The 2016 World Series was the championship series of Major League Baseball's (MLB) 2016 season. The 112th edition of the World Series, it was a best-of-seven playoff between the National League (NL) champion Chicago Cubs and the American League (AL) champion Cleveland Indians, the first meeting of those franchises in postseason history. The series was played between October 25 and November 2 (although Game 7 ended slightly after 12:00 am local time on November 3). The Indians had home-field advantage because the AL had won the 2016 All-Star Game. This was the final World Series to have home-field advantage determined by the All-Star Game results; since 2017, home-field advantage has been awarded to the team with the better record. Many consider the 2016 World Series to be one of the best of all time, due to the underdog story behind both teams, the games being tightly contested, and the series going the full distance.

The Cubs defeated the Indians 43 to capture their first World Series championship since 1908, and their first while playing at Wrigley Field. The deciding seventh game, won by Chicago 87 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 31 deficit to win a best-of-seven World Series.

The Cubs, playing in their 11th World Series overall and their first since 1945, won their third championship and first since 1908, ending the longest world championship drought in North American professional sports history. 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, fell 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.

The 2016 World Series was highly anticipated; the two teams entered their matchup as the two franchises with the longest World Series title droughts, a combined 176 seasons without a championship. At the series' conclusion, numerous outlets listed Game 7 as an instant classic, and the entire Series as one of the greatest of all time.

The Chicago Cubs are an American professional baseball team based in Chicago. The Cubs compete in Major League Baseball (MLB) as part of the National League (NL) Central division. They play home games at Wrigley Field, located on the city's North Side. The Cubs are one of two major league teams based in Chicago; the other, the Chicago White Sox, is a member of the American League (AL) Central division. The Cubs, first known as the White Stockings, were a founding member of the NL in 1876, becoming the Chicago Cubs in 1903.Throughout the club's history, the Cubs have played in a total of 11 World Series. The 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. The 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. Since the start of divisional play in 1969, the Cubs have appeared in the postseason 11 times through the 2020 season.The Cubs are known as "the North Siders", a reference to the location of Wrigley Field within the city of Chicago, and in contrast to the White Sox, whose home field (Guaranteed Rate Field) is located on the South Side.

Through 2021, the franchise's all-time record is 11,087–10,521 (.513).