How to turn your points into 5-star stays and lay-flat flights
Use my exact system to find award availability, transfer points strategically, and avoid wasting them on bad redemptions
This is the Window Seat Travel Hacking series, your guide to turning everyday spending into five-star hotel stays and lie-flat flights. The goal? Help you make the most of the money you’re already spending so you can book the luxury travel experiences you used to only dream about.
If you haven’t yet read my Travel Hacking 101 guide, start there.
You’ve opened the right credit cards. Hit the minimum spend. Watched your points balance slowly rise and maybe even hit six figures.
But now comes the part no one teaches you: how to actually use them. That’s what this guide is for.
I’ll walk you through exactly how to turn those points into luxurious travel—the kind that gets you lie-flat seats on flights to Japan and suites in St. Tropez—without ever touching your bank account.
I’ve been there: I turned one million points earned in a year into $25,000 worth of luxury travel (all for less than $3,000 in fees). It took months of trial and error, but now I know how to squeeze every last drop of value from a points stash. And I want you to know how, too.
Read on to get:
A breakdown of how to know if you’re getting a good redemption (or wasting your points)
My favorite tools for finding flights and hotels that can be booked with points
Real strategies for avoiding the most common redemption mistakes plus tips to 2x–10x the value of your points stash
A peek at my own personal redemptions, with the full breakdown: points, cash, and point values included
📄 A downloadable cheat sheet of every travel loyalty program you can transfer to, sorted by credit card issuer
You’ve opened a credit card with a strong sign-up bonus and hit the minimum spend—congratulations! That’s half the battle. Now you have your precious stockpile of points, waiting to be turned into the vacation of your dreams. This is a critical juncture, because it’s where most people go wrong.
Usually one of two things happens at this point, and both are bad. The first is total analysis paralysis. Overwhelmed by info, people freeze. They keep earning points without ever using them, promising themselves, I’ll figure it out eventually! They watch the number rise, comforted by the ever-expanding digits. But points aren’t like money in a savings account—hoarding just to have a high balance is not a flex.
Why? Points are a notoriously unstable currency. Value can drop and programs can change their policies among other things, so you’re much better usin’ ‘em than losin’ ‘em.
The other thing that happens, which I suspect is more common, is using points poorly—aka wasting them on low-value redemptions. Instead of being smart and strategic about making sure to stretch your points as far as possible, they might just jump on the first attractive offer they see. 400K points for a business class flight? If you have the points, that might seem like a no-brainer. But without doing the math on what those points are actually worth, you could be getting a terrible deal. Why would I want you, my dear reader, to only get one luxury experience when you could get, say, four or five instead?