Need help with neighborhoods for buying a condo in?

Hi chicago,

Im looking to move and potentially buy a condo in chicago but im having a hard time looking into neighborhoods because the youtube videos dont give a good insight for someone with my needs. I live in Madison, WI right now which I do like but I think its a little too sanitized for me and the condo market there doesnt really have good options for what im looking for. Im a single guy who intends to stay single and I would want a 2 bedroom condo, perhaps with a little art studio as well?

What I want in a neighborhood: -good walkability/transit access -diverse neighborhood, a decent mix of people that doesnt lean too hard to one specific group -doesnt need to be in the cleanest, safest area as long as you can be safe minding your own business -i like a lot of divey places to eat and hang out at, I cant stand "millennial burger" type places. -decent LGBTQ and arts scene