Never understood why Ferris Bueller took place in Chicago, but Cameron wears a Wings sweater.
Who knows, I see people sporting St. Louis Cardinals hats in Chi all the time.
The late John Hughes was originally from Michigan and was a big Wings fan. Within the Hughes family there is a bit of a Redwings/Blackhaws rivalry.
http://www.grantland.com/story/_/id/9221556/filmmaker-john-hughes-nhl-fandom
Some people are just contrarian. When I was in high school I rooted against all the home teams, just to be rude.