Positioning flights, explained

Good morning from New York City, the “Windy City” (or something like that).

Let’s talk about some important travel things:

• 🤓 Travel Trivia Tuesday

• ✈️ Positioning flights, explained

• 💳 Three awesome merchant offers

• 🌎 Travel Trivia Reveal

🤓 Travel Trivia Tuesday

The answer is waiting a little farther down… keep scrolling 👇

✈️ Positioning flights, explained

One of my favorite tactics in the points-and-miles world is positioning flights.

I use the term all the time, but it’s worth revisiting and giving you some concrete tips.

A positioning flight is when you book a cheap flight to a different city to take advantage of a good deal from that city.

It generally means your travel will be less convenient. But it also helps you save a LOT of points or money.

For example, I regularly tell you about points deals on Virgin Atlantic. You can fly from New York to London for 6,000 miles on a regular basis, which is such a good deal:

If you live in Charleston, West Virginia, you might read that and think, “Well, I guess I can skip this section.”

No. No, no, no.

This is exactly where positioning flights come into play. You could book a cash flight for $67 to Newark, spend the day exploring New York City, then catch that cheap Virgin Award flight to London.

You could even spend the night in New York to give yourself an extra little adventure and some buffer time (which is what I usually do).

Compare that to award flights to London directly from Charleston, and you can see how this could make sense.

Delta and American both charge 27,000-37,000 miles for the same trip (or even double that, depending on the date).

Sure – you’ll pay more cash and spend more time in transit, but if getting the best possible deal is your priority, positioning flights are the move.

This is especially true if you’re traveling with multiple people, where doing this could save you tens or hundreds of thousands of points.

Before you run off and book your trip, there are some caveats:

1. Be careful about the costs

In the example I gave you, you’re paying an extra $175 to save 30,000 points, which can be a good deal.

But if your positioning flights (or onward award deal) have higher taxes OR require multiple extra nights in between, the math might not work.

2. Two flights means two itineraries

The biggest risk of positioning flights is being on two separate bookings…

If your positioning flight is delayed or canceled and you miss your connecting flight, neither airline is on the hook to help you.

That’s why I always like to give myself at least a one-night buffer when I position like this (and this is where hotel free night awards can be perfect!).

Additionally, use a card with good travel protections to cover most situations where things go wrong.

3. This is not the “convenient” option

If you value convenience over savings, positioning flights might not be for you. It will definitely add time to your itinerary.

However, I look at this as a positive. I’ve used positioning flights in all kinds of cool cities around the world, and I treat it as a fun opportunity to explore a new place rather than a hassle.

Bottom line

When award deals are available from cities you don’t live in, don’t assume you can’t take advantage of them.

Positioning flights can unlock good deals and comfortable premium long-haul flights if you’re willing to be a little flexible.

💳 Three awesome merchant offers

I said it once, I said it twice, and now I’ll say it… thrice: Merchant offers are the single most underrated way to save money on credit card annual fees.

Let me refresh your memory right quick:

Merchant offers are targeted, limited-time discounts or statement credits you get when you use a specific card at a specific retailer.

And right now, this bank has a bunch of new targeted offers that could save you tons of money on airfare and accommodations.

Personally, I’ve seen all three of these offers on this card, but you might see them on different cards.

Virgin Atlantic and Aer Lingus

Two of the big ones are rebates for spending on flights with Aer Lingus and Virgin Atlantic:

As you can see, the spending requirements are both pretty hefty, but there are two reasons you might still want to pay attention.

If you’re flying a family to Ireland on Aer Lingus, this could be a great way to get a nice return on an expensive airfare purchase.

This round trip from Boston to Dublin costs just under $400.

Flying a family of four round-trip would cost you around $1,600, triggering the merchant offer to save $250 – netting a 16% return, which is cool.

If you have this offer on the same card as me, you’ll also earn 5x MR points on the purchase, or about 8,000 points total.

If you’ve ever wanted to fly Virgin Atlantic Upper Class (a.k.a. business class), you may have been deterred by the sky-high taxes and fees.

For example, this flight from Tampa to London next month costs just 32,000 miles in business class, but has cash fees of almost $600.

If you’re flying round-trip as a couple, you’re looking at over $2,000 in cash fees. But with a merchant offer like this, you could at least save a couple hundred bucks to ease the pain.

Airbnb offer

The other interesting offer is to save $50 after spending $250 on Airbnb. This is way better than the other offers for two reasons:

• Airbnb has a massive variety of accommodations around the world

• The spending threshold is super reasonable

For travelers who prefer staying in homes to hotels (or for families who need more space), this is an easy way to save $50 toward the annual fee of whichever card you get this offer on.

The fine print

Merchant offers are targeted. You might see all of these, some of them, or none of them. You also might see other cool offers that I don’t see.

You generally need to activate these offers, and some of them might have terms (like requiring flights to depart from the U.S., for example).

Basically, always activate your offers, read the fine print, and book carefully.

🌎 Travel Trivia Reveal

A few minutes ago, we asked which airline was the first to offer rewards…

If you chose American Airlines, congrats — you know who started the points obsession.

American kicked off the airline loyalty era in 1981 with the launch of AAdvantage, the first modern frequent-flyer program that let travelers earn miles and redeem them for flights and upgrades.

Delta followed later that same year with its own program (which eventually became SkyMiles), while Europe took a bit longer to jump in. KLM launched its original frequent-flyer program in 1991 (now part of Flying Blue), and Lufthansa rolled out Miles & More in 1993.

So yeah… if you’ve ever booked a worse flight just to keep your status, or planned an entire trip around points — you can thank American for starting it all.

If you want to nerd out more about the history of frequent flyer programs, check out this article.

That’s all I’ve got for you today, amigos.

Have a nice day, and I’ll see you tomorrow.

Ciao,

40.7128° N, 74.0060° W

With contributions by McKay Moffitt