Anne Van B.
Google
Wright Plus organizes a yearly house walk that lets you through select rooms at select private residences for about a $100 price during one weekend every summer. It's a great event, though lately the tour seems a little more limited in the rooms you are allowed to see. This is understandable as it really is up to the family who owns the place. The money goes to the charity for preservation of the buildings so that is good. Kids from the neighborhood set up lemonade stands along the way so make it worth their time, and spend the fifty cents!
the main cluster of homes is usually a decent walk away from the solitary homes on side streets, so I recommend starting far and working your way closer. You'll really need to spend all day to see everything. Parking is a problem so take the CTA if you can.