I almost fell for this offer (almost)

Good morning and welcome back to Daily Drop, the baseball of newsletters — where every day is a slam dunk… or… a touchdown…?

Whatever. Let’s talk travel:

• 💳 The IHG offer that almost got me

• 🧳 Wyndham’s new subscription might just pay for itself

• ✈️ Southwest’s 40% off sale ends tomorrow

• 💬 Lounge Highlight: A Milan-bound masterpiece

💳 The IHG offer that almost got me

So I got this email from IHG the other day — you know, the kind that makes you squint at your inbox like, “Is this actually good, or are you just trying to make me do math before coffee?”

The deal:

Earn 8,000 bonus IHG points when I spend $5,000 on my IHG One Rewards Premier Credit Card between now and January 15th (3 months).

Now, I actually like IHG points. They’re probably my favorite non-transferable currency — simple, flexible, and very easy to squeeze value from.

But when I started crunching the numbers, things got messy.

The IHG Premier earns:

• 10x points on IHG stays (great, but I’m not dropping five grand on hotel nights anytime soon)

• 5x points on travel, dining, and gas

• 3x points on everything else

Travel and dining are better purchased with other cards that earn 3x or 4x transferable points.

If you spent that $5,000 on non-categorized purchases, you’d end up with 15,000 IHG points. But here’s the kicker: if you used a 2% cash-back card for that $5,000, you’d earn $100 back instead.

And with IHG’s frequent points sales (where they go for around 0.5 cents per point), that same $100 could buy you 20,000 points.

So even if you love IHG, the math says the IHG Premier loses this round.

BUT wait…

If we throw in that 8,000-point bonus, suddenly you’re at 23,000 points total, which does beat the cash-back scenario.

So… case closed? Swipe the IHG card?

Nope.

Because, as you might remember, I’m already chasing a different offer — that juicy Delta upgrade promo that earns me 50,000 Delta SkyMiles for the same spend.

In fact, even if you ONLY care about IHG, the Chase Sapphire Preferred® Card gives you 75,000 transferable points after spending, you guessed it, $5,000 in three months.

That’s 80,000 total points, which you can just transfer to IHG (sometimes with a bonus).

Here’s the real takeaway:

Whenever you see these kinds of “spend X, earn Y” promos, it’s worth comparing them to your other options.

Sometimes they’re solid, but often you can earn way more of the same type of points by channeling that spend into a better offer.

So yeah… nice try, IHG. You almost had me. 😉

🧳 Wyndham’s new subscription might just pay for itself

Wyndham woke up today and said, “You know what? Let’s be Amazon Prime… but make it travel.”

They just launched Wyndham Rewards Insider, a $95-a-year travel subscription that comes with:

• Automatic Gold status (fancy)

• Discounts on hotels, flights, cruises, and car rentals

• Ticketmaster perks so you can literally earn points for going to concerts

Plus, for a limited time, you’ll get two extra months and a 7,500-point bonus when you sign up — enough for a free night at tons of Wyndham properties.

So if you’d normally spend about $95 on that hotel night, you’re basically getting 14 months of status, perks, and points for free.

No catch, no scammy fine print (well, except the auto-renew thing — cancel anytime, yada yada).

If you actually like what you get over those 14 months, you can renew.

If you don’t? You’ve effectively traded $95 for a free night and some discounts along the way. Not a bad deal.

Now, the real-talk part:

• You can earn Wyndham points on all kinds of travel and other purchases, but only when booking through this new portal, which means you’ll be skipping your usual cashback or points portal.

• If Rakuten is offering the same multiplier on the same purchase, you might end up with less valuable Wyndham points instead of your sweet, sweet transferable ones.

• There’s also a non-zero chance that prices for flights in the Insider portal are inflated, though it just launched, so we’ll have to see how the math actually lands.

Still, I’ve gotta hand it to Wyndham — they’re getting weird in a good way.

No other hotel chain is out here mixing loyalty status, Ticketmaster perks, and flight discounts into a subscription model.

It’s new. It’s experimental. It might even be genius (it’s not). Now, let’s see if Hyatt and Marriott follow suit. 🤞

✈️ Southwest’s 40% off sale ends tomorrow

Good ol’ Southwest is back at it again with one of those classic, blink-and-you-miss-it flash sales — this time offering up to 40% off base fares when you use promo code 40SALE by tomorrow (October 23).

Some important details:

• Book by: Tomorrow (October 23)

• Travel window: December 3, 2025 – March 4, 2026

• Excluded routes: Inter-island Hawaii and a bunch of holiday blackout dates (obviously a conspiracy between Santa and the DOT).

• Not valid on fancy business fares

• Read all of the terms here

In reality, the deals are kind of a mixed bag. Some routes, like Indianapolis → Baltimore, are nearly the full 40% cheaper. 👇

The nice thing about Southwest sales is that they also apply to award flights, which is the case here.

But…

There’s some weird shit going on. For example, I found a flight from San Francisco to Denver, where the points price is discounted by… 0 points.

Still, if you’re flying Southwest this winter or early spring, it’s worth checking — even a small discount beats paying full price for an in-flight pretzel.

If you do go the cash route, use a Southwest co-branded credit card to earn some big boy bonus points. 👍

💬 Lounge Highlight: A Milan-bound masterpiece

One of our Daily Drop Lounge members just pulled off a chef’s-kiss redemption for a 2026 anniversary trip to Italy — booking two one-way business-class tickets from DC to Milan on British Airways (via Cathay Pacific) for 63,000 points + $282 each.

That’s about 5.3 cents per point of value — a redemption so good it probably deserves its own Aperol Spritz. 🧡

They learned everything through Daily Drop — positioning flights, transfer partners, and more – and it all came together in one glorious booking.

Now they just have to figure out how to get home. 😅

👉 Join the Daily Drop Lounge to share your own wins, get ideas from other travelers, and find your next redemption story.

That’s all for today, folks! I’m working on a fun section for you tomorrow that I think you’ll be excited about, so make sure to tune in.

Take care and have a great day. ❤️

50.0647° N, 19.9450° E

With help from my cool friends Tiffany “cat mom” Eastham and McKay “queen of the 0.5 selfie” Moffitt