Questions and Answers

Your recent story about being unchecked in reminded me about a weird situation last year we had. My wife and I. travel a few times a year. Not that long ago we traveled from Boston to Chicago to run the Chicago marathon. We booked our roundtrip flights on Southwest. We checked in via mobile app, boarded and flew into Chicago on that flight. However the next morning I received an email from Southwest saying “Sorry we missed you” etc. I found it funny at first since I was reading this while in Chicago after previously flying the “missed flight” the night before. However his is the kicker: Southwest automatically cancelled my return flight back to Boston for that following Monday per their policy! So my wife and called customer service but that was useless. Every person we spoke would just refer to their system and say “but you missed your flight”. It was like being in the twilight zone. They just kept saying there was nothing they can do and that I had to book and repay for a whole new flight. Their only advice was to call their corporate headquarters days later after the holiday weekend and try to get reimbursed. Thankfully my wife started posting on social media that weekend while we did our tourist thing in Chicago tagging Southwest mocking them with selfies in Chicago. One of their social media staff members picked up on this and at least got a new return flight without having to repay. When we got back to Boston I still contacted headquarters to let them know of the issue so it wouldn’t happen again to me or someone else. They basically thought I was crazy and was making it up. I told if they didn’t believe they could just refer to existing video from Logan or Midway gates showing me get on and off the flight lol. I eventually gave up but of course it still bothers me to this day. I wasn’t trying to get any vouchers or miles/points from them. I just wanted them to own the mistake/problem, address the issue and fix it so it didn’t happen again. Ever since then I never book round trip flights together. I book them separately as my understanding is all airlines have this policy of cancelling return flights if you “miss” your initial flight. Even if you didn’t lol. What would you have down differently?

With Southwest, I never buy a roundtrip ticket, always two one-way tickets. This way I am protected because the return flight would not be cancelled if something like what you had described had happened.
Another benefit of doing that is that if Southwest fare decreases after you bought your ticket, you can easily rebook just that segment which decreased in price. If you have a roundtrip ticket, and one segment decreases while the other increases in price, you cannot just rebook one segment, you would need to rebook both, which might negate the cost savings.

We always book two one way tickets also. Since we always have the companion pass it also makes changes with that significantly easier than with a round trip. We also use southwest to position for international flights so if something happens with the other flights our entire itinerary is not compromised.