Chicago is heading into October with something it has experienced only a handful of times in more than a century of baseball. Both the Chicago Cubs and Chicago White Sox are in the postseason.
The 2026 season marks only the fourth time the Cubs and White Sox have reached the playoffs in the same year. The others came in 1906, 2008 and 2020. And because the 2020 season was shortened to 60 games with an expanded playoff field, this is only the third time it has happened during a full regular season.
The last time was 2008.
Go back to the first time, and the story gets even better. In 1906, the Cubs and White Sox didn’t just make the postseason. They played each other in the World Series. The Cubs entered after a remarkable 116-win season, but the White Sox defeated their crosstown rivals four games to two.
One hundred and twenty years later, both sides of Chicago are playing October baseball again.
And each team has taken a very different road to get there.
Cubs return to October
The Cubs finished the regular season 89-73, taking second place in the National League Central behind the Milwaukee Brewers and earning the No. 5 seed in the National League playoffs.
It is the Cubs’ second consecutive postseason appearance and the first time they have reached the playoffs in back-to-back seasons since their four-year run from 2015 through 2018.
It wasn’t an easy road. The Cubs opened the season strong, then endured a 10-game losing streak and fell to just three games over .500 by June 20. From there, they turned the season around, winning 48 games the rest of the way.
Pete Crow-Armstrong delivered one of the biggest individual performances of the Cubs’ season, while Alex Bregman and Seiya Suzuki were also key pieces of the lineup.
Now the Cubs head west to face the San Diego Padres in a best-of-three Wild Card Series at Petco Park.
It is a rematch of last year’s Wild Card Series, when the Cubs eliminated San Diego in three games at Wrigley Field. Chicago also had San Diego’s number during the 2026 regular season, winning five of their six meetings.
White Sox complete a historic turnaround
If the Cubs’ return to October is a success story, what happened on the South Side may be even more remarkable.
The White Sox finished 84-78 and earned the sixth and final American League playoff seed. They are back in the postseason for the first time since 2021.
Consider where they came from.
The White Sox endured three consecutive seasons with at least 100 losses, including their brutal 41-121 season in 2024, which established the modern-era Major League record for losses.
Two years later, they are playing postseason baseball.
The White Sox became the first team in Major League history to reach the playoffs after losing at least 100 games in two or more consecutive seasons.
Miguel Vargas and Munetaka Murakami emerged as two of the biggest offensive forces in the turnaround, while a young roster that entered the season with modest expectations kept itself in the American League Central race almost until the end.
The Sox ultimately finished one game behind Cleveland in the division but still earned their ticket to October.
Their reward is a trip to Houston to face the Astros in a best-of-three Wild Card Series at Daikin Park.
There is an interesting twist. Houston won the AL West with an 81-81 record, giving the Astros home-field advantage as a division champion even though the White Sox finished with three more victories.
When, where and how to watch
Both Chicago teams begin their postseason Tuesday, Sept. 29, and both Wild Card Series are played entirely in the higher-seeded team’s ballpark.
The White Sox face the Houston Astros at Daikin Park in Houston. Game 1 is Tuesday at 4 p.m. CT. Game 2 is Wednesday, Sept. 30 at 4 p.m. CT. If necessary, Game 3 will be played Thursday, Oct. 1, with the time dependent on how many Wild Card series remain.
The Cubs face the San Diego Padres at Petco Park in San Diego. Game 1 is Tuesday at 9 p.m. CT, followed by Game 2 Wednesday at 9 p.m. CT. A deciding Game 3, if necessary, will be played Thursday, with the time again subject to the other Wild Card results.
Tuesday and Wednesday’s White Sox and Cubs games are available on Peacock and NBC Sports Network. Thursday’s television schedule will depend on which series require a third game.
ESPN Radio is also providing national radio coverage throughout the MLB postseason.
So Chicago enters October in a position it rarely gets to enjoy.
The Cubs are back looking to build on a second consecutive postseason appearance. The White Sox have gone from a record-setting 121-loss season to the playoffs in just two years.
For only the fourth time in history, the North Side and South Side are playing postseason baseball at the same time.
And somewhere in the distance sits the tantalizing piece of Chicago baseball history that has happened only once before.
A Cubs-White Sox World Series.
