4 Flights, 15 Hours. Why I spent my Saturday flying around the country to earn airline status

Normally I tend to shy away from flying on Southwest Airlines, but with their recent promotion offering a companion pass for booking and flying two flights or one round trip and the fact that I still had Southwest flight credit from a price change on a flight back in March, I decided to spend my Saturday on a status run to secure the companion pass. To earn the Southwest Companion Pass you typically need to fly 100 one way flights or earn 125,000 miles in a year. When you achieve the companion pass, a companion is able to fly with you on any flight for only the taxes and fees of a flight. I will give the companion pass a try in the Winter and decide if it is worthwhile to try to achieve it via credit card sign up bonuses in the future. Since I have had airline status of some form since my first status challenge with American Airlines in 2018 and achieving Platinum status, I have shied away from flying low cost carriers like Southwest and Spirit unless absolutely necessary. But, now that my wife and I had our first child in August, flying Southwest might be a better choice in the near future when traveling domestically, if not just for the checked bags as well as being able to preboard. After picking a day to fly I searched Southwest’s site for the cheapest one way flights as well as a schedule that would make sense. Since Southwest does not operate on the same hub and spoke route system as most airlines, it is actually quite difficult to find same day round trip out of a city like Milwaukee. It also seems Southwest return flights are significantly more expensive when trying to return on a weekend from what you would typically consider a destination city to a city that people would be visiting from, in this case, Milwaukee. After searching and searching and not being able to find a decent routing that would be short and inexpensive, I decided to turn this trip into a two-tiered status run and use a return flight to reach AA Gold Status; which I was only a few Loyalty Points away from obtaining.

I figured my best chances of making this run a success where to leave on one of the first flights of the day which in this case from MKE was to BNA. I also wanted to make sure I was flying somewhere where I would have a few options to get home in the event of a delay or cancelation. I booked the flight from MKE to BNA for around $95 (using credit from a previous flight) and then searched for the least expensive and shortest connection time from BNA,  which was a flight to MIA ($90) where I could get a return flight back to Milwaukee using flight credit that I had after receiving EU261 compensation for a cancelled flight from PHL to MKE in April. The total out of pocket cost for this status run which will secure me a Southwest Companion Pass as well as AA Gold, was around $50.  Depending on how much I am able to use the companion pass in January and February I will easily be able to get $400-$1000 in value out of that and with AA Gold, I envision being able to get quite a bit of value out of as well once my OneWorld Sapphire status via Royal Air Maroc expires in March.

Is it crazy to book 3 flights with a total of 4 stops in one day to chase status on an airline? Maybe for some people, but I have found that having any status with an airline makes the experience of flying so much better, even as it seems upgrades are harder and harder to come by in 2022. I am writing this as I am on my 3rd of 4 legs, from MIA to PHL before connecting to Milwaukee and so far the day has gone forward as planned and I have not experienced any delays or major issues.

Once my Companion Pass is issued, I already have a few family trips planned where we will be utilizing the pass. I will update as soon as I receive my companion pass and am able to apply it to booked flights for a review of the companion pass.