On September 24, 2026, Chicago had two postseason tickets — and they arrived within minutes of each other. The Cubs beat the Miami Marlins 2-1 at Wrigley Field; the White Sox crushed the Kansas City Royals 9-1. It’s only the fourth time in MLB history that both Chicago teams have reached October together: 1906, 2008, 2020, and now 2026. The most staggering part isn’t the rarity of the date — it’s that one of those two teams lost 121 games just two years ago.
The Day Chicago Punched Two Tickets to October
The Cubs closed it out first. Matthew Boyd threw seven innings of one-run ball, and in the final regular-season night at Wrigley, Pete Crow-Armstrong stole his 40th base of the year in front of the home crowd. That steal completed one of the more remarkable individual achievements of the season: 45 home runs and 40 stolen bases, making Crow-Armstrong the seventh player in MLB history to join the 40-40 club — and the first in Cubs history.
Minutes later, the notification came in from Kansas City: White Sox win, 9-1. Just like that, both Chicago teams were in.
From 121 Losses to October: The Most Dramatic Rebuild in Recent Memory
For the Cubs, the path was bumpy but the destination was rarely in serious doubt. They lead the majors in runs scored and slugging percentage, rank second in home runs, and their fielding run value of 70 per Baseball Savant puts them more than 25 points clear of second place. Still, they dropped ten straight in August, Cade Horton went down for Tommy John surgery in April, and Alex Bregman played through facial fractures from a foul ball late in the season. This is their second consecutive postseason — the first time the Cubs have done that since their four-year run from 2015 to 2018.
For the White Sox, the story is something else entirely. In 2024 they set the modern MLB record with 121 losses. In 2025 they posted their third straight 100-loss season. And on September 24, 2026, they clinched a postseason berth. The leap is so extreme that they already hold the record for most wins by a team coming off at least three consecutive 100-loss seasons. The rebuild wasn’t magic — it was years of work that only feel sudden because the starting point was so brutal.
- The 2021 draft produced Colson Montgomery and Sean Burke.
- Munetaka Murakami signed from Japan in December 2025.
- Murakami and Tristan Peters both made the 2026 All-Star Game.
The Fourth Time — and What Comes Next
The only time both Chicago teams met in October was 1906, in the only all-Chicago World Series. The White Sox won that series 4-2. Since then, sharing October has been almost unheard of — just 2008 and 2020 before this year.
The Cubs enter as an NL Wild Card team, still jockeying for seeding with the Padres and Phillies. The White Sox clinched a postseason spot, but as of September 24 they were still in a half-game battle with the Cleveland Guardians for the AL Central title — their exact seed still to be determined.
What is clear: Chicago baseball has never seen a day quite like this. Two tickets, two teams, two completely different stories arriving at the same place on the same afternoon.
