Welcome to The Upgrade List if you are new. If you’ve been here, welcome back!
Every Friday, this newsletter is going to do one of these 3 things for you:
Help you stop stalling and actually book trips
Show you how to get more $$ out of your trips w/ exclusive perks
Drop a free trip design straight to your inbox
Now let's get into it.
JO'S TAKE
I'm typing from an airport gate, which is actually the perfect setup for today's upgrade.
The lesson: stop herding points.
I needed a last-minute flight to San Francisco. I had 17K Southwest points sitting in my account, and the flight was 19K. Two thousand points short, but I had my Chase Ultimate Rewards.
Chase transfers to Southwest 1:1 and the points usually land within a day (in my case instantaneous). Two minutes later, I was 2K richer and booking a flight without coming out of pocket (with the exception of the $5.60 tax).
That's the whole point of points. Not stockpiling. Not "saving for someday."
This week's upgrade tip: always check BOTH redemption options
Before you click "book" on a full-points Southwest fare, run the same flight through Cash + Points. Southwest will show you up to five mixed redemption options starting as low as 1,000 points. Sometimes the blend is a better value than going all-in on points — especially if you're light on points but flush on cash for a different trip coming up, or vice versa.
A nice change that kicked in this January: the cash portion of a Cash + Points booking now earns Rapid Rewards points, tier qualifying points, and Companion Pass qualifying points. You're no longer giving up earnings just because you slid some points into the mix.
Pro move: Pull up the same flight in two browser tabs. One priced in points, one in Cash + Points — and compare what each option actually costs you in your weakest currency this month.
Transfer bonuses worth eyeing this week
A few that could make a redemption sing if the route lines up:
Chase → Air France/KLM Flying Blue: 20% through May 27 (great for European award space)
Capital One → Qantas: 20% through May 31 (their partner chart still hides gems)
Citi → Leaders Club: 25% through May 16 (niche, but useful for indie luxury hotels)
Amex → JetBlue: 10% through May 11 (small, but JetBlue points are decent on transcons)
Skip the Chase → Marriott 65% bonus — even with the bonus, you're trading roughly 2¢ Chase points for ~1.15¢ Marriott points. Math doesn't math.
THE TAKEAWAY
Points are a tool, not a trophy. If a redemption today saves you real money on a real trip, take it. The "perfect" award you're saving for may never come and devaluations usually arrive first.
See you next week. Maybe with a longer one.
Talk soon,
Jo