Tomorrow, I’m taking my first Southwest Airlines flight in about 5 years. We’re headed to Baltimore for a family event. My wife and mother-in-law both had expiring Southwest flight credits so it made sense to use Southwest for this trip.

I have a long history with Southwest Airlines. It goes back to the late 90’s when I was living in South Florida and Southwest was making their first big national push out of the South West and West Coast routes they had flown for a couple of decades. I was living near Fort Lauderdale airport and Southwest moved in to start competing with Delta, Continental, US Air and other airlines that flew the north-south sunshine routes to Fort Lauderdale, Tampa, Orlando, Jacksonville, etc.

I was traveling every week for consulting work and was an airline free agent as I didn’t live near a hub and I much preferred nonstop flights (and frequency of options) to where I was assigned for projects instead of keeping loyal to one airline. I was assigned to a several month project in Nashville in late 1998 and Southwest was the best option. They had an early morning flight to Nashville that made a quick stop in Jacksonville on the way (you could stay on the plane) and then a non-stop flight home in the late afternoon that met my needs.

Before I began flying Southwest, I joined the Rapid Rewards program. Back then, you would earn a credit for each one-way flight (including changes and stops) and when you had 16 credits, you could redeem them for a free round-trip ticket good for one year for any Southwest city pair. There were no fare class restrictions or points per dollar to calculate.

Here’s the kicker: American Express had an ongoing promotion with Southwest at the time where you received double Rapid Rewards credit for booking Southwest tickets with your Amex card. My company had me use a corporate Amex card to book all my travel, so now I was earning a free Southwest round-trip ticket every four weeks (eight one-way trips). The Southwest footprint was still pretty limited back then. You couldn’t fly to New York City or Boston yet (only Islip and Providence/Manchester), but they had opened up flying to Baltimore-Washington, Chicago Midway and a few other places.

The check-in and flying experience was also different back then. There was no online check-in. If I had a 7am flight at Fort Lauderdale, I would show up at 6am when the gate opened to stand in line to get a plastic card with a number on it. If I got 1-30, I was good to get an aisle or window seat near the front. If I got 31-60, I was probably OK for an aisle or window a bit further back and so on. You handed these cards to the gate agent as you entered the jetway.

I remember earning so many free flights that we couldn’t use them all. We visited my wife’s brother in DC and took a trip to New Orleans, but we also gave away a few of the tickets to family and friends as they were easily transferrable.

So why did I stop flying Southwest? I stopped traveling for work for 18 months or so when our oldest daughter was born and then I started traveling to Atlanta every week. Back then, you had two choices for Atlanta travel: Delta and Air Tran. Living in South Florida, Air Tran still had the bad reputation of Valujet (which they had purchased following bankruptcy) and the horrible crash in the Everglades back in 1996. Many people would never fly Air Tran because of this. Anyhow, I stuck with Delta and really forgot about Southwest, especially after we moved to Atlanta in 2002.

After the move, we flew Delta mostly but also Air Tran when it made sense. Air Tran had a similar program to the old Rapid Rewards where they used flight credits instead of points. Then, in 2012, Southwest finally entered the Atlanta market when they purchased Air Tran. They sold off the non-737 Air Tran planes and took over the small hub that Air Tran had established in Delta’s home.

We started flying Southwest again when my kids were traveling for sports. My oldest had oversized lacrosse goalie gear and sticks we had to check so the two free checked bags really helped save on costs and the lack of change fees helped when we needed to change flights if they got knocked out of tournaments earlier than expected. I never loved the stress of having to check-in exactly 24 hours before the flight, the lack of assigned seats (especially if we had a bad boarding number) and the fewer overall flights between each market compared to Delta. But, Southwest did the job.

After the sports travel ended, my wife and I mostly switched back to Delta. Once we got the Amex Platinum cards which gave us SkyClub access and I earned Medallion status, it was a much more pleasant experience flying Delta than any other airline. These days, I’m not too thrilled about flying Southwest, but I know many love it thanks to the Companion Pass, which is a great money-saver for families. I also don’t find the prices to be too competitive relative to the value I get from Delta these days.

What do you think of Southwest Airlines?

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