Flying Southwest, Then, now, and in the future.

southwest liveries

3 Generations of Southwest Liveries

Despite most of my premium travel over the last few years, I’ve flown Southwest Airlines a lot in my life. Having grown up on Long Island, New York, Southwest was the perennial option for flying out of Long Island Islip’s MacArthur Airport. I remember the old days of standing in line to get a colored numbered plastic boarding card (it was most often brown for some reason), and then queuing up. I also remember the face to face seats at the exit rows. Those were fun and awkward at the same time.

In college, I would make the trip from Northeast, DC up to Baltimore-Washington Airport to fly home, or most other places, because back then, other than the occasional Independence Air (anyone remember that?), Southwest was actually pretty cheap.

Now I fly Southwest less often, usually opting for American Airlines, but I still fly Southwest on routes that make sense, like to Orlando, Jacksonville, and to Key West back when they flew that route. The reason being frequency of flights and nonstop flights. In fact, on my latest trip to Florida, I chose the middle seat in both directions. Neither flight was completely full, but I made the calculated decision that sitting in the first 4 rows, while less comfortable, would mean I would be able to disembark more quickly.

Observations about the experience

For the flight down, my wife and I were both in the second half of C group. I actually chose to use a backpack, rather than a carry-on, for fear of having to gate check a bag.

So of course, boarding, I expected the worst. But, would you believe, that there was still overhead space over row 4, as I boarded with C38? I was pretty surprised too.

The gentleman next to me had already made himself comfortable by the time I arrived, but was happy to let me in. He was kind of innovative, too. He had a double carbiner, which he had an empty bag hanging from. Over the course of the 2 hour flight, he used it as a garbage bag for himself and others. He was generous to accept neighbors trash, which was a nice gesture. He also sang out loud to his music, but he was nice, so it wasn’t a big deal.

On the window, I had a guy watching the free Dish Network TV that Southwest offers, on his iPad. The headphones never came off.

The flight down, there was no issue with the arm rests. Usually, sitting in the middle seat, you get options to both arm rests, or so general convention goes.

The flight home was different, I had a sleeper on the window, who had the arm rest most of the time, the aisle seat occupant was more standard, with the half use of the arm rest. The positive of the sleeper, however, was that he left the window shade open.


Somewhere over North Carolina, I think.

All that said, Is there still such a convention of arm rest use? I just don’t know anymore.

Final Thoughts

I joked on Twitter that flying Southwest helps me stay in touch with the people.

Proper Airline

In reality though, if you have no status and fly a few times a year on routes that Southwest flies, they do seem like the best option. You get peanuts, pretzels, a beverage, streaming TV, and the option the pay for wifi. Heck, if you like to check bags, that’s free too!


The big caveat about Southwest though, is that they just aren’t always cheaper anymore. Their method of distribution–aka how they market and sell their flights–means that you must separately check Southwest prices vs checking Kayak to see how all compare, which does add a step. That step sometimes means they can demand a higher fare (for those folks that don’t bother checking other airlines).

But at the end of the day, Southwest isn’t a bad choice to fly, at least for sub- 2 hour nonstop flights.

What do you think? Is Southwest better than flying domestic economy on the legacy carriers?

12 thoughts on “Flying Southwest, Then, now, and in the future.

  1. Totally agree that WN is better than the legacy carriers in economy. You are right that you need an extra step to check WN fares but that’s just the way it is. BTW, if price is comparable, I would use JetBlue since their seats are much better for me at 6′ 5″.

    • @JohnnieD – Its been a while since I’ve flown JetBlue, but I’d definitely give them a shot too, in Y. Flew them Transcon, just before the East Coast’s “Snowmeggedon” back in 2011 I think. It was definitely a comfy flight (for Y!)

  2. Trevor, we worked, last year, on a CP, and have since flown Southwest to DC, to Jamaica and have flights booked into San Diego and out of San Francisco this summer. Will do SOMETHING on SW in the fall.

    Because we are at MSP, we always fly through somewhere–the first two times, it was MDW. It’ll be DEN and PHX, this summer. I don’t mind stopovers, nor do I mind spending an extra $50 for A group boarding, if the two of us are flying for a total of maybe $50 + 20K miles.

    I appreciate the greater level of comfort in the seats, and the always cheerful and frequently cheeky attitude of the flight attendants is lovely. The ONLY time I wasn’t enchanted was flying from Jamaica to Chicago. The (male) flight attendant pointedly failed to notice when a woman asked for something, and was Mr Congeniality (“Is that better, Bro?”) to the men!

    • @MickiSue – Southwest does fly to Cancun now – maybe its time to checkout the new Hyatt all inclusive? I can totally see the value of Southwest, although I haven’t forked over $40 for A Group boarding…
      I find your comment about your MBJ-MDW flight interesting, because while I see a whole lot of “fun” from WN flight attendants, what you describe is not the kind’ve “fun” I see… (e.g. your Mr. Congeniality piece) – I would think, that type of behavior would be unacceptable… unless meant in good fun. At least unacceptable in the old Southwest I used to know.

  3. I had a great flight back from ft4rl on southwest yesterday. On the flight down, I used 17k miles&more miles to fly in UA first. I travel a lot compared to most people, but less than most travel hackers (much less than Trevor!). I had such a great time and the ease of getting there and back has really made me ask myself why we don’t take more weekend trips during these often cool and grey spring months (not to mention winter, but I already know to head somewhere warm if I can in January).
    That’s in some ways apropos of nothing, but with southwest points easy enough to earn and their flexibility and the fact that they fly a lot of places nonstop from MDW, it really makes a weekend trip to somewhere nice an easy option.

    • @Jamie – I really do enjoy that Southwest actually provides more inflight amenities than the legacies. I truly do. I especially appreciate pretzels (because I’m not a nut fan – perhaps I’m nutty enough already!). I have flown into MDW – usually have pretty good flight attendants, even one that pointed out the “ruff” of his apartment!

  4. “The big caveat about Southwest though, is that they just aren’t always cheaper anymore.”

    They can be cheaper if you watch the fares and rebook when it drops. I love that SW has free cancellation because it means that by the time my trip arrives, I know I have the lowest fare.

    • @HeavenlyJane – You’re right, they are willing to give you money back, but as I recall, its not back to your CC, its just money you end up needing to spend again on Southwest sometime in the following 12 months. Still pretty awesome though.

  5. I LUV SWA! Though I do not travel near the likes of you and your readers, I check SWA first every time and often will have a backup plan booked on SWA, as American has left me stranded, and we have trust issues. What other airline lets you cancel 10 min before you board and give you your “money” back? Points AND money!

  6. I am not Southwest’s biggest fan. For being a LCC, they are almost always higher than AA on the routes from PHL/BWI. I dislike their boarding process immensely and their lack of a decent same day change policy. Sure the free bags are nice, but I get those on other airlines for holding their branded cc. All that being said, I had never realized there was armrest etiquette! Your rules make sense to me.

    • @Brandi – Kudos for being candid! I personally love Southwest’s history and the Herb Kelleher lore, but you are right – their prices aren’t always the lowest, and you do feel like you should get a cowbell when boarding sometimes. Have you not noticed some sort of armrest etiquette? I always thought it was an unspoken rule, but maybe not?

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