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I have a home-based business. So, I'm completely flexible, and the local job market wouldn't matter.
It really only comes down to where would I enjoy myself the most.
I've considered NYC, but I have family there ... and, well ... I'd rather not be too close to them.
Do you enjoy cities that are urban/walkable where you don't have to rely on a car and can walk around, bike, take the train/bus, cabs/uber, etc or do you not care? What about cost of living considerations?
By the way, Chicago does have beaches (30+ of them). Not an ocean (a big ass lake that you can't see the other side of that has small waves) but a lot of people hang out at them doing normal beach stuff for the ~3 or 4 months per year they are open. There are a few beaches right downtown actually.
Chicago is awesome. I moved to Austin from Chicago and you don't realize what an amazing city it is until you leave (granted I love Austin too). Chicago has great art scene, great sports, amazing food, four seasons...Xmas time is truly awesome in Chicago, character, and all the amenities of any other city. I'd pick Chi-town.
Both cities are great with all of these really. I think it depends on what type of city you want - Chicago is the more urban and walkable city and LA does have some of that, but it's not at the same level. Public transit is a little easier to use/more far reaching in Chicago, more cabs, etc. But if you don't care about that, then.....what else is there that you care about? Types of people? Cost of living? Diversity? Both cities for food you can pretty much get any type of cuisine you want (though I will give the overall nod to Chicago in food, LA is great too). Music scenes are a little different but both cities have a lot of different types covered. LA has more bands centered there due to the record industry, but it doesn't mean that all of them are necessarily going to be playing there.
I'm thinking LA would be a better music city for the reason you mentioned.
However, some of the best musicians I know were raised in and still live in Chicago. Not interested in the industry, but I do know the industry attracted A-list musicians.
Diversity?
I'm black. But, I know that both LA and Chicago are very, very diverse. At the same time, my interests are such that, my being black wouldn't make me lean more towards one city more than the other. Not overly concerned about race relations. I grew up in a southern town where race was a REAL issue, and I was still indifferent to all of it.
I'm kind of 'it is what it is' about a lot of things. lol. Life is in no way perfect. People aren't perfect - and I have no expectations of being loved and embraced by everyone.
COL is important if there is really no difference between LA and Chicago based on my criteria. If LA was heads and shoulder above Chicago in those areas, then I'd choose LA.
It's very hard to beat the bang-for-the-buck proposition that Chicago offers. But the two cities offer different cultures and lifestyles based on the respective environments in which they're situated, and that's not just about weather. Chicago is a great place to live if your interests revolve around the types of activities that a highly urban and urbane environment can provide. But if your hobbies revolve around outdoor activities, your options here are very limited in Chicago compared to Wast Coast cities. It sounds like you're more the former type than the latter, so Chicago seems like your better bet as it has all the features and amenities you're after at a substantial discount compared to L.A.
Of course. I'm just very methodical. I'm the type of guy who reads the instruction booklet in it's entirety before he attempts to operate a device.
Well, you definitely won't have a problem finding musical festivals in Los Angeles. The biggest one is Coachella, though it's not in Los Angeles. Same goes for food. Lots of variety. Ever been to Farmers Market here in LA?
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