✈️ Earn Companion Pass from one trip

Estimated read time: 4 minutes and 47 seconds

🥱 Good morning and welcome back to Daily Drop!

I’m writing this while my body thinks it’s 3 a.m., my brain thinks it’s breakfast time, and my stomach thinks it’s still in Tanzania. Jet lag is a democracy, and apparently every part of me gets a vote.

Anyway, let’s get into it:

• ✈️ Earn a Companion Pass from one trip

• 🧐 Would you rather: 25k points or $500?

• 🌎 Unlock the world (and protect your data in the process)

• 🤓 Travel Trivia Reveal

✈️ Earn a Companion Pass from one trip

Southwest just dropped an epic opportunity on us… but we need to act quickly.

Here’s the gist: If you book one round-trip (or two one-ways) on Southwest before August 28, you’ll unlock a Companion Pass that’s valid Jan 6 to Mar 6, 2026.

That means for two full months next year, you can bring someone along on your Southwest flights and they’ll just pay the taxes/fees (usually $5.60 each way).

That’s huge — especially since it lines up with long weekends like MLK Day and Presidents’ Day.

Here’s how it works:

• Step 1: Register (don’t skip this part or your flights won’t count).

• Step 2: Book one round-trip or two one-ways before August 28 (tomorrow).

• Step 3: Fly that trip (or trips) by November 15.

• Step 4: On January 6, 2026, the Companion Pass lands in your account. Pick your buddy and start booking!

What counts (and what doesn’t):

• ✅ Regular revenue tickets, award bookings, and cash + points bookings do qualify.

• ❌ Basic fares don’t. Neither do flights booked before registration.

• ❌ If you change your flight after the booking window, that can also kill the promo.

Why this is awesome

• It’s basically a “try-before-you-buy” Companion Pass without grinding 100+ flights (or putting massive spend on your Southwest card)

• You can book your own January/February flights now, then tack on your companion for free after January 6 (as long as there’s still a seat).

• Award flights work to trigger it — so you can qualify using points and then use the pass on cash bookings later.

Smart plays

• Go cheap to qualify: Grab a dirt-cheap round-trip or two short one-ways this fall.

• Save it for expensive trips: Cash in the Companion Pass on pricier winter getaways when flights are expensive.

• Flexibility: You can change your companion up to three times in that window — so yes, in theory you could bring your partner in January, your mom in February, and your bestie in March. 😉

Bottom line: If you ever thought about trying the Companion Pass lifestyle, this is the easiest possible way to do it.

Book something small now, and then treat someone to a free trip next winter — whether it’s ski slopes, sunshine, or just a Valentine’s getaway.

🧐 Would you rather: 25k points or $500?

When the [[ chase-sapphire-reserve.name ]] relaunched, the limited-time offer was pitched as a big deal: 100,000 points plus a $500 travel credit.

It sounded great at the time — because who doesn’t like an extra $500?

But now that the limited-time offer has ended, the “regular” offer on the table is 125,000 Ultimate Rewards points. And the funny thing is… that’s actually better. 😏

Here’s why:

Example 1: Phoenix to Paris in Premium Economy

Let’s look at a real booking. A flight from Phoenix (PHX) to Paris (CDG) in Premium Economy currently sells for around $1,703 in cash.

Instead of paying cash, you could transfer points to KLM/Air France’s Flying Blue program and book it for 30,000 miles + $177 in taxes thanks to this month’s Promo Rewards.

Even if you had to add 5,000 points from your stash of Ultimate Rewards points, the “extra” 25,000 points from the new offer would nearly cover the ticket. That’s close to triple the value of the $500 credit (even when accounting for the taxes and fees).

And if you’re aiming higher, that same flight in business class is just 60,000 miles — which means your points could easily be worth over five cents each.

Example 2: A Hyatt stay near Philadelphia

Not planning to jet off to Europe? No problem. You could instead transfer those points to Hyatt.

Take this Hyatt Place in Mt. Lauren, New Jersey, where rooms cost $184 per night after taxes. With World of Hyatt, the same room is just 5,000 points per night.

That means 25,000 points can cover five nights that would otherwise cost nearly $1,000. Again, that’s double the value of the old $500 credit.

Oh… and don’t forget that all of this is on top of the 100,000 points you also get from the welcome offer. 😉

Flexibility wins every time

This is the heart of it:

• That $500 credit was tied to one portal and had an expiration date.

• Points can be used in the portal or transferred to over a dozen airline and hotel partners.

• They don’t expire as long as you keep the account, and you can save or stack them for bigger redemptions.

The takeaway

When you line them up side by side, the question becomes: Which is better — $500 locked to one option, or 25,000 points you can use flexibly across the world?

The math (and the examples) point overwhelmingly to the latter. Which is why the “regular” offer is, somewhat surprisingly, the best version yet.

While points are the obvious choice for me, I can understand why some would prefer the travel credit instead… so tell me:

🤓 Travel Trivia Reveal

Yesterday, we had a little interactive trivia… y’all cast your votes for what you thought was the right answer, which is… Fes, Morocco! 🇲🇦

The ancient “Medina of Fes” is officially recognized by Guinness World Records as the world’s largest car-free urban area, with more than 156,000 residents getting around without a single car in sight (donkeys, however… are fair game 😌).

The Medina is a UNESCO World Heritage site where you can find old tanneries, copperware stalls, tons of rooftop cafes, and some pretty sick architectural gems… all without dodging any cars. 

It’s walkable and widely considered Morocco’s cultural capital. So if you’re planning a trip through Northern Morocco, take a stroll and take it all in.

Read more about the walkable Medina of Fes.

That’s all for today, folks! I’m curious to know if any of you will go for that Companion Pass deal… so tell me:

Dengan senang hati,

6.9175° S, 107.6191° E

With contributions by Tiffany Eastham, McKay Moffitt, and Benji Stawski