Chicago baseball fans may be putting away their postseason gear for the winter, but 2026 gave the city something it has rarely experienced with both the Cubs and White Sox playing postseason baseball.
The two teams reached the postseason in the same year for just the fourth time in history, joining the 1906, 2008 and 2020 seasons. The Cubs and Sox also clinched bracket positions on the same day within minutes of each other, giving fans across the city reason to celebrate. This year was the first year that both teams clinched a spot in the playoffs on the same day.
Although neither team reached the championship round, this season gave fans of both teams plenty to look forward to in the future.
For the Cubs, this marks the second consecutive year the team got to play postseason baseball, building on a campaign that featured an MVP-caliber year from star center fielder Pete Crow-Armstrong. The Cubs overcame injuries to their pitching staff, periods of inconsistency and a difficult summer to secure a postseason berth.
The Cubs run ended quickly, however. The team had the best offense in the National League in 2026 and scored the most runs but was held to just one run in two games against the San Diego Padres.
On the other side of town, the White Sox made history. The team became the first ever to make the playoffs immediately after having back-to-back seasons with 100 losses. In fact, the team set the record for the most losses in major league history in the 2024 campaign where they lost 121 games.
The Sox came out blazing in the Wild Card round against the Houston Astros, sweeping the series in two games on the road. The dagger came in game two when second baseman Chase Meidroth hit a three-run home run late in game two that gave the Sox the insurance needed to finish the job.
The Sox would ultimately lose to the Cleveland Guardians in the next round in heartbreaking fashion, setting the record for strikeouts in a postseason game with 21 strikeouts in game five. Nonetheless, the team overachieved in virtually every metric. With all the young talent, and a strong farm system, the best is yet to come at 35th and Shields.
