Book smarter, not harder

Haaaappy (long) weekend, my friend!

Personally, I think you should spend your bonus 24 hours doing something responsible… like booking a trip.

I hear that’s what all the cool kids are doing. 😎

Meanwhile, I’m writing to you from Porto, where I’m currently trying to outwalk my newfound pastel de nata addiction.

While I take a breather between bites… here are some quick ways to make your next trip a reality.

😌 So, Hyatt’s changes weren’t actually that bad (and here’s why). 

💙 You could be earning 14x points (or more) on United flights. 

🏨 This underrated hotel chain is offering instant status (you don’t even need elite status to qualify!).

💰 Mike has a million Marriott points… and here’s how.

💳 You can transfer UR points to Southwest with a 30% bonus through June 5.

🎥 Are humans or AI better at planning travel? Find out in this week’s Daily Drop YouTube video.

🏆 Our Favorite Pick: Two ways to book cheaper flights

Airfare is feeling a teeny bit crazy these days.

One minute you’re looking at a $59 one-way on Google Flights… the next, United wants 18,000 miles and your remaining sense of joy for the exact same route.

So this week, we wanted to highlight two practical ways to spend less on domestic flights: one using points and one using a budget airline promo that’s… surprisingly decent?

Book United flights using partners

So there’s this sweet spot… and it involves booking United flights through Air India’s Maharaja Club program.

And yes, I know that sounds random. 🙂

But thanks to Rove Miles transferring 1:1 to Air India, it’s suddenly become a very practical way to book United flights for (way) fewer points than United itself charges.

We’re talking short domestic flights for as little as 3,500 Air India points one-way.

Even Hawaii can price surprisingly well.

Yeah… NOW you’re for sure paying attention.

Mike found United flights to Honolulu for just 13,500 Air India points when United was charging well over 20k miles for the exact same seat on the exact same plane.

Almost 10,000 points in savings just for a few extra clicks on the ‘ole laptop? Done.

And honestly, the sneaky-good part here is the earning side.

Rove lets you earn miles on hotel bookings, and certain stays are even marked “Loyalty Eligible,” meaning you can sometimes double dip with:

• Hotel points

• Elite nights

• Promos

• AND Rove Miles

In other words: Because Rove points transfer to Air India, you can earn enough miles for United flights just by booking hotels. 👇

Some of the earning rates on boutique and non-chain hotels are also kinda wild.

A quick 2-night stay can pretty easily earn enough miles for one of those shorter United flights.

So yeah… Air India sounds super niche on paper, but it might just be one of the cheapest ways to book United flights right now.

👉 You can dive even deeper into these examples in this newsletter.

Frontier launched a decent promo?

Now for the opposite end of the airline spectrum. 😅

Frontier is currently running a promo where you can earn 5,000 bonus Frontier miles every time you book an eligible round-trip cash flight (up to four times total).

And because Frontier flights are sometimes cheaper than my sad airport lunch, this can actually be a solid return on very little spending.

For example, the following round-trip flight from Denver to Austin is about $56 total:

… and booking that trip (with this promo) would earn enough bonus miles to basically book the same flight again.

Idk about y’all, but I loooove a “buy one, get one” situation, or in this case, a “fly one, get one.”

Here are some quick deets:

• Register by May 31

• Only paid round-trip flights qualify

• You have to book directly with Frontier

• Travel must be completed by Aug. 31

• You can earn up to 20,000 bonus points total

Now look… is Frontier suddenly boujee? Nah, fam.

But if your goal is simply to “get somewhere for as little money as possible,” this is honestly a decent low-effort flight promo.

And speaking of low-effort wins…👇

👀 Did someone say Daily Drop Pro sale?

ICYMI… It’s Memorial Day weekend.

And just because we love you (and are always looking for a reason to show it), we’re running a quick sale on Daily Drop Pro.

Quick reminder: Daily Drop Pro is our in-house tool, where you can get personalized points (and cash) flight deals, access to our pro community, and more.

You can even search your exact trip to compare flight and hotel options across different programs — then follow step-by-step instructions on how to transfer points and book it all.

Right now? You can lock in a sweet, sweet $50 off your first year (sale ends May 26!).

That’s it, y’all. I just love an easy “yes,” don’t you?

🌍 Week in Review

• Monday: ✈️ Save 30% on award flights from the U.S.

• Tuesday: ✈️ Book United flights for WAY fewer points

• Wednesday: 🤯 Earn 14x points on flights

• Thursday: 😬 Oops, I have a million Marriott points

• Friday: 🏨 Hyatt’s changes aren’t actually that bad

Alrighty, sweet fam.

These Porto hills aren’t gonna climb themselves. 

Love you lots, and I’ll see ya real soon. ❤️

Byeeeeeeee,

40°39'41.4"N 73°56'22.0"W

With contributions by Mike Dodge and Sam Anthony.