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Having grown up in and around Chicago, I have no clue where to tell you to look in specific.
It sounds like you need an 'aging' area, full of elderly people who won't bother you, unless you get on their lawn. Oaklawn is pretty close to that, but its a bit too old and they are dying so its starting to turn over. I'm sure somewhere out there you will find the right combination.
Honestly I'd still move somewhere more fun and trendy just so you can make fun of the people there. My sister lived briefly in 'Boystown' doing the starving artist bit, and even going to the supermarket was entertaining.
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