The World Series are set to last between 25 October and 2 November, if the series is taken to a Game Seven, which would conclude half a week before the All Blacks take on Ireland at the 61,500-capacity Soldier Field in the first match of their tour to the USA and Europe.
The Cubs are scheduled to host Games Three, Four and Five of the series, where the series would be beginning to peak, meaning more media coverage, more hype and rising viewing figures in Chicago and the United States.
During that time period would be roughly when the All Blacks, who took on the USA Eagles in front of a sold out crowd at the same venue in 2014, dot down in Chicago to prepare for their test against the Irish, before playing them on November 6.
If the Cubs come away with a historic title within the next week, the task of exposing and expanding the All Blacks' brand in Chicago and the United States will be made more difficult, with the key reason for hosting an All Blacks test in the United States being for both financial and brand exposure purposes.
Other highly popular sports in the region could also restrict the amount of attention Steve Hansen's side receives in the States.
The city's NHL side, the Chicago Blackhawks, face off against the Dallas Stars on the day of the All Blacks' test against Ireland, while also hosting three games in the week leading up to the test.
Interest in the NBA will also be high with the 2016-17 season being just a few days old, and the Chicago Bulls will also be playing three games during the week of the test.
Fortunately for the New Zealanders, Soldier Field has already sold out for the match like it did the last time the three-time world champions played there, meaning the All Blacks won't need to drive ticket sales on their day off.
The All Blacks then travel to more familiar territory following the Ireland clash in Chicago, facing of against Italy, Ireland - again - and France in Rome, Dublin and Paris in the following weeks.