Southwest gets cheap again

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Are you on board with this whole cold-plunge trend? If you are, this crazy itinerary could take you to TWENTY of the hottest (or… coldest?) spots on earth to plunge right now.

It's been over 72 hours since this Newsletter was published, so some info and links might be out of date or expired.

Are you on board with this whole cold-plunge trend? If you are, this crazy itinerary could take you to TWENTY of the hottest (or… coldest?) spots on earth to plunge right now.

Goooood morning and welcome back to Daily Drop, the Rice Krispies of newsletters. We’re sweet, addictive, and we’ll have you coming back for seconds (without the adverse health implications 😉)!

Here’s what’s inside today’s bowl of goodness:

✈️ Southwest is selling flights for $39

When I used to live in the US of A, Southwest was my homie.

While living in Baltimore, I dated a girl who lived in Indianapolis. I would book $40 nonstop Southwest flights ALL the time to visit her, and I just fell in love with the airline.

It’s because of a few reasons:

  • They have amazing service and staff

  • They have flexible booking policies, like flight credit even for nonrefundable fares

  • As I mentioned, they USED TO have crazy cheap prices

That last point has changed a lot over the years, and Southwest has become less of an ultra-low-cost carrier.

Thankfully, they just launched a sale that hearkens back to the days of yore, with flights for as little as $39.

A screenshot from Southwest's website showcasing their new $39 sale

Here are the deets:

  • You must book your flights by 11:59 pm on January 25

  • Valid for Tuesday and Wednesday travel from February 6 through May 22

  • A 21-day advance purchase is required to get the sale prices

  • No promo code is needed—just book directly with Southwest

  • No blackout dates or routes (nice 😎)

  • The discounted fares are only for the “Wanna Get Away” fare class (the nonrefundable one)

Overall, this is pretty good (but not very good). I hate these Tuesday and Wednesday travel deals, as it makes the upside of the sale very restrictive and inaccessible for many. 😓

Still, there are some excellent deals available.

For example, if you live in the Windy City and want a warm winter getaway to Los Angeles, you could fly there nonstop for under $100, which is not half bad.

A screenshot showing a sample flight on Southwest from Chicago to Los Angeles for $90

Or, if you live in the Washington, D.C. area and want to fly to Indianapolis to visit my ex-girlfriend (tell her I said hi, by the way), you could fly for just over $100.

It’s no $40 flight, but it’s still cheaper than the other U.S. carriers. 🤷🏼‍♂️

A screenshot fro the Southwest website showing a sample flight from Baltimre to Indianapolis for $104

In terms of the dirt-cheap flights that Southwest is advertising, it seems there aren’t many routes that offer the low $39 price. Here are the ones I was able to find, though:

  • Chicago (MDW) to Cincinnati (CVG)

  • Minneapolis (MSP) to Chicago (MDW)

  • Louisville (SDF) to Chicago (MDW)

A screenshot fro Southwest's website showing a $39 flight from Chicago to Cincinnati
A screenshot fro Southwest's website showing a $39 flight from Chicago to Minneapolis
A screenshot fro Southwest's website showing a $39 flight from Louisville to Chicago

Some of these routes are actually popular and might be useful for some of you, so it’s great to see that there are at least a few ways to get dirt-cheap flights.

If you decide to stock up on Southwest flights for the winter, make sure you use a good travel credit card to maximize your points.

I know a lot of you have credit cards with the airline in question, thanks to some epic welcome offers last year, so use those if you want to earn some extra points from this purchase. 🤘🏼

🍪 Tasty Travel Tidbits

💰 Alaska Airlines shopping portal bonus

Not all deals can be a mic-drop, pick-your-chin-up-off-the-floor type of baller deal.

Some are just respectable, wholesome, and cheeky (say it in a British accent 🇬🇧) types of deals that are still worth a mention.

Enter the Alaska Airlines shopping portal bonus which is running through January 26, 2024 👇

Screenshot of the Alaska Airlines shopping portal bonus

Now we love a good shopping portal around here at Daily Drop. It’s an excellent way to boost your points if you’re already planning to make a purchase.

Many bank issuers and airlines have their own portals, as seen here with Alaska, so you could very well be partial to one over others depending on who you’re loyal with.

The current bonus is as follows:

  • Spend $150, earn 400 bonus miles

  • Spend $300, earn 1,200 bonus miles

If you’re someone who frequently flies Alaska or just wants to earn more Alaska Airline miles… then this is a nice little bonus.

Currently, Alaska miles are valued around 1.8 cents a piece, so this makes that bonus worth up to $21.60 if you hit the $300 spend.

And these bonus miles are on top of whatever additional miles you would earn from the amount of your purchase (e.g. 2X, 3X, 8X miles per dollar from a given retailer).

Though the monetary value isn’t groundbreaking, remember that Alaska miles can be redeemed for flights not only on Alaska Airlines, but also for Oneworld partner airlines which include some heavy-hitters like American, Cathay Pacific, and Qatar (among others!).

In case you didn’t know, we started a podcast. It’s called the Daily Drop Podcast.

Every week (and sometimes more often), Megan and I sit down to talk about travel hacking in a way that we simply don’t have space to do in this newsletter.

We think it’s a lot of fun, so check it out by clicking here, going on YouTube, or searching for us wherever you get your podcasts.

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That’s all for today, my friends! I just arrived in Jakarta, a city even more steamy than Bangkok (who knew that was possible?).

But enough about where I am…

Where are you in the world right now?

If you're traveling, where at?

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See you tomorrow ❤️

Mike Dodge
Head Writer, Daily Drop

6.1944° S, 106.8229° E

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