I mean, yes, Madison is heavily planned. But so is any city you build on an isthmus. You have to heavily plan the layout or it won't work. At the same time they made a north-east flowing layout. Now it may be a "grid" if you rotate a grid 45%, but when someone generally thinks of "grid", they think of a grid oriented in cardinal directions. Obviously, this is not possible in Madison because of two giant lakes.

Minneapolis has more of a "grid" layout that most people would consider a true "grid" layout.

Milwaukee and Chicago obviously have grid layouts on steroids because of their history and the nature of the original people inhabiting those places. They are places built for moving men and material to the front so to speak. And they don't too much care what they have to do to make that possible. Giant hill of rock in the way? They'll happily blow right through it. City keeps flooding because it's basically a swamp/marsh? No problem, they casually lift the entire city into the air and continue right on building. Just a whole lot of things most other places probably wouldn't do.