ahead to some degree, 2) often return to the same region within a certain period, and 3) often don’t fully maximize the generous stopover allowance. If those describe you, then this type of nested booking should be a technique you always keep up your sleeve.


Once you start thinking about putting trips in-between other trips, the travel possibilities grow exponentially. With nested trips, you’re looking at a more involved trip-planning process, but in return, you might be able to see more places you want to see, and perhaps even save miles by maximizing the stopover policies in situations when they’d otherwise go to waste.

Best of all, unless you’re engaging in back-to-back ticketing to skirt around fare rules, nested tickets are a perfectly above-board booking method that won’t at all get you in trouble with the airlines. Time to get out your calendars and world maps and let me know what sort of creative journeys you’re able to come up with!