Urban and culturally rich, not for everyone
Move to Chi if you want:
* A walkable, urban environment with distinctly city-like streetscapes
* Coffee houses, jazz joints, blues bars, comedy pubs, greasy spoons and similar that are open till 4AM
* Bookstores and so on that are open till midnight or thereabouts
* Other stores open till ten or thereabouts
* Great symphony, opera, ballet, galleries, museums and theaters all concentrated near each other, or located in convenient, walkable parts of town
* Grand and beautiful architecture
* Metro transit running twenty four hours (busiest two lines) or twenty hours (the other lines)
* A decent, second-tier concentration of creative culture
* Decent professional-class opportunities
* A city with immense civic pride, fascinating history and a strong, unique, cohesive sense of place. There's no mistaking you're in Chicago -- this ain't Anyplace, USA.
If you're seeking these things, move into a loop-adjacent neighborhood, or one on the north-side near a stop on the Red, Blue or Brown lines. You'll need to be ready to pay at least $1000 a month for a one bedroom, much more close to the loop. Make sure your job, if you have one, is in the loop or on the same train line as you.
Stay away if you:
* Are conservative, culturally or financially. Chicago is high-tax and highly redistributive. Aside from some outlying, suburban neighborhoods, this is an extremely liberal city. Low-income women get their abortions paid for by the government. Plus, the city is in terrible, terrible financial shape and taxes will be stiff to climb out of it. I can't emphasize this enough. If you hate taxes and have no interest in putting serious skin into Chicago's long climb back to solvency, stay away. You will hate it progressively more until you leave in a screaming rage.
* Are uncomfortable with being vigilant about crime. The city's violent crime rate is below the likes of Atlanta, Houston, Miami, Philly, Charlotte, DC and even Minneapolis, though you wouldn't know it listening to the national media. That said, robberies and murders happen. Some city neighborhoods in the south and west are incredibly dangerous. Occasionally, innocent people are caught in the crossfire of stupid young men trying to kill each other. Be ready for that.
* Need the cultural vibrancy, density and all-round excellence of New York City. NYC soundly beats Chicago on every single urban metric. It's more sophisticated, more pedestrian-oriented and its amenities and businesses are uniformly, measurably superior. Its creative environment and opportunities for creative-class professionals leave Chicago in the dust. If you're looking for NY, stop reading now and move there. Chicago is its own thing, and that ain't going to be enough for you. Just swallow the extra expense and go to NY.
* Need to be somewhere that's growing and relevant. LA, SF, Seattle, Boston, DC, and of course, NYC are better choices if this is important. Chicago is a giant, slow-burning star, and it's getting relatively less relevant by the day. You need to be comfortable with that.
* Can't deal with the city's legacy of corruption and mismanagement. It's getting better, but the problem is large and there's still a long way to go.
* Can't deal with locals, both newcomers and old-timers, moaning and griping and proclaiming the city's doom. Even the city's newspapers do it. It's a favorite local pastime. According to these folks, Chicago has been lurching to its demise since the turn of last century. It really starts to wear, and you need to switch off to it, while not blinding yourself to the city's challenges.
If that hasn't driven you into NYC's loving arms, then... welcome to the suck, friend.