Chicago Cubs vs Chicago White Sox Prediction 5/16/2026 Today’s MLB Picks

In this article, we will formulate a Cubs vs White Sox Prediction for this MLB matchup on Saturday, May 16th in the second game of this series. Let’s take a look at the prediction for this MLB matchup.

Chicago White Sox Preview

The Chicago White Sox have a 22-22 record this season and are sitting in the second place of the AL Central. They have a 12-10 home record and are coming off a 5-10 loss at home against the Cubs. They will face the Mariners and the Blue Jays next.

The White Sox have a .234 batting average this season, .324 OBP and .401 Slugging percentage. Chicago’s pitching staff has a 4.35 ERA and 1.37 WHIP. Chase Meidroth is the team’s best hitter with a .277 batting average. Colson Montgomery leads the team in RBI with 30, and Munetaka Murakami adds a team‑high 15 home runs.

Davis Martin (R) is the projected starting pitcher for the White Sox, and he has a 5-1 record, 1.62 ERA and 1.00 WHIP.

Chicago Cubs Preview

The Chicago Cubs have a 29-16 record this season and are sitting in the first place of the NL Central. They have a 11-11 away record and are coming off a 10-5 win on the road against the White Sox. They will face the Brewers and the Cardinals next.

The Cubs have a .247 batting average this season, .343 OBP and .404 Slugging percentage. Chicago’s pitching staff has a 3.80 ERA and 1.19 WHIP. Nico Hoerner is the team’s best hitter with a .264 batting average, also leading the team in RBI with 29. Ian Happ adds a team‑high 10 home runs.

Jameson Taillon (R) is the projected starting pitcher for the Cubs, and he has a 2-2 record, 3.94 ERA and 1.14 WHIP.

The Chicago Cubs @ the Chicago White Sox Betting Trends: May 16, 2026

• Probable Starting Pitcher: Davis Martin      Record this season: 5-1      ERA: 1.62
• Home Record: 2-0
• Last 5 against Cubs: –

Why the Chicago White Sox will win

• The White Sox have won six of their last seven games as home underdogs after playing the previous day.
• The Cubs have lost four of their last six games as favorites against American League opponents following a win.
• The White Sox have covered the run line in each of their last eight games as underdogs against National League opponents following a home loss.
• The Cubs have failed to cover the run line in nine of their last 10 games against AL Central opponents following a win.
• The White Sox have led after 5 innings in four of their last five night games.

• Probable Starting Pitcher: Jameson Taillon      Record this season: 2-2      ERA: 3.94
• Road Record: 1-2
• Last 5 against White Sox: 1-0

Why the Chicago Cubs will win

• The Cubs have won each of their last nine games against the White Sox following a win.
• The White Sox have lost 19 of their last 20 home games against NL Central opponents following a loss.
• The White Sox have failed to cover the run line in 14 of their last 15 Saturday night games against teams that held a winning record.
• The Cubs have covered the run line in each of their last six Saturday games against AL Central opponents.
• The White Sox have lost the first inning in three of their last four games against NL Central opponents that held a winning record.
• The Cubs have led after 5 innings in eight of their last 10 night games against American League opponents.

Total Runs Facts

• Each of the White Sox’s last four games have gone OVER the total runs line.
• Six of the Cubs’ last seven games have gone UNDER the total runs line.
• The ‘Inning 1 UNDER 0.5 runs’ market has hit in each of Jameson Taillon’s last seven road appearances as a starter.
• The ‘Inning 1 OVER 0.5 runs’ market has hit in seven of the White Sox’s last eight games as underdogs.

Chicago White Sox Player Prop Facts

• Miguel Vargas has hit a home run in each of the White Sox’s last two home games against opponents that held a winning record.
• Miguel Vargas has recorded at least one hit in each of the White Sox’s last 17 games as underdogs.
• Davis Martin ranks 2nd amongst qualified players for Earned Run Average (1.62) this season.

Chicago Cubs Player Prop Facts

• Jameson Taillon has recorded a win in each of his last four appearances with his team as a road favorite against AL opponents.
• Jameson Taillon has recorded five or more strikeouts in five of his last six appearances against AL Central opponents.
• Alex Bregman has recorded at least one hit in each of the Cubs’ last 10 night games.
• Michael Conforto has hit a home run in two of his last three road appearances against the White Sox.
• Pete Crow-Armstrong ranks 10th in the league in Steals (11) this season.

Matchup/League Facts

• The White Sox rank 30th in the league for doubles this season (52).
• The White Sox rank T4th in the league for home runs this season (59).
• The Cubs rank 1st in the league for on-base percentage this season (.343).
• The Cubs rank 1st in the league for walks this season (210).

Cubs vs White Sox Prediction

The Cubs are 9-1 in their last 10 meetings against the White Sox and are 5-1 in their last 6 visits in Chicago.

In this Cubs vs White Sox Prediction, the Cubs are coming as -115 road favorites. Davis Martin takes the mound for the White Sox and he has been elite this season, he has given up one run or less across his last five starts and has been unhittable at home with a 0.77 ERA. Taillon has been weaker on the road for the Cubs, who also rank just 23rd against right-handed pitching in the month of May, so I like the value with the home dog today. Take the White Sox on the moneyline.

Nikos Lagouretos's Pick: Chicago White Sox ML