The Chicago Cubs has won 3 World Series Ring in year 1907, 1908 and 2016.
Throughout the club’s history, the Chicago Cubs have played in a total of 11 World Series.
Furthermore, in 1906 Cubs won 116 games, finishing 116–36 and posting a modern-era record winning percentage of .763, before losing the World Series to the Chicago White Sox (“The Hitless Wonders”) by four games to two.
However, the Chicago Cubs won back-to-back World Series championships in 1907 and 1908, becoming the first major league team to play in three consecutive World Series, and the first to win it twice.
Most recently, the Cubs won the 2016 National League Championship Series and 2016 World Series, which ended a 71-year National League pennant drought and a 108-year World Series championship drought,
Both of which are record droughts in Major League Baseball. The 108-year drought was also the longest such occurrence in all major North American sports
1907 Chicago Cubs World Series Ring

Chicago Cubs came back strong from their shocking loss in the 1906 World Series. The Detroit Tigers’ young star Ty Cobb came into the Series with the first of his many league batting championships.
With pitching dominance over the Detroit Tigers and Cobb, the Cubs allowed only three runs in the four games they won, while stealing 18 bases off the rattled Tigers.
Each game was umpired by the two-man crew of Hank O’Day and Jack Sheridan.
The Cubs claimed their first world series ring after a 4-0 dominance over the Tigers.
1908 Chicago Cubs World Series Ring

This series was a re-match of the Chicago Cubs and the Detroit Tigers.
Chicago Cubs brought home their title in five games for their second world series ring. This was the only 2 world series ring won by the franchise until 2016.
Curse of the Billy Goat
The Curse of the Billy Goat was a sports curse that was supposedly placed on the Chicago Cubs Major League Baseball (MLB) franchise in 1945, by Billy Goat Tavern owner William Sianis.
It lasted 71 years, from 1945 to 2016. During game 4 of the 1945 World Series at Wrigley Field, Sianis’s pet goat, named Murphy, was bothering other fans, and so the pair were asked to leave the stadium.
Outraged, Sianis allegedly declared, “Them Cubs, they ain’t gonna win no more,” which had been interpreted to mean that the Cubs would never win another National League (NL) pennant, at least for the remainder of Sianis’s life.
Therefore, the Chicago Cubs lost the 1945 World Series to the Detroit Tigers, and did not win a World Series championship again until 2016.
Also, the Cubs had last won the World Series in 1908. After the incident with Sianis and Murphy, the Cubs did not play in the World Series for the next 71 years until, on the 46th anniversary of William Sianis’s death.
Above all, the “curse” was broken when they defeated the Los Angeles Dodgers 5–0 in game 6 of the 2016 National League Championship Series to win the NL pennant.
Later, the Cubs then defeated the American League (AL) champion Cleveland Indians 8–7 in 10 innings in game 7 to win the 2016 World Series, 108 years after their last win. Claiming their 3rd world series ring.
2016 Chicago Cubs World Series Ring

The Chicago Cubs defeated the Indians 4–3 to capture their first World Series ring since 1908, and their first while playing at Wrigley Field.
Furthermore, the deciding seventh game, won by Chicago 8–7 in ten innings, was the fifth World Series Game 7 to go into extra innings, and the first since 1997 (which, coincidentally, the Indians also lost).
It was also the first Game 7 to have a rain delay, which occurred as the 10th inning was about to start. The Cubs became the sixth team to come back from a 3–1 deficit to win a best-of-seven World Series.
Also, the Cubs, playing in their 11th World Series overall and their first since 1945, won their third world series ring and first since 1908, ending the longest world championship drought in North American professional sports history.
On top of that, it was the Indians’ sixth appearance in the World Series and their first since 1997, with their last Series win having come in 1948. Cleveland manager Terry Francona, who had previously won World Series titles with the Boston Red Sox in 2004 and 2007.
Felling short in his bid to become the third manager to win his first three trips to the Fall Classic, after Casey Stengel and Joe Torre.