Chicago Cubs

Chicago Cubs vs Chicago White Sox Prediction, Odds and Picks for Today, 05/16/26

Rate FieldCHSN, MARQ, WCIU
Cubs
29-16
Cubs
Today
White Sox
22-22
White Sox
Chicago White Sox
Google News

Cubs vs White Sox Pickswise Expert Predictions

Money Line Pick
CHI White Sox Win(-105)

The Chicago White Sox couldn’t contain the Chicago Cubs offense on Friday night that erupted for 10 runs, helping them cruise to a 10-5 victory. Today, the White Sox are hoping for a different outcome as they send one of their more reliable starters to the mound, Davis Martin. On the season, Martin is 5-1 with a 1.62 ERA, 1.00 WHIP, and has struck out 52 hitters in 50 innings pitched. For the Cubs, they’ll hand the ball over to Jameson Taillon who is 2-2 with a 3.94 ERA, 1.14 WHIP, and has struck out 40 in 45.2 innings pitched. 

The Cubs offense was quiet over their last five games, until last night. Looking at their last 10 days, the Cubs are averaging 10 runs per game and hitting .203 while they hold a 3.48 team ERA. For the White Sox, they’re averaging 5 runs per game and hitting .262 in that same span, while holding a 4.70 team ERA. A big concern heading into this matchup, and we saw it last night, was the White Sox bullpen. Martin will be facing a tough Cubs squad, and he’ll need to eat up plenty of innings if he wants to keep his team in it. Despite the White Sox bullpen struggling last night, I like Martin and the White Sox in this spot. The White Sox did a great job at hitting the ball last night, and I trust Martin on the mound a lot more than I do Sean Burke. Look for the White Sox to rally behind Martin and help him pick up his sixth win of the season.

Cubs vs White Sox prediction: White Sox ML (-105) at the time of publishing. Playable up to -125.

Photo of Jason Fragomeni

Jason Fragomeni

Jason Fragomeni is a MLB sports writer for Pickwise who lives in New York and is a huge fan of the New York Yankees and New York Giants. Jason is a data/statistic fanatic and he’s learned how to apply statistical analyses into the sports betting world. Jason uses data every day to help him determine what picks have the greatest probability of winning, which has helped him when it comes time to make a wager. Jason has been in the sports industry for over 10 years now, and has a wealth of knowledge surrounding sports and is a sports bettor by hobby.
Read more about Jason Fragomeni