No Valet, No Problem: Why Moving from LA to Chicago Might Be the Best Thing You Ever Do

You land in Chicago, suitcase full of hoodies, sunglasses still perched on your head, and the first thing you notice is the sky: big, blue, and—let’s be honest - often threatening. Los Angeles taught you to worship sunshine and dodge traffic; Chicago will teach you to worship neighborhoods and dodge potholes. You’re not in a city of freeways and canyons anymore. Here, the city is a patchwork of blocks, each with its own stubborn personality, and you’ll need to learn the rules fast.

Let’s start with the rough stuff. Every city has its “maybe not after dark” zones, and Chicago’s Englewood and LA’s Skid Row could swap horror stories over a cup of burnt coffee. Englewood, all boarded-up houses and dreams deferred, is the kind of place that makes headlines for the wrong reasons. Skid Row, meanwhile, is less a neighborhood and more a cautionary tale, a place where the American Dream went to die and never got a proper burial. Both are reminders that cities, for all their beauty, are built on fault lines—sometimes literal, sometimes social.

Then there’s the gentrification two-step. In LA, Highland Park is ground zero for the artisanal invasion: old bungalows now sporting yoga studios and vegan taco joints, locals priced out by the latest wave of “creatives.” Chicago’s Logan Square is running the same playbook - murals, microbrews, and a parade of new residents who can’t decide if they’re saving the neighborhood or just raising the rent. Over in Pilsen, the paint is still fresh on the murals, but the condos are rising fast, and every block is a tug-of-war between tradition and transformation. Echo Park in LA knows the feeling: the old guard side-eyeing the new, everyone arguing over who belongs.

But then you find the places that make the move worth it. Lakeview is Chicago’s answer to Santa Monica - minus the ocean, but with a lake so big you’ll forget you ever cared about saltwater. It’s got joggers, dog parks, and enough brunch spots to keep your Instagram busy. Wicker Park is Silver Lake’s Midwestern cousin: a little grittier, a little less curated, but with the same sense that something weird and wonderful could happen on any given night.

And then, just when you’re starting to miss the palm trees, you stumble into Lincoln Square. It’s not flashy. It doesn’t need to be. Lincoln Square is what happens when a neighborhood decides it’s enough just being itself. It’s walkable, it’s warm (in spirit, if not in temperature), and it’s packed with people who actually know their neighbors. The festivals spill into the streets, the bookstores are still standing, and the sense of community is something LA could only dream of. You came for the job, the adventure, maybe even the pizza. You stay because Lincoln Square feels like home, even if you have to buy a better coat.

So yes, the weather’s worse. The traffic is different, but sometimes just as maddening. But Chicago’s neighborhoods - especially the ones that don’t try too hard - are what you have to look forward to. You’ll trade your endless summer for four honest seasons, and if you’re lucky, you’ll find that what you lost in sunshine, you gained in soul.