From Brent Kelley,
Your Guide to Golf.
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Definition: Chicago is a golf game whose format is based on golfers beginning their rounds with negative points. In Chicago, players start with a negative amount of points, based on handicaps, then add positive points during the round. The idea is to get from the negative to the positive, clearing your "hurdle" (the term used for your starting total of negative points) by as much as possible.

Negative points begin at -39 for scratch golfers. A 1-handicapper starts with -38, a 2-handicapper with -37, and so on up to a 36-handicapper who starts with -3 points.

During the round, positive points are added on this basis:

• Bogeys are worth l point
• Pars are worth 2 points
• Birdies are worth 4 points
• Eagles are worth 8 points

Not everyone will be able to clear their hurdle, so the highest point total - whether that is 15 or -15 - wins.

Chicago can be a tournament format for individual stroke play, or a betting game among buddies. The winner might get a set amount agreed upon before the round, or the differential in final points can be used, with each point worth a set amount.