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Based on this interesting little article i found.
Context: IOTL, there was dispute between the US states of Wisconsin and Illinois over the boundary dividing them, especially over the city of Chicago, which would prove useful a few years down the line as an outlet for Lake Michigan. Through the manoeuverings of a lawyer sympathetic to Illinois named Nathaniel Pope, Illinois managed to wrest the Chicago area and the lands to its west from the territory of Wisconsin in 1818, setting back the latter's statehood by thirty years.
But what if the "Chicago strip" had gone to Wisconsin instead? Could Illinois, now dominated by its southern portions, end up becoming a slave state?