At least in my experience, Chicagoans are really super friendly about people who are lost/clueless and are quick to point you in the right direction.

Our windows are pretty new. I think they are drafty, to the point where they should have storm windows or something, but maybe the walls were just really cold? I don't think our walls are... actually... insulated. I mean, with something other than newspaper. When we eventually gut this place (plaster and lathe walls with wallboard covering them, burying a lot of vintage woodwork) insulating the walls is totally on the agenda.