pittsburgh: I am 16 right now and I am looking to go to college and someday live in Pittsburgh or Chicago as a sports writer/reporter/broadcastor. Which city do I have a better chance at getting a job in sports, Pittsburgh or Chicago? Pittsburgh has the Pirates, Steelers, and Penguins. Chicago has the White Sox, Cubs, Bears, Bulls, Sky, Blackhawks, and Wolves.|||Chicago is way bigger than the Burgh. It's a funny question because I'm moving from Pittsburgh to Chicago in August. The bigger city is always going to have mor opportunities in my opinion. They are both wonderful cities to live in. I've never been further west than Topeka, Kansas, but of the cities I've been to east of there, Chicago, Pittsburgh, and Boston are my favorites.