An all‑Chicago Fall Classic this October is highly unlikely, but historically the odds have never been great.

Bradford Doolittle notes that when the White Sox and Cubs both finish as contenders, the assicurated chance of a Windy City World Series is about 63‑to‑1. Over the modern era, there have been only 11 seasons where both teams were in contention on Aug. 17, and just three back‑to‑back years of dual contention.

The only times both clubs made the postseason are 1906, 2008, and the shortened 2020 season. In 1906, the Cubs won a record 116 games and the White Sox topped the AL, setting the stage for a historic showdown.

The best odds for an all‑Chicago series came in 1907 (2.8‑to‑1) and 1906 (3.3‑to‑1), yet the 1906 World Series was the only time the rivalry reached the Fall Classic, with the South Siders winning in six games.