The Chicago Cubs (72-53) and Chicago White Sox (65-58) meet for another round of the Crosstown Classic or Windy City Showdown, whatever you call, it's a meeting the city of Chicago looks forward to. The White Sox went 2-1 versus the Cubs in the first half of the season. The White Sox outscored the Cubs, 22-21. The White Sox have won three consecutive games, four of the last five, and six of the previous eight. The offense has been cooking in the past week with an MLB-best 37 runs scored over the past six games. The White Sox are hitting .285 (2nd) and top three in SLG, OPS, and OBP during that span. The Cubs offense on the other hand is scoring runs, but not getting on base as often as you'd think. The Cubs have a .219 batting average (21st), but have scored the second-most runs (31) behind the White Sox in the last six games. The two teams are atop of the standings as well when it comes to home runs in that span with 11 and 12. Luis Castillo and Shota Imanaga take the mound at Wrigley Field for opener — let's see how many runs we get tonight! Let’s dive into tonight’s matchup and find a sweat or two. We’ve got all the info and analysis you need to know ahead of the game, including the latest info on the how to catch first pitch, odds, recent team performance, player stats, and of course, our predictions, picks & best bets for the game from our modeling tools and staff of experts. Follow Rotoworld Player News for the latest fantasy and betting player news and analysis all season long. Game details & how to watch White Sox at Cubs
Date: Monday, August 17, 2026 Time: 8:05 PM EST Site: Wrigley Field City: Chicago, IL Network/Streaming: MLB TV
Never miss a second of the action and stay up-to-date with all the latest team stats and player news. Check out our day-by-day MLB schedule page, along with detailed matchup pages that update live in-game with every out. Odds for the White Sox at the Cubs The latest odds as of Monday:
Moneyline: Chicago Cubs (-161), Chicago White Sox (+150) Spread: White Sox +1.5 (-155), Cubs -1.5 (+128) Total: 8.0
Probable starting pitchers for White Sox at Cubs
Monday's pitching matchup (August 17): Luis Castillo vs Shota Imanaga
White Sox: Luis Castillo
2026 stats: 110.2 IP, 4-9, 4.96 ERA, 1.35 WHIP, 101 K, 35 BB
Cubs: Shota Imanaga
2026 Stats: 137.1 IP, 8-9, 3.74 ERA, 1.10 WHIP, 130 K, 29 BB Who’s Hot? Who’s Not
Pete Crow-Armstrong is hitting .230 in August (14/61) with four home runs and 12 RBI Alex Bregman is hitting .276 in August (16/58) with five home runs and 14 RBI Seiya Suzuki is hitting .291 in August (16/55) with three home runs and 13 RBI Munetaka Murakami is hitting .189 in August (10/53) with four home runs and six RBI Colson Montgomery is hitting .179 in August (10/56) with 26 strikeouts and four walks
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The Cubs are 61-64 ATS The White Sox are an MLB-best 74-49 ATS The Cubs are 67-56-2 to the Over, ranking sixth-best The White Sox are an MLB-best 70-51-2 to the Over The Cubs are 27-35 ATS at home, ranking fifth-worst The White Sox are 35-27 ATS on the road, ranking fifth-best
Expert picks & predictions for tonight’s game between the White Sox and the Cubs Rotoworld Bet Best Bet Please bet responsibly. If you or someone you know has a gambling problem, call the National Gambling Helpline at 1-800-522-4700. Our model calculates projections around each moneyline, spread and over/under bet for every game on the MLB calendar based on data points like past performance, player matchups, ballpark information and weather forecasts. Once the model is finished running, we put its projection next to the latest betting lines for the game to arrive at a relative confidence level for each wager. Here are the best bets our model is projecting for Monday's game between the Cubs and the White Sox:
Moneyline: NBC Sports Bet is recommending a play on the White Sox on the Moneyline. Spread: NBC Sports Bet is leaning towards a play ATS on the White Sox at +1.5. Total: NBC Sports Bet is recommending a play on the Over on the Game Total of 8.0
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