My brother recently moved to Chicago, which kind of coincides with an interest Nicole and I have both developed in Chicago architecture. For Christmas he sent us a fantastic gift: the DVD/book set Lost Buildings.
It's the portable version of a 2004 This American Life stage show done by Ira Glass and cartoonist Chris Ware about their friend Tim Samuelson's obsession with Chicago architect Louis Sullivan. The story is fascinating, and Chris's drawings are spectacular (see above).
It's hard to find, but right now you can still buy it at the NPR Shop.