1 year SW Companion Pass: how we travel the country for nearly free
6 Cities: Orlando, FL; San Francisco, CA; Baltimore, MD; Chicago, IL; Nashville, TN; and Denver, CO
Those were the vacation spots my girlfriend Tiffany and I chose to visit between March 2018 and March 2019. That amount of travel was certainly above average for us as a couple: during that time we were, in fact, the paradigm of the broke millennial. As it happened, that same period saw her complete a 2-year MSW program (while working full time and self-financing her coursework). I, for my part, left a W-2 job for the life of an entrepreneur and a revenue-free first business quarter. For these stresses, on top of all the everyday ones, we chose to vacation more rather than less: to pour more time into our health personally and as a couple, and to help keep us sane during the predictably difficult life path we had chosen for ourselves.
How did we make it work? After a (2-3 month) period of research, a dozen targeted credit cards I took out (and paid off) and a wholesale systematization of my personal and business financial practices, we were able to pay for all of our flights with 120,000 units of monopoly money known as Southwest Rapid Rewards Miles and $134.40 in taxes & fees.
I'm going to state that again, for emphasis:
We had 6 amazing adventures last year for $22.40 out of pocket, per flight.
Wanna see how I got there? Let's dig in:
Background: Essential listening on this subject is ChooseFI podcast episode 007:
It is an excellent starting point to explain what the Southwest Companion Pass is (as is, not surprisingly, Southwest Airline's website), with links to other, more in-depth resources into the phenomenon known as "Travel Hacking" across the blog-o-sphere.
How did it work for me?
Certainly the most financially efficient way of unlocking the Companion Pass tier is through opening personal & business credit cards through Chase Bank. Depending on when you read this post, the point offerings on the cards will possibly if not certainly be different; unfortunately that means you'll have to do some of your own Googling to find out what's being offered currently...
For reference, here is what they are offering, as of the publication date in the photo.
You could say I got lucky; you could say I figured out, with some research, how to game the system...
Either way, in October 2017 they were offering 50,000 point bonuses for their Premier and Plus (now discontinued) cards. After reading through a few blog posts on the subject, I found out that it was not disallowed for applicants to apply for two credit cards on the same day (this is now not allowed).
After being immediately approved (solid credit score, born out of a decade of good payment history in high school & college) I received both credit cards in early October. With some careful accounting, the bonus spend tiers were achieved and paid out to my Southwest Rapid Rewards account in January 2018.
I added their third card offering (the SW Business card, alongside another 60k points) in the summer, totaling just under 200,000 miles to spend over the next ~23 months. This also unlocked the "holy grail of travel hacking" The Southwest Companion Pass, described below:
With a purchasing queue well into 6 figures, and a BOGO sale on flights being run every day of the year, beginning in early February we set out to see how far we could stretch them...
They send you a physical card, though you don't need it to actually fly...
Trip 1: Orlando
One day experiencing Harry Potter World at Universal Studios, one at Epcot. Hotel paid on standard credit card ($~80/night through Hotwire), transportation was mostly free shuttle buses, and breakfast was served at the hotel.
Cost of round-trip flight: $22.40 and ~27,000 points
Trip highlight: sake & selfies at Epcot's Japan venue
Trip 2: San Francisco
We didn't actually go to Golden Gate City (though we'd love to!), but for our big trip to Thailand it was several hundred dollars cheaper to fly to Singapore and Krabi/Bangkok from San Fran than it would have been departing from our home hubs of Tucson or Phoenix.
Cost of round-trip flight to SFO, to board international flights: $22.40 and ~15,500 points
Approximate savings on trip to Asia from SFO vs. PHX: $250 per round trip ticket
Cost of trans-Pacific flight per person: $550 (she found a great deal)
Trip highlight: visiting an elephant preserve run by an indigenous tribe outside of Chang Mai, northern Thailand.
Trip 3: Baltimore
A week of Smithsonian Museums tours, the biggest blue crab food festival in Maryland and a walking tour of one of the oldest cities in the nation. It was done on the cheap, as we were visiting friends who provided housing and most of our meals. DC's robust public transportation system helped us get around as well as a borrowed car.
Cost of round-trip flight: $22.40 and ~24,500 points
Trip highlight: Annapolis Rotary Club Blue Crab Feast
Trip 4: Chicago
A chance to see Lin-Manuel Miranda's Hamilton live in the Windy City, a tour of my favorite brewery (New Glarus, in Wisconsin) and a week-long escape from the Tucson summer heat, all while visiting a friend who had recently moved away; we had been missing him. Most lodging was free, though a few nights were paid with Chase Ultimate Rewards points accumulated through the "Chase Gauntlet" referenced in the ChooseFI podcast above. Rental car paid with Capital One Venture points.
Cost of round-trip flight: $22.40 and ~21,500 points
(bonus: we discovered on this trip that a Priority Pass lounge had opened in TIA; Priority Pass is a benefit to 7 cards listed here among others, including the Marriott Bonvoy. So now, we get $56 to spend on beer/coffee & food just before each flight, so long as we can find departing flights leaving after 8am; a nice incentive to no longer flirt with missing the initial outbound flight every trip...)
Trip 5: Nashville, TN
Visiting my parents and college buddies for the Christmas holiday season, with a beer festival, a Nashville Hot Chicken walking tour and a visit to country music row wrapped in. Short and sweet, and home in time for Christmas and the TSA shutdown.
Cost of round-trip flight: $22.40 and ~21,000 points
Trip Highlight: Family Christmas photo, per tradition
Trip 6: Denver, CO
Our friend's 30 birthday was excuse enough to rent a 10-man cabin in the ski town of Steamboat Springs in the middle of February. Knowing Denver is a major hub for Southwest on the west coast I figured I could find a deal, and I did:
Cost of round-trip flight: $22.40 and ~9,700 points
So there we have it! Easy, frugal, flexible... and free! Annual fees aside, we did not carry a balance on any of the credit cards I took out. All of the bonus points we used to transact were accumulated on, as Mindy Jensen loves pointing out in the Money Show, "normal items that we would have bought anyway." The cost? Decent credit, adult-level discipline in your personal financial life, and a few blog posts' worth of financial literacy...
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