Good morning everyone, I hope you all had a great weekend.  The Easter Bunny took a liking to me and gave me a small box of See’s Candy, but enough about me and my love / addiction to sweets.  A few days ago, I needed to make a change to an existing Southwest Airlines reservation, but I booked it as a roundtrip flight (San Francisco to San Diego).  I wanted to change my trip so that I would be able to fly from San Francisco to San Diego, but return from Orange County and fly into Oakland (I know we have all done that a few times, right?).

Long story short, when you want to change a roundtrip Southwest Airlines flight, you cannot change the departure and arrival cities for a leg of your reservation.  I could probably change the return flight to fly San Diego to Oakland, but that wouldn’t work for me.  I also couldn’t cancel just the return flight either.  Lastly, if I canceled the entire reservation, I would end up paying much more since my outbound flight from San Francisco to San Diego had gone up in price since I originally booked the flight.

Luckily, I have a secret weapon when it comes to making complicated changes to Southwest Airlines reservations… Twitter direct message.  Unlike Ben who wrote Why I Don’t Bother With Airline Customer Service Via Twitter Anymore, I have gotten great customer service from Southwest Airlines, Virgin America, Alaska Airlines, and JetBlue (among many other companies).  I have sent direct messages to Southwest Airlines in the past and they were always very quick to respond and always provided great customer service.  In this instance, I clearly explained that I wanted to cancel the return flight but keep the outbound flight intact.  A few minutes later, my direct message was seen and my reservation was updated.  I then had a travel credit available which I used to book my return flight from Orange County to Oakland.  The entire process took about 20 minutes.

In contrast, if I had booked San Francisco to San Diego as one reservation and San Diego to San Francisco as a second reservation, I could have easily changed the second reservation to fly from Orange County to Oakland.  That entire process would have taken me probably 2-3 minutes.  In 99% of cases, 2 one way Southwest Airlines flights will cost the exact same price as a roundtrip Southwest Airlines flight.  Learn from my mistakes and always book 2 one way flights with Southwest Airlines.

Before I show you another Southwest Airlines direct message conversation, let me share my Southwest Airlines booking process.  Whenever I travel, I prefer to fly Southwest Airlines, if the routing, timing, and price is right.  Even if the price is higher than I think it should be, I prefer to book with Southwest Airlines, even if the flight is several months into the future.  Like clockwork, Southwest Airlines sends out emails every Tuesday morning with their latest fare deals.  And also like clockwork, I check all my existing Southwest Airlines flights for price drops.  Most of the time the price is the same or higher than when I booked, but sometimes the price has dropped significantly.  I’ve written about rebooking existing Southwest Airlines flights in the past (PSA: Check Existing Southwest Airlines Flights for Price, then Rebook). I’ve probably saved $500+ in the last 12 months from rebooking existing Southwest Airlines reservation and the process only takes a few minutes once a week of checking existing reservations and rebooking them at the lower price.

During one of my rebooking sprees, I was trying to rebook my brother’s flight to a lower price, but the Southwest Airlines website was erroring out on me.  I tried 3 times in total and always got an error message.  I then sent Southwest Airlines a direct message explaining the problem and they were able to rebook the flight for me and refund me 2,085 Southwest Airlines points.  Not bad for doing a little research and sending them a short direct message.

It also goes without saying (but I will say it anyway), you need to have good records of how much each Southwest Airlines flight cost (either in money or in points) and have the booking reference number handy.  You also need to keep track of your Southwest Airlines travel funds because you only have 1 year to use them from the date with which you originally booked the Southwest Airlines flight.  In very rare instances, an airline will have a much cheaper price than one of my existing Southwest Airlines reservations and I will sometimes book that new flight and cancel my existing Southwest Airlines flight.  That can also be a double edged sword since Southwest Airlines might lower their price in the future.  Ugh, sometimes saving money on travel is so complicated.

If you have any questions about my See’s Candy (don’t bother asking, it will be all gone by the time you read this), about rebooking Southwest Airlines flights, or about contacting Southwest Airlines on Twitter, please leave a comment below.  Have a great day everyone!

P.S. Pro tip from a sweet tooth, check out CVS, Walgreens, and Rite Aid this week for discounts on leftover Easter Candy :)