Flying Southwest Airlines With a Family: Three Ways We Were Surprised

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We all have images in our head of how we think things will go, but sometimes the script of real life doesn’t play out the way you imagined. Sometimes it is far worse or more challenging than expected, but sometimes things work out even better than you hoped. Our first family flight on Southwest Airlines in a number of years surprised me in a few ways, and most of them were for the better.

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Before we get into the three ways I was surprised on our most recent Southwest Airlines flight, let me add a little background as to why our traveling family doesn’t regularly fly on a pretty family-friendly airline. We flew Southwest regularly when we lived in Austin years ago, but for the past eight years, we have lived a bit north of Houston. Southwest operates out of Hobby Airport, which is on the south side of Houston. Getting all the way through Houston is often very time-consuming and unpleasant, which is not how we like to start and end family trips.

Secondarily to the geography barrier, we have elite status with United that makes flying them pretty easy and comfortable with early boarding, E+ seats, etc. However, when the price differential between United and Southwest using cash or miles was absolutely staggering for our flight to Costa Rica, we decided it was time to again hit the skies with Southwest.

Family boarding still scored us seat 1C

For our outbound flight, we ponied up the extra cash to purchase Early Board Check-In that scored our family spots in the A boarding group. However, we decided to not spend that extra $15 per person on the return and just roll the dice to see what boarding positions we would get at exactly 24 hours before check-in. Our boarding group numbers at 24 hours out were in the B group, but since Southwest offers family boarding between the A and B groups, we would board before they ever got to our assigned numbers.

I figured we would be able to get seats together, but likely towards the back of the plane during family boarding. I’m sure that is often the case for those boarding between the A and B groups, but on this particular day, family boarding resulted in Josh scoring his favorite seat of 1C! The rest of us were just behind him together in Row 3. This was a truly pleasant surprise and it made for a comfortable ride home with a quick exit towards customs and immigration ahead of the other 150 or so passengers on the plane.

Cups with lids, can I get an amen

While we haven’t flown a ton in recent years on Southwest, my family of four does fly a good amount. We have learned what to expect in most routine airplane related situations. On our recent Southwest flights, we encountered something so helpful, but exceedingly rare, during the drink service. When my kids ordered their normal drinks of juice for the two-year-old and ginger ale for the eight-year-old, something magical happened. The drinks were brought to us not just with those little blue stir-stick straws we sometimes see on other airlines, but with actual lids and straws.

Giving the kids cups with lids is such an obviously positive move for everyone involved, but it is one that most other airlines within the United States have missed. We usually pour my youngest daughter’s drink in her sippy cup, but having a cup with a lid is such a simple but effective family-friendly win.

It was surprisingly normal

My Southwest flights of years gone by were often a little different in some ways than my flights on other airlines. I remember bottles of wine being given away to winners of various onboard contests. Flight attendants (and occasionally passengers) would sing over the intercom with some frequency. The onboard atmosphere was often less stuffy and more relaxed than on a traditional US air carrier.

I don’t know if things are still toned down because of their relatively recent heartbreaking incident, but our flights on Southwest felt pretty much like every other flight we take. Sure, the boarding and open seating process is unique and a little stressful when one of your kids has a ‘potty emergency’ right before your group is set to board. Otherwise, flying Southwest felt just like flying economy on Delta or American or United.

If your family is hoping to fly Southwest, know that their Rapid Rewards points are easy to generate as they are a 1:1 transfer partner from the Chase Ultimate Rewards program and cards such as the Sapphire Preferred. There are also Southwest credit cards available for the taking if you want to rack up more Rapid Reward points that way. Learn more. As an added bonus, those points earned with the Southwest credit cards will count towards earning the valuable Southwest Companion Pass so that your companion can fly with you by paying only the cost of taxes on the flight.

Geography will keep us from being super regular Southwest passengers, but you can bet that we will fly with them again before another eight years pass. I’d love to hear if anything surprises you when flying Southwest these days!

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  1. Open seating policy plus lap child is a wonderful combination. Any empty seats on the plane? Bring the car seat on and stake your claim for a free extra seat. It’s policy.

    With children, open seating plus tight connection plus delayed flight is terrible. Sometimes better to misconnect.

    • Agreed on connections…I choose to avoid WN when traveling with kids if I have to connect. 10 years ago our connection time of 1.5 hours was killed off to the point that our connecting plane was waiting for us…but was fully loaded. Boarded in a full sweat with 6 month old twins, a 4 year old and a 7 year old. We sat away from our older kids since no one was willing to change seats for us. Absolutely miserable way to get to Disney World. Now idontflyswa for connecting flights…

      • However, on the return flight the 7 year old was pulled out of her seat to carry the treat basket up and down the aisle…their customer service is typically fantastic.

  2. Southwest is my favorite, especially for personal travel. My four-year-old calls it the “peanut plane” and LUVs the heart logo. I like the ability to rebook with no fee and the included checked bags. So ironic that the original “discount carrier” now offers the fullest-featured product.

    You do still encounter particularly wacky employees — one recent gate agent put on a quiz show and Rubik’s cube contest — but that is indeed much rarer than it used to be.

  3. I live Southwest. I don’t understand why people refer to the line up as cattle call. I would much rather know my exact place in line than a vague zone. I have never paid for early check in and never gotten anything later than a B. There are 5 of us and with a B have always gotten seats together.

  4. I haven’t flown them, however, reps were at a bbq festival in Texas and they handed out all in one silverware with Southwest on the side! It really boosted my impression of them. This paired with other things I have heard, I may just try them. I’m still nervous about those first come, first serve seats though.

    • Don’t worry about the first come first serve. The first time I flew with them, I had heard nothing about how they operate. I was different for me. At that time, I was flying at least 8 times per month for work from Philadelphia to Raleigh. Later, Southwest stopped direct flights to Raleigh from Philly, but I still opted to continue flying Southwest. This increased my flights to at least 16 times per month. I became so used to the Southwest boarding that the few times I had to fly other airlines, I realized how cumbersome the other way of boarding was. It took less time to board Southwest than other airlines. I wonder why it takes so long when the seats are assigned. Not only that, flying certain airlines, like American, makes me feel so degraded because I am NOT in the elite group so I board on the tail end of the boarding call. It is ridiculous!

  5. Hi! I’m new to your blog and loving it. Your posts about the Andaz Costa Rica helped us decide to book it (for Feb 19), and I’m so happy to see your recent posts about traveling there with kids! (We will have a 2.5 year old when we take that trip.) I was so interested to see that Southwest flies to Liberia, yet I see that the flights from Houston stop completely in Dec 18/Jan 19. I know that SW only puts out so much of their schedule, and I’ve called them to ask about their schedule for next year and gotten nothing. Do you have any inside info on whether that flight is going away, or if it will be back in Feb 19? It’s hard to know if we should wait or consider booking another airline for our dates. For whatever reason our dates in Feb are super expensive for flights, so trying to weigh everything and not wait too long and lose other options. Thanks 🙂

    • You are 100% correct that the Southwest schedule does not extend past early January 2019 just yet. Normally that isn’t a huge deal, but I think that route specifically is somewhat seasonal so I am not 100% sure if they normally operates in February. The good news is that the schedule should extend until early March on June 28th so you can find out soon.

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