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When you subscribe to From the Tray Table’s email newsletter, you automatically receive my five most underrated travel hacks as a thank-you for joining.
These aren’t your typical “take the 6 a.m. flight to avoid delays” hacks. These are the esoteric tricks that most travel bloggers and influencers aren’t talking about.
But one hack in particular has clearly struck a nerve and caused some confusion.
Judging by the replies in my inbox, it’s worth explaining how I saved over $10,000 this year using a tactic called trip nesting.
So let’s break it down.
What is trip nesting?
Trip nesting is a money-saving strategy for frequent travelers.
Instead of booking each trip as a simple round-trip from the U.S., you use multiple round-trip tickets arranged like puzzle pieces to build your ideal itinerary for much cheaper.
That sounds abstract, so I’ll use a concrete example.
Earlier this year, I visited Europe a few times. Most travelers would buy three round-trip tickets from the U.S. to Europe. So, one round-trip flight for a visit in February, another in April, and another in June.
That works, but it’s not the cheapest way to fly, especially if you want to sit in the pointy end of the plane.
That’s because flights departing from Europe (and other points outside of the U.S.) often cost dramatically less than the same flights departing from the U.S.
Trip nesting takes advantage of that.
Expensive way: three round-trips from New York
Once I knew I had three trips to Europe, my next step was to figure out how to use trip nesting to save.
To better illustrate the example, I’m going to use business-class fares for similar dates in 2026.
For simplicity, let’s assume that all three of my European trips are to Frankfurt (though the same logic applies to any other international destination).
If I booked three standard round-trips from New York to Frankfurt, the prices would look like this. (Note that I’m looking for the cheapest business-class fares on a mainline carrier).
- Feb. 4 to Feb. 11: $5,193
- April 3 to April 15: $$4,262
- June 11 to June 16: $5,859
Total: $15,314 for six flights in business class.
Booking flights with trip nesting
Instead of three normal round-trips, here’s what I’d book instead with the nested version:
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- One-way from New York to Frankfurt (Feb. 4): ~70,000 points
- Round-trip from Frankfurt to New York to Frankfurt (Feb. 11 to April 8): $3,106
- Another round-trip from Frankfurt to New York to Frankfurt (April 15 to June 3): $2,895
- Finally, a one-way flight from Frankfurt to New York on June 16: ~70,000 points
That totals $6,001 and 140,000 points.
Even if you value points at 2 cents each, the “all-in” cost is roughly $9,000, about $6,000 cheaper than the three normal round-trips.
Tips and tricks for nesting flights
Redeem points for one-ways
One-way paid business-class flights can be extremely expensive, but one-way award redemptions are often reasonable when you find saver award availability.
My go-to programs for Europe:
- Air France/KLM Flying Blue
- Air Canada Aeroplan
- United MileagePlus
So in above example, I’d redeem Air France Flying Blue miles, Air Canada Aeroplan points, or even United MileagePlus miles for the one-way flights.
There are a handful of other valuable programs for redeeming one-way long-haul flights to and from Europe, but those are three of my favorites.
Alternatively, you could pay cash for the one-ways, but you might end up spending more on the one-ways than you would on simple round-trips starting in New York, negating the value of nested trips.
Consider multi-city fares
If your next trip doesn’t start where your last one ended, book a multi-city itinerary as part of your nested trip strategy.
So, say you need to get from Frankfurt to New York, but plan your next flight in a few weeks from Boston to Zurich.
Book a single multi-city trip:
- Departing Frankfurt to New York
- Then from Boston to Zurich in a few weeks
You’ll still take advantage of the cheaper pricing for flights departing Europe, and you won’t need to worry about purchasing positioning flights for your next leg.
“Throw away” your return
If you can’t find award availability for the one-way flight, you could still end up saving by buying yet another round-trip ticket.
After all, one-way cash fares are often more expensive than a round-trip, especially in business class.
Just push your return date far into the future (and hope for a big schedule change or delay), that’ll entitle you to a refund for the remaining leg.
Worst comes to worst, you lose the value of the return ticket. And best-case scenario: you end up getting a refund for the return flight that you weren’t planning to take.
Final thoughts
Trip nesting looks complicated at first glance, but once you see the structure — one-ways on the ends, cheaper ex-Europe round-trips in the middle — it should click.
And the savings can be massive.
Now that you know everything you need to know about trip nesting, you probably have a few questions. Sound off in the comments, and I’ll do my best to reply.
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