Goodbye Chicago: Why I’m Saying Goodbye to Chicago and Leaving Chicago

Jamison Webb
4 min readSep 8, 2017

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I was born in the beautiful city of Ft. Myers, Florida, and raised across the Caloosahatchee River in Cape Coral — “Home to Everyone’s Great-Aunt” as it is nicknamed due to everyone’s great-aunt living there. And while not an underpopulated area by any stretch of the imagination—Southwest Florida’s year-round population is approximately 1.2 million until the winter, when the snowbirds come down and it grows to 4.9 billion—I felt a desire to someday move away from these quaint coastal paradises and make my way to “the big city”. Lost Angeles? Bostown? Nü York? Which of these Ameritropolises would I someday call home?

It was a question that went unanswered through most of my college years, until one night at what we used to call “a mp3 party”. As I regaled the guests in attendance with my tips for remembering all the U.S. Vice Presidents (Tompkins was 6th / he was no goon / and the 7th was / racist John C. Calhoun!), my ears, so hungry for the latest indie-folk sounds, picked up on what sounded like a choir-boy singing about…demented serial killer John Wayne Gacy?

“What is this?” I asked the woman next to the mp3 machine.

“It’s Sufjan Stevens. The album is called ‘Illinois,’” she responded.

Jeez! Excuse me for asking!

All the same, the music spoke to me. Illinois….Chicago. I had gotten my answer. I had to move to Chicago immediately.

Two years later, I moved to Chicago. I was full of hope and excitement. What would I encounter in this great city that Carl Sandburg once so poetically called “this great city”?

As I pulled into Chicago city limits, I was awed by the sights and sounds around me. There was Lake Union Park! And Pike Place Market! And the Space Needle! And the Seattle Museum of Art! I was overwhelmed. Yes. Chicago is where I belonged.

Seven years later, I realized I was living in Seattle. This explained why everyone spoke with such a heavy Seattle accent. You know the one? “Hooo-low, I lahrve een Syattle. I larhve toe drynk Strawbucks cough-cough-fee.” The worst!

Three years later, I moved to Chicago. This time I wanted to be sure I was in the right place, so upon arriving, I asked the man at the toll booth, “Is this Chicago?”

“Yes, it is,” he replied. “Welcome!”

Damn. This big city was gonna be tough. I just had to be tougher.

But now, after three hours of living in this city, I have come to realize that, no matter how tough I am, Chicago isn’t for me. And frankly, it’s not for anyone.

Chicagoans love to talk about how great the food is in the city. “You gotta try a Chicago hot dog,” they say. Hey, buddy, I don’t “gotta” do anything. Fuck you.

And they love their sports here. Go Bears! Go Cubs! Go Bulls! Um, ever heard of “Go read a book”?

I will admit that I went to a Cubs game to see what all the fuss was about. First, I was told by the security man that I could not bring in my collection of hunting knives (they’re conversational icebreakers, you cretin!). Then when I finally got inside the stadium after I left my knives with some children outside, I went to the men’s room only to see people URINATING into the large basin meant for washing hands. Filth, thy name is Cubs fan! Also Tony, thy name is Cubs fan, because that’s who I sat next to at the game until I left in the middle of the seventh inning when a Joe Mantegna concert broke out from the press box.

Chicagoans love to brag about Lake Michigan. “It’s a great lake,” one guy told me. “I don’t think it’s that great,” I said. “No, you don’t understand, it’s one of the great lakes,” he said. “Look, buddy,” I said, “the only ‘lake’ I think is great is Lake Bell…she’s one of my favorite actresses!!”

Then there’s the natural spring I found hidden deep within Lincoln Park that promised everlasting life to any one who drank from it. The less said about that, the better.

The straw that broke the camel’s back was the job hunt. My degree is in Russian literature with a specialization in the works of Aleksandr Kuprin. Job interviewers loved to point this out to me. Here was one such exchange:

JOB INTERVIEWER (an ASSHOLE): I’m sorry, sir. I don’t think this job is right for you.

ME (a GOOD, SMART MAN): And why not?

ASSHOLE: Your experience is in the works of Aleksandr Kuprin, and we specialize in the works of Leonid Andreyev here. Kuprin’s straightforward chronicling of the lives of ordinary Russians at the onset of the 20th century runs in almost complete opposition to the more expressionist techniques of Andreyev, especially in his more politically charged writing.

I mean, he was right, but you can’t be nicer about it??

So, it is with a heavy heart that I must leave Chicago. I have no plans to ever return, except for a wedding next month and a concert the month after that and then a two-month stretch next summer where I am housesitting for a friend and then another wedding after that and then two more weddings after that. But, for now, that’s it.

And what’s next for me? Let’s just say I’m bound for a place known for its great food, its authentic people, and its incredible music scene. That’s right. I’m moving to a shack in the woods.

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