Well, I read your post. I'll share some nightlife enjoyment in chicago city.
Chicago Magic Lounge
Kingston Mines
Jazz Showcase
Andy's Jazz Club & Restaurant
Royal George Theater
There are some attractive and night club to enjoy the night. So I think you go there so must explore these clubs. All is very charming but my favorite "Royal George Theater". Last month, I am visited this city and go this club with my lover. We was very enjoyed this club. I wish I'm go there ones more time with my family. What do you say about this?