My Wife and I Are Flying Roundtrip to Cabo for Less Than $100, Here’s How

Alexandria and I are in Cabo San Lucas, Mexico for the next week. We’ll spend mornings running along the beach, enjoy afternoon poolside drinks at the Hyatt, hopefully get some scuba diving in and maybe some bouldering at Lovers Beach too. But it’s not technically vacation for us, we just happen to spending a week away.

While here, we’ll still be working, just remotely. And we’ll also volunteer some of our time to Los Cabos Humane Society. So, why did we decide to just work from Cabo for a week? Well, because Southwest flies here and two roundtrip tickets from Boston cost us less than $100.

How are we flying to Cabo for less than $100?

As you can see in my receipt above, I booked the ticket using 27,792 Rapid Rewards Points, paid only for taxes, and Alex flies free with me via the Southwest Companion Pass.

What is the Companion Pass? In my opinion, one of the best perks in travel! If you earn 110,000 Southwest Rapid Rewards points within a calendar year, then for the following year, you get to chose one person to fly free with you whenever you fly Southwest.

If you don’t currently have the Southwest Rapid Rewards Visa card, the signup bonus on that card is your best bet for ensuring you earn the pass. It’s currently 40,000 Rapid Reward points after spending just $1,000 in the first 3 months. Once you get that, you can reach the 110k with a little effort by using some of the links I’ll drop below.

With the Companion Pass, after you book a ticket, whether on cash or points, you simply add your Companion to your itinerary and you’re on the way with a two for one hot deal. Now, if you do earn the pass, where will you go?

We frequent the Southwest Getaway Finder to scan where and when we can hop a flight for the best deal. Just set your departure city, departure date, and budget (dollars or points) to start exploring options!

Venturing beyond U.S. borders

Southwest is typically my go-to airline for domestic flights and I generally fly Delta for international destinations, but starting back in 2014, Southwest began upping its international game. At least across Latin America.

I’m hopeful they’ll continue to expand, but for now, you can fly Southwest to the following countries:

  • Aruba
  • Belize
  • Cabo San Lucas/Los Cabos
  • Cancun
  • Cuba
  • Grand Cayman Island
  • Liberia, Costa Rica
  • Mexico City
  • Montego Bay
  • Nassau, Bahamas
  • Puerto Vallarta
  • Punta Cana
  • San Jose, Costa Rica
  • Turks and Caicos

That being the case, when I first earned Companion Pass, Alex and I started prioritizing where we wanted to use our points to fly, vs. pay for a ticket. If we go to visit our friends up in Buffalo, NY, or want to spend a weekend in Chicago, we’ll just pay for the ticket (well, mine at least and she goes free) and earn the points on the travel. Whereas when we look at visiting family across the country or jetting off to Liberia, Costa Rica, we’ll cash in on those points.

Cabo had been on the list for a while and we figured it would be a nice little getaway together after I got back from my near month in Alaska climbing Denali with the Between The Peaks boys. Plus, we’re big Hyatt fans (part of their World of Hyatt rewards program too of course!) and when the Hyatt Ziva Los Cabos resort opened its doors in 2015, we knew we had to check it out at some point.

But how sustainable is the Companion Pass and keeping a topped up rewards account? It’s actually easier than you might expect if you know the tricks and earning of points stays a top of mind priority. My brother and his wife have had Companion Pass since 2012 now, and Alex and I are coming up on year three.

How to keep up your Rapid Rewards point balance

Once you’ve got over 100,000 Rapid Rewards points, ideally the 110k you need to earn Companion Pass, then it’s actually fairly easy to keep your point balance up. There are a few easy tricks, certain shopping portals or rewards booking sites, like Rocketmiles, that give you bulk bonus points for simply buying what you probably normally buy anyway.

And then of course if you are using the Southwest credit card, whether Plus or Premier and Personal or Business, regularly for everyday personal/business expenses, the points just stack up! And then you use them to go awesome places!

Really though, it’s not a vacation 😉

Being able to head off to some beautiful beach in Mexico for a week is simply part of the lifestyle we’re making a priority to pursue. We both crave flexibility and are designing a life that gives us just that.

For years I’ve studied travel hacking tips and tricks and have become well versed at taking advantage of these programs and perks so that we can just jet off whenever we can or want. More and more, the trips have become less of a “vacation” getaway, and more just, we happen to be somewhere else for a little while with no major interruption to our lives. And that’s the goal. To make travel part of everyday life. Because 2 weeks vacation time is bullshit. And I’ll leave it at that!

Comment below if you have questions about the Rapid Rewards program, the Southwest Visa card, earning and using points, Companion Pass, Rocketmiles, or digital nomad life in general. I’m always happy to help!

*Follow-up from Cabo!

Jonathan Ronzio
Jonathan Ronzio

Founder & Host

Founder, Explore Inspired | CMO, Trainual | Co-Host of The Stokecast Podcast | Mountain Athlete | Award-Winning Adventure Filmmaker | Keynote Speaker

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