There’s no doubt that Chicago loves baseball, although the hearts of passionate fans are divided between either the Cubs or the White Sox. Each team can boast three World Series titles apiece, while the Windy City Showdown series currently favours the White Sox by 65-63.

Considering the relative success of both franchises, it’s actually quite remarkable the Cubs and the White Sox have met just six times in the postseason, with the White Sox also leading that series 4-2. Even more incredible taking their histories into account, these two baseball teams have met just once in the World Series, way back in 1906, with the White Sox victorious.

Despite the slim chances of that unique event ever being repeated, both the Cubs and the White Sox are enjoying strong 2021 regular season campaigns. Respectively, both teams are within the top three of the American League (White Sox) and the National League (Cubs) standings.

The White Sox currently top the AL Central with relative comfort, boasting an impressive .619 win percentage at the time of writing. Third in the overall MLB standings, they are genuinely considered one of the leading candidates to win the 2021 World Series, according to many of the leading online sportsbooks.

Meanwhile, the Cubs are also looking strong this year with their .571 win percentage. They are locked in battle with the Milwaukee Brewers for leadership of the NL Central, albeit with a big run differential advantage over their divisional rivals. Despite being amongst the top ten teams in the MLB at present, sportsbooks consider the Cubs as longshots for the World Series.

While both teams are doing well, there’s every chance of the two Chicago franchises continuing their form into the postseason. Just imagine the euphoria amongst baseball fans in the city if both teams made it all the way to a historic second World Series encounter. Along with being in utter defiance of the latest baseball odds and probabilities, it would be fascinating for the sport.

Before getting too excited, however, check out some betting information first and read this article from about which sites offer the best casino and sportsbook promotions. Odds and offers can vary more than the form of our beloved Chicago baseball teams, over the last few years. That’s why it’s always good to read plenty of reviews, make comparisons, then bet safely and securely.

In terms of individual chances, the Cubs boast a more consistent record of reaching the MLB Playoffs. In five of the last seven seasons, they have participated in the postseason, even going all the way to win the 2016 World Series, beating the Cleveland Indians 4-3. That year Kris Bryant won the MLB Most Valuable Player Award.

By comparison to the Cubs, since the Chicago White Sox last reached and won the World Series in 2005, and they have only managed to reach the postseason twice in the last fifteen years. Nevertheless, they are widely tipped as genuine World Series contenders this year and who knows, it could be duelling against the Cubs. So, it’s all to play for!

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