I believe that I live on the west side, primarily because I don’t want to be a “north sider.” (To date, I’ve never lived east of the river and north of Madison — only on the south and west sides.) Newspaper reports have ceased referring to Wicker Park as “west side” and just call it “near northwest” or don’t assign a side to it, assuming that everyone will know where it is.
In any case, Craig Z. picked up on the odd schism between west and north; in a comment to Eric Zorn:
The only reason people will argue with this is that they are going to say, “I live in a nice neighborhood! We are not on the West Side!”
In Chicago parlance, “West Side” means ghetto, crime, ignorance, hopelessness, decline, decay, futility. It means empty lots, shut-down factories, abandoned dreams. Most of all, it means the ’68 riots that broke out after Martin Luther King Jr. was assassinated, from which some neighborhoods have never recovered.
In fact, these borders shift in the media depending on what type of story is being reported. In Chicago’s Near Northwest, if a trendy new restaurant opens, it’s on the “North Side,” but if someone gets shot, it’s on the “West Side.” This is true even if the shooting occurs north and east of the restaurant!