Making the best of an accidental stopover in Chicago

There are few things more frustrating to a traveler than flight delays. My return to Europe was preempted by a ridiculous almost three-hour delay at MIA. But after spending a month driving in Miami, I’m officially all out of fucks to give. Life is too short for silly things like aggravation.

So what could have delayed a flight so severely? Apparently planes have a thing called a log book, that is required to be maintained and carried on board every flight. The crew of the previous flight misplaced it, so we had to deplane and wait for a copy to be made from the computer records. That took two hours.

In the meantime, I waited on a rocking chair listening to Matt and Kim who make all airport delays feel like a fun music video featuring a pink rocking chair. Mostly I wasn’t worried because I didn’t actually have a connection in Chicago; we were going to continue on the same plane to Düsseldorf.

Or so I thought.

After other numerous delays, including a thunderstorm that we had to wait to pass in order to land in Chicago and traffic on the runway, I arrived in Chicago and asked when the plane was expected to continue to its final destination. At that point, I was told that the flight to Düsseldorf had already departed.

These kinds of epic fuck-ups are so common at O’Hare that they have several areas with phones for rebooking travel every three feet. The person on the phone didn’t even really understand where I was, despite having my itinerary in front of her. There was no information about the flight anywhere. And the next available flight was the following day.

Then I went to baggage services where they told me my bag was being held for my rescheduled flight and it would go on to my destination. If I wanted it the same night, I would have to wait 45 minutes. I’m skeptical about this bag making it to Germany, but I’m also not about to drag my stuff all over Chicago for 18 hours when they can just keep it. They gave me an overnight pack which contains tiny versions of essential toiletries. And that, kids, is why you should always carry extra underwear in your carry on.

I know this sounds like a logistical nightmare but remember, situations are only shitty and aggravating if you perceive them to be. I love Chicago and I haven’t been here in years. So I hopped on the blue line and headed into town. I booked a hotel (which I’ll be billing AA for later) on the way to city center because God bless Chicago transit which is mostly above ground or is equipped for cell service.

But instead of going to the hotel, I went straight to Giordano’s for a deep dish pizza. This is actually not the first time I’ve gone straight from the airport to Giordano’s. But it is the first time I’ve tried to eat one of these by myself (Spoiler alert: I failed).

Chicago Deep dish pizza

So what can you do in less than 24 hours in Chicago? Actually, kind of a lot.

  • You can enjoy a Cubs game while you try to stuff down an entire deep dish pizza.
  • Try walking in an unfamiliar neighborhood before you realize these aren’t the quiet crime-free streets of Prague; this is Chicago, so you call an Uber.
  • You end up wondering why you ever thought Chicago would be a cool place to live and then your Uber driver is super friendly and helpful and you remember why.
  • You can go to Millennium Park at night and check out the bean.
  • You can go up Willis Tower which is open until 10 pm. Because you haven’t been since it was the Sears Tower and before they installed that crazy glass ledge.
  • You can see a good concert. Because if you accidentally land in a great music city like Chi-town, concerts are the first thing you should look up.
  • Or you can just drink a lot of Goose Island because your flight doesn’t leave until 3 pm the next day.
  • You can walk along the Chicago river so you can see why it’s called the Windy City.
  • Eventually crash in your hotel room for the night and consider yourself fortunate to have a relaxing night of sleep between your two flights.
  • You can have breakfast at Stan’s Donuts or you can just eat the rest of your deep dish pizza for breakfast.

With the right attitude, all your pitfalls can be unexpected gifts, like an unplanned night in your favorite US city and free upgrade on an international flight for your troubles. When life gives you lemons… eat a whole deep dish pizza (and make your airline pay for it).

Millennium Park

2 thoughts on “Making the best of an accidental stopover in Chicago

  1. My home town. Deep dish pizza is a must(and kudos for choosing Giordanos). Not bad public transportation for an American major city. And you should take in a White Sox game.Fuck the Cubs. I would rather see Buckingham fountain than the Bean. A trip to the top of (what will always be )the Sears tower is great. Yes indeed,people there are very friendly. Living in Miami,I definitely miss the people.And the seasons.But not freezing my ass off for too many months out of every year. Spot on about the concerts. Last summer that was practically all I did.And drink too much beer. Although 9.5 times of the 12 near death experiences I had in that city (I spent too much time in the Heights and the South Side in my youth – doing things no one should be doing),still I consider it one of the best places on Earth.

  2. You can totally do a lot in Chicago in 24 hours. I usually go for quick 2-day trips for work and manage to pack whatever little free time I have with lots of fun stuff 😉

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