How One Man & His Wife Got $4k in Flights from a Southwest Companion Pass & You Can Too

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My law school buddy, Ray, asked to write a piece about his experience getting $4,000 worth of flights for $257 with the Southwest Companion Pass. Of course, I said yes because I have never been able to personally review the best deal in travel hacking. I’ve added a section at the bottom about how you can get the Southwest Companion Pass today and copy what Ray and his wife have done. Take it away, Ray:

The Southwest Companion Pass is often called the best deal in travel, and after having it for 21 months through December 2015, I have to say: The Southwest Companion Pass is the best deal in travel. From April 2014 to December 2015, I took seven trips, six with my girlfriend-cum-fiancée-cum-wife, Lauren, and the airfare cost only $257.* That’s 13 tickets for an average cost of less than $20. The retail price was over $4,000! Here’s how I did it, and the trips I took.

Getting the Pass

Since I live in Houston, I regularly travel on Southwest and earned a lot of extra points by traveling to Dallas, Austin, and San Antonio for work. Southwest gets dumped on by a lot of travel blogs because they don’t have any luxury or elite services. But that’s the wrong way to think about Southwest. Don’t think of Southwest as a bad airline for elite travelers, but as the greatest bus service in the world! Southwest is great for getting from point A to point B and even has wifi on most planes, allowing my wife and me to watch Astros games during the recent playoff run.

Earning the Southwest Companion Pass was one of the easiest travel hacks I’ve ever done. You need to earn 110,000 Rapid Rewards points in a calendar year and basically everything (except transfers from Ultimate Rewards counts toward that number.) Southwest has two personal credit cards and one business credit card. I simply signed up for both personal cards, the Southwest Plus card during a 50k bonus and the Southwest Premier card a month later. I made sure to hit the minimum spending requirements of $2,000 per card in early 2014. That gave me 104,000 points, and with another $6,000 in spending on one of the cards, I had the Companion Pass.** Now is a great time to sign up for the cards yourself, as you’ll have the pass for the rest of 2016 and all of 2017 as soon as you get to 110,000 Rapid Rewards earned.

Once I had the Companion Pass, check out what we were able to do.

The 2-for-1 Trips

The best part of the Companion Pass is that it works for any flight you’re on, whether you pay for ticket or use points. And since you just earned 110,000 points, that’s a lot of cheap travel coming your way. In fact, all of these trips, I booked my own ticket with points, and Lauren flew for just the taxes.

Trip 1: Outer Banks, North Carolina, 4 Segments, $10, 22,995 pts

I qualified for the Companion Pass on April 7, 2014, just in time to fly my then girlfriend and me to Norfolk, Virginia so we could spend a week in the Outer Banks. My entire extended family rented a giant house in Corolla, North Carolina, and we had a great week teaching my parents drinking games, playing poker, and consuming massive amounts of Fireball. It was also the first time Lauren got to spend a week with my entire family. Somehow that went okay.

My ticket was 22,995 points and $5. Hers was $5.

Trip 2: Ft. Lauderdale, 4 Segments, $22.40, 24,615 pts

In October we planned a quick trip to Ft. Lauderdale to see Lauren’s aunt, and after three years of dating, Lauren was expecting me to pop the question there. I surprised her a few days early, making this trip a celebratory vacation now that we were newly engaged. We spent a few days in Ft. Lauderdale, and then I got a swanky hotel in South Beach for our final night (also using points), which led to us eating at a drag brunch. Great trip.

My ticket was 24,615 points and $11.20. Hers was $11.20.

Trip 3: Los Angeles, 2 Segments, $11.20, 30,598 pts

With wedding planning in full swing, I needed a quick break, and so headed off to Los Angeles to catch my buddy’s short film at a festival.  This was the only trip I took without Lauren, but if she wanted to come it would have only cost the $11.20 in taxes.  It was a one-day trip, but with points that’s no big deal.  For less than $12, I hit up a film festival, Hollywood night clubs, and Manhattan Beach in 36 hours.  A+++++++, WOULD BUY AGAIN.

We Got Married!

No travel here, but with the wedding in the bag we spent the following weekend using up the remainder of my Southwest points and booked four trips over two months. Here we go!

[Scott: And I was there with a pre-printed apology note for any trouble I might cause.]

Trip 4: Washington, 4 Segments, $22.40, 20,564 points

After our wedding, we had to jet up to Washington to see one of my best friends get married. We landed very late, but still got some great food, went to a great wedding, and then spent Sunday sightseeing in the nation’s capital. Southwest flies into Reagan (DCA), which is the most convenient airport in the world. Our flight home was scheduled for the day when all of Southwest’s computers went down. We expected mayhem and got it, but somehow this still worked out in our favor. We got involuntarily bumped from our return flight, but I was able to book flights home on United for $1,300 and got compensated from Southwest for almost $2,000, netting about $700. Woot! Southwest basically paid me to take all these trips. Go Companion Pass!

My ticket was 20,564 points and $11.20. Hers was $11.20.

Trip 5: Cancun, 4 Segments, $147, 26,238 points

Southwest has been adding a ton of international destinations in the last few years, so Lauren and I jumped at the opportunity to take a mini-moon to Cancun, which is one of the easiest cities to visit in Mexico. We booked an all-inclusive resort and spent the weekend surrounded by British and Russian nationals on “holiday” and had ourselves a wonderful weekend. From Houston, this was incredibly simple with a two-and-a-half hour flight each way and a nearly empty international terminal at Houston-Hobby. We were at the resort four hours after leaving the house and sailed through customs on the way home. Even better, Southwest and United are currently engaged in a price war over this route, so we’re likely to do this again. Weekends in Mexico for under $1000? Sign us up. We’ll definitely also be taking advantage of Southwest’s other international destinations, including Cabo San Lucas, Montego Bay, Belize City, and Nassau.

My ticket was 26,238 points and $73. Hers was $73. The only reason these flights were more expensive than the others was the exit tax from Mexico.

Trip 6: New York City, 4 Segments, $22.40, 15,614 points

My cousin got married this November, and so we were off to NYC. While Southwest originated in Texas and was for many years just the airline you took to Vegas, if you look at Southwest’s current routes you’ll see they now fly almost anywhere: from Portland, Maine to Seattle, Washington. I was surprised we could fly Southwest to Newark, but quickly booked it and had a wonderful weekend in New York, with all the same extended family Lauren met in the Outer Banks. Somehow both my parents and my aunt and uncle ended up featured in Humans of New York. (It’s pretty hilarious reading 4,000 comments about how your dad needs to wear socks with his shoes.) The wedding was gorgeous and we spent Sunday in Manhattan, catching the matinee of the amazing Hamilton musical and then walked around the Village, eating amazing Italian and finishing the night in Washington Square park as it showed off its solidarity with Paris.

My ticket was 15,614 points and $11.20. Hers was $11.20.

Trip 7: Las Vegas, 4 Segments, $22.40, 32,595 points

Our final trip, we spent 31 hours in Vegas, which is more than enough time to do Vegas. We caught a Cirque show, and while we were barely breaking even, our final black jack session netted $600, making this trip both profitable and extremely fun.

My ticket was 32,595 points and $11.20. Hers was $11.20.

The End of the Companion Pass

My Companion Pass expired at the end of 2015, and I really miss it. Being able to take your wife on any trip, practically for free, is amazing, and the past two years saw us go from dating to married. It would have been entirely different without the Pass. It was an incredible set of trips and after going to seven cities the only thing I’m missing is Southwest Points. Had I paid cash for all these trips it would have cost at least $4,000, and I never would have booked one-night trips to LA or Vegas. But with the Companion Pass and enough points, Southwest is simply the greatest bus service in the world.

Thanks to Scott at MileValue for showing me how to make it happen and for helping us book our honeymoon with flat bed Business Class seats to Chile. Southwest doesn’t offer service to South America or lie flat beds, but for domestic and Central American travel, the Companion Pass can’t be beat.

*Plus the $69 and $99 annual fees on the Southwest personal cards.  Still, that’s 13 tickets for $425, or $32 a ticket.

**Note that, technically,the Companion Pass rules are ambiguous on whether credit card sign up bonuses count,but so far Southwest is still happy to give it out to flyers who qualify this way.

How You Can Do What Ray Did (by Scott)

Read this post in full, which explains step-by-step how to get the Companion Pass for $3,142 in free flights.

Right now the Premier Personal and Premier Business cards have 50,000 point public offers after spending $2,000 in the first three months. Just meeting both minimum spending requirements puts you well over 90% of the way to a Companion Pass for the rest of 2016 and 2017.

If you don’t have a business, though, you need to get the Premier Personal and Plus Personal cards. The Plus does not currently have a public 50,000 point offer. However, current cardholders can refer you to the offer and pick up some bonus points for themselves. Here is a MileValue reader who you can email for a referral to a 50k Plus offer: [email protected]. Feel free to leave your information in the comments if you can also refer people to a 50k Plus offer.

Who can top the value Ray and Lauren got from his Companion Pass?