Chicago - Don't Move Here if You Like Nature and A
After living in Chicago for 11 years, in a variety of neighborhoods—Gold Coast, Roscoe Village, Lincoln Park, South Loop, and the Loop—I can definitely say I have a pretty good grasp on the city. I'm a thirtysomething business owner.
Speaking for myself, I find Chicago a very difficult place to be happy in, so hard, in fact, that it's had a negative impact on my health and actually triggered real depression!
This message is mainly for sensitive people who might be affected by climate and the lack of access to nature. I find that there aren't too many of "us" in Chicago, that those who are here moan about it but they're just the type who aren't "affected" by these things as much. I get that.
For the rest of us, consider the fact that there are whole months where the sun sets before 4:30 p.m. Speaking for myself personally, as soon as daylight savings time kicks in, something goes haywire in the brain and my sleep starts getting affected. Ordinarily I could fight this with going outside and "resetting" myself with some greenery and bright sunlight but that's not an option here when it gets cold and cloudy. So you are really in a bind. For me it's meant being absolutely miserable from November until March - or later.
You'll find a lot of people who work out here, but there's really not a "healthy" lifestyle to speak of. You kind of have to patchwork it with trips to Whole Foods, an occasional 5k, etc., if you can be bothered. If you don't drink (I don't), you'll find yourself an outcast at like 95% of things.
Nature—pretty much nonexistent, except for the parks by the lake and Northerly Island. (All of which are far less accessible in winter). Yes, there are folks who go hiking in nearby forest preserves, and love it, but do you really want to go through all the trouble of driving at least an hour through ugly areas and possibly traffic? And what if you don't have a car? And yes, you can bike in the winter, but are you kidding?
If you're really creative the train can take you to some nice places - the Dunes, Hyde Park, Geneva - but that's a hassle and again, summer activities.
Overall, I find the city to be just ugly—the buildings, the streets. Nothing charming about it, except maybe places like Old Town. The skyline is pretty from afar but get up close and I find the buildings don't really "mix" well.
If you're reasonably friendly, and join organizations, it's easy to meet people, but like anywhere, true friends are trickier to find. In the business world there's an overt "I'll scratch your back and you scratch mine" mentality.
If you must live here, I would urge you to try to live near Grant Park in a building with a view of the park and the lake—I've been much happier when I've lived in places with this view (and will make this sort of place the last place I live here). I realize that's expensive, but it's the only way I've found to make living here tolerable. Try to avoid living in and around "concrete canyons," for reasons of mental health. Also beware that living downtown means lots of NOISE so try living on a floor above 15. Live near within walking distance of a grocery store. I had good luck with a building called 1130 S. Michigan.
Crime—I've been lucky to not be a victim all these years, but I had a friend get his head bashed in leaving a Streeterville gym at 7:00 p.m.
Chicago is a good place for business activities, cultural options (rich theater scene, etc.), and can be paradise for those from Midwest schools looking to drink and socialize. And socializing in general. The lakefront trail, particularly the southern portion, is a delight in the summer. But that's just not enough to keep me here.
Oh - a couple more things. The isolation - Chicago is 700 miles away from anything interesting (The Smokies, etc.) and to get there you'll likely have to go through dreaded O'Hare, possibly the most depressing airport on earth. Flying south during the winter is a good idea, but the last time I did it, I was delayed 3 days in South Carolina because of snow in Chicago. So "getting out" during winter can REALLY be a hassle.
The el is functional but crumbling. You'll have to cope with an hour+ ride to O'Hare from the Loop; is this acceptable for a world-class city?
I'm presently looking to relocate to either Charleston, SC or San Luis Obispo, CA. I know every place has issues but there's got to be somewhere that's better to live than here.