Here is the good, the bad, and the ugly about flying Southwest Airlines –

I just returned from a same day business trip to St. Louis, MO to speak at the Global Business Travel Association – St. Louis Chapter. I had a busy week at work so decided to fly down early in the morning and fly back home after my meeting the same day. I only fly Southwest Airlines about once a year so I wanted to share with you my observations about what was good, bad and ugly about the airline. Here you go!

Good #1 – The flights were not like clockwork (Like they used to be), however, they operated within 20 minutes of the expected arrival and departure times. Not great but Good. 
Bad #1 – Southwest’s famous cattle-call calls for a massive line up to get on the plane. I hate standing in line and if you fly Southwest you wait in one line after another. (There will soon be big changes you can read below)
Ugly #1 – The Southwest Airlines computer system has to be 40 years old. They really are very limited when things get complicated. 

Good #2 – Bags fly free – This is a giant advantage for many travelers who now understand that many airlines will charge you $35 to $150 each way for you to check on luggage. 
Bad #2 – A round trip flight from Omaha to St. Louis was over $500. Southwest is now often the most expensive airline for last minute travelers.
Ugly #2 – Southwest seems to run a $59 airfare sale every other week, however, I have never been able to find even one time in 10 years that I could find one of these sale fares. Very deceptive. 

Good #3 – Southwest offers many direct flights from secondary cities like Omaha, NE. Some of these flights allow you to have a one day meeting and be home in your own bad the same night. Here are their direct flights from Omaha. 
Denver, Colorado, 
Chicago, Illinois, 
Dallas, Texas, 
Las Vegas, Nevada, 
Orlando, Florida, 
Phoenix, Arizona, 
Nashville, Tennessee, 
Houston, Texas.
Bad #3 – Southwest tries to prevent you from comparing their prices to other airlines. Generally speaking, they only allow prices to be found on their website and they are not listed on other online travel sites. Many people just visit southwest.com and assume they have the lowest prices. Not so my friend.
Ugly #3 – Southwest does not currently offer assigned seats, however, they recently announced that starting in 2025 they plan to offer assigned seats.