So basically the earlier you get there the closer to the stage you'll be.
Stefan, The Aragon Ballroom is awsome, never noticed a problem with the sound, have seen lots of shows there. It is a couple miles if that East of Lake Michigan/Lake Shore Drive but on the Northside not in the greatest neighborhood, any place you stay downtown will be a short cab ride or train ride away. Another mile or so is Clark Street which if you take back south will lead you to where all the bars are, I know the good dives to go to
Going both nights, VIP for Pinkerton. Already booked my flight up from Baton Rouge, will get on hotel in a few weeks. There aren't any hotels around the venue, your best bet will be to look downtown.
I was definitely going to one of the cities for this tour, and Chicago (in addition to being an awesome city) was the best fit. Low ticket prices and GA make me a happy camper.