Rules
The game of Chicago is played in a similar fashion to nine-ball and rotation, where balls must be played in order starting with the 1 ball. In Chicago, all fifteen balls are used. The money balls are the 1, 5, 8, 10, 13 and 15. These six balls are racked to the front of the rack with the 1 ball at the head of the rack. A player continues his turn as long as a ball is pocketed. A score is kept as to how many money balls are made by each player.
Once all balls are pocketed the players will "settle up" based on the amount of money balls they made during the game. The loser pays the winner a previously agreed upon amount multiplied by the difference in money balls between the two players (i.e., if Player A makes five money balls and Player B makes one then Player B owes Player A four times the amount of the wager.)
The game can also simply be played recreationally for points instead of money.
As well as the 1, 5, 8, 10, 13, and 15 balls being money balls (also called "Ways"), the number value of each ball pocketed by a player is added up at the end of each game (i.e. 1 ball = 1, 12 ball = 12). The player(s) with at least 61 cumulative points, or a majority of points (the cumulative sum of all balls is 120) gets a 7th Way, or point. This prevents the game from ending in a tie.
This game can be played by up to 4 players. The 3 and 4 player format is team based, and decided by the following: 3 Players: The player who pockets the one ball is solo for the duration of the game, and competes against the other two players, who are now teammates, and shoot alternately against player one. 4 Players: The player who pockets the one ball remains alone until the lowest numbered money ball is pocketed by another player, making them teammates. For example: player 1 pockets the one ball, and player two pockets the five ball. They are now teammates, and competing against players three and four, who are also now teammates. If player one pockets the one ball and the five ball, the player who pockets the 8 ball becomes teammate to player 1. If the 1, 5 and 8 ball are pocketed by player one, the 10 ball then becomes the pairing ball, and so on.
Fouls: If you do not hit the object ball it is considered a push. In the event of a push you have the option to either take the next shot or give it back to the person who pushed. If there are two fouls in a row the next player in rotation gets ball in hand. Scratches (Cue Ball hit into pocket) results in ball placed behind headstring.
Special considerations: Roundhouse: A roundhouse occurs if a player or team pockets all money balls on the table (1, 5, 8, 10, 13, 15). This results in double points being awarded to that individual or team (or 2x the money per Way). In this case the 61 points rule for the seventh Way does not apply.
Squarehouse: A squarehouse occurs if a player or team pockets ALL balls on the table, without an opponent pocketing a single ball. This results in quadruple points being awarded to that individual or team (or 4x the money per Way).
Read more about this topic: Chicago (pool)
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—Samuel Butler (1835–1902)