What should my friends and I do on our trip to Chicago?

My friends and I (all 27F) will be in Chicago for a week in September. This will be our 4th or 5th time going, so we are avoiding all touristy things. We plan to go to the green mill (as all of us are musicians) and like hanging on the beach playing card games, but we need to find more to do ahead of time. We want to focus more on experiences and food this time.

Do you guys have any suggestions on things to do/places to go/food to eat?

I prefer to find more mom and pop stuff when traveling to live more like a local, so please give me all your personal favorites!

Common interests we have:
Music
Books (specifically USED books)
Good food - any kind except soups; the kind of hidden gems you wouldn’t find on your own.
Experiences rather than shopping/tourism

TIA🤩