💘 The ultimate flight hack for couples

Estimated read time: 5 minutes and 19 seconds

Good morning from New York City!

By the time you read this, I’ll be in a country known for jazz music, seafood, and for being the fashion capital of the continent on which it lies.

… can you guess where that is? (hint: it’s not in Europe) 😉

While you copy and paste that into ChatGPT to solve for you, let’s dive into the newsletter:

• ✈️ Earn Southwest Companion Pass from a credit card

• 🏨 Marriott’s new global promo is live

• 🎥 Ultimate guide to Hilton Honors

• 🔒 Before using airport Wi-Fi… turn this on

✈️ Earn Southwest Companion Pass from a credit card

Southwest co-branded cards just rolled out their big once-every-year-or-two welcome offers – the ones that include a year of Companion Pass and a stash of points after meeting the minimum spending requirements.

If you’re not familiar, the Companion Pass is basically Southwest’s cheat code.

Here’s how it works:

You book a flight with cash or points, add a companion as long as there’s an open seat on the plane, and just pay the taxes and fees.

You can use it as often as you want, on any route Southwest flies, through February 28, 2027.

If you snag one of these offers early, that’s potentially around one full year of BOGO flights.

What makes this round especially spicy is the combo:

• You get tens of thousands of points as part of the welcome offer

• … plus an instant year of buy-one-get-one flights

• … which means you can book the primary traveler with those bonus points

• … and still bring someone along for almost nothing

Example: Weekend in Cancun

Let’s say you live in Kansas City and want to take your boo on a quick 3-day vacay to Cancun.

Southwest flies this route nonstop (which is cool, by the way), for as few as 8,000 points each way:

If you get one of these card offers, you can use your welcome offer points to book this, then add your companion for ZERO extra points.

That’s two people, round-trip to Mexico for 16,000 points and the cash fees.

Oh, speaking of the cash fees…

It’s important to know that while the companion doesn’t have to pay the base fare or points, you will still be on the hook for any taxes and fees.

In the above example, that’s $146 round-trip. But for domestic flights, it’ll be just $5.60 each way.

Stack with the card’s benefits

The nice thing about this system is that by holding a Southwest co-branded card, you’ll get benefits like free checked bags.

That means you can book a basic fare without worrying about whether or not your significant other will be able to bring their 50-pound hair dryer.

If you’re flying with a plus-one (partner, parent, friend, situationship, or emotional support human), this is one of the strongest shortcuts we've ever seen.

🏨 Marriott’s new global promo is live

Marriott just launched its first big global promotion of the year. And while it’s not one of their wild “double everything” events, there’s definitely solid value here if you’ve got paid stays coming up.

Between February 25 and May 10, Marriott Bonvoy members who register can earn bonus points AND bonus elite night credits on qualifying stays.

Here is how the two main components work:

Part 1: 2,500 bonus points per paid stay

You’ll earn an extra chunk of points on top of the normal earnings whenever you check out.

It’s not life-changing, but if you’ve got multiple short stays coming up, the totals add up fast.

Part 2: 1 bonus elite night credit per brand you stay at

This is verrrrrrrrrry intriguing. 🧐

Aside from Hyatt with their Brand Explorer perk, we rarely see hotel chains encourage members to try out different brands.

But with this Marriott promo, you’ll earn one bonus elite night credit per unique brand you stay at during the promo period.

Please don’t forget to stack

As always, you can stack this offer in several ways:

1. Use a portal like Rakuten

2. Use a Marriott co-branded card to pay for stays

3. Earn elite bonuses and points for being a Marriott member

A detailed example

That’s a lot to think about, so let me give you a simple example and break down exactly what you’d earn.

Let’s say you want to spend three nights in Portland, Oregon. You could hotel hop between these three hotels, spending one night at each property:

In total, you’d spend $378 for three nights. Not bad, honestly.

Let’s also say you have at least one Marriott co-branded card, which earns 6x points per dollar on Marriott stays. Most of these cards offer at least Silver status as a perk, which will add some extra bonus points.

Here is what you’d earn:

• 2,268 points from your card spend

• 3,780 points from being a Marriott member

• 378 points from Marriott Silver status

• 7,500 bonus points from the promo (2,500 per stay)

• 3 elite nights

• 3 bonus elite night credits (one for each stay at a unique brand)

In the end, that’s a nice haul for a relatively cheap 3-night stay.

As I mentioned earlier, you can also stack this by using a portal like Rakuten, which is currently offering 1.5x points or 1.5% back when shopping at Marriott.

This isn’t a life-changing portal bonus, but free points are free points. 🤷🏼‍♂️

And just to cover the bases, let’s specify the fine print:

• Only valid on cash stays

• You must register for this offer by April 26

• Valid for stays between February 25 and May 10

If you run into trouble with Marriott’s website, don’t worry – it’s not you, it’s them.

Their site has been glitching all day today and is giving major “2005 Limewire” vibes – I can’t tell if clicking something will search for a hotel or download 47 viruses onto my computer.

In all seriousness, if you do run into tech issues on their website, you can always call customer service and ask them to register you for the offer.

Anyway, Marriott’s new promo is a great way to rack up some extra points and nights toward elite status on your next stay.

🎥 Ultimate guide to Hilton Honors

Hotel loyalty programs can be confusing… And at first glance, you might think it’s not worth learning the ins and outs.

But I’m here to tell you that it might not be as complicated as you think.

In this week’s Daily Drop YouTube video, Brendan gives you the SparkNotes version (throwback reference for you naughty kids) of Hilton’s program.

Here’s what you’ll get in the video:

• How to earn Hilton points

• How to earn and use Free Night Awards

• A simple explanation of elite status

• How to maximize your points value

If you want the no-nonsense version of the program, check out our 10-minute breakdown here:

That’s it for today, my friends. I hope you’re as excited about all of these deals as I am. It’s good to see things finally start to pick up in 2026!

Have a great day and ba suba,

40.7128° N, 74.0060° W

With contributions by McKay Moffitt