As a matter of existence, airport delays have always been relegated to the domain of news. They were always in the camp of things that existed but happened to other people. That is, I suppose, until it happened to me. After spending a night at the airport, I’m now an Expert on Airports and thus more than qualified to write my full thoughts on the Horror that is Airport Delays.


On 10/15, I booked a flight from MDW to SJC on 12/24 to go home before flying out to Taiwan. I had already resigned myself to the fate of brushing shoulders against everyone else like a can of sardines, but I figured it would all be OK. (This leg of my journey was mainly limited by the flight out to Taiwan, which was difficult to schedule.)

A week out from the flight, we all saw the oncoming disaster called Winter Storm Elliot. (As a side note, having grown up in sunny San Jose and having gone to school at cloudy Berkeley, I suppose I’ve never lived through what half of America calls a proper winter. Now I have.) Watching the weather forecasts, we in the office couldn’t do much but hope for the best as the onslaught came. The worst of the storm, I supposed, would be Thursday, when the storm hit its zenith in Chicago. Indeed, that day was quite miserable – Friday was at least a bit sunny and Saturday even bearable. On Saturday morning, I saw the sun and naively thought the odds of a cancelled flight would be low. Boy was I wrong.

A Slow Descent (Into Madness)

The red flags began. Oh boy did it go downhill. The first major red flag was that my flight was already delayed from the start of the day. Interesting, I thought. Doing some deeper digging (thanks @Flightaware!), I saw that the first leg1 of my plane’s route from Baltimore to Midway was cancelled. So it became an open question in my head as to how they would go about finding a replacement flight and replacement crew to staff the remainder of those flights.

As the day progressed, the delay on my flight went from one hour to two, from two hours to four, and peaked at six hours. As my boarding time neared, under good advice2 from my parents, I left to the airport before my flight’s original scheduled departure time. And there, I waited. And waited. and waited …

At around 7:30 central time, about two hours after my flight was scheduled to leave, I received a call from my dad: “Was your flight cancelled?” Checking Southwest, he was totally right – I was sitting in a separate area from the boarding area, so I missed announcements.

I packed my bags and spedwalk to the boarding area. On the way, I found a separate flight to Oakland departing at 10:30, and figured I might as well ask to join the waitlist there. As a result, I got in line for customer service for that terminal.

I wasn’t that far back in line, but boy did people take forever. I became an expert in estimation in that two grueling hours of waiting for some ~10 people ahead of me (Godspeed to all the people behind me). I found that the time taken at the customer service desk was largely a function of the number of people in a party. It averaged 15 minutes per person, so a party of 4 took an hour. (They really did!) I suppose there are hidden parallels between restaurant wait times and airport support desks as a function of the number of people waiting! (I would’ve thought that airport support time was a function of the number of parties of people)

But I digress… In line, I booked two tickets in advance as insurance and then some – one for 12/25 (the next day) and one for 12/26 (two days later).3 Some two and a half hours later, I made it to the front of the line. Talking to the helpful people there, they said that the Oakland flight was beyond booked. When I first got in line, there were maybe 6 people on the waitlist. It had since grown to 9+ and counting. My odds of making it were beyond low. They transferred my flight to the next free one, on 12/25, which happened to be exactly the same as one of the flights I booked (which I cancelled shortly thereafter). At my request, they also placed me on the waitlist for the first flight out the next morning at 9AM. And of course, the voucher – they gave $200 travel credit to everyone who waited in line.

The Brightest Night

Night was me roaming around, sleepless. For my first hour of sleep, I tried to sleep head to the side on a table. This really obnoxious tiktok kept playing in the background – something about autodispensing popcorn in Midway and different flavors. (I suppose the commercial worked; I still have nightmares about popcorn.) After that first hour, I decided to pack my stuff and walk around. Towards the front of section A’s food court, I found these tall comfy chairs, and very luckily there was one left. I took it, put on sunglasses, and fell asleep all the way until sunrise.

The Fateful Day

I woke up bright and early at 5AM, hungry to eat a bagel from Einstein Bros that I had eyed the night before. (Waiting in line for Southwest support took until past 10, which is when all the stores closed.) Boy was that bacon egg and cheese the saddest bagel to have existed – the bacon was OK, but the cheese wasn’t melted, and the egg tasted like foam. I downed my coffee and headed over to the waiting area for the first flight of the day.

To keep things short, after two hours of waiting, I ended up getting on the flight. That was perhaps the most grateful I’ve been in a while – I suppose it really takes losing something to really appreciate having that thing back. The thing that surprised me most was that the plane had around 15 seats missing, which amounted to perhaps 10% of the seats. How was that possible? Furthermore, I had checked the flight in the morning, and there were no empty seats available! Either way, I landed in San Jose safe and soundly four hours later.

Oh, so what happened to my original flight had I not taken the waitlisted flight?

I went back and checked, and it turns out the flight was cancelled yet again. This time, it seems for the same reasons! The originating flight didn’t make it out of Virginia, causing the Midway to Oakland leg to get cancelled. Boy was waiting in the airport the right decision.

In Retrospect

So what should we make of the delays? Was it anyone’s fault? In retrospect, it was a fairly unlucky set of circumstances. Weather caused flights to be cancelled, which had cascading failures downstream. But I suppose that’s not the full story – had the airlines cancelled the flights ahead of time instead of cancelling them after everyone had already gone to the airport, maybe it would’ve been a much better outcome for everyone involved. So, some retrospectives:

On the Airline

  1. The line of communication between passengers and the airline broke down. This was suboptimal for quite a few reasons:
    1. Customers resorted to selfish actions (myself included): Once we lost the guarantee of a safe flight home, it became a free-for-all, and people overbooked flights. This undoubtedly impacted the system many times over and helped no one. It’s basically the textbook definition of a negative externality.
    2. Customers were left in purgatory. I didn’t hear about a rebooked flight; there was no official communication about what to do next. Furthermore, to think that the next direct flight (that I’m writing this on) still has 15 empty seats – that’s just unacceptable.
    3. Related to point 1, but it likely made all the lines of support overcrowded as well. It’s somewhat akin to the stampeding horde problem or even the bank run problem, but once the situation seems even a little out of control, it will quickly spiral to very out of control.
  2. There was no reason for the flights to be cancelled as late as they were. It seemed that the reason for cancellation was due to a combination of short-staffing and plane availability. I understand the want of optimism, but in this case, it doesn’t seem like there existed a universe where the flight actually took off. Cancelling them all ahead of time more optimistically and committing to a plan of communication might have saved everyone lots of pain.

Personal Takeaways

  1. You’re really at the mercy of an airline to Do the Right Thing. When you inevitably need to take an impacted flight, all you can do is show up on time and pray for the best.
  2. It might be prudent to think ahead of time for backup plans: would you be OK with spending the night at the airport? If so, it might be a good idea to pack a pillow and blankets and mentally prepare yourself to spend the night.

Cheers to everyone I met on the way

Though this journey was quite painful, I must still give thanks to everyone that I met on the way. To those whose flights to Rochester, NY, were cancelled, I hope you either found a way back home to where you came from, or that you found the next flight to Rochester. To a friend of a friend who I miraculously bumped into while waiting for the first flight of day – I suppose it was only God’s will that made us cross paths in the airport. I know I gained some of my sanity back, even if I did think I was hallucinating for a moment.

And to Southwest snacks, thanks. (I’d just appreciate better communication next time, but it seems like they improved on it for the second cancelled flight.)


  1. For the uninitiated, Southwest operates by scheduling their planes on multi-destination journeys, and tickets are sold for legs of that flight. My flight was the second leg of the day. 

  2. I heard stories last night of people checking in after their flight’s original departure time since they knew their flight would be delayed, but were turned away instead since they didn’t check in on time! 

  3. I recognize that this is pretty bad in aggregate – one can imagine that, in the limit, if everyone in the same position as me did this, the airlines’ problems would be compounded and then some. I don’t have much to defend myself with except that I think there were much more elegant ways they could’ve solved this problem, and that this behavior is largely a function of last resort and fear rather than irrationality.