Me: “Stop being such a diva, just suck it up and fly economy.” — Also me: “No.”

Well, we knew it would happen sooner or later — I’m finally getting on a plane again. After 16 months or so, I’m heading back to Chicago next month to see my family for the first time since the pandy started, and I’m pretty excited about the trip. Unlike your garden variety #AvGeek, however, I’m not particularly excited about the flight. I’ve written in the past about my fear of flying (which is specifically more of a fear of turbulence causing me to have a massive panic attack), and one of the key ways that I manage that fear is by actually flying. A big part of my particular issues with flying involve anticipatory anxiety, and having a recent example of a flight that was perfectly fine really helps tamp that down for the next flight.

For years, I’ve tried to take a flight every couple months, even if it was just a short hop up to Seattle or down to LA (sometimes even just for the day). My last flight was coming back from Seattle after a work trip in mid February of 2020, and I was considering it as preparation for a trip to France in April that never actually happened. That’s 16 long months for my flying anxiety to fester and grow, and now that there’s a physical flight for it to glom on to, the inside of my brain has been pretty turbulent lately (LOL).

Because so much of my issues on the plane are exacerbated by claustrophobia, it makes a huge HUGE difference to fly in first class. It makes such a difference that I pretty much won’t fly in economy anymore — even if I’m traveling for work, I’ll pay the difference to upgrade to first (and god help me if I ever start working for a company with a stricter travel policy). Of course, sometimes it’s unavoidable — like flying around Europe, for instance. So, I know that I can do it, but I certainly don’t like to, and those flights are always more difficult for me.

What a diva, right? “Sir Jordan will only consent to travel in the firste classe cabine, and his champagne must be delivered in a proper glass flute and served at a perfect 39.4 degrees.” It honestly makes me feel a little ridiculous, but hey — I like what I like. (More accurately, I hate what I hate, and I really hate flying in economy.) However, this trip to Chicago is really stretching the limits of how far I’ll go to avoid an economy seat.

See, I’m really having a tough time with this upcoming trip, so I started focusing on finding something I could get excited about. A first class recliner seat with a couple extra inches of width and legroom on an Amercian 737 isn’t really cutting it in that department. Sure, those couple inches do make a pretty huge difference, but it’s still mostly a snooze. Plus, I was trying to use miles to fly on a specific day (luckily I have a shitload of those saved up), so I was never going to be able to be that choosy about my flight.

While there wasn’t much going out of San Francisco, I did find a flight from LA to Chicago on an American 787-9 with award availability. I’ve flown the 787-8 configuration before, and while it was a real treat for a domestic flight, I don’t know that I’d love it for a 10+ hour flight. The 789 has a better seat — in fact, it’s probably my favorite business class seat looks-wise. And, while tons of airlines use this same basic seat (with various customizations), I’ve never actually flown it before (unless you count British Airways’ 787 first class, which is a heavily modified version).

Photo courtesy of American Airlines, provided with extreme courtesy and courteousness.

Now, the one problem with this flight is that I don’t live in LA, and American wasn’t giving me a good routing from SFO to Chicago via LAX. That meant that I would need to make a separate booking for the SFO-LAX leg, which introduced all kinds of other issues. JetBlue had a flight, but it was at 8:30 AM, and I hate waking up early. (DIVA!) Delta had some flights, but they were expensive. It finally occurred to me to check Oakland instead, and both Delta and Southwest had some reasonable options. I ended up picking Delta, for the sole reason that the flight is on an E175, and I really like the single first class seat on the left side in those planes. It was a $200 flight that would have cost 27,500 SkyMiles, so instead I used the “pay with miles” feature for the first time and burned 20,000 miles off the top of my Delta balance. Not a great redemption, but I have a decent amount of SkyMiles right now, and I’d rather spend them than watch them devalue.

The end result, of course, is that whereas I could have acted like a normal person and taken a very simple 3 1/2 hour flight from SFO to Chicago for a fraction of the cost, I decided to spend 45,000 miles on a one-way flight to Chicago with an unnecessary connection and a 3 hour layover in LAX for no reason except that I wanted to fly on a widebody. (Let’s not forget that it’s not too far in the past that 45,000 miles was enough to fly you from San Francisco to Frankfurt in business class through Aeroplan (RIP)).

One of the benefits of my strategy to accrue as many miles as possible in as many programs as possible is that I can make a horrifying redemption such as this one and not really miss the points. And it seems to have worked, since I am actually more excited than nervous about this flight from LA. Oh, and on the return leg, I have a United 777 with Polaris seats to look forward to — and that one’s a direct flight. It’s been four years since I’ve enjoyed a Polaris cabin, so I’m excited about that as well.

A real glam shot of a Polaris seat. Courteously, United was courteous enough to offer me this photo courtesy of United.

So I’m all set for my first trip in over a year… Now I just need to hope they don’t hit me with an aircraft change.

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