Why My Family is Flying Southwest for the First Time in Seven Years

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The last time we flew Southwest as a family my now second-grader was a one-year-old toddler on her way to Disney World for the very first time. It was so long ago that I hadn’t even yet started this blog. I think we selected Southwest for that trip because I earned some Southwest credits from flying around Texas from my job with the state that we needed to use before they expired. This was way back when 16 Southwest credits = one free round trip, but they expired if you didn’t hit the mark in time, so we used them while we could. When we lived in Austin we flew Southwest pretty regularly not just for work but also for fun. We stopped flying them almost seven years ago after that trip to Orlando primarily because once we moved to the Houston area, the airport they served in the area, Hobby, was simply not at all convenient for us.

We live north of Houston and can get to Bush Intercontinental within 30 – 35 minutes or so if traffic isn’t bad. However, to get to Hobby you basically have to walk through the fires of Mordor, AKA get all the way through the traffic pit of Houston. That can take hours, is very stressful, and is not at all the way we like to start and end a trip.

So for close to seven years, we have not really ever even considered flying Southwest…until today. Last summer Josh and I had a fantastic trip to the Andaz Costa Rica, and after falling in love with not only the property, but also the on-site kid’s club and the ladies that watch the little ones there, we decided to return for a family trip next summer. At just 15,000 Hyatt points per night with an included kid’s club, it was a no-brainer decision.

I’ve had the hotel award nights booked on points since shortly after our last trip, but I’ve been watching and waiting for United to make some saver awards available from Houston to Liberia as the schedule for next summer opened up, but it simply hasn’t happened. Paid flights on United or any other similar airline are $500 – $1,000 each, and prices are often towards the higher end of that range for the nonstop flights we would want.

Because the airfare pieces weren’t coming together, I had all but scratched this destination from next year’s list when I decided to check Southwest. I knew they started a Houston – Liberia route a year or two ago and their international prices are often quite fair even when others have clearly gone nuts.

While their booking window currently only extends until the first week of June 2018, that was enough for me to determine that they are going to be the clear winner in this contest. In fact, they will be what saves this trip to Costa Rica because I’m not giving United thousands of dollars for a three-hour round-trip journey or connecting in Canada to secure a saver award, which are United’s only real options. I know other options may present themselves as we get closer to next summer, but I strongly prefer to book our “big” family trips well in advance and last summer United wasn’t stellar about saver availability on this route even close-in.

United award availability to Costa Rica

Instead of the $800 – $900 or 70,000 miles per round trip that United currently wants to travel from Houston to Costa Rica next summer, Southwest is only charging 8,856 points each way + taxes. For a round trip that comes to 17,712 Rapid Reward points + $75.02 in taxes and fees. Keep in mind that even if United had saver awards available, they would be 17,500 miles each way and the same taxes and fees as booking through Southwest.

For the four of us, that would come to a grand total of 70,848 Rapid Reward points + $300.08 in taxes and fees. That is still a decent chunk of points and change, but a manageable one. You can transfer Rapid Reward points from Chase Ultimate Rewards 1:1 if you are running low. Since only standard awards are available for our preferred dates, booking via United for the same exact dates and routes (albeit from the closer Houston airport) would cost 300,000 United miles + $300.08 in taxes and fees. I don’t know about you, but that price differential is more than enough to get me to drive through Houston this one time for our flights.

With Southwest, we will also have access to $8 per day per device satellite-based WiFi (on enabled aircraft) which I’m sure Josh will use, free live and on-demand television which I’m sure the kids will use, free checked bags that I hope we don’t use, and the time-honored tradition of fun and exciting open seating. Honestly, that part really makes Josh raise an eyebrow, so I won’t be shocked if he wants us to do the $15 Early-Bird Check-In to help secure a higher boarding group position by having the computer check us in at T-36, but we’ll see. Since we have a kiddo six or under travel with us, the worst we would do is boarding after the A group during the family boarding time even if we forgot to check ourselves in at T – 24.

I recently flew on Southwest with a friend on a short hop from Austin to Houston, so I have personally flown them once in the past seven years and it was a totally fine short flight. However, returning to the Southwest travel experience with my family will be a change of pace for us, but one that I actually welcome. I mean, worst case scenario they serve sparkling wine, and we have beautiful Costa Rica waiting for us on the other end of the journey.

Best case scenario is we don’t mind the drive through Mordor to Hobby as much as we used to now that the kids will be 3 and 8, we have a great flight, and the Companion Pass comes into real discussion as a travel tool our family can use to save a ton…especially if the heavily rumored Southwest Hawaii flights become a reality in the near future!

If Southwest is a good fit for your family, remember the 60,000 point credit card offers are said to only be running for a few more days until October 4, 2017, and if you time it right those bonuses can help you earn almost two years of a Companion Pass.

Head here to learn more about available credit cards and their bonuses. 


Editorial Note: The opinions expressed here are mine and not provided, reviewed, by any bank, card issuer, or other company unless otherwise stated.

The responses below are not provided or commissioned by the bank advertiser. Responses have not been reviewed, approved or otherwise endorsed by the bank advertiser. It is not the bank advertiser's responsibility to ensure all posts and/or questions are answered.


  1. FWIW we frequently fly Southwest with a 9- and 5-year-old, never select Early Bird, and never have any problem whatsoever finding four seats together.

    • Great! That was my experience years ago, too, but my husband is a bit obsessed about seats, so we’ll see how far I can push my luck. Ha!

  2. I fly Southwest 90% of the time and even if we don’t get an A boarding pass and have to board with family boarding, I always get seats for 6 of us all together.

  3. We’ve taken many many Southwest flights the last two years (gotta maximize that Companion pass!) and we always board family boarding after group A. Typically from our experience we can find empty rows (6 seats across) right before or right after the exit row seats. Never a problem as long as you don’t have to be at the very front of the plane.

  4. Just got back from the HOU/LIR Southwest R/T. Great flights, wonderful service in LIR. Also, the airport in LIR was a breeze and modern. Just be prepared for high price food and snacks. FYI the wifi is not reliable between LIR and the Yucatán peninsula. The flight times are also so convenient. Customs was a breeze on both ends.

  5. Gosh, Mommy Points, bully much?

    You said: “I mean, worst case scenario they serve sparkling wine, and we have beautiful Costa Rica waiting for us on the other end of the journey.”

    Here are just a couple of facts and figures courtesy of Southwest …

    This year (2017) is the 23rd year Southwest has appeared on FORTUNE Magazine’s Most Admired Companies list until 2009, it was called America’s Most Admired. Southwest has appeared in the Top 10 the majority of the time.
    Southwest is America’s largest airline in terms of originating passengers with 24 percent market share. (Based on data available from the U.S. Department of Transportation (DOT) as of March 31, 2017.)
    We are the only domestic airline with a decades-long history of returning capital to Shareholders.
    Southwest is the only domestic airline with 44 consecutive years of profitability.
    Southwest has been #1 in the DOT Consumer Satisfaction Ranking for 22 of the last 26 years.

    Named a Best Employer in Forbes’ 2017 list
    Received the Readers’ Pick for Best Frequent Flier Program (U.S.) by SmarterTravel
    Highest ranking Low-Cost Carrier in the J.D. Power 2017 North America Airline Satisfaction Study
    Named Program of the Year for Rapid Rewards® Program and recognized for providing the Best Loyalty Credit Card, the Best Airline Redemption Ability and, for the fifth consecutive year, the Best Customer Service by the Freddie Awards
    Named Domestic Carrier of the Year by the Airforwarders Association for the eighth consecutive year
    Named as one of Corporate Responsibility Magazine’s 100 Best Corporate Citizens 2017
    Designated a 2017 Most Valuable Employer for Military by Recruit Military
    I hope that all of these accolades don’t screw up your blog … uuuh, I mean your trip.

    • Stefanie, I think you missed the part where I said I was looking forward to flying Southwest again and that distance to then airport was the primary reason I stopped. The sparkling wine comment was largely a joke. While it is a slightly different experience, that isn’t bad a bad thing, just different. I have no issues at all with Southwest. I’m pretty sure I’ve voted for Rapid Rewards for some of the above-mentioned awards. 😉

    • Stephanie, I have no problem flying Southwest, but you’re pushing WAY too hard. You look like a paid tout or an employee when you go that far. Maybe ease up a touch.

  6. Ha, I just made the drive back up from Hobby to far north Houston. Hardy to 610 east loop to I-45 is the way to go. It took me a shade under 40 minutes to reach the grand parkway!

  7. You will not have a problem getting seats together if you do family boarding. Do not spend the extra money. We flew with our 10 week old on his very first flight back in June and there was plenty of space when we boarded.

    • I forgot to mention the flights were OAK – SNA, otherwise known as DISNEYLAND and the planes were completely full. We were one of the last in a long long line of families to board and there was still plenty of space for us to choose from. Please tell him you. will. be. fine.

  8. United is a diagrace. 300,000 miles? Last year we had a short 2 day trip to Chicago and when I looked at the prices Southwest was the clear winner. It was a 40 minute flight from MSP but it was perfect. I woukd fly them if prices makes sense.

  9. We fly Southwest most of the time. International trips are paid for with points on other airlines. The prices are good. Don’t love the open seating and many times the two of us are sitting separately in different rows on flight. For a family with young children my advice would be to purchase early boarding. I think I have been reading your blog for 4 years now.

  10. I have been considering taking my family there for spring break. Only hesitation is food. I heard it is expensive. Might have to split between Andaz and the Westin.

    • Food price does look expensive to an American on the menu. All restaurants charge a mandatory 13% tax and 10% service charge normally included. At my visit to Marriott ‘s Guanacaste the Marriotts burger and fries was $17.00. As a Marriott silver we got a 10% discount. The adjusted price was about $10.50, with discount and plus tax’s, and it was very good. Dinner’s were in the $25 range and breakfast around $15 including drink. All reduced by 10% then included the total of 23% tax’s, not bad. Service was terrific.

  11. I fly Southwest 10 times or so a year. Half with family half for business. Not my preferred carrier, but their route network in California is difficult to beat (as well as pricing). My one piece of advice – $15.00 Early-Bird check in is a no brainer for the family traveling together. That’s $120 I would charge today FWIW.

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