Could the Cubs and White Sox Meet in the 2026 World Series?

The Chicago Cubs and the Chicago White Sox played each other on Tuesday, August 18, with first pitch at 7:05 p.m. Central Time. Fans gathered at Wrigley Field, the Cubs' home ballpark, to watch the game.

The matchup was part of the annual Crosstown Classic, a series of games between Chicago's two Major League Baseball teams. The event is known for drawing large, energetic crowds because of the strong rivalry between the two clubs.

Beyond the excitement of the game itself, the matchup has raised a bigger question among baseball fans and analysts. Could the Cubs and the White Sox both make it to the World Series in 2026, possibly even facing each other?

A World Series between two teams from the same city would be extremely unusual. Historically, this kind of matchup, sometimes called a Subway Series or, in Chicago's case, a potential 'Crosstown World Series,' has happened only rarely across the history of Major League Baseball.

Analysts have been discussing the odds, or chances, of both teams reaching the postseason and eventually the World Series. This depends on each team's performance and their position in the playoff race, the competition among teams to qualify for the postseason.

For now, fans on both sides are focused on the excitement of the Crosstown Classic itself. Whether a Cubs-White Sox World Series happens in 2026 remains uncertain, but the idea has captured the attention of baseball fans across the city and beyond.