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PSA: Southwest Airlines will Cancel Reservations if Multiple Flights Booked on Same Day to Different Airports

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Good morning everyone, I hope you all had a great weekend. A few days ago, I received an email from Southwest Airlines that my San Francisco to Orange County (SFO-SNA) reservation on Friday, June 30 (Fourth of July vacation) was canceled. What happened to my Southwest Airlines reservation? I definitely did not cancel that flight.

SFO-SNA Cancelled Southwest Airlines Reservation Email

I tried to rack my brain to see what could have happened. I checked the Southwest Airlines website to see if the flight was canceled or had a schedule change. Nope. Everything looked fine online.

Search SFO-SNA Southwest Airlines Flights

I then checked my other Southwest Airlines flights to see if any of them were messed up too. Nope. Everything looked correct… except for my San Francisco to Phoenix (SFO-PHX) reservation. That flight was supposed to be on Friday, July 14, but my Southwest Airlines confirmation email said that I booked the SFO-PHX flight on Friday, June 30 – the same day I was flying SFO-SNA for my Fourth of July vacation. Uh oh, that is not good.

I had originally booked the SFO-PHX flight for Friday, July 14 using Southwest Airlines points, but then I wanted to use those Southwest Airlines points for another flight, so I canceled that reservation and used my Southwest Airlines travel credit to pay for that flight instead.  I must not have been paying attention, since I booked the wrong date.  Sadly, this is not the first time I have booked a flight (or hotel) on the wrong date.

Wrong SFO-PHX Southwest Airlines Reservation Email

My only guess (later confirmed by Southwest Airlines via Twitter direct message) is that if you book multiple flights that leave on the same day to different airports, Southwest Airlines will automatically cancel one of your reservations.  I’m not sure how the system determines which flight to cancel – maybe it was the reservation booked first or maybe the flight departing first. Either way, it’s not fun to fix.

Luckily, I have always received amazing customer service from Southwest Airlines via Twitter direct messaging.  Here is my conversation with Jennifer on Twitter.  She did confirm that Southwest Airlines will cancel a reservation if the same passenger books multiple flights to diferent airports on the same day.  I asked her if she could move my SFO-PHX flight on June 30 to the same SFO-PHX flight on July 14 and restore my SFO-SNA flight on June 30.  It was a big ask and I was hopeful that Southwest Airlines could help me out (yet again).  My previous Southwest Airlines post also highlights my amazing experience with Southwest Airlines via Twitter direct messaging: PSA: Book 2 One Way Flights on Southwest Airlines & Direct Message them on Twitter.

After anxiously waiting a few hours, I followed up with Southwest Airlines to see if they could help.  Like magic, Jennifer was quick to respond and was able to fix both of my reservations.

Twitter Direct Mesage with Southwest Airlines 4-27-2017

Midway through our Twitter conversation, I received multiple emails from Southwest Airlines regarding my revised SFO-SNA and SFO-PHX reservations.  I’m so glad I reached out to Southwest Airlines right away and that they were able to fix both of my reservations very quickly.  If I had to fix these reservations on my own, I would have had to pay an extra $70 since my SFO-SNA flight has gone up by $70 since I originally booked the flight (luckily the SFO-PHX flights were the same price).

All in all, another good reminder that I need to be much more careful when booking flights and double check that I am not booking multiple flights on the same day to different airports.  If you have a similar situation, I would love to hear about your experience.  If you have any questions about my experience, please leave a comment below.  Have a great day everyone!

P.S. If you are reading this post on Monday, May 1, don’t forget to enter my 4 year blogiversary giveaway for a chance to win a $10 Amazon eGift Card.  Good luck!

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7 thoughts on “PSA: Southwest Airlines will Cancel Reservations if Multiple Flights Booked on Same Day to Different Airports

  1. Elijah

    I am not surprised by this given their no overbooking policy now. I am also not surprised by the Twitter team being awesome!

  2. Mark O

    I did this about a year ago with no issues so they must be policeing it better now. I did it when I wasn’t sure which location of the CFP my team was going to so I booked both a couple of weeks early to lock in the cheaper price.

    1. Grant Post author

      I’m pretty sure I’ve done it in the past too without any problem. Not sure when they implemented this “feature” or why now. I wish they would just send an email informing me of multiple reservations instead of just cancelling one.

  3. Hoang


    I thought I did mention to you about this issue 2 months ago. I was told by SW customer service they upgrade their computer system. I mentioned to her about our case since my wife is a consultant so we are not sure when she will get the next job so we need to book 2 flights same day from different departure and destination: DAY to CHS or CMH to BWI. She said she understand the issue and will put the note but then she came back said nothing she can do due to the computer program.

    1. Grant Post author

      Now I remember our conversation. I guess there is no way to override the system. I wonder if you leave off a SWA Rapid Reward Number or using a middle name/initial if that might work.

  4. Pingback: The Complete Guide to Southwest Airlines

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