Like most people, I gravitate strongly to books, movies, and shows that relate to places I enjoy or have some sort of connection to. The smaller or more unique the place, the better.
I get my Chicago fixes via podcasts from Nick, Milt, and Jake (I wish Roe Conn offered more podcasts). Madison comes from Ultimate Outdoors.
I still have not found the perfect North Woods piece of entertainment, but the Starvation Lake novels come pretty close. They may be set in northern Michigan rather than my preferred Wisconsin, but the mysteries and settings are excellent. I just cannot get enough of these books lately.
Now I need the perfect Chicago novel (Stuart Dybek has the short story front covered) and some Boundary Waters fiction. I've been told I could simply just satisfy this need by writing them myself. I'm trying.