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One of the interesting things about ‘travel hacking’ and the broader points/miles game is that loyalty programmes are always evolving and so you’re always learning new things. Or, sometimes, remembering things you had forgotten.

On a recent trip, I decided to use up some American AAdvantage Miles I’ve had for years and accidentally (re)discovered a rather useful tip. In my case, it ended up saving me about 50% of the miles I thought I was going to have to redeem.

What are you on about?

I needed to fly from Miami back to Europe. I didn’t mind too much where exactly, as long as I could sort out a reasonable connection home.

Initially, I searched for award space with American Airlines itself straight back to London. Business Class was available (with a connection in Charlotte) for 112,000 miles, which seemed a little steep:

My schedule was pretty flexible, so I started looking at alternatives. I quickly found availability to Vienna for just 57,500 miles, which seemed an excellent price these days for transatlantic Business Class (bearing in mind the negligible taxes/surcharges).

On closer inspection, the interesting thing was that the routing was via London. In fact, it was the exact same itinerary as the 112,000 mile award, but with an additional BA flight to Vienna tagged on:

Basically, by adding an additional leg, I could save 54,500 miles – nearly 50%. On the face of it, that may not make much sense, but if you think about it in similar terms to how cash prices for flights work (where indirect, less convenient, routes are often cheaper than direct flights), you can understand how the AA algorithm priced it.

Was this a fluke?

Not at all.

I can’t promise you will always find something similar, but it’s a feature of how AA’s award pricing works these days and is therefore surprisingly common. For example, I could have booked the same award, but ending in Stockholm instead at the same rate:

I don’t have any American Airlines Miles, so why is this useful to me?

Over the last few years, airline programmes have increasingly moved towards ‘dynamic pricing’ models. The basic idea is that there should be closer alignment between the cash price of a flight and the number of points/miles required for the same flight.

Most points/miles collectors hate dynamic pricing, because it generally removes a lot of the outsized value available. But, there are circumstances (like my example above) where it can also work in your favour – particularly if you can be flexible about when/where you want to fly.

Each programme is slightly different, with its own quirks. The principle though of flexibility and being willing to think a little bit outside the box is something that can be applied to pretty much all of them. I’ve already seen some very interesting things about the new Virgin Atlantic pricing model that I’ll be running some more experiments on soon.

Bottom line

American Airlines’ award pricing can offer surprising sweet spots if you’re willing to be flexible with your final destination. By adding an extra leg to your journey – counterintuitive as it may seem – you could save up to 50% on your miles redemption.

While this specific example involves AA miles, the broader lesson applies across many loyalty programmes: sometimes the less obvious routing offers the best value. In an era of increasing dynamic pricing, thinking creatively about your redemptions and being flexible with your destination can unlock significant savings.

P.S. – As Andrew points out in the comments below, you don’t necessarily need to take the last flight: “If stopovers are allowed you could book to fly the last leg a few days later, have your back checked to LHR (in this case) and quietly drop the last leg if you didn’t want to fly it. If stopovers aren’t allowed it might be able to work in a long layover (less than 24 hours) and try to get the check in agent to short check your bag to LHR”. That said, it’s not something you want to do too frequently, as loyalty programmes can take a bit of a dim view…