The Original Chicago Trivia Board Game

From BoardGameGeek:

This game is just what it sounds like, a Trivial Pursuit type game using trivia that is entirely about Chicago. It's broken into six categories: History/Geography, Big Bucks, Politics, Sports, Entertainment and PhD. The game is very hard, even for long time Chicagoans. The questions are extremely difficult to begin with and you can lose category chips for wrong answers in some situations, including the last question to win which your opponents get to choose.