Was this directed at me? (Confused by spelling, should be 'John') Or does JP have a second home in Chicago? Well, a group of cute young Notre Dame girls at my place would be a no brainier! I'd be happy to lead the tour! Just not sure what Anne would think.
Agree that if even remotely affordable, stay downtown. Doesn't matter where, you can get anywhere with the train or bus, as Dan said, As long as you're not right next to Cabrini Green (there are no hotels right next to Cabrini Green, so just relax!). But if they want to step outside and be in the middle of it all, sure, The Mag Mile would be great. The best shopping will be right there for her to spend your money!