Chicago is the Best & Worst City Ever

Prompt it, louder!
5 min readJul 11, 2023

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The ups and downs of the windy city.

A painting I made out of pure emotion

It’s a city that’s exciting. It’s a city that’s inviting. We heard it best from Daniela Monet in Victorious. Her one-woman show about this city was a great example of the many contradictory characteristics we have. The scene was endearing and entertaining, but her singing was straight- up horrible. Well, that’s a great microcosm for Chicago. This duality goes into the weather, the politics, and the people. Let’s get to it.

Chicago Weather

We’ll start out easy. The weather in Chicago is alright. It’s not bad, and it’s certainly not good. Some days we have beautiful sun and not a cloud in the sky. The next, it is bat-shit crazy; tornados, floods, and blizzards are some of the disasters that strike here. However, nothing is ever completely destroyed, so who cares? Our morale stays especially strong anytime of the year. Yet, in secret, Chicagoans are intensely influenced by Mother Nature.

Some may think of the rapid-changing climate as a problem, but I can’t complain. In the middle of winter when it’s below freezing, I’m dying for a spring day, and that’s what we get here. One day it’s a polar vortex, and the next it’s 50 degrees Fahrenheit and the sun is shining. Nevertheless, something I cannot stand by is the nastiness of the water. It rained so hard the other day, the locks at Navy Pier opened up, and now there’s a swim ban because of the sewage flowing into Mama Michigan. Yet Chicagoans swim anyway. We’ll swim in the flooded streets if we feel like it.

Then there’s winter in general. After living in Duluth, Minnesota for four years, I realized our winters are super mild. Chicagoans don’t care about my comparison; it still sucks even with some sun here and there. If you’re from Chicago, you may know of an unwritten rule called ‘dibs’. This is when it starts snowing and people put up all different kinds of objects to save their parking spot. If you’re aggressive enough, you earn a nice ‘n shiny spot to park your vehicle; that’s extremely coveted around here. You shoveled your car out, so you are entitled to that spot for the next five months. It sounds stupid until you take your neighbor’s spot and find your tires slashed the next morning.

Chicago Politics

The aforementioned situations almost sound political, and that is because Chicago weather and politics are wicked similar. It’s called the windy city literally and figuratively (weather and politics respectively). They change day to day. Overall, the politics around here are progressive, but this city does NOT escape the drama.

In fact, Illinois politicians are some of the most corrupt out there. We pay taxes for every-f**king-thing, and to be quite frank, I have no clue where that money goes. Chicago Public Schools (CPS) are struggling, our homicide clearance rate is the lowest in the country (35%) and the ‘L’ (elevated subway) tracks haven’t been cleaned in years. These are all proof that the money we pay does not go towards helping our citizens.

Of course, this city is an abortion safe haven and marijuana is legal, so that’s cool. We are union heavy, and are known to side with the people almost every time. Also, we just voted in a former teacher as our new mayor who seems to actually give a s**t about the people who live here. Hooray!

Chicago is also known for a few revolutions. On the note of abortion rights, the Jane Collective was formed and run throughout Chi-town. Other revolutions, more than worthy of mention, include: the Chicago railroad strike of 1877, the Haymarket riots, the Red Summer of 1919, the Memorial Day Massacre of 1937, the Chicago Freedom Movement (MLK) and many more. Some are to be proud of, and most represent a time to mourn. There have been the most powerful activists and the most cruel perpetrators participating in it all. One thing in common with these movements is how Chicagoans never stop fighting. And we never will.

Chicago people

As you’ve learned, people from Chicago are pretty wild. We have some of the best and some of the worst people in the world. The gangs and organized crime are plentiful, and always have been. However, the average Chicagoan is here to work, laugh and have fun.

I’m sure you’ve heard of Al Capone. If not, he was a big ol’ Mafioso in Chicago’s south side. He was a big, tough guy in this city. So tough that during prohibition times he was active in the trade. Unfortunately, his era included the Valentine’s Day Massacre. In 1929, seven gang members were lined up and gunned down by four what’s-his-names; two disguised as the police. Everyone involved in this was not innocent. This is part of the bad people of Chicago, back in the day.

Nowadays, the mob is not in the news as often. There’s a perception that they are not active anymore, which is untrue, but also unspoken about. The threat in this day in age are the South and West side gangs. Children are being recruited and committing crimes they can’t even process themselves. The citizens of Chicago are scared to do anything. I don’t blame them. Even if the murder rate was decreasing the amount of guns roaming around is scary in and of itself. Luckily, Chicago didn’t even make the top ten list of the most dangerous cities in the US last year. Don’t ask about the stats from 2019, we’re on the ups.

Now, the good people of Chicago. We exist. Even though you can get robbed at gunpoint in any neighborhood, you can also talk to any Chicagoan about your life’s dwellings in all the same spots. We, Chicago people, have an ability to be personable with anybody. We love to talk, but never to a point of annoyance. Chicagoans know how to crack a joke, throw ya some sarcasm, or give you a motivational life excerpt at the drop of a hat. However intimidating this city can be, the people here are always ready to welcome you. It’s the best ‘little’ big city ever. What amazing city doesn’t have some downfalls? I guess you’ll have to see for yourself.

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Prompt it, louder!

A little Chicago lady finding anyway to unleash my raw, unadulterated creative beast ;) I give myself prompts and improvise from there!