The Chicago Cubs and Chicago White Sox both begin best-of-three Wild Card Series on Tuesday, September 29, 2026. It is the first time since 2020 that both Chicago teams have made the postseason. Both teams open on the road: the White Sox in Houston against the Astros, and the Cubs in San Diego against the Padres.
Key Takeaways
- This is only the fourth time in history that the Cubs and White Sox have reached the same postseason. The previous pairings came in 1906, 2008, and 2020.
- The White Sox are the first team in MLB history to reach the playoffs after three straight seasons of 100 or more losses, following records of 61-101 in 2023, 41-121 in 2024, and 60-102 in 2025.
- The Cubs finished the regular season 89-73, and the White Sox finished 84-78.
- Neither team plays a home game in the Wild Card round. Home postseason games in Chicago are possible only if a team advances to the best-of-five Division Series.
- The White Sox open in Houston at 4 p.m. and the Cubs open in San Diego at 9 p.m. Chicago time on Tuesday. Games 1 and 2 of both series air on Peacock and NBC Sports Network.
- Chicago is the only city with two MLB franchises to have both teams in this year’s postseason.
The White Sox Turnaround Rewrites A Losing Stretch
The White Sox reached the postseason after one of the deepest slumps any franchise has climbed out of. The club lost 101 games in 2023, a franchise-record 121 in 2024, and 102 in 2025. No MLB team had ever followed three straight seasons of 100 or more losses with a playoff berth before the White Sox clinched with a 9-1 win over the Kansas City Royals on September 24.
The final stretch was bumpy. The White Sox gave up their hold on the American League Central and ended up with the final AL Wild Card spot, which set up a road series against the Astros. The team’s 48-33 record at Rate Field shows how much home games have mattered for the White Sox this season, and it is one reason a return trip to the South Side for a Division Series would have extra weight.
The Cubs Return For A Second Straight Postseason
For the Cubs, October baseball is becoming a habit again. The club clinched its second consecutive playoff trip with a win over the Miami Marlins at Wrigley Field on the same day the White Sox clinched. Pete Crow-Armstrong also joined MLB’s 40-40 club during that game. The Cubs have once again chosen Matthew Boyd to start Game 1 of the Wild Card Series.
The matchup is a rematch. Last season, the Cubs beat the Padres in the Wild Card round and then lost to the Milwaukee Brewers in the Division Series. This time San Diego, at 91-71, hosts every game of the series.
A Division Series Would Bring October Business Back To Both Ballpark Neighborhoods
The Wild Card round has a direct economic effect: none of it happens in Chicago. With both series on the road, the bars, restaurants, and merchants around Wrigley Field and Rate Field will host watch parties instead of sellout crowds. For Chicago’s two ballpark neighborhoods, the real economic stakes start only if a team advances.
A Division Series win or two would change that quickly. Postseason home games bring full stadiums, pregame and postgame crowds, and national TV attention to neighborhood businesses that depend on the regular season to carry them through Chicago’s winters. In Wrigleyville, where the neighborhood economy is closely tied to the ballpark schedule, an unexpected October home date adds business at a point in the year when foot traffic usually drops. Around Rate Field on the South Side, a first home playoff game since 2021 would give nearby businesses a crowd they haven’t seen in years.
The Red Line Crosstown Scenario Is Now On The Table
If both Chicago teams win their Wild Card Series, they could host postseason games on the same day. The CTA Red Line runs past both ballparks, with Addison station at Wrigley Field and Sox-35th station at Rate Field. A same-day doubleheader would put two postseason crowds on the same line within hours of each other. That would test transit capacity and draw attention across the city.
That scenario depends on four wins across two best-of-three series in two cities. It isn’t a prediction, but it is the version of October that fans on both sides of Madison Street are already thinking about.
A Rivalry With Little Shared Postseason History
The Cubs and White Sox rarely peak in the same season. They met in the 1906 World Series, which the White Sox won four games to two. In 2008, both teams lost in the Division Series. In 2020’s shortened season, both were eliminated in the Wild Card round. Neither franchise has ever gotten past the first round in a year when the other also reached the postseason.
That history is what makes this week’s double opener stand out. For Chicago, Tuesday brings two road games, two late nights in front of the TV, and a chance that October baseball could return to both ballparks.
FAQs
When Do The Cubs And White Sox Play In The 2026 Wild Card Series?
Both teams open on Tuesday, September 29, 2026. The White Sox play the Astros in Houston at 4 p.m., and the Cubs play the Padres in San Diego at 9 p.m. Chicago time.
Will The Cubs Or White Sox Play Playoff Games In Chicago?
Not in the Wild Card round, because every game is played at the higher seed’s ballpark. Chicago would host postseason games only if the Cubs or White Sox advance to the Division Series.
How Many Times Have The Cubs And White Sox Made The Playoffs In The Same Year?
This is the fourth time. The previous seasons were 1906, 2008, and 2020.
What Record Did The White Sox Set In 2026?
The White Sox became the first team in MLB history to reach the postseason after three straight seasons of 100 or more losses. They lost 101 games in 2023, 121 in 2024, and 102 in 2025.
Where Can Fans Watch The Cubs And White Sox Wild Card Games?
Games 1 and 2 of both Wild Card Series air on Peacock and NBC Sports Network. White Sox games are also carried on ESPN Chicago 1000 AM radio.
