I use to think flying was magical. Now, it’s just annoying and stressful. Airlines keep cutting basic amenities in hopes of getting customers to pay more for flights without dramatically raising the “base” fare. This is unfortunate but understandable. Airlines have to make money to stay in business and costs keep going up, particularly for jet fuel. Airlines can’t raise rates if other airlines don’t also raise their rates. So, once one airline starts charging for what use to be a basic amenity, the others are going to follow. With Southwest also caving to investor pressure and charging for bags, well, the customer experience is only going to get worse from here.

On February 7, 2023, in the State of the Union address, President Biden suggested that the government should crack down on “junk fees.” No doubt coincidentally, on February 20, 2023, United announced “. . . an improved family seating policy that makes it easier than ever for children under 12-years old to sit next to an adult in their party for free – including customers who purchase Basic Economy tickets.”. As someone who has a United credit card, and flies United’s Basic Economy with a child under 12 fairly frequently, this is rubbish. They’re not lying, exactly, it’s just that the “makes it easier” is doing a lot of work in that sentence. Both my kids were born before United charged anything extra for seats. I’m not particularly impressed by United’s magnanimity in maybe trying to seat families together now.

When I book a ticket with Julian, my youngest kid, I rarely get the option to reserve a no-extra-charge seat. Even the awful back-of-the-plane-right-next-to-the-bathroom seats aren’t available. Though, United is, of course, happy to offer me the option to pay for “better” seating. Julian is eleven now, and also has a lot of experience flying, so I don’t succumb to the uncertainty of whether or not the airline is going to assign us seats together. I just wait them out. So far, United has been successful in seating either Jaeger or I next to Julian and it’s not unusual for us to get Economy Plus seating for free. However, if I were a new parent, I might not be willing to take the risk that United won’t mess up seating. (Ok, I probably would take the risk under the assumption that the flight attendants would move heaven and earth to avoid providing free babysitting for me.)

On my flight this last weekend, it appears that United assigned a kid, probably a 3-year-old, an Economy Plus seat in a row by himself with his mother directly behind. (I know that the parents didn’t book it this way because I had looked at the seat map just hours earlier, wondering where Julian and I were going to end up, and those seats were unassigned.) Clearly, that’s not a good option for the kid, the parent(s), the other passengers, or the flight attendants. Of course, Corporate United never has to deal with the fallout from this scenario. The flight attendant was successfully able to negotiate with another passenger, who likely paid for their seat, to move and the situation was resolved. The mom sat in a row with her infant and toddler and the father sat somewhere else in the back. Fun.

Charging for bags is also now universal. I’m old enough to remember when most airlines allowed customers to check bags for free. Then, they started to charge for checked bags but not carry-ons. Not surprisingly, many people, not just the efficient business travelers, stopped checking bags and just flew with carry-on bags. Then, the airlines started charging for carry-on bags or restricting who is guaranteed carry-on space. It’s almost traditional now to hear the gate agents spend a good 20 minutes per flight pleading with passengers to check their bags for free, after they’ve gone through the inconvenience of security with them¹. As far as I can tell, if you need to fly with checked bags, which I usually do for vacations with kids, the best bet is to get an airline credit card. I now have three airline credit cards: United, Alaska, and Southwest. These cards currently cost me $344/year which is still cheaper than paying for bags.

My most recent credit card is the Southwest one. For the past couple of years, my kids and I have met up with my parents at a summer camp. Southwest offers the only reasonable itinerary for our specific situation². Because I’m not only bringing clothes but also bedding, I need to check two bags. Up until this year, that hasn’t been a problem. However, now Southwest charges for bags: $90/bag for a round trip. Since I have two bags, that’ll be $180. For one trip. Their credit card costs $99/year but each passenger gets a bag for free. So, I “saved” $81 by getting the credit card, with just this one trip. I looked for other options but nothing else made sense. So, with reluctance, I resigned myself to yet another credit card.

Of course, this meant I had to unfreeze my credit. Fortunately, as long as I remember my login information, temporarily thawing credit is pretty easy these days³. After thawing, I had to wait a few minutes before I could apply for the Southwest credit card. I already had a United card, which is also administered by Chase, so I don’t know if they did a full credit check on me or already had the info they needed. Regardless, when I tried 30 minutes later, I was immediately approved. This all was a bit tedious but worked the way I expected. Then things got complicated. Naturally, Chase and Southwest want you to start booking flights as soon as possible. So, once I was approved, they sent me a one-time link which would allow me to book my flight with the perks the new credit card provided. They’re very clear in the instructions that you can’t close your browser, or click the back button, or do anything else that might make you lose the temporary credit card number and this is the one chance before getting the card to book the flight.

I already knew the flight I wanted so I went through all the steps and, on the very last page, I saw it did indeed have my new credit card entered as the payment method. However, when I clicked the very final button, it gave me an error. Not, mind you, a helpful error. An error that just contained numbers. After some searching, it seemed this particular error could only be solved by calling Southwest, which I did. I don’t remember how long I was waiting on the phone but it was long enough that my Southwest session expired and I lost the credit card information.

I explained the situation to the agent and she was apologetic and suggested I call Chase to see if they could give me the number. That sounded extremely unlikely to me. I pointed out that Southwest’s website was the one that had an issue so it seemed reasonable that Southwest be the one to resolve the issue. I told her the main reason I applied for the credit card in the first place was for the free bags so if she could just credit my account with two free bags for the trip, that would work well enough for my situation⁴ Eventually, she put me on hold and talked to someone else to figure out what she could offer me. In the end, she reserved the ticket for me, without me paying anything, and told me to call in once I had the card to pay for the ticket. She also told me it was important I jot down the confirmation number because she wasn’t able to email it to me and it wouldn’t necessarily appear on my account. I emailed myself the confirmation number. Though, when I logged into my account I saw the confirmation also.

That brings us to today. I received my Southwest credit card in the mail yesterday and called today, with some trepidation, to pay for my reservation. I was concerned because the reservation was no longer showing on my account so I worried that a mistake had been made and the reservation was only good for the initial 24 hours. To Southwest’s credit, this was not the case. When I eventually got through to a person, she had some issues getting me the original price I had seen but, after placing me on hold, she got the price updated and I was able to pay for the tickets. I now have an emailed confirmation, a pending charge on the credit card, and the flight shows up in my Southwest account so all seems to be fine. In retrospect, my $81 savings was probably not worth the three hours I spent dealing with this. My only consolation is that since I only use airplane credit cards for booking flights, and I pay off my full balance each month, Southwest isn’t going to make much money from me via the credit card.