Baseball is a game of ghosts. If you grew up watching the NL Central in the early 2000s, seeing the Houston Astros vs Cubs on a marquee still feels like a division rivalry, even though Houston packed its bags for the American League over a decade ago. It’s a matchup that carries weight.
Honestly, the distance between these two franchises since the 2013 realignment hasn't cooled the heat much. When the 2026 schedule dropped, fans immediately circled the late May series at Wrigley Field. There is just something about the Crawford Boxes in Houston or the ivy in Chicago that brings out the weirdness in both clubs.
What happened the last time they met?
The 2025 season gave us a three-game set at Daikin Park that was basically a microcosm of modern baseball. High-leverage relief, veteran heroics, and a few "wait, who is that?" prospect moments.
Houston took two out of three in that June series, but it wasn't easy. The opener saw the Astros' Yainer Diaz and newcomer Cam Smith—yeah, the guy the Cubs actually drafted but later traded away—both launch three-run homers. That had to sting for the North Side faithful. Brandon Walter earned his first MLB win in that game, which is the kind of stat that only matters to die-hards but tells the story of how Houston develops pitching on the fly.
Then you had the finale. A classic 2-0 grind. Jose Altuve, who seems to be aging in reverse, hit a two-run shot in the fifth inning off Jameson Taillon. Framber Valdez did Framber Valdez things, tossing six shutout innings.
The Cubs did snag a 12-3 blowout in the middle game, proving that when their lineup clicks, they can still bully anyone. Matt Shaw, a name you're going to hear a lot more of, was a monster in that series, racking up doubles and driving in runs like he'd been in the Bigs for a decade.
The 2026 Outlook: Houston Astros vs Cubs
So, what’s the vibe for May 22–24, 2026?
Wrigley Field is going to be rocking. The pitching matchups are already looking juicy. We’re likely looking at Cade Horton—who has basically become the Cubs' undisputed ace after a dominant second half in '25—going up against Houston’s newest weapon, Tatsuya Imai.
The Imai signing was the talk of the winter. The Cubs were heavily linked to the Japanese star, but the Astros swooped in and grabbed him. Seeing him debut his stuff against a Cubs lineup featuring Seiya Suzuki and Ian Happ is going to be appointment television.
Key Matchups to Watch:
- Jeremy Peña vs. Dansby Swanson: Two of the smoothest shortstops in the game. Swanson is the veteran leader, but Peña’s glove is still a highlight reel waiting to happen.
- Yordan Alvarez vs. The Friendly Confines: Yordan hasn't played at Wrigley often. If the wind is blowing out toward Waveland Avenue, he might actually break a car window.
- Josh Hader in the 9th: Hader was nearly perfect against the Cubs in 2025, converting two saves in that June series. Chicago needs to find a way to get to the Astros' starters early to avoid the "Hader Curtain."
Why the "Expert" Predictions Often Fail
Most analysts look at these teams and talk about run differentials or Pythagorean win-loss records. That’s fine for a spreadsheet. But when you look at Houston Astros vs Cubs, you have to factor in the Joe Espada vs. Craig Counsell chess match.
Counsell is known for being a tactical wizard with his bullpen. He’ll pull a starter in the fourth inning if the data says the third time through the order is a trap. Espada, on the other hand, has kept that Houston "next man up" culture alive. Even when stars like Kyle Tucker have been sidelined, the Astros find a way to plug in a Zach Dezenzo or a Cam Smith and not miss a beat.
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The Weird History You Forgot
Did you know Houston actually has a winning record against Chicago all-time?
It’s true. Despite the Cubs' century-long history, the Astros have held their own since 1962. Before the move to the AL, these teams played 18 times a year. It was a bloodbath. They never met in the postseason—which is a crime, really—but the regular-season battles between Jeff Bagwell and Sammy Sosa are legendary in the South and the Midwest.
Nowadays, the games are rarer, which sort of makes them feel more special. It’s interleague play that actually works.
Practical Takeaways for Fans
If you’re planning on betting or just following the 2026 series, keep these nuances in mind:
- Watch the Wrigley Wind: It sounds like a cliché, but it’s the biggest factor in Chicago. If it’s blowing in, the Astros’ power-hitting style gets neutralized.
- Bullpen Depth: Houston’s relief core, led by Bryan Abreu and Hader, is deeper on paper, but the Cubs' farm system has started producing high-velocity arms that are harder to scout.
- The "Ex-Factor": Keep an eye on Cam Smith. Players always play harder against the team that traded them. He was a first-round pick for Chicago in 2024 and is now a cornerstone for Houston.
Actionable Next Steps:
- Check the weather forecast 24 hours before the May 22nd opener; Wrigley is a different park at 50 degrees versus 80 degrees.
- Monitor Jeremy Peña’s health—he had rib issues in the last series against Chicago and his defensive range is vital for Houston's pitching staff.
- Secure tickets early for the Wrigley series, as the 2026 matchups are expected to be sellouts given both teams' standing in their respective divisions.