United's Big Loyalty Update, Giveaways, Deals, and More

Hello from my return to reality!

If you’ve been following closely on social media, Jill and I had our first couples’ escape since becoming parents over a year ago.

Finding the time to take the trip wasn’t easy, but we’re grateful for the memories (and the grandparents who allowed us to make it happen).

We ended up being hosted by the Four Seasons Costa Rica, a property that I’ve been longing to return to since my first (and only) stay there twelve years ago. I’ll have plenty more to share, but I can confidently say that it’s still the ultra-lux Costa Rican escape I remembered.

Speaking of returning to reality, this morning I woke up to news that I predicted would happen soon enough.

Read on for more, including my first newsletter giveaway and limited-time gear deals.

This newsletter is brought to you by ABC Getaways — explore stays and book now at the lowest rates. Learn more and XXX.

United started the week with a big loyalty update.

The announcement that’s practically worth an entire newsletter is the headline buried at the end of the United email that introduces a “dynamic approach to PlusPoints upgrades.”

Before you get too worried, nothing is changing between now and February 2027.

And the good news is that the airline isn’t increasing Premier status thresholds next year, and it’s also introducing more ways to earn PlusPoints and receive upgrades on award tickets.

(TL;DR: expect the waitlist to get even longer than it is today, but more upgrade opportunities are always better.)

But all of that news is secondary to the big announcement about PlusPoints.

Right now, if you want to use PlusPoints (United’s upgrade currency) to upgrade your flight, you need somewhere between 10 and 80 points to do it. The number of points required is listed in an easy-to-read chart.

Starting next February, the airline will move to dynamic pricing.

There are more questions than answers right now, but the basics don’t paint the most rewarding picture.

United will vary the number of PlusPoints required for an upgrade based on demand, cabin, and other factors, meaning that the upgrade price will differ from flight to flight, just like it does in cash.

We still don’t know how waitlists will work in the new dynamic pricing model, nor do we know how frequently prices will change, but this is a move I predicted would happen earlier this summer.

The writing has been on the wall ever since United introduced a new PlusPoints exchange that allows you to convert upgrades into bonus miles or travel credit. The redemption rates were so skewed that I wondered whether this could signal the end of PlusPoints upgrades as we know them.

Those who fly to Europe on Tuesdays in October will probably find more value with the new dynamic program. Everyone else should hope that the folks in Atlanta or Fort Worth aren’t reading this newsletter and thinking about copying this move.

I’m putting the finishing touches on my holiday gift guide (should hit your inbox later this week), but in the meantime, it’s worth calling out some of my go-to products that are still an excellent deal this holiday season.

AirPods 4 with active noise cancellation are still just $99.99 from Amazon (44% off). These are probably the best travel earbuds you can find for under $100.

(Here are the other travel tech essentials you need to pack, including one you probably forget.)

Away is offering up to 20% off many staples. Grab the Bigger Carry-On for $265, or the Featherlight Weekender for $133. Shop other sale items here, and grab the travel backpack I use for $228 (sadly, not currently on sale).

Finally, the best travel diaper bag/backpack combo, Dagne Dover’s neoprene diaper backpack, is on sale for 30% off. If you’re a parent (or know one), this is the only bag they need. Trust me.

Well, this was way more controversial than I expected.

When I go to the airport, I want to look at the screens and quickly find my flight status on the board.

I can’t do that with United’s new FIDs (flight information displays), and I thought many of you wouldn’t be able to either.

But judging by the replies I got on Instagram, it seems like some of you think this new layout is more intuitive than the old one. (If you have strong feelings, hit the reply button and tell me what you think. Maybe I’ll anonymize some of the best replies and share with everyone.)

One of my goals with this newsletter is to introduce you to the off-the-beaten-path tips, tricks, and hacks I use to elevate my life.

One such example is Chase’s Trip Delay coverage, included with the Chase Sapphire Reserve® and Chase Sapphire Preferred® cards.

As winter approaches, it’s worth keeping this perk top of mind if weather snarls your journey.

It’s saved my family and me thousands of dollars this year alone and could do the same for you, too.

If you’re not yet a Sapphire cardholder, consider using my links when applying.

Long-time followers know I love to spread the holiday cheer this time of year by brokering an exchange of airline upgrades and hotel free-night certificates. No bartering, just helping people share their transferable benefits.

I’m planning to do the same this year, but it’ll be limited to newsletter subscribers. (Much easier to handle all the forms via email than social media.)

I’ll have more to share on this later this week, but stay tuned and tell your friends to subscribe if they want in.

One day, I’ll have some spare time to write stories about everything happening on the beats I’m most passionate about.

Until then, enjoy this news-you-can-use section highlighting everything you may have missed since my last newsletter.