All Articles

The Ex-Resident's Guide to Chicago

By mid-June, the Young Family will be living in Colorado. While this move is positive overall, I also feel a certain trepidation: Chicago was where I launched The Machine, re-ignited my love for software, and kindled a new dedication to speaking. It’s also where I lost my religion, morphing from a lukewarm christian into a staunch atheist.

So, yes. This City and I; we have a history. Six years of awesome, messy history.

Heading north was our first inter-state move as a couple. It’s where our daughter was born. Additionally, Chicago has even improved my career in many ways. But for every creative thought that was born, cared for, or dismantled here, I see thousands more out west.

Why is that? I certainly don’t think it’s the classic, 20-something wanderlust. I’ll elaborate on specific reasons in a later post, but for now, please accept this short list — a Ex-Resident’s Guide, if you will — as a street-level dispatch on what it means to leave the city behind, and as I do so, you wiser.

Riding the C.T.A.

Live by the one or more transit lines, but not closer than a few blocks.

Most city dwellers will instinctively abide by this rule, unless they’ve acquired the ability to sleep through minor earthquakes and ear-splitting explosions. There’s nothing I hate more than constant noise, especially at night, so we live closer to the bus lines than trains.

One night listening to “stand clear, the doors are closing,” on repeat will explain why this is a very wise choice.

Gritty, grimy.

Avoid Wrigleyville at All Costs

Let’s play a round of Chicago Trivia! At this specific moment in time, Wrigleyville is dominated by what social class? The “dude-bros”, to be sure.

This social animal is prone to public drunkenness and all manner of untoward social behavior. They’re especially fond of the Cub’s constant portrayal as a long-suffering underdog, who will, one day, stage a glorious comeback. The 'bros and compatriots will one day, bask in that glorious, winning light while rafting down the whiskey river. But until then, it’s PBR by the gallon.

Joshua Wentz

Expect Northern Hospitality

There’s a camaraderie among Chicago residents. A thick outer hide that, when it isn’t preventing our ability to feel a foul political wind, keeps us warm during months of sub-zero temperatures.

Jokes aside, residents are friendly. I don’t know if that’s the resigned “we may as well go to hell together” mentality; but even if that is the case, it’s useful.

Chicago is also home to many genuinely talented artists, who are also, just behind the hide, very kind souls. Pictured above, my friend Joshua Wentz (who has made several appearances on this blog.)

Use Headphones

If you plan to frequently ride the C.T.A., I recommend purchasing a set of noise-canceling, decent-quality earphones. You’ll find many passengers who clearly flaunt this rule of public transport, but conscientious persons will avoid blasting some tinny rap song openly.

If you want to throw-down, do it right and bring the subwoofers. Okay?

Navy Pier and the Magnificent Mile…

…aren’t that great. Thanks to the sidewalk-clogging tourists, locals often struggle to walk. But that’s not a huge issue, because most of us tend to shop in our own neighborhood.

We only go downtown for the hospital, or if a visitor insists on violating local customs. Get out of The Loop: you won’t regret it.


So there you have it. Several tongue-in-cheek pointers to make your visit a bit more pleasant. Welcome to Chicago.

Published 26 May 2016