Baseball is booming in the Windy City. In 2026, both the Chicago Cubs and Chicago White Sox qualified for the postseason — with both teams making it by virtue of the Wild Card. The Cubs finished the 2026 regular season with 89 victories, while the White Sox, despite losing their hold over the AL Central, won 84 games this year in a massive bounce-back campaign.

Both teams will be playing Game 1 of their respective Wild Card series on the road on Tuesday, with the Cubs facing the San Diego Padres and the White Sox squaring off against the Astros. This marks a rare occasion in the city of Chicago; as pointed out by Jon Morosi of MLB Network, this will only be the ninth time that the Cubs and the White Sox will be playing a postseason game on the same day.

The first six days in which both the Cubs and White Sox simultaneously played a playoff game came all the way back in 1906, when the two teams based in the Windy City faced off in the World Series.

It wasn't until 102 years later when both teams would play postseason baseball on the same day (October 2, 2008) once more, and then it would take another 12 years before this phenomenon would happen again (September 30, 2020).

Article Continues Below

The rarity of this occasion just shows that Cubs and White Sox don't tend to be good at the same time. While the Cubs did make it to the postseason last year and were expected to make it this year once again, the White Sox have completed their remarkable turnaround by qualifying for the postseason this year.

It was just in 2024 when the White Sox set records for putridity by winning just 41 games, and in 2025, they fared better much not by much — finishing with a 60-102 record.

Can both Chicago-based teams continue their strong 2026 by making it deeper into the postseason?