There Really Is Nothing Like Chicago in October
The Cubs are heading back to the postseason for a second straight year, Pete Crow-Armstrong has joined baseball’s 40–40 club, and a familiar October phrase has moved from graphic language into the team’s actual Wild Card wardrobe.
The Cubs clinched in the final home game of the regular season at Wrigley Field, beating Miami 2–1 after a season that refused to travel in a straight line. They experienced two separate 10-game winning streaks, later absorbed a 10-game skid and navigated a long list of injuries before finally locking in the postseason berth.
The payoff is a second consecutive October appearance — the first time Chicago has done that since the four-year postseason run from 2015 through 2018.
And because baseball apparently enjoys narrative symmetry, the opponent is San Diego again. The Cubs eliminated the Padres in last year’s Wild Card round. This time, the series moves west to Petco Park.
“Nothing Like Chicago in October” works because it describes more than weather. It describes what happens when the city starts measuring evenings in playoff innings.
One Clinching Day Produced Two Cubs Stories
Pete Crow-Armstrong stole second base in the first inning of the clinching game and became only the seventh player in Major League history to record 40 home runs and 40 stolen bases in the same season. No Cubs player had done it before.
That achievement gave September 24 a split identity. One side belonged to the team’s return to October; the other belonged to a player putting a historic number beside his name. Readers following the latter can explore the Pete Crow-Armstrong search archive.
The Best External Image for This Design Is Almost Too Perfect
At 2026 Wild Card media availability, Pete Crow-Armstrong was literally wearing Cubs apparel reading “NO TIME LIKE OCTOBER” — the same cultural phrase driving this design.
That visual is useful because it removes any doubt about whether the phrase belongs to the current moment. It is not a generic fall slogan being retrofitted onto Cubs colors. It is part of how the organization itself is packaging the 2026 postseason.
A City-First Graphic Instead of a Player-First Graphic
Royal blue, varsity red and four Chicago stars turn the postseason phrase into something closer to a city banner than a conventional player shirt.
View the Chicago October piece →The four red stars are the smartest part of the composition because they pull the idea beyond baseball. They bring the Chicago flag’s visual grammar into a Cubs postseason context. The shirt therefore reads in two directions at once: North Side baseball and city identity.
That is important in a year when both Chicago clubs reached October. The Cubs and White Sox took radically different roads, but the city enters the postseason with baseball alive on both sides.
The 2016 Memory Is Still in the Room
Every Cubs October exists in conversation with 2016 whether the current roster wants that comparison or not. Ten years have passed since the World Series championship ended the franchise’s 108-year drought. Enough time has passed for that run to become a true memory object rather than merely “the recent title.”
The current team is not trying to recreate 2016. Its identity belongs to a different roster, a different competitive cycle and a different Chicago. Yet the anniversary adds another layer to the phrase “Nothing Like Chicago in October.” Cubs fans know exactly how large an October can become.
Now the Story Moves to San Diego
Chicago opens the best-of-three Wild Card Series at Petco Park with Matthew Boyd scheduled opposite Michael King. The Cubs are the No. 5 seed; San Diego earned home field as the No. 4.
For a design built around place, it is interesting that the first October games happen far away from Wrigley. “Chicago in October” travels. The city’s playoff identity is carried into another ballpark before there is any guarantee of a home postseason game.
The Cubs Archive
The wider Chicago Cubs collection connects the season’s player milestones, postseason phrases and Chicago-specific visual language. The broader MLB collection places the Cubs inside a postseason field full of dramatically different stories.
Frequently Asked Questions
When did the Cubs clinch the 2026 postseason?
Chicago clinched on September 24 with a 2–1 victory over the Miami Marlins at Wrigley Field.
What did Pete Crow-Armstrong accomplish that day?
He stole his 40th base to become the first Cubs player and seventh MLB player ever to produce a 40-homer, 40-steal season.
Who do the Cubs face in the Wild Card Series?
Chicago faces the San Diego Padres in a rematch of the 2025 Wild Card round, this time at Petco Park.
Why does the design use four red stars?
The stars connect the Cubs postseason phrase to the visual language of the Chicago city flag.
Follow the North Side’s October through the Chicago Cubs archive.
Nothing Like Chicago in October Shirt captures the Cubs’ 2026 postseason return with royal blue, Chicago red stars and the playoff phrase already appearing around the team during Wild Card week.