> grown organically around us over a few hundred years But in the case of Chicago, nobody really lived there until recently. I'd bet that in the last thousand

> grown organically around us over a few hundred years But in the case of Chicago, nobody really lived there until recently. I'd bet that in the last thousand years or more, there were never more than 500 people living in the general area until 1820 or so. The first Europeans in the area were the French, who saw it as an amazingly good logistics hub for shipping between New Orleans and their settlements in what is now Quebec. But they had no real interest in living in Chicago any more than Native Americans - up until the "Raising of Chicago", it was a pretty terrible place to live! If you are in Chicago and come across a road that is not on a grid with intersections at 90 degree angles, there is a fairly good chance that it is centuries-old Native American path. For example, Milwaukee Ave was a path that led to (what is now) Milwaukee, Michigan City Road was a path that led to (what is now) Michigan City (where it met up with the path that went from (what is now) Detroit to (what is now) Rock Island Illinois on the Mississippi River).