Not sure if this is the reality, but it is certainly the perception among those of us not from Chicago:
Wrigley = Trendy, Frat Party, Hot College Girls, Beer, Beer, and more Beer
White Sox = Real Baseball Fans.
If I had to choose, I would go with the Cubbies, just because they are such a lovable loser. The moment they finally win the Series, they will cease to be lovable to us outsiders.