Baseball in Chicago is like thin crust and deep dish pizza—people either swear by one or the other. Cubs or White Sox. North Side or South Side. There’s no middle ground. And every time the two teams square off during the regular season, it’s a celebration, a grudge match, and a civic tug-of-war all wrapped into one. This weekend, the Cubs and White Sox are meeting again, and the first three games will be played at Wrigley Field. The timing is perfect. The weather’s warm, the fans are loud, and both sides of the city are ready to prove who really runs this town.
The Cubs and White Sox have always felt like they exist in different baseball universes, but the interleague format gave fans something they’d always wanted—bragging rights. When MLB introduced interleague play in 1997, one of the matchups that drew instant attention was the so-called Crosstown Classic. Sure, the New York Yankees and Mets had the Subway Series, and the Los Angeles Dodgers and, at the time Anaheim Angels battled for Los Angeles, but Cubs vs. White Sox had a little more feeling of a rivalry. A little more spite. A little more grit. And maybe it’s because the two teams had so rarely faced each other before then.
Before interleague play became a thing, the Cubs and White Sox only met in exhibitions. They played a few games at Comiskey Park or Wrigley Field, but they didn’t count. They were like backyard games between two brothers who both wanted to win but would still go home to the same house. Then, in June of 1997, everything changed. The first regular season series between the two teams was held at Comiskey Park, and it was electric. Frank Thomas and Sammy Sosa hit bombs. The fans were louder than a playoff crowd. It felt personal.
That 1997 series set the tone for what would become one of the most heated interleague rivalries in baseball. It’s never really mattered how good or bad either team is in a given year. Even when one team is at the bottom of the standings, winning the Crosstown series becomes their postseason. In 2000, the White Sox were on their way to a division title while the Cubs were floundering, but when the Cubs took two of three at Wrigley in July, it felt like they’d won a trophy. In 2008, both teams were in first place in their divisions when they played each other—rare air for this rivalry. The White Sox swept the Cubs on the South Side. Then the Cubs responded with a sweep of their own at Wrigley. It was theater. It was beautiful.
Over the years, the Crosstown games have produced some unforgettable moments. Remember the fight in 2006? A.J. Pierzynski ran over Cubs catcher Michael Barrett at home plate, and Barrett responded by punching Pierzynski in the face. Benches cleared. Fans lost their minds. That was more than just a baseball moment—it was the soul of this rivalry on full display. Grit, emotion, and a refusal to back down. The same thing that’s in the air every time these two teams meet.
Wrigley Field, with its ivy-covered walls and party-in-the-bleachers vibe, is a world away from the South Side’s blue-collar edge. When the White Sox come to Wrigley, it feels like an invasion. When the Cubs go to Guaranteed Rate Field, Sox fans let them know they’re not welcome. It’s one of the few interleague rivalries where the crowd mix creates a stadium split in personality. You hear dueling chants in the stands. Families wear different jerseys. Friendships are temporarily suspended. And every at-bat feels like it matters just a little more than a regular Tuesday night against the Marlins.
The Cubs hold the edge in the all-time interleague series, but the White Sox have had their moments. During their 2005 championship season, they took four of six from the Cubs. In 2021, the Sox again went 5-1 against the North Siders, asserting themselves during a year when the Cubs were breaking things down and rebuilding. Of course, Cubs fans still have 2016 in their back pocket—a season where they broke a 108-year drought and finally brought a title back to Wrigleyville. The Sox fans might respond, “Yeah, but we did it first, and we only had to wait 88 years.” That’s the thing about this rivalry. Even the championships become talking points in the never-ending game of one-upmanship.
Now here we are in 2025, and the Crosstown series is as spicy as ever. The first three games this weekend at Wrigley will kick off another chapter in the saga. Maybe it won’t have playoff implications. Maybe both teams are still trying to figure out their identities. But none of that matters when Chicago’s two baseball families meet. These games are about pride. About proving that your side of the city bleeds just a little bit stronger. It’s not about standing in the wild card race—it’s about not having to hear it from your cousin at the next barbecue.
For the players, it’s also special. Guys like Nico Hoerner and Dansby Swanson know what it means to play in front of a packed Wrigley crowd during this rivalry. And even though the rosters turn over every couple years, the vibe stays the same. You come into this series and you feel it. The energy. The pressure. The intensity. Rookies become legends in these games. Veterans can turn into villains in one inning. And the managers feel it too. They know their postgame quotes will be parsed and replayed if they lose. It’s more than just three games.
Here’s the thing, folks: For fans, this is the good stuff. These are the games you circle when the schedule comes out. It doesn’t matter if it’s Friday at 1:20 or Sunday night under the lights. Cubs and Sox is destination baseball. Maybe you’re watching from Murphy’s rooftop. Maybe you’re at home on the couch with your Sox gear on, booing the Wrigley crowd through the screen. Either way, you’re invested.
With that… As the Cubs and White Sox get ready to clash at Wrigley this weekend, expect the unexpected. Maybe someone will hit three home runs. Maybe there’ll be a walk-off. Maybe there’ll be another fight or a controversial call. Whatever happens, it’ll be part of the long, colorful, often chaotic story of baseball in Chicago. It’s not just a rivalry—it’s a tradition. And for one weekend, this city forgets about the standings and just roots with its heart. Cubs or Sox. Pick a side.
If you cannot play with them, then you should pick one of them to root for!