A significant number of Chicago's citizens (the ones who aren't fleeing the city, anyway) aren't originally from here, and as a result, they find themselves having to adjust when they first move. Whether they're here for work or college, chances are they're entering an environment that differs vastly from the town or city they came from. Fortunately, it doesn't take too long to get used to the Chicago way. These are some of the things they'll have to get used to:
Navigating the grid. Chicago's street system is built on a grid that makes getting around incredibly easy. Just say a block number and a cardinal direction and any Chicagoan should, at the very least, be able to produce a visual in their mind as to where that is with relative ease. Also helpful when giving or receiving an address to a place is to name the nearest major intersection. Instead of giving an exact address, people will more often than not give the nearest intersection of where they're at, even if they aren't at the corner. It's just easier that way and something seemingly everyone does.
The expressways have names. Listen to any traffic report on the morning news or someone complaining about their commute and you'll notice that the numbers of the expressways are never used. Everyone refers to them by their names, whether it's the Dan Ryan, Stevenson or whatever expressway.
Bi-polar weather. Chicagoans always rejoice at the first sign of sunshine in spring, even though that's been known to change at the drop of a hat (even in May). Be prepared for anything the elements could possibly throw at you, because it might happen. These erratic atmospheric patterns and prolonged periods of bad weather also help to make summer in Chicago a religious experience.
Salt stains are everywhere in winter. Speaking of the long winter, the sidewalks and streets are constantly salted to keep the city from becoming an ice rink. As a result, everything is stained with the stuff. If you're not careful, you'll get it all over your shoes and the bottom of your pants. If you live here, get used to sacrificing at least one pair of shoes to the winter gods each year.
The politicians will never cease to amaze you. If you've ever watched the news in your life, you know Chicago has somewhat of a reputation for churning out crooked, incompetent politicians. They pass ordinances that make you scratch your head, and they somehow find new and creative ways to tax you. They will most certainly get involved in nefarious shenanigans for their personal benefit at the expense of you, the ordinary citizen. And you know what the amazing thing is? That could all happen over the course of one day and it'd still be a slow news cycle.
The diversity of neighborhoods. One truly great thing about Chicago, though, is how it's made up of tons of neighborhoods, each with their own unique flair. Once you find your routine and develop relationships with people, you'll find that the range of things to do across town is incredibly wide. You can go to a small concert in a hipster venue, go on a date at an upscale restaurant, act like a drunken imbecile at a baseball game and so much more. Having the option to do all of this (over the course of one day if you plan it right), is something that shouldn't be taken for granted.
Perpetual construction. There's an old joke about Chicago that says the four seasons around here are "almost winter, winter, still winter and construction," and it really isn't that far off from the truth. Something is always in repair, whether it's the expressways, downtown streets or CTA lines. It's an inconvenience, but eventually you get to the point where you factor construction into your commute and delays don't faze you.
Getting into arguments about food with out-of-towners. You're not a true Chicagoan until you find yourself in the trenches of the great battle of defending Chicago cuisine to that of other cities. Once you've gotten to experience it all, you'll come around to the fact that Chicago-style food is not only the best to eat, but it's the correct way to eat. Putting ketchup on hot dogs? Grounds for a crucifixion. A dipped Italian beef? Much better than a dry hoagie in New York.