For a two-team town — city to be more precise — Chicago has experienced less than its share of baseball glory.
The Cubs spent forever and a day seeking World Series glory, and the White Sox have much more often than not been on the outside of the postseason looking in.
That history is what makes a day like Thursday all the more special.
There were the Cubs at Wrigley Field, defeating the Miami Marlins to clinch a spot in the playoffs.
And at just about the same time, there were the White Sox down in Kansas City, winning against the Royals to claim their own spot in the postseason.
With the two Chicago teams in opposite leagues, the only way they could meet in the postseason is the World Series.
But hey — it’s happened once before, so why not again?
Cubs, White Sox Make Chicago Baseball History
It’s rare that the Cubs and White Sox make the playoffs in the same year.
According to MLB Network’s Sarah Langs, it’s just the fourth time it has happened.
They first pulled off the feat in 1906.
Then they did it in 2008, and then 2020.
And now in 2026.
Of course, many more teams make the playoffs now than they used to. Back in 1906, it was just the league pennant winners, and they went straight to the World Series to face off.
That 1906 World Series was won by the White Sox, 4 games to 2. It was a pitching-heavy series where White Sox starters Ed Walsh, Nick Altrock and Doc White all had sub-2.00 ERAs for the series. And the White Sox got two wins over Cubs legendary starter Mordecai “Three Finger” Brown to help win the series.
Amazingly, each team in that series used just four pitchers across the entire series.
There’d be a few more arms called upon if there was a Chicago World Series in 2026 — and the travel would certainly be simple.
Improbable Feat
Of course, the Cubs entered this season as postseason probables.
The White Sox? Not so much.
They had gone 41-121 two seasons ago and 60-102 last year. They weren’t viewed as a contender by most prognosticators.
But for most of the year, the White Sox led the AL Central Division. It’s not a given that they get the division crown now, but they at least did enough to ensure they’ll have the league’s third-and-final Wild Card spot, at worst.
The Cubs had to work for it, too, because the Milwaukee Brewers won the NL Central, and so it’s also a Wild Card berth for the Cubbies.
At this point, they’ve both done the most important part. They’ve walked through the door into the playoffs. Now it’s time to put on a Chicago show.
Cubs, White Sox Make Rare Chicago Baseball History