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.|||That depends on what city will have a job opportunity when you graduate and if they are hiring. It is too far into the future, so for now, concentrate on your education. I wouldn't worry about it until your junior year and maybe you can do some interning by then.