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With Cubs and White Sox both on a postseason trajectory, Chicago is ready for October baseball

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CHICAGO — If you walk around the city of Chicago right now, there’s an energy that is palpable. That’s because for the first time in nearly two decades, good baseball is being played on both sides of town.

Even with the city’s other marquee sports teams, Chicago is a baseball town, and with two of MLB’s oldest franchises, the intra-city rivalry between the White Sox and the Cubs runs deep. That said, historically, when one team is good, the other typically is not, which usually takes some of the steam out of their annual six-game slate.

But this season, with less than six weeks to go, both the White Sox and Cubs are on a postseason trajectory. With the conclusion of their three-game set at Wrigley Field — the Cubs took the first two contests in walk-off fashion before the Sox rallied in the finalethe 66-60 Sox lead the AL Central, and the 74-54 Cubs have a comfortable hold on the first NL wild card. The last time the Cubs and White Sox were both this good this late in the regular season was 2008.

"It's an amazing atmosphere, and playing in front of these crowds in Chicago is really nice," White Sox first baseman Munetaka Murakami said Tuesday.

This week’s late-season clash between two teams with their eyes on the postseason deserved a playoff atmosphere, and the games didn’t disappoint. The contests featured highlight-reel moments, momentum swings, defensive gems, multiple lead changes, extra innings, walk-off hits and even a lengthy rain delay.

And that’s before mentioning the star power, headlined by Cubs center fielder and MVP contender Pete Crow-Armstrong, who delivered leadoff and walk-off heroics in Games 1 and 2, and Sox slugger Murakami, who stunned the Wrigley crowd with a blast to the video board on Tuesday.

From opposing dugouts, even the managers couldn’t help but enjoy the high-stakes environment of this Crosstown Classic.

“It’s fun when you can sit next to your family member, your best friend, your uncle, and you’re cheering for a different team,” Cubs manager Craig Counsell said. “That’s who gets rewarded in these games more than anybody.”

Said Sox manager Will Venable: “I thought, just as a fan of baseball, watching all these guys play how they did and the talent that was out there, the way they played — just big-time players making big plays and doing cool stuff in a great atmosphere. It's just a cool place to play.”

Munetaka Murakami sends one off the jumbotron! pic.twitter.com/QxDHvbCNk1

— Chicago White Sox (@whitesox) August 19, 2026

The White Sox, with a four-game lead in their division, and are six weeks away from their first division title since 2021. They’ve been arguably the biggest surprise in baseball this year, and following three consecutive 100-loss seasons, their rise to the tier of the AL’s best teams has been pretty unprecedented. 

Meanwhile, for the second year in a row, the Cubs, who are five games back of Milwaukee in the NL Central, are headed toward hosting a wild-card series to begin the postseason. But after an offseason and trade deadline in which they pushed their chips to the middle of the table, they’re looking for more than just a playoff appearance.

“I think we've had stretches this year early where we've been the hottest team in baseball, and then the coldest team in baseball, and then the hottest team in baseball again,” third baseman Alex Bregman said. “But I feel like the main thing in the second half is just being consistent and playing consistent baseball, and I feel like we've done a good job of that in all three phases of the game.”

Between these two Chicago teams, there’s clearly respect for what each has accomplished this season. And with both squads being talked about as among the best in their respective leagues, it’s not hard to appreciate what the other is doing.

“I thought they did a great job at the deadline,” Cubs president Jed Hoyer said of the Sox earlier this month. “They’ve put themselves in a great position. They’ve put themselves in a position to get a bye. They’ve got a really good young team.”

While MLB teams don’t often like to use individual series as a measuring stick, this week’s meeting at Wrigley Field felt like an appropriate temperature check for these two teams. The three tightly contested games proved without a doubt that the Cubs and the Sox are both prepared to play postseason baseball. 

Even more apparent is that the city of Chicago is ready, too.

Is a Crosstown World Series a pipe dream? Probably. There’s a lot that would have to happen for that to become a real possibility. But the fact that there’s a non-zero chance of Cubs vs. White Sox in the Fall Classic has many in Chicago letting their imaginations run wild.

“Sign me up. Yeah, I’m in for all the fun. Everything,” Counsell said with a wry smile before this week’s series began. “You want to hype it up? I’m in for all of it.”

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