As of the end of 2016, how many times have the Chicago Cubs won the World Series?

3 [Three Times]

After a crazy, action-packed series against the Cleveland Indians, the Chicago Cubs won their third World Series in 2016. They first won a championship on Oct. 12, 1907, beating the Detroit Tigers. Only a year later, the Cubs came back as defending champions on Oct. 14, 1908, again facing the Tigers and coming up triumphant. But it wasn’t until Nov. 2, 2016, nearly 108 years later, that the Cubs went back to the World Series and won it all. Source: mlb.com

The Chicago Cubs are an American professional baseball team based in Chicago, Illinois. The Cubs compete in Major League Baseball as a member club of the National League Central division, where they are the defending World Series champions.