Updated: September 12th, 2016

Today, I was in the airport rather early eager to go home.  I started a new job today and my employer booked me on the last flight out.  The problem?  I was already done for the day and so I was there nearly four hours early.  I wanted to get home earlier.  My problem was that I wasn’t on a full fare ticket.   This is one place where Southwest really differs from others.  With the big carriers, you are likely to pay a fee to take an earlier flight, Southwest approaches it differently.    You see with Southwest, you can only fly standby if you are on an Anytime (refundable) fare*.  This means if you are flying a heavily discounted Wanna Get Away fare, taking an earlier flight may cost you some money. You may or may not like it but from a business perspective, I totally get it.

Now, you may have noticed that I appended that statement above with an asterisk. That’s because a few weeks ago, I discovered that you didn’t always have to pay the fare difference to fly home early.  This was one of those many occasions where I ended up to the airport (Dallas Love Field as usual) rather early.  I noticed there was an earlier flight on the board, so in a bold and daring move, I went to the gate agent to ask my standard “beg for standby” leading question “So…you have any room on the 7 o’clock flight?”. The agent took my boarding pass and looked at my original fight and told me your flight is delayed, so we can let you fly earlier with no fare difference.  I smiled, thanked the agent, and gladly took my new boarding pass because that means getting home to my beautiful wife several hours earlier.  The only problem, my shiny A-19 boarding pass was now C-2.  That meant I could be high-centered.  Luckily though, I remembered, that those with A-List can board after the A group boards.  That meant I still got a decent seat.

Unfortunately, for me tonight my flight wasn’t that delayed. It was tonight, when I learned that they could only waive the fare increase, if your original flight was delayed by 15 minutes or more.  Unfortunately, the board at Love Field didn’t show any flight delay, however the gate agent said it was actually delayed by a few minutes.  He recommended coming back a bit later to try my luck again.  After about 45 minutes, I returned and he informed me that they made an “executive decision” to let those of us with later flights get on the earlier one.  I took my new boarding pass and was ecstatic. This time it meant getting home over three hours earlier.

Update as of September 12th, 2016: Southwest now gives A-List and A-List Preferred members free standby upgrades as long as it’s within two hours of the original flight to the same destination.

You’ll hear me say this over and over again in this blog, but kindness kills with Southwest.  Be nice to the gate agents, flight attendants, captains, whomever you meet.  Being nice will get you farther than anything with Southwest.  When you are asking the gate agent to let you on an earlier flight, it’s that smile and kindness that are going to get them to bend the rules a little.  Remember that, when you are trying to get home a bit earlier and it’s sure to get you far.