If you are a walker then it’s a rather walkable city, if not a few bus rides can help. I really enjoy street art, murals and good graffiti and all. Chicago was a great city for that. Plenty of art to be found. You can go online and make a pretty good map, there are some famous pieces to see and there are some districts packed with art. If you follow that map you will probably find some new or unknown pieces along the way. I’m sure new pieces are added on a regular basis. I would suggest using some of your favourites as landmarks. Its a large and confusing city it’s nice to know where you are sometimes, my best one was the giant red flamingo.