First, a confession. I did, actually, leave Chicago last year. I moved 50 feet north of Howard Street, and now live in Evanston. It wasn't on purpose--I couldn't find a house in Chicago that met my needs of neighborhood, price, and timeline. But "stone's throw" was pretty much invented to describe how close I am to the city.
I came to Chicago nearly 40 years ago for a man. In the intervening years, I lost the man, but added a couple of great native Chicago offspring, who came to the same conclusion that I did: you don't have to leave Chicago, because everything you need is here.
We have bars, music, theater, art, from the scruffy neighborhood to the world class variety. We have a popcorn-worthy political sideshow, and some of the nation's most inspiring public figures like Barack Obama and Jesse Jackson Sr. (We also do corruption the best.) Our architecture is unparalleled anywhere in the world. Great housing stock and actual zoning laws, because of that whole thing where the city burned down that time, and instead of just giving in to the moneyed interests, we actually did something about the danger.
We have a forever open and free lakefront, with the greatest stretch of free public beach in the world.
It's not all sunshine and lollipops, of course. Although I've spent my whole time in Chicago in the last truly diverse neighborhood of Rogers Park, we have some of the worst segregation in the country, as well as pockets of bad violence (though not the citywide apocalypse that the national media would have you believe), a dysfunctional school system (again, not the sewer that is widely reported), and racist police system (this one is worse than reported.) It would be really nice if people on the west side could get somewhere other than the Loop with public trans other than nausea-inducing buses (circle line anyone?). But our neighborhood system means that we actually know our neighbors, and have honest-to-god local shops, and even, still, some light (and even heavy) manufacturing.
We have jobs, and summer youth programs; the museums are free to residents in February, and the beaches are free always, to anyone. We're midwesterners, too, so we're super friendly, and have a Goldilocks attitude toward pace--not too slow, not too fast; we're just right. Our downtown sidewalks are crowded but not packed, and there's always room for a picnic or a pick up game in one of our beautiful parks. We'll start a conversation, even with a stranger, with a little bit of hobnobbing, and then get down to business before you get uncomfortable, or bored. And we're pretty good at business, too.
This is not to say we're pushovers. Never ever ever tell a Chicagoan that the Pacific Northwest, or Texas, or New York does X better, or does it in a certain way (which we also do exactly the same way here, so that's always a little puzzling), at least not if you ever want one of us to feed you ever again. Don't disrespect our pizza, our hotdogs, our ice cream, our beer, or our sports teams, all of which are the best (science fact). Don't like them? Don't consume them. And remember we're laid back midwesterners, so we'll be cool with that!
There's lots of reasons to leave Chicago. It's not "home." You want to be close to farflung family. You can't handle the weather, which I hear they also have in other places, sometimes accompanied by things like hurricanes, nor'easters, and earthquakes. We'll be sorry to see you go, as long as you're leaving for personal reasons, and not because you feel the need to blame someone.
Chicago's a great place. There's really no reason to leave. But if you do, check in on Facebook every now and then. If we're not busy at the beach, or the ballpark, or a downtown festival, or a museum, or having a great time with our friends, we'll be sure to say hi, and see how you're doing.