Whether you recently moved to Chicago or are born and raised, we’re sharing a few rules and reminders to help navigate city life.
Get Familiar With the Grid
Have you been on Lower Wacker, and your GPS goes berserk? Take a wrong turn on a six-way intersection because Google Maps erroneously told you to? The apps can’t always save you, but at least Chicago’s grid system is pretty easy to learn. And if you’re bad with directions (same) get a portable charger!
People Ask What High School You Went To
If we meet, and you say you’re from Chicago, there’s a high likelihood your fav newsletter editor is going to ask where you went to high school. It’s an easy way to connect, figure out if we have any mutuals, and tell you that Michelle Obama went to my high school 🐬 #ShouldveBeenADolphin
Be Thoughtful With Chicago Nicknames
Call us the Second City, the Windy City, the City in a Garden, or the City of Big Shoulders. But please don’t say “Chi-Raq.”
A resident uses an ironing board to save a parking spot in Chicago in 2021. (Scott Olson / Getty)
Form an Opinion on Dibs
Once snow falls, dibs season will be upon us. Chicagoans use objects — like traffic cones, chairs, and even religious icons — to reserve parking spots they’ve shoveled out. Illegal and controversial, dibs are part of Chicago winters.
Chicago Suburbs ≠ Chicago
I’m going to hold your hand when I say this: If you are from the suburbs and only parachute into the city for Lollapalooza, you are not from Chicago. It’s not a hard-and-fast rule — lots of people who live in Chicago suburbs have connections to the city. But how do you talk about Chicago? How do you engage with the city when you’re here? If you want to claim Chicago, we just ask that you embrace all of it.
Keep Your Eyes Open
Shoutout to my dad who ingrained this essential Chicago rule into me as a kid. In any big city, you’re going to want to be aware of your surroundings. That means looking both ways when crossing the street, but also keeping an eye out for flyers and architectural gems.
Stop Comparing Chicago to New York
Listen, Chicago knows it’s not New York. We’re cleaner. We’re cheaper. We’re Midwest nice. And we’re helluva lot smaller! No, we don’t have a complex about it (or at least not all of us).
Understand Chicago’s History
Chicago is a city of neighborhoods rich with different cultures and things to explore. But those neighborhoods are also segregated. Being familiar with that history will help you understand the challenges different areas of the city face and give you a baseline for nearly every story we cover.
