I wouldn't necessarily expect you to know this but Milwaukee is east of the Mississippi. The Mississippi runs along the western WI border with MN through the Twin Cities southward. Milwaukee is in South Eastern WI on the shore of Lake Michigan just about 80 miles or so north of Chicago.

Regardless your point is well taken the Midwest is much more spread out than New England for sure. I also feel like the Midwestern cities are "newer" i.e. they were founded after the advent of modern urban planning which I think makes a difference.