For the first time in franchise history, the Chicago Cubs and Chicago White Sox clinched playoff berths on the same day. On Thursday, September 24, the White Sox beat the Royals 9-1, and minutes later the Cubs edged the Marlins 2-1 to punch their own ticket. Two Chicago clinches, one afternoon, something the Windy City had never pulled off at the same time.
A Windy City First
Per USA Today’s Bob Nightengale, it was the first time in Chicago baseball history that both teams clinched postseason berths on the same day. The timing made it surreal: the White Sox wrapped up in Kansas City, and within minutes the Cubs finished off Miami. For a city used to its two teams taking turns, having both punch in together on the same afternoon was a genuine first.
Only the 4th Time Ever
Both Chicago teams reaching the postseason in the same season is rare air. According to MLB’s Sarah Langs, it has happened just four times in over a century of baseball: 1906, 2008, 2020, and now 2026. The 1906 edition is still the most famous, the only all-Chicago World Series, which the White Sox won 4-2 over the heavily favored Cubs. Fans on both sides have waited a long time for another shared October.
How Each Team Got In
The White Sox story is the stunner. They reached the playoffs a year after losing 100-plus games for the third straight season, including a modern-record 121 losses in 2024, a turnaround we broke down in our White Sox clinch story. The Cubs, meanwhile, are back for a second straight postseason, clinching a National League wild card behind a strong all-around year. Both are in as wild cards for now, and final seeding will not be set until the regular season ends on Sunday.
Follow the 2026 MLB Postseason
Both Chicago teams are dancing. Here is everything you need to track the Cubs and Sox through October, with printable schedules and brackets:
Wondering how the seeds shake out? Our 2026 MLB playoff tiebreaker rules guide covers every scenario.
Could Chicago Get Another Crosstown World Series?
Here is the dream: the Cubs and White Sox can only meet in the World Series, exactly like 1906. Both have work to do, and the road runs through the wild card round first, but for the first time in a long time a Red Line World Series is at least on the table. Chicago would lose its mind, and the rest of us would happily watch.
