Hello from my final (and most rewarding) flight of the year!
I’m flying JetBlue from Fort Lauderdale to Punta Cana, which will be my 25th unique destination for the airline’s viral 25 for 25 challenge.
If you’re just tuning in, this means that I flew to 25 unique JetBlue destinations in the last six months of the year. You might be wondering: Is Zach really such a glutton for punishment? (After all, JetBlue’s operational performance didn’t exactly make it easy to fly the airline consistently.)
Well, by completing the challenge, I earned 25 years of Mosaic 1 elite status and 350,000 TrueBlue points. I’m compiling a full recap (including how much I spent on the challenge), but my early math indicates that I’m coming out way ahead.
As for destination number 25, I purposely saved the best for last. I knew we’d want to end the year with some R&R, and what better place to do it than the Caribbean.
We’ll be on island time through the new year, but don’t worry: I’ll still find enough reasons to hit your inbox again in the coming days, including with my full 25-for-25 recap.
In this edition
The fight for Chicago
Perhaps the most fascinating storyline in aviation these days is what’s happening in Chicago.
American and United both operate massive hubs there, and neither airline is backing down. They’ve sparred over marketing campaigns, gate access, routes, and just about every lever you can pull to win market share.
The latest move came on Friday. Less than 24 hours after American announced three new Chicago routes, United announced that it would also add three flights from O’Hare. And guess what?
They’re the exact same flights that American announced — just with more frequencies.
If you’ve got strong feelings about how this turf war ends, hit reply and tell me who you think ultimately wins the battle for Chicago — and why.
Gifts, rebates, and points
You don’t need me to tell you that Christmas is just days away.
Fortunately, I have a few easy gift ideas that are still available for last-minute delivery.
AirTags four-pack for $64.99 (lowest price of the season)
Plus, check out my 20 best holiday travel and lifestyle gifts for 2025
A few additional tips to maximize your spending:
Check Amazon for credit card discounts
Get up to 40% off when paying with Amex points ($60 max discount)
Get up to 40% off when paying with Discover cash back ($50 max discount)
Get up to 40% off when paying with Citi ThankYou points ($50 max discount)
Earn extra points — for free — with Bilt
Sign up for a free Bilt Rewards account, link a credit or debit card, and earn bonus points on lots of everyday spend — in addition to your normal points from your credit card company.
Reminder: you don’t need to be a renter to sign up for a free Bilt Rewards account.
Boosted offer: Free $25 to restaurants
InKind, the free dining rewards app, is offering a boosted referral bonus through Jan. 31. If you sign up using my link, you’ll get $25 off your next $50+ meal.
I’ve saved hundreds over time with InKind (my two favorite overpriced juice bars, Raw Juce and Juice Press, are on it). So are thousands of other neighborhood spots.
Here’s my referral link if you haven’t signed up yet.
Digital ID works!
When Apple announced last month that Digital ID is officially live, I couldn’t wait to try it. (Long-time followers know I’m just as obsessed with tech as I am travel.)
Well, I just tried it, and here’s what happened.
I placed my iPhone on the NFC reader of the Idemia identity verification machine at the TSA checkpoint.
My phone immediately prompted me to authenticate and share my Digital ID. After a quick Face ID and photo, I was fully verified without needing to take anything out of my wallet.
The best part? Digital ID works with a valid U.S. passport, meaning that it satisfies the Real ID requirement. So if you’ve been procrastinating (and the new $45 fee is now scaring you into getting your act together), at least you can use a Digital ID to clear security, for free.
Watch how it all worked (along with detailed instructions on how to use it) in my 25-second video recap.
Last-minute elite push
We’re down to the last few days of the year, which means it’s time to take a hard look at your loyalty accounts.
Are you close to hitting the next status tier with your favorite airline or hotel? If so, a last-minute push could be worth it.
If you’re chasing elite status with Delta or United, remember that status is largely spend-based. Instead of flying aimlessly to rack up segments, booking (or upgrading to) a single higher-fare ticket can earn a meaningful chunk of status credit in one shot.
Pro tip: If you already have upcoming flights booked, call customer service and ask about upgrading your fare class. That’s often cheaper than buying a last-minute upgrade to business or first class.)
Hotel elite status usually requires actual nights, so you may need a last-minute mattress run at a cheaper property to lock things in.
Alternatively, you could use your cobranded credit card to hit status-qualifying spend thresholds, but make sure your transactions post to your account on or before Dec. 31. (I often prepay bills like insurance at year-end if I need to bridge a small gap.)
And one final reminder: if you fly American, your elite year doesn’t wrap until Feb. 28, 2026 — so you’ve still got time.
Light up the nights

It’s the last day of Hanukkah, which my waistline will appreciate. (It spells the end of latke and jelly doughnut season.)
And as my family and I have been lighting up the past eight nights, my laptop also joined the glow-up party.
Apple just launched a new software feature, dubbed Edge Light, which essentially adds a built-in ring light to your webcam during video calls. You can tweak both the brightness and the color temperature, and it’s been surprisingly helpful in low-light settings.
Download MacOS 26.2 today to turn on your Edge Light (and keep those Hanukkah vibes going all year long).
Upgrade giveaway update
Here are the latest stats on my United upgrade spree.
104 ineligible submissions (people don’t read instructions…)
27 upgrades processed
17 long-haul flights
34 eligible upcoming upgrades
These upgrades haven’t been processed because I’m basically out of PlusPoints donations. If you have any to share, please reply to this email so we can keep spreading the holiday cheer.
News you can use
Hawaii connection: Southwest announced that it would add a new nonstop route from Hilo (on the Big Island) to Las Vegas starting on Aug. 6, 2026. This will mark the first time Hilo will be connected to the mainland since United pulled out of the market in 2023.
Feed me, airport lounge edition: Aside from a recent stealthy devaluation, American has been on a roll. The airline just announced a menu revamp for its Admirals Clubs, bringing things like bagel and waffle bars to the airport.
Going big for Boston: Another turf war has been unfolding for years in Boston, where Delta has been chipping away at JetBlue’s dominance. JetBlue is now trying to remind Bostonians that it’s invested in the local market with a new special livery dedicated to Boston. JetBlue isn’t limiting the aircraft to Boston routes, though it’d be pretty cool (but probably too operationally challenging) if it did.


