👀 Hilton guts award rates overnight

Estimated read time: 4 minutes and 35 seconds

☕️ Good morning and welcome back to Daily Drop — the only thing more addictive than your morning caffeine (and without the withdrawals, I hope).

We’ll keep doing what we do best: sharing news, deals, and tips to make travel more rewarding, with a little extra gratitude for the journeys we get to take.

Here’s what’s on deck today:

• 🏨 Hilton devalues… again (and this one’s brutal)

• ✈️ Southwest sale: up to 50% off (ends tomorrow)

• 🛎️ Should you buy Marriott points with a 40% bonus?

• 💺 Win from the lounge

🏨 Hilton devalues… again (and this one’s brutal)

Hilton Honors has quietly made changes to its award rates yet again, and not in our favor. Overnight, the cost of a standard room award at top-tier properties jumped from 200,000 points to 250,000 points per night.

That’s the second increase just this year:

• Early 2025: most expensive hotels capped at around 150,000 points

• Spring 2025: that ceiling climbed to 200,000 points

• Now: the cap has shifted to 250,000 points per night

Because Hilton doesn’t publish an official chart, these hikes often slip in without warning. In less than nine months, Hilton’s “standard” award pricing has inflated by nearly 67%.

And remember, this is only the floor for standard rooms. Premium rooms remain fully dynamic and can run several times higher.

What this looks like in practice

I recently stayed at Eichardt’s Private Hotel in Queenstown for my birthday back in July, using two Free Night Awards.

• In May, a standard room was 140,000 points

• Then it crept up to 170,000 points

• Today, the same room costs 200,000 points 👇

That’s a 43% increase in just a few months at a single property. 😬 

The silver lining

Hilton’s Free Night Certificates (FNAs) still work at any standard room, no matter how outrageous the price. So even as the numbers climb, one annual FNA can still unlock a 250k night.

That’s why I keep the [[ hilton-honors-american-express-aspire-card.name ]]. It comes with an annual FNA, automatic Diamond status, resort credits, and more.

Even though Hilton points aren’t my go-to currency anymore, the math still works out for those one-off luxury splurges. Personally, I’ve shifted most of my hotel strategy toward World of Hyatt and IHG, which are far more stable.

Bottom line

Hilton keeps moving the goalposts, and its points are proving less reliable for consistent value. Unless you’re holding co-branded cards or FNAs, it’s getting harder to justify collecting Hilton points over some other programs.

✈️ Southwest sale: up to 50% off (ends tomorrow)

Southwest just launched a massive sale, slashing up to 50% off base fares across the U.S., Hawaii, Puerto Rico, and international routes.

Here are the key details:

• Book by: tomorrow night (September 12) at 11:59 p.m. PT

• Travel window: September 30, 2025, to March 4, 2026 (some routes/dates vary)

• Promo code: MILLIONS

• Blackout dates: heavy restrictions around Thanksgiving, Christmas, New Year’s, and Presidents’ Day

• Other restrictions: certain routes (Hawaii, international, PR) are only valid on specific weekdays

As always, make sure you check out the sale page for full details and blackout dates.

Let’s look at an example. Since I’ve been sick and bingeing Breaking Bad for the last few nights, I figured Albuquerque was a good place to start.

A nonstop from Albuquerque (ABQ) to Baltimore (BWI) in October is down to $132 each way (normally $249) — almost the full 50% discount.

The same flight costs just 10,500 Southwest points each way if you’d rather book with miles. That’s a solid redemption.

And it’s not just long-hauls: a quick Baltimore–Chicago hop comes in at only 4,000 points each way (+$5.60 in taxes) for the Basic fare.

That’s a crazy value for a domestic nonstop. 👇

If you go the paid route, use a Southwest co-branded card — it’s your last chance to score an elevated welcome offer of 100,000 bonus points before the offer ends on 9/18/25 at 9:00 AM EST!

With these cards, you’ll maximize points earning, keep benefits intact (like free bags), and stack even more value on top of the discount.

🛎️ Should you buy Marriott points with a 40% bonus?

Marriott Bonvoy is running a “mystery” points sale with bonuses up to 40% — and from what I’ve seen, most people (myself included) are getting the full 40%.

So… should you buy?

The answer is: sometimes. Unlike Hyatt’s frequent sales (which are almost always worth a look), Marriott’s math is a little more hit or miss.

Let’s look at New York City

Take this Residence Inn in Midtown Manhattan. Cash rates are an eye-watering $706 per night. But with points, the rate comes out to about 50,000 points per night.

Thanks to Marriott Bonvoy’s 5th night free perk, a five-night stay would cost 212,000 points instead of $3,530 in cash.

Here’s where the sale shines: you could buy 210,000 points for $1,875 during this promo, top up the balance with just 2,000 more points (from Membership Rewards points, Ultimate Rewards points, or Bilt Rewards), and walk away saving over $1,600.

Not every redemption looks like that.

While this deal works in places with inflated cash rates like New York, the math is rarely the same in other places.

Take the Courtyard in Edinburgh. A five-night stay runs 200,000 points, but the cash rate is only $166 per night — about $830 total.

Buying those points, even with the 40% bonus, would cost $1,812. That’s more than double what you’d pay in cash — and you’d lose out on the points you’d normally earn from the cash booking.

The bottom line: Marriott’s points sales can occasionally unlock huge savings in markets with sky-high hotel prices (think NYC, London, or resort towns).

But more often than not — especially abroad — buying Marriott points ends up being a bad deal.

So if you’ve got a specific, expensive stay in mind, run the math before the sale ends on September 17. Otherwise, it’s probably best to sit this one out.

💺 Win from the lounge

Today’s Daily Drop Lounge win is a masterclass in stacking. 🥞

One reader booked a hotel for their partner’s work trip through the Southwest portal, which alone earned them 21,000 Southwest points.

But they didn’t stop there — they paid with their Bilt Mastercard, earning an extra 2x points on the purchase. Those Bilt points are especially valuable here because they can be transferred directly to Southwest, making them just as useful for future flights.

This is the magic of stacking — a single hotel booking turned into a pile of points, elite perks, and a practically free flight for a second traveler.

A perfect reminder that sometimes the best redemptions come from maximizing the earning side of the points and miles game.

If you want more wins like this (or to share your own), come join us in the lounge.

That’s all for today, folks! I’m off to eat more chicken soup, pound cough medicine, and daydream about my next trip. ✈️

Have a great day,

6.9175° S, 107.6191° E

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