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Short Answer: White Sox

The Chicago White Sox won three World Series ... 1906, 1917, and 2005, while the Chicago Cubs have only won two ... 1907 and 1908.

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The Chicago White Sox have won three World Series -- in 1906, 1917, and 2005. The Chicago Cubs won in 1907 and 1908.

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14y ago
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Q: Which Chicago teams who won the most World Series?
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