Reddit reviews City of the Century: The Epic of Chicago and the Making of America

Northwestern Territory, yes. But Illinois has a greater claim on Wisconsin rather then the other way around.

If it makes you feel better, Wisconsin was basically deforested to build Chicago (pre-fire, 1871. Source: William Cronon's "Nature's Metropolis")

And the Green Bay-Chicago rivalry transcends football. After the revolution, Chicago, St. Louis, Green Bay, and Cincinnati all competed to be the nexus for trade and goods moving from the western frontier to the East Coast and on to Europe. Chicago actually lagged for several reasons: Shipping would include an annoying portage from the Illinois to Chicago Rivers, and Chicago was an ice or mud locked malarial swamp for much of its early history.

But while the other cities invested heavily into their water passages, Chicago gambled and came up big on the newer technology of railroads. After most of Chicago burned to the ground in 1871, Green Bay began to attract significant investment from New York and Boston betting Chicago would take decades to recover. (Source: Donald Miller's "City of the Century")

The hands down best book on Chicago history (and I've read almost all of them) is The City of the Century by Donald Miller it can be had on Amazon for 0.01 (plus shipping)

City of the Century by Donald Miller. Epic read, but totally worth it.