Best places for arts, culture, and music?

I’ll be visiting Chicago from the 19th-26th to check out the neighborhoods I may want to live. I’ll be seeing my favorite jazz player, Alabaster DePlume, and I’m excited to see the Chicagohenge. But in the midst of driving around and getting a feel for the place, where do the creatives go?

I’m a writer where I currently live, both typewriter poetry and a journalist for my local magazine. I love art, opera, jazz, and slow, cozy spaces to lounge and take in the environment. Maybe a bit of people watching.

What places should I check out? Where should I spend my nights?