Over the next few weeks, I am going to do a series on the hotels and airlines I like/fly/stay at. While this information is all available else where on the interwebs, I hope to provide some perspective about my travel strategy.

Since I will be flying Southwest later this evening, I figured that there was no better place to start.


What I Like

-2 free checked bags on every flight. Boots + skis only count as one bag, if you’re into that. I, personally, have never been charged an oversize fee for my skis, even though they clearly are.

-flexibility. All flights are refundable (to SW credit). You can change your flight up to 10 minutes before you fly.

-you can pick any available seat on the plane when you board. This is determined by your boarding order, which is dependent on when you check in for your flight. You can check in as soon as 24 hours ahead of time. You can bypass this by paying extra to be automatically assigned a number, but this blog is about saving money while traveling, so I just set an alarm on my phone or deal with it if I forget.

-the Southwest Companion Pass. If you earn 100,000 eligible points in 1 calendar year, you will earn the companion pass. This thing is great because whoever you designate as your companion can fly with you for only the cost of the security fee on any paid or award ticket as long as there is a seat available on the plane for purchase. (Note that credit card bonus points do currently count toward that 100,000 points)

What I Don’t Mind, but Isn’t Ideal

-Fixed value points. I know every time I earn a Southwest point that it is going to be worth approximately the same thing. Currently about 1.67 cents. Decreasing to approximately 1.5 early next year. Yes, I can usually get more value out of that from other mileage currencies, but I can still often find round-trip flights for under 10,000 points on SW. Those RTs on UA, DL, AA, or others would almost always cost 25,000 miles. So yes, it is a fixed value system, but there is still value to be had.

What I Don’t Like

-Southwest sometimes flies into the smaller airport in a city. Chicago for example. Southwest only services to and from MDW, which is fine when I want to go to Chicago, but a lot of the time when I am heading to Chicago, I want to be at ORD to fly somewhere else. It is either not cheap, or a pain in the butt to get from MDW to ORD (in my opinion) so I will not fly Southwest if I need to get to ORD. Ever. I will take Amtrak (cheap ish, convenient ish), or Megabus (cheap), or use Avios (usually convenient). But I will not fly Southwest.


I like Southwest. I fly Southwest a lot (relative to my number of segments). Often times Southwest is the cheapest option (for domestic flights that I am looking at). I find that the planes are always clean. The staff is usually very friendly. Flying Southwest is generally a good experience. I think there is a lot of value to their program, especially if you have someone you like to travel with and can secure a companion pass and because of the fact that you have free changes to tickets until 10 minutes before departure.