The Humphrey House blog details a total, top-to bottom green remodel - keeping many original features but altering the underlying materials and design to make it as energy-efficient as possible - of a beautiful 1920s Chicago bungalow. This is probably the most complete houseblog I've read in a long time. They carefully document every single project (in photos and drawings) - including the little mistakes that we all learn from -  in the seemingly-endless quest to turn this drafty but pretty home into a showcase of modern green technology, techniques and materials.

They are also maintaining a list of trusted Chicago contractors in the sidebar, so if you're looking for someone to take on a modernization project on an older home in that area, this is a great place to start.