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15 Trips in 2 Years: How One Family Maximizes the Southwest Companion Pass

Jan. 17, 2019
11 min read
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In our traveling family, we overcome some extra challenges and logistical issues when traveling with my 7-year-old son with special needs. But -- we never let any of those challenges stop us and one thing that helps our family do what we do is having the Southwest Companion Pass. With it, we've taken 15 family trips in the past two years. Here's how we maximize our travel with this fantastic tool from Southwest that lets a companion fly for just the cost of taxes and fees -- no matter if you paid cash or Rapid Rewards points for your own ticket.

The freedom to travel in your family's hands.

Why We Got the Companion Pass

I first heard about the Southwest Companion Pass several years ago but didn't give it much thought because all my elite status was with American Airlines. But after our second child turned 2, and the realization that most flights on American Airlines out of our hometown of Austin would require a connection, I started to take a harder look at air travel options. Now that both of our kids were beyond the age where they could fly free as a lap infant, the days of buying three tickets for the four of us were over.

I read up on the now defunct Southwest Marriott Travel Package trick and became intrigued. Once upon a time, you could buy a Marriott Travel Package using points that included both hotel nights and a bushel of Southwest points that counted toward the Companion Pass. Since my wife and I both had a ton of SPG points from years of using the Starwood Preferred Guest® Credit Card from American Express, we both did our first conversion in late 2016. We did the same conversion the next year as well and both my wife and I earned a Companion Pass.

While the method we used to get the Companion Pass for two years is no longer available, but the sign-up bonus points from Southwest's personal cobranded credit cards count towards the 125,000 you need to earn in a year to earn the Companion Pass, so it is still within reach even if you don't fly Southwest all the time.

15 Trips in 2 Years With the Companion Pass

My wife and I have each had our Southwest Companion Pass for just over two full years, and we did our best to take full advantage of the buy-2-get-2 free air travel system we created for our family. In fact, we may have gone a bit overboard, booking trips on a dime simply because we knew we could buy two tickets and get two free. "Sure. Let’s go to Cancun for this long weekend. Direct flights and two fly free? Book it!" That was all part of the fun.

In the past two years, we have taken 15 family trips (six international and nine domestic) on Southwest, all using the Companion Pass. Much of the time we "paid" for the tickets we had to purchase to use the pass using Southwest Rapid Rewards points. You can still use the Companion Pass to fly someone with you for just the cost of taxes even if you book the first ticket using points. If your Rapid Rewards points balance is dipping low, you can even transfer points in 1:1 from Chase Ultimate Rewards cards such as the Chase Sapphire Reserve, Chase Sapphire Preferred Card and Ink Business Preferred Credit Card.

We saved thousands of dollars on airfare by having the passes. Though more accurately, the Southwest Companion Pass allowed us to have experiences and create memories that we probably wouldn't have had without it.

Cancun, Mexico
Cancun, Mexico (Photo via Shutterstock)

On top of the savings, Southwest's flexible ticketing rules made it easy to say yes to a travel idea. If someone was sick on the day of the trip, just rebook with no exchange fees. If the weather looks bad for the weekend on the beach, just cancel the flight and use the credit within a year with no fees if you booked with cash. If you booked with Rapid Rewards points, simply redeposit the points without fees. These rules are absolutely amazing and very rare in the airline world.

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Image by Vitali Kozhar / EyeEm / Getty Images

Where the Companion Pass Took Our Family

To give a flavor of what's possible, here is where the Southwest Companion Pass took our family over the last two years.

Nassau, Bahamas

We visited twice in 2018. With an easy connection from Austin to Nassau (via Fort Lauderdale), this was my family’s top destination pick.

Haydon making sand angels in the Bahamas thanks to the Southwest Companion Pass.

Both times we stayed at the amazing Grand Hyatt Baha Mar. On our second trip, we had at least five employees say they remembered us from our past trip. The attendant in the Club Lounge even remembered my drink preference, which was just one example of great service at a resort that is bookable for 20,000 World of Hyatt points per night.

Grand Hyatt Baha Mar Club Lounge

Flights to Nassau can sometimes be expensive so we used a combination of points and cash. On our second trip, two round-trip flights were pricing at $700, including all taxes. This was more than we would have liked to pay, but we had to book the more expensive flights due to the kids’ school schedule. Factoring in the passes, the price wasn't nearly as terrible as if we didn't have them.

Cancun, Mexico

We visited Cancun three times in the last two years: twice in 2017 and once in 2018. With flight times at around two hours, this is a no-brainer for a quick getaway from Austin. From our hometown, Southwest has one and sometimes two nonstop flights a day to Cancun. This makes it a great last-minute trip for anyone who wants fun, sun and a tremendous overall value. Don't forget, if you are going for a weekend and the weather looks bad, just cancel the flight and use that credit later. Just make sure your hotel can be canceled until close-in, too.

Westin drinking a Chocolate Milk
Westin drinking a chocolate milk

On two of those trips we stayed at the family-friendly and all-inclusive Hyatt Ziva Cancun resort using World of Hyatt points. (If you're short on Hyatt points, they transfer at a 1:1 ratio from Chase Ultimate Rewards.)

Since we were able to book weekend airfares off-peak, tickets were $340 for two round-trips tickets, including taxes. That’s $170 each for round-trip to Cancun, or really $85 each round-trip if you factor in the Companion Passes.


We made it to Orlando once in 2017 and 2018. It's again an easy choice out of Austin, and many other Southwest cities. We had gotten fares as low was $97 for two one-way tickets. The return flights are often a bit pricier as we like to return at the peak times (along with everyone else).

Westin and Haydon on the Teacups.

Las Vegas

Vegas was on our hit list once a year the last few years. How could the gambling capital of the US be one of our family's top choices? Simple. Have you ridden the tall escalator at Aria, ran into Elmo himself on the streets or stood in a shoe? That is what happens for families in Vegas -- along with a whole lot of other things. It's a little wacky, but a lot of fun. Plus, we have a lot of family and friends around the area so we spend a lot of time with the family at buffets or walking around the town sightseeing.

Westin standing in a show!
Westin standing in a shoe!

Your Family Can Do It, Too

To have the freedom to move about the country (and beyond), get your family the Southwest Companion Pass. That slashes your cash or award prices in (almost) half immediately, assuming you plan to bring someone along with you. When planning out your travels, keep in mind that most international destinations will still be more expensive than domestic due to the additional taxes. Taxes and fees can be over $100 per person when flying back to the US from countries like the Bahamas, plus factor in that everyone will need passports for the international spots.

Taxes aside, we love looking at the Southwest route map and dreaming about where to go next. We like to start with the furthest away destinations (like Aruba) and map out how to get there using the ever-evolving Southwest line-up of nonstop, direct and connecting flights.

Naturally, we are awaiting the news that Southwest has the approvals to start flights to Hawaii very anxiously. With Hawaii, you won't have to deal with high taxes and passports, making it an exotic but attainable destination with the Companion Pass once Southwest planes are in the air.

Rainbow over Tunnels Beach on the north shore of Kauai, Hawaii (Getty Images)

Bottom Line

I have to add a word of warning that getting BOGO tickets on Southwest can be addicting. Your child might even end up with a swim-up chocolate milk bar themed birthday cake after all of those fun trips to beach destinations. Perhaps we need to brush up on "How Not to Spoil Your Kids With Miles and Points" since the first thing our son now asks when going on a trip is if the hotel is going to have a bellman.

Westin's 7th Birthday Cake
Westin's 7th birthday cake

But in all seriousness, the Southwest Companion Pass is a sincere boon for our family. Travel is a priority for us, so we make a travel budget each year and use Southwest Rapid Rewards points and Southwest Companion Pass to take as many family trips each year as we possibly can on our budget. We have seen more family members in the past two years than the previous five years combined -- all because we could book our air travel with a buy-2-get-2 deal thanks to two Companion Passes.

Heading to the beach!
Featured image by Getty Images
Editorial disclaimer: Opinions expressed here are the author’s alone, not those of any bank, credit card issuer, airline or hotel chain, and have not been reviewed, approved or otherwise endorsed by any of these entities.