How to Book a Nested 2-in-1 Trip

We’ve seen countless cheap premium cabin fares from Europe to the US. However, cheap flights from the US to Europe seem to be much less common. That’s great for people that live in Europe, but doesn’t really help you if you live in the US.

Buttttt you still want in on some of those sweet, sweet premium cabin deals. Are you out of luck? NO! Of course not!

What do you mean by a “nested 2-in-1 trip”?

You don’t need Leo to pull off “Tripception” (image courtesy of Warner Brothers)

Before you ask, no – this isn’t a buy-one-get-one sale. This is trip-ception – booking a trip within a trip. The thought process is pretty simple. Traditionally, if you wanted to take two trips to a destination, most people will just book two return trips to the same city (with a week at each destination). In this case though, you’d book one return trip several months apart. Then, you’d fill in the rest with points or a cheap cash fare from your home country.

Why would someone do that?

In most cases, people who do this fall into two categories: people who want to take two trips to a destination and people who want to save money. Let’s use the example from the beginning of the article. A great premium cabin deal just popped up. Maybe it’s a business class deal from Europe to the US or incredible Cathay first class deal from Vietnam to North America. The only problem is that the flight starts from your desired destination instead of your home country. Even if you wanted to skiplag, you can’t skip the first portion or the airline will cancel the rest of your ticket.

That leaves you with two options: book the deal and figure out the rest later or miss out on the deal. For the sake of this article, let’s assume you want to book the deal. How can you “figure out the rest”? Let’s look at a few of your options.

WARNING: nested trips are not for the faint of heart. May cause excitement, but also stress. Proceed at your own risk/enjoyment.

The Easy Way

In a perfect world, you’d just be able to book a couple round trip flights from your home airport. Maybe you book two return fares from your home airport with a week at your desired destination.

Maybe you snagged a great deal from London to the West Coast. Then a couple weeks later, another deal from LA to London pops up and you book that to fill in the rest of your dates. Great, problem solved. Unfortunately, life isn’t that easy.

Using Points

Let’s use the Cathay example again. In that case, the flights departed from Vietnam and flew to several North American destinations. Let’s say you booked from Hanoi to New York. Right now, your itinerary would look like this:

Original Cathay Routing HAN-HKG-JFK (screenshot from

You’re incredibly excited because you just booked 30+ hours in one of the world’s best first class seats for under $1,000. In this case you have two problems though:

  • You still have to get to Vietnam
  • Once you get to Vietnam, your return flight ends in Vietnam

This is where the magic of points and miles comes in. For just 50,000 Alaska Airlines miles, you’d be able to book a one-way flight in Cathay’s business class from anywhere in the US to Vietnam. In total, you’d spend less than $1,000 and 100,000 miles for two trips to Southeast Asia in first and business class. That’s a pretty phenomenal value.

Using a little of both

Sometimes, there’s no one-size-fits-all solution and you need to be flexible. In this case, let’s say you were able to get a great first class return fare from Europe and a one-way business class flight back to the US. You’ve gotten most of the legs taken care of with cash tickets, but you’re still missing the outbound flight.

Unfortunately, direct one-way cash tickets from the US to Europe are usually prohibitively expensive, often costing more than the same round trip fare.

One-way international fares vs round trip

I don’t know about you, but I’m not overly eager to shell out a couple thousand bucks for a one-way coach ticket. In this case, it likely makes the most sense to just use points for the flight back across the pond.

What We Did

To show you how this works in practice, let’s walk through what we did for a trip we recently booked. If you’re not interested in reading about my recent experience with this, feel free to stop here. If you’d like to see how we made this work in practice, keep reading.

For our 2-in-1 trip, we wanted to visit Asia and then fly back to the States to visit family. We started out by buying one round trip fare to Singapore on Qatar Airways.

So how the heck did we turn this…

Screenshot from

…into this?

Screenshot from

Step 1: Book a return trip from London to Asia

Our original booking: LHR-GOT-DOH-SIN return flight on Qatar (screenshot from

Not too long ago, there were some pretty decent cash fares running from Europe to Southeast Asia on Qatar Airways. We’ve been wanting to go to that region for a while now and to be able to do it in Qsuites sealed the deal. We booked our flights several months apart, with the return flight coming five months after the departure.

Step 2: Book a cheap one-way flight from Asia to the US

Adding on SIN-PVG and PVG-DFW-CLT (screenshot from

Since we wanted to get back to the States, it didn’t make sense to backtrack to London, only to buy another return ticket. Instead of flying for close two days straight, we decided it would be easier to continue eastward. We were able to find a great one-way premium economy fare on American from China to the US and booked that.

Step 3: Book a cheap one-way flight from the US to London

If you’ve been paying attention, you’ll remember that one-way flights from the US to Europe can be incredibly expensive. Most times, we’ve booked these expensive one-ways using points and miles. However, I was able to snag a one-way through an OTA for only $300 on United. I booked the daytime flight to try to minimize my loss of sleep. Would business class have been nicer? Of course! That said, I can live in the back for six or seven hours at that price.

Adding on a one-way from CLT-IAD-LHR (screenshot from

Step 4: Book a cheap one-way flight to Asia using points

Adding a cheap positioning flight (LHR-PRG) and points flight (PRG-ICN) (screenshot from

For those of you who read the blog on a regular basis, you might remember a post about one of the best business class redemptions out there. If you have American Express Membership Rewards, you can transfer 25,000 points over to Etihad Guest to book a one-way business class ticket from Prague to Seoul on CSA Czech Airlines. We saw this as a great way to use our UK Membership Rewards points. It was definitely worth the $50 positioning flight from London.

If you don’t have any Amex Membership Rewards points, you can create them pretty easily. For example, the American Express Gold Card is offering a 50,000-point welcome bonus when you spend $2,000 within the first months of opening the card. That’s nearly enough points to fly round trip in business class on Czech Airlines from Prague to Seoul!

Step 5: Fly back on the originally booked flight from Step 1

Once you’ve reached this point, you’re pretty much done. We’ll fill in the rest and any intra-Asia flying with points or cheap cash tickets. That’s how you go from one trip to this:

Adding some intra-Asia flights and flying back on the original return fare (in orange) SIN-DOH-GOT-LHR (screenshot from

Final Thoughts

Booking a nested 2-in-1 itinerary can seem intimidating on the surface, but in reality, it’s not that hard to do. It’s a great way to take advantage of the best deals, especially if they don’t originate in your home country.

What’s your favorite way to turn one return fare into multiple trips?

Author: Stephen Hoechst

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  1. Are you able to write out in bullets how you this would work? makes it easier to understand. i.e
    CLT to LHR
    LHR to SIN with stopover in DOH


    Post a Reply
    • Agree! Or with dates on it. I’m really trying to follow this, but it’s not clear. Thanks!

      Post a Reply
    • Updated the article to include notes on the screenshots. Hope that helps make it a little more clear 🙂

      Post a Reply


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