✈️ Fly to Hawaii with 40% off

Plus, I'll tell you about my favorite hotel points trick, and Delta has launched some winter deals.

Estimated read time: 4 minutes and 47 seconds

🚢 Celebrity Cruises is kicking off Black Friday early with up to 75% off a second guest on sailings booked by Dec. 9th. The deal covers trips through May 2027 (exclusions apply), and you can find more details here.

Good morning from Hangzhou, China - the city whose beauty inspired generations of art, poetry, and folklore.

And hopefully, today’s newsletter can inspire you to book some nice trips:

✈️ Southwest 40% sale (today only)

If you’re like me, you love the cold. It’s great. There’s nothing more refreshing than a crisp, snowy winter’s eve.

But most people are not like me. No, most people are dreading the winter. And folks - winter is coming.

Winter is Coming meme

Thankfully, our friends at Southwest have given us another good excuse to book a warm tropical getaway to Hawaii with a hefty 40% sale - but only if you book your flights today!

Here are the details:

  • Book by TODAY (November 14th) to get 40% off both points and cash fares

  • Valid for travel from December 3rd through May 22nd, 2025

  • There are some blackout dates

  • You must use promo code HAWAII40

Overall, this is great. After some random searches, I found mixed results.

This flight from Las Vegas to Lihue has multiple options for around 12,000 Southwest points one-way, which I think is a pretty solid deal:

Las Vegas to Lihue for 12,000 Southwest points

There are also some solid cash deals, too.

I found flights from the Los Angeles area to Honolulu for around $150 bucks, but I also noticed that on some dates, the cheapest flights are actually the non-discounted ones…

Los Angeles to Honolulu for $147 one-way

Anyway, this is a great deal for anyone looking to book a getaway, whether it’s next month or six months down the road.

If you want to rack up some Southwest points, you can sign up for a co-branded credit card (which just released some elevated offers) or a card like this one, which allows you to transfer points to Southwest.

🏨 Buy IHG points with a 100% bonus

A lot of people ask me how I can afford to live in hotels all year round. Especially really nice ones.

And while I earn points in creative ways, occasionally get a new card, and sometimes just pay cash, there’s one strategy that not enough people consider when it comes to getting excellent bang for your buck with hotels.

I’m talking about applying for this co-branded credit card (which allows you to get every 4th night free when using IHG Points) and buying IHG Points when they have a 100% bonus.

It just so happens that… well, you know:

Buy IHG points with a 100% bonus

That’s right, folks. The 100% IHG points bonus is back again.

This combination of tools is a super cost-effective way to combine points and miles strategy with a cash budget.

For example, many of the hotels I’ve lived in this year are super cheap ones, like this one in Jakarta, which only costs 4,250 points per night.

Holiday Inn Jakarta for 4,250 IHG Points per night

Four nights here would run 12,750 points thanks to the 4th-night free perk from this card.

To simply buy those points with a sale like this one, I’d only have to pay $95… to book a FOUR-night stay.

And since it’s a Holiday Inn Express, I even get free breakfast there (because every guest gets free breakfast there)!

Buying 14,000 IHG Points for $95

That’s obviously an extreme example.

But you don’t need to live in a cheap country to get value out of this combo… In fact, even booking hotels right at home in the U.S. is a good deal.

To prove my point, let’s look at the most expensive city in the country - New York, baby!

This Kimpton Hotel in Times Square can cost as few as 20,000 points per night.

Kimpton Hotel in New York City for 20,000 IHG Points per night

Okay, first of all… Holy f****** s*** 

That’s a CRAZY deal. Especially when you consider the cash price hovers close to $300 on the same nights… which, honestly, is also not terrible for New York…

The same hotel for $287 per night with cash

Anyway, simply BUYING the 80,000 points you’d need to book four nights (again, assuming you have this card) would cost you just $400.

Since these four nights would otherwise cost well over $1,000 if paying cash, you can see how this is the optimal choice.

Here’s the bottom line:

IHG is offering a 100% bonus when buying their points.

Whether you live on the road like me or you just want to save a bunch of money on a short trip, this is a GREAT strategy that you all should be considering.

🎁 Delta’s “Winter Your Way” event

Delta fans should be feeling jolly over this one 🎅🏻

And that’s because Delta is officially kicking off the holiday season with a solid selection of winter deals for earning bonus miles in a variety of ways 👇

Delta winter your way event

The festivities officially launched yesterday, granting early access to Delta Medallion Members and airline cardholders, but as of today, November 14th, the general public has wiiiide open access to these deals as well!

Here’s what you can earn:

  • 5x miles per dollar on Delta gift cards (for $400+)

  • 4x miles per dollar on rental cars booked with Delta Cars through February 2025

  • 4x miles per dollar on Delta stays through February 2025

  • 4x miles per dollar on Delta Cruises for travel through June 2025

  • Get 10% more for your miles when booking Delta Vacations for bookings through December 2025

  • Earn extra miles from 1,000+ retailers when using SkyMiles Shopping

These winter deals will be available to take advantage of until December 4, 2024. If you’d like more details on these Delta deals, you can head over to their promo page.

Now, are these deals and bonus miles worth it?

I wouldn’t go out of your way to buy gift cards or book a cruise just because of this, but if you’re a Delta die-hard and have been thinking about making one of these purchases anyway, then yes, of course!

Honestly, 4-5x miles per dollar is a great earning rate, and I will never say no to “bonus” anything… Especially when it’s points or miles 😏

And even though Delta’s loyalty program and redemptions have been on decline (womp, womp), there are still some really useful ways to use your SkyMiles.

There are plenty of relatively cheap domestic flights within the U.S., like this popular route from Seattle to San Francisco starting at just 4,500 miles 👇

And even though many Delta flights departing from the U.S. will cost an arm and a leg in miles, you can use your SkyMiles to book flights on their SkyTeam partner airlines.

For example, this route from Paris to Dubai features the longer, six-hour leg of this itinerary in ITA Airway’s stunning business class for just 42,500 miles (or 25,000 miles for economy if you’re trying to stretch your miles!).

Anyway, there are still plenty of ways to get max value out of your Delta miles, so if you’re able to earn some bonus miles along the way, that’s even better!!

That’s all for today, folks! I hope you all have a great day, and I look forward to seeing you tomorrow to finish off the week.

Cheers,

Mike Dodge
Head Writer, Daily Drop

30.2741° N, 120.1552° E