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The latest edition of the Crosstown Classic begins Monday night as the Chicago White Sox (65-58) take on the Chicago Cubs (72-53) to open a three-game series at Wrigley Field in Illinois. The crosstown rivals last met in mid-May at Rate Field, with the White Sox earning a 2-1 series victory, including a 10th-inning walk-off two-run home run by Edgar Quero in the finale.

The White Sox continue to be a surprise team this year, leading the AL Central after entering the season without particularly high expectations. The Cubs, meanwhile, are coming off a series loss to St. Louis over the weekend but have enjoyed a successful season of their own, entering Monday with the fifth-best record in MLB and holding the top National League Wild Card spot.

Cubs left-hander Shota Imanaga is set to make his 25th start of the year in Monday night’s opener, bringing a 3.74 ERA into the matchup. The White Sox will counter with veteran right-hander Luis Castillo, who’s enduring one of the worst seasons of his career. This will be Castillo’s third start since being acquired from Seattle at the trade deadline, and although he struggled in his White Sox debut, he’s coming off an excellent start in which he tossed seven shutout innings of one-hit baseball while also recording a season-high 10 strikeouts in a win against Cincinnati.

White Sox vs. Cubs Odds

Hard Rock Bet Sportsbook lists the Cubs as home favorites for Monday night’s Windy City showdown:

  • Moneyline: Cubs -155, White Sox +145
  • Run Line: Cubs -1.5 (+135), White Sox +1.5 (-145)
  • Total (Runs): Over 8.5 (+105), Under 8.5 (-115)

Hard Rock Bet’s 10Ā¢ Summer Sale is giving players another reason to get in on the MLB action throughout August. Qualifying pregame Moneyline, Run Line, and Total markets feature reduced-vig dime lines, meaning tighter odds and more value on eligible wagers.

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White Sox vs. Cubs Predictions for the Crosstown Classic

Don’t miss out on the chance to get in on the Crosstown Classic Monday night, so head over to Hard Rock Bet Sportsbook and check out the Stats Hub for baseball betting insights and trends to help make picks like the one below:

Cubs vs. White Sox Best Bet: Cubs Moneyline (-155)

Depending on which version of Luis Castillo the White Sox get, Monday night’s series opener could very well turn into a pitchers’ duel. Both starting pitchers have had plenty of success at the big league level, but with how the season has gone for each of them, the advantage goes to Shota Imanaga.

Imanaga had a rough outing his last time out, but before that, he allowed only one earned run against the Los Angeles Dodgers in his first start of August and had posted a 1.53 ERA across five starts in July.

The kicker here could be that the Cubs haven’t necessarily been scoring a ton of runs lately, averaging just 2.75 runs per game over their last four. The Cubs do, however, have one of the best run differentials in MLB this season.

While it doesn’t have much to do with this season since the only meeting between the two teams took place at Rate Field, the Cubs have won six consecutive games against the White Sox at Wrigley Field.

  • Cubs vs. White Sox Moneyline Pick for Aug. 17: Cubs (-155)

Top 5 Most-Bet Player Props for CWS-CHC

Pete Crow-Armstrong, Munetaka Murakami, and Miguel Vargas each hit a home run Sunday and are among the league leaders in home runs this season, making their home run props the top three most-bet player props heading into first pitch Monday night:

  1. Pete Crow-Armstrong – Over 0.5 Home Runs
  2. Munetaka Murakami – Over 0.5 Home Runs
  3. Miguel Vargas – Over 0.5 Home Runs
  4. Pete Crow-Armstrong – Over 0.5 Hits
  5. Shota Imanaga – Over 5.5 Strikeouts

White Sox vs. Cubs Game Info

  • šŸ“ Where: Wrigley Field, Chicago, IL
  • šŸ“… Date: Monday, Aug. 17
  • ā° First Pitch: 8:05 PM ET
  • šŸ“ŗšŸ’» TV/Streaming: MLB.TV
  • ⚾ Probable Pitchers:
    • White Sox: Luis Castillo
    • Cubs: Shota Imanaga

More Ways to Bet

One swing can cash your ticket, but until then, Florida players can keep things interesting with Real Money Games powered by Past Motor Racing, only on Hard Rock Bet. It’s another way to stay engaged between plate appearances.

Referenced odds are subject to change.

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Michael Hennelly

Michael has been an active sports contributor for multiple publications since graduating from Penn State in 2024. While sports play a major role in his life (in the best way), he also enjoys spending time with family and friends. Contact Michael at michael.hennelly at hardrockdigital.com.