Why I Don’t Fly Through Chicago

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Photo by Tim Dennert on Unsplash

No offense, Chicago, I’m sure you’re a wonderful city and maybe one day I’ll get to spend some time in you.

But it seems that I have no luck with Chicago and airplanes. Now, to be honest, one issue was predictable. My parents came to visit for Christmas and had to fly from the UK to Raleigh.

I told them not to fly through Chicago. I told them. But it was cheap, so they booked a flight through O’Hare in winter. I hear the groans already. The year was 1999.


The second biggest snowstorm in the history of Chicago. They were on the last plane to land. They were stranded for three days.

My personal experience with Chicago is, well, not that dramatic, but both times I’ve flown through (rather than to…no issues when it was my end destination) Chicago were, well, entertaining in a less than fun way.

Why I Don’t Fly in Dry-Clean Only Clothes

Nope. It wasn’t bodily fluids. While on a flight from DC to Chicago, we hit an air pocket.

At the precise moment the poor flight attendant was pouring my drink.

Yes, it was Coca Cola.

She was more upset about it than I was. I was, thankfully, going somewhere with laundry facilities…

Then There Was Our Trip to Jackson Hole

This trip is why I’m not ever trying to fly the same day an all inclusive vacation starts again, by the way.

Jackson Hole, Wyoming. It’s kind of the middle of nowhere unless you’re a skier. In the summer it’s a gateway airport to Yellowstone. But it’s tiny and pilots hate it. The approach is, shall we say, interesting, involving a 90 degree turn between two mountains. It’s an airport where co pilots don’t land the plane, if you know what I mean.

Needless to say there’s no direct flights there from the DC area. There are, in fact, only about four summer flights in and out of Jackson Hole, across all airlines. So I was choosing flights not so much by where the interim airport was, but what the price, schedule and layover times were.

This gave us an outgoing flight through DFW (Dallas-Fort Worth) and a return flight through, yup, Chicago.

“It’s July 4. We’ll be fine.”

Yeah, those are words you don’t say. Because of the massive price difference, we were flying American. On the way out, we had a delay out of National because American doesn’t trust pilots to record their own weight and trim. There’s no indication this has any safety impact. This resulted in a stressful flight — were we going to get stranded in Texas. Thankfully our flight to Jackson Hole was delayed as well. We made it to our destination just in time for Happy Hour. Which at that point I needed.

So on the way back…we get to the tiny Jackson Hole airport with plenty of time. This airport has like three gates, zero jetways, a tiny souvenir store and a restaurant with a kitchen in the dividing wall so they can serve both sides of security.

We were there for five hours.

The spectacular mountain view was not helpful.

Our plane, apparently, broke down at…well…DFW.

And like a fool I’d booked us on…the last flight out of Chicago.

This flight was the only one of the four flights we had tickets on that left on time.

Without us.

So there we are in Chicago, at like 9:30pm, without our luggage and at the mercy of American.

“Here are your meal vouchers. You can use them at the airport or the hotel.” They then gave us directions to the hotel shuttle.

We were driven to our hotel, between the strip club and the porn shop. No, I’m not making this up.

We get off only to see what the hotel doesn’t have.



Pro tip: If you are ever stranded in Chicago, it turns out there are multiple pizza delivery joints near the airport who will gladly take your airline vouchers.

So, we got our real Chicago pizza.

Which we had to wait three hours for because it was July 4th and everyone in the city was ordering pizza.

I am never flying through Chicago again.

Until next time it saves us $300 each…

Written by

Freelance writer, freelance editor, novelist and short story writer. Jack of many trades. https://www.jenniferrpovey.com/

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