Cubs, White Sox 2020 World Series Odds: All-Chicago Finale A Real Possibility

Written By Joe Boozell on September 21, 2020 - Last Updated on March 3, 2021

It’s been a tumultuous year in Chicago, to say the least, but the city’s baseball teams have served as a few rare bright spots.

The Cubs and White Sox are in first place in the NL and AL Central, respectively. And both have realistic World Series hopes.

Here are the 2020 World Series odds at Illinois‘ five online sportsbooks.

Cubs, White Sox 2020 World Series odds

DraftKingsFanDuelPointsBetWilliam HillBetRivers
White Sox+1000+1000+1000+1000+1000
Blue Jays+4000+3600+4000+3500+4000

The White Sox are 10-1 to win the World Series across the board, while William Hill is most bullish on the Cubs’ chances.

The Southsiders are in the midst of their best season in a very long time.

In 2005, the Sox won the World Series and notched 99 regular-season wins. That was good for a .611 winning percentage.

Fast-forward 15 years and the Sox have a gaudy .642 winning percentage — adjusted for 162 games, that’s a 104-win pace.

White Sox outlook

The biggest reasons for Chicago’s dominance? Tim Anderson and Jose Abreu, who are strong 2020 AL MVP candidates.

Anderson is slashing .360/.395/.601, while Abreu is slashing .335/.381/.651. Abreu leads the AL in WAR, with Anderson about .6 wins behind him.

The Sox have a +75 run differential, tops in the AL and third among all teams behind the Dodgers and Padres. The record is excellent, and the advanced numbers say they are every bit as good as their record indicates.

Run prevention has also been a low-key strength for the Sox this season, as they rank fourth in baseball with a 3.53 team ERA. And yet, that’s their perceived weakness going into the postseason.

Lucas Giolito and Dallas Keuchel inspire confidence out of the first two slots in the rotation, as they should. Keuchel has a 2.04 ERA, and Giolito ranks third in the AL in strikeouts.

But there’s uncertainty after that duo. Rookie Dane Dunning will likely be Chicago’s No. 3 playoff starter; he was injured all of 2019 and hadn’t pitched above AA before this year.

With that said, he’s been excellent in 2020, compiling a 2.33 ERA in five starts. But the Sox are putting a heavy burden on someone with single-digit MLB starts.

Dylan Cease is the Sox’s likely No. 4 starter, and he walked seven batters in his most recent start. His 3.52 ERA is solid, but he’s been the beneficiary of good luck. Cease’s FIP is an ugly 5.92, and he rarely makes it past the 5th inning.

Are the White Sox good enough to win it all? Of course. Are they the best team in the AL? One could reasonably make that case.

But the holes are real, and Chicago’s World Series hopes likely rest on Dunning and Cease.

Cubs outlook

The Cubs season in 2020 is, like a lot of things, weird.

They are leading the NL Central by 3.5 games at 31-22. But with a run differential of just +21, their expected record is 29-24, suggesting they’ve been a bit lucky.

The Cubs’ two best offensive players are Ian Happ and Jason Heyward (1.3 WAR apiece). Two of their worst players are Javier Baez and Kris Bryant, who are both hitting around .200. If the Cubs want to have any shot of making a deep postseason run, they need Baez and Bryant to return to form.

The good news for the Cubs is that they have one of the best 1-2 pitching duos in the game in Yu Darvish and Kyle Hendricks. Darvish and Hendricks both have sub-3 ERAs, and the former is striking out 11.5 batters per nine innings. Since the opening round of the playoffs is best-of-three, that’s huge.

But like the White Sox, there are questions after that.

With a 4.91 ERA, 36-year-old Jon Lester is on his last legs. Alec Mills has been solid, but he was a journeyman before 2020 and isn’t going to scare most teams (unless you’re the Brewers on an NFL Sunday).

The bullpen, the Cubs’ biggest question mark going into the season, has exceeded expectations.

And unlike the White Sox, the Cubs have a clear powerhouse in their league in the Dodgers, who are the best team in baseball. Los Angeles has a .704 winning percentage and is the consensus World Series favorite.

Is this really the year the Cubs and Sox could meet in the World Series?

The Cubs and White Sox haven’t met in the World Series since 1906. Chicago baseball fans have long fantasized about a crosstown finale.

There’s a legitimate (albeit outside) chance it could happen in 2020 … and it wouldn’t take place in Chicago, or with fans in the stands.

That’s because the World Series is set to take place in Arlington, Texas, at the new Globe Life Field.

Bizarre? Sure. Hilariously on brand for 2020? You bet.

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Joe Boozell

Joe Boozell has also been a college sports writer for since 2015. His work has also appeared in Bleacher Report, and Growing up, Boozell squared off against both Anthony Davis and Frank Kaminsky in the Chicagoland basketball scene ... you can imagine how that went.

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