Why the Red Wings shirt instead of Blackhawks?

I don't know. I'm sure there is some explanation.

On a side note, I know John Hughes wasn't actually a Cubs fan, although that was the only local team shown. Wrigley is sort of iconic though and in the right part of town to make sense for the film.

Maybe Cameron and his family moved from Michigan to Illinois?

I figured to make Cameron an outcast.

There's no rule saying you have to like the team from the city you live in.

I mean, really, how many times will you look under Jabba's manboobs?

Gordy Howe was John Hughes'(?) favorite hockey player, I think.

I remember reading that Cameron's Dad was a huge Blackhawks fan so he wore the Redwings jersey to make his Dad mad.

John Hughes was born in Michigan.

A nod from Hughes to his hometown. He says it on the DVD commentary.