While I can’t speak to many of your logistical questions about living or studying in Chicago, since our D is just finishing school and so far has only lived and studied in Evanston, I will say that there seems to be something special happening in Chicago’s theatre scene recently. From what I understand the city has long been known for amazing acting (think Steppenwolf, Goodman, Chicago Shakespeare, Lookinglass, etc.), but more recently there seems to be a thriving MT scene taking shape as well, both downtown and in the surrounding suburbs. Last I checked there are over 150 theatre companies operating in and around the city (including some really interesting storefront companies who share spaces), and it seems that there is also increasing exchange of talent and ideas between Chicago and NYC. Here’s an article that speaks to some of this…
Best of luck in your decision, and I hope others can add suggestions for great local voice, dance and acting coaches as I’d be interested in that as well.