My favorite show of all time, Seinfeld, always seemed to work in the odd Chicago sports reference - which I love. Perhaps the most well known is in The Limo episode when George and Jerry pretend to be O'Brien and Murphy and think they are headed to see Michael Jordan and the Bulls play the Knicks at Madison Square Garden. ...
But my personal favorite was just so absurd - it's The Heart Attack episode from Season 2, when Jerry finds out that George did not have a heart attack.
One of the items Jerry wants from George when he dies is his Blackhawks jacket...what?! How random is that? Do you have any favorite inane Chicago sports references in movies, TV or music?
Rick Armstrong 
Mike Knapp 
Kanye West always has good Chi-town references....like Showbiz Pizza (where a kid can be a kid!) in Gold Digger
I guess that can count, but 'Ye is from Chicago. I'm talking about Streetlife rapping about Candace Parker on "Starter" off the Wu-Tang joing "The 8 Diagrams", stuff like that...