The World Series: Chicago Cubs and Cleveland Indians Betting Preview


The Cleveland Indians will face the Chicago Cubs in this year’s World Series, which means that one of these teams will end their long championship drought. The first game of the Fall Classic takes place on Tuesday, October 24th at Progressive Field in Cleveland. It will be televised on FOX.


Game 1 starters will be Jon Lester for the Cubs and Corey Kluber for the Indians. Chicago has announced starters for the first three games. Jake Arrieta will start Game 2. Kyle Hendricks will go in Game 3 and John Lackey in Game 4. Cleveland has tentatively announced Trevor Bauer for Game 2 and Josh Tomlin in Game 3.

Series Prices

At, the Cubs are big favorites, currently going at -195 to win the World Series. The Indians, the underdogs, are at +170. If you’re looking to bet the Cubs, you can get a slightly better price at where they are at -190.

Those interested in MLB proposition will have a large list of markets to choose from for the World Series. All three of our top-rated sportsbooks (which are shown below), have a lot of betting options when it comes to props and alternative lines.

October 2023 Safest Betting Sites

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  • 1
    100% Up To $2,500
  • 2
    50% Up To $250
  • 3
    100% Up To $1,000
  • 3
    100% Up To $750
  • 4
    50% Up To $1,000
  • 4
    Bet €10 To Get €30
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    100% Up To £30

Field of Dreams

Baseball is happy when they get a large market team, especially one with such a large fan base as the Cubs. The Indians are a small market team, but the city has been much more on the map since LeBron James guided the Cavaliers to an NBA Championship in June.

Also, aside from the Chicago Cubs, a team that saw their last World Series title all the way back in 1908 – the Indians have second-longest World Series drought. They haven’t won a title since 1948.

World Series Prediction and Free Picks

Using the odds above at BetOnline, I am partial to the Indians. These teams may be a lot more evenly matched than the odds appear. It’s tough to lay close to -200 when the Indians pitching staff, especially when their bullpen has been lights out. If these guys get a lead, the game almost always seems to be over.

Let’s also remember that series pricing has lower limits than major markets, making it less efficient in many cases. Every red blood Chicagoan male is going to be betting the Cubs in this series. If we’re looking for value, I think it’s easy to say that it’s with the Indians.

Let’s also remember there’s a fair bit of luck involved with baseball. It’s seven games, anything can happen, which is why I’m partial to getting upside with the underdog and staying away from heavy favorites.

Check back on our free picks page for picks on each game in the series, including Game 1.

Joseph Falchetti

Joseph Falchetti - Editor-in-Chief, Pro Sports Bettor and Casino Expert

Joe is the author of the majority of sports betting pages on SBS and he serves as a gambling consultant to our content team. He's been mentioned on as a gaming analyst, and his articles have been linked by larger publications, such as the New York Times.

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