White Sox vs. Cubs Lineup: No Colson Montgomery? A Big Night for Luis Castillo, More

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After a series sweep against the Detroit Tigers, the Chicago White Sox will face the Chicago Cubs in a much-anticipated Crosstown series. With a lefty on the mound, the White Sox will go with their righty-heavy lineup.
Game Info
Who: Chicago White Sox (65-58) vs. Chicago Cubs (72-53)
Where: Wrigley Field
When: 7:05 CT
Watch: CHSN, WCIU TV
Listen: ESPN Chicago WMVP 1000 AM
Chicago White Sox Lineup
1. Chase Meidroth, 2B
2. Munetaka Murakami, 1B
3. Miguel Vargas, 3B
4. Randal Grichuk, DH
5. Braden Montgomery, RF
6. Brenton Doyle, CF
7. Sam Antonacci, LF
8. Luisangel Acuña, SS
9. Jake Rogers, C
Will Venable will roll with a righty-heavy order against Cubs starter Shota Imanaga. The red-hot Chase Meidroth will lead off, followed by Munetaka Murakami and Miguel Vargas, per usual. Randal Grichuk will be DH'ing in the cleanup spot. Grichuk has not hit a home run since June 24 but has gotten the job done with a .299/.319/.493 slash line in his last 30 games.
Braden Montgomery, on a mini hot streak of his own, will bat fifth. One player who is absent in Monday's game is shortstop Colson Montgomery. While Colson has struggled overall in the past couple of months, he hits better against left-handers and is likely getting a scheduled off day.
Tristan Peters will also be out of the lineup, with Brenton Doyle facing the left-hander. Sam Antonacci will be in the lineup. It looks like Venable is finally giving him reps against southpaws. Luisangel Acuña and new addition Jake Rogers will round out the lineup. Rogers is slashing .261/.333/.435 against lefties this season in a limited sample size (23 at-bats).
Chicago Cubs Lineup
1. Pete Crow-Armstrong, CF
2. Seiya Suzuki, RF
3. Michael Busch, 1B
4. Alex Bregman, 3B
5. Ian Happ, LF
6. Nico Hoerner, SS
7. Pedro Ramírez, 2B
8. Michael Conforto, DH
9. Carson Kelly, C
On The Mound...

Chicago White Sox - Luis Castillo, RHP
It has been an up-and-down first two starts for Luis Castillo, who was acquired from the Seattle Mariners at the trade deadline. In his first start against the red-hot Boston Red Sox, he faltered, giving up five runs in four innings. In his next start against the Cincinnati Reds, he pitched seven shutout innings, giving up just one hit and striking out 10 batters. That's the Castillo the White Sox will need to have in order to defeat the Cubs on Monday.
This Cubs team has seen Castillo a lot from his time with the Reds. Alex Bregman, Michael Busch, MIchael Conforto, and Ian Happ all have home runs in their careers off of Castillo. Nico Hoerner also has had a solid career in 11 at-bats against Castillo.
Chicago Cubs - Shota Imanaga, LHP
The left-hander gave up seven runs in just three innings in their last matchup in 2025. Imanaga has a 3.74 ERA this season in 24 starts. While he has put it together in his last seven starts (2.31 ERA), he has still given up a lot of home runs this season (28).
The White Sox could have a field day against Imanaga if the ball is flying at Wrigley!

Matthew Singer is a contributor for White Sox on SI. Before joining SI in 2026, he worked for Heavy as an MLB contributor and Cubs on SI. Singer has a master's degree in sports journalism from the Walter Cronkite School of Journalism and Mass Communication at Arizona State University. He loves sports more than anything in the world.