Dear Troops,
First off, welcome! We’ve been anticipating your arrival in our city, where the wind blows like our reported crime rate, so hold on to your MAGA hats and ski masks. The weather changes hourly; prepare for simultaneous sunburn and frostbite. Our humidity smells like Italian beef, and in the winter, our streets are slicker than President Trump’s legal team at a deposition.
Your deployment was unsolicited, but we’re friendly Midwesterners. Neighbors will hand you a rusted lawn chair and a passive-aggressive note about parking “dibs.” Accept both. You’re family now.
Your odds of success for this mission will be as easy to decipher as the standard Midwestern “yeah, no” or “no, yeah,” but don’t let that discourage you from enjoying a slice of our city—and deep dish—while you’re here. Extra sassage.
We already have a myriad of militia defending the right to drag brunch, improv comedy, and the Portillo’s punch card. If offered Malört, accept. It’s not a drink, it’s a test of character and liver function.
Our topography is deceptively simple: flat, gridded, and paved with salt residue. Expect sudden gusts of civic pride (“Go Bears!” chanted as a question) and potholes large enough to swallow your Humvee, along with any sense of purpose.
Forget the Bean. It’s already under the protection of Instagram influencers. The lakefront looks inviting, but it’s a trap. One wrong step and you’re in a volleyball league with six lawyers wearing matching neon T-shirts.
A few final tips to help you fit in:
- Never call it “Chi-town.” That’s a felony in three wards
- When at Wrigley Field, order an Old Style and ignore the scoreboard
- Never say “yes and” to a stranger for fear of a spontaneous improv sketch
- When locals say sauce it always sounds like a slur
- Name-drop Studs Terkel. It’s our version of diplomatic immunity
- Riding the CTA is like dating in Chicago: confusing, delayed, and occasionally smells like giardiniera
- At our jazz clubs, if you make eye contact with the upright bass player for more than three seconds, you’re legally part of the rhythm section
- If confronted, claim you’re filming a reboot of The Fugitive
Godspeed. Remember, we’ve been practicing corruption since Al Capone, so don’t try to outdo us. We still have democracy, though, and it might just be the one thing in town you can’t bribe.
Warm regards,
A friendly Chicagoan
(Also known as the middle-aged woman behind the counter at The Weiner’s Circle)
PS: The real war is over ketchup on a hot dog.
