The Cubs-White Sox Rivalry (also known as the Crosstown Classic, The Windy City Showdown, Red Line Rivalry,[citation needed] City Series, Expressway Series,[citation needed] Crosstown Series , or Crosstown Showdown) refers to the rivalry between two Major League Baseball teams that play their home games in Chicago, Illinois. The Chicago Cubs of the National League play their home games at Wrigley Field located on the city's North side, while the Chicago White Sox of the American League play their home games at U.S. Cellular Field (previously known as Comiskey Park) on the city's South Side. The terms "North Siders" and "South Siders" are synonymous with the respective teams and their fans.

As of June 19, 2009, the all time series is tied 34-34. There have been six series sweeps since interleague play began: four by the Cubs in 1998, 2004, 2007, and 2008, and two by the White Sox in 1999 and 2008. The Chicago Transit Authority's Red Line runs north-south through Chicago's neighborhoods, stopping at Wrigley Field and US Cellular Field.

The rivalry between the two teams and their fans dates back to the founding of the American League. In 1900, Charles Comiskey moved his Saint Paul Saints minor league franchise to Chicago. It is believed that the Cubs owner at the time was not happy, and filed a suit against Comiskey.

After talks, it was decided that Comiskey could move his team to Chicago, pending that Chicago was not used in the title of the team name, and that the team play south of 35th Street. In response, the team was renamed the "White Stockings," which had been the original name of the Cubs from 1876 to 1889. The establishment of a new team in the city was a direct challenge to the National League franchise, which had been the idea behind the formation of the American League.

As the AL gained in popularity (with cheaper prices on admission and alcohol), the NL recognized the equality of the AL. This recognition did little to stem the rivalry between owners, players, and fans. While teams in New York City (such as the Yankees, Giants, and Brooklyn Dodgers) routinely played against each other in World Series matchups throughout the 1940s and 1950s, the two Chicago teams only met once in the 1906 World Series, a celebrated event that seemingly put the city on hold for a full week.

The heavily favored but young Cubs (who had won 116 games in the regular season) lost in six games to the veteran and pitching-strong White Sox, "The Hitless Wonders."

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