Illinois has become one of the biggest legal sports betting markets in the country since it started taking online wagers in June of 2020. That’s not surprising considering Chicago is a sports-obsessed town in which Al Capone ran a dog racing track and countless illegal betting shops throughout the 1920s.

It’s also home to one of the best rivalries in baseball, with the White Sox and Cubs set to meet for the first time this season August 6-8 at Wrigley Field.

The 2021 Crosstown Classic is sure to attract a ton of betting interest at Illinois sportsbooks as the only show in town, with the Bears still in training camp, and Bulls and Blackhawks off until the fall. And while the Cubs have enjoyed the upper-hand lately, things have changed dramatically on the North Side in recent months.

The Cubs have split or won their season series with the White Sox every year since 2014. The two teams split four games in 2019 and six games in 2020, with the White Sox taking two of three at Wrigley last season. The White Sox also lead the all-time series 68-63, and it’s dead even at 32-32 for regular season games at Wrigley.

While the Cubs have definitely turned the tide in this rivalry lately, it’s possible the White Sox could be favored in all three games on betting apps, depending on the pitching matchups. Kyle Hendricks has been the only consistent, reliable Cubs starter this season, and sportsbooks could favor him in a potential game against Dallas Keuchel. Elsewhere, the storylines are pretty clear – advantage, White Sox.

The White Sox are one of the best teams in baseball and enjoy a big lead in the AL Central. It’s been a bit of a bumpy road and the hiring of manager Tony La Russa – a move many questioned in the offseason – predictably led to internal tension in the early months. But an excellent starting rotation and a strong lineup filled with young bats has the White Sox poised to win their division for the first time since 2008.

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The Cubs were sellers at the deadline as time expired on their unprecedented six-year run of success, which included their first World Series in more than a century. Letting go of Kyle Schwarber and Yu Darvish in the offseason hurt even more in retrospect given the seasons they’re having in Washington and San Diego, respectively.

The Cubs have hovered around .500 all season but might have some value as an underdog in this series. They’re 31-20 at Wrigley this season and the White Sox are just 25-26 on the road. MLB betting fans should keep in mind, however, the Cubs aren’t used to opposing fans invading their home field. It might be not-so-friendly confines for the Cubs with thousands of Sox fans in attendance, especially if the Cubs ship star players like Kris Bryant and Anthony Rizzo before the trade deadline.

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As for Over/Under betting, we can blindly recommend the Under on the total in all three games. The wind gets plenty of attention but bookmakers always adjust their MLB odds to take it into account, and it’s just as likely to blow the other direction and help pitchers. The Under has hit at a 56.7% clip at Wrigley this season, making it the second-best Under park in the majors behind Nationals Park.

One thing is for sure – the weather will be warm, the drinks will be flowing, and the betting action will be off the charts all weekend as the Windy City Showdown returns to Chicago.