Downtown Madison is sandwiched between 2 lakes, and most of the city orients North East for the roads that run between them.
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.
This is presuming that Madison roads "work", but they don't! They're a mess.
Note also that the state capitol was originally built at the present site in 1837, before the rise of the automobile. And North Hall, the first building on the University of Wisconsin campus, was built in 1851. I'm not aware of any grand road plan.
Another interesting thing not talked a lot about online is that these midwest cities typically have a ton of documented (or not?) underground tunnels. There used to be a cool website for the Twin Cities (Minneapolis/St. Paul) that showed them off. My parents recall walking from the University of MN to further parts downtown where you can transition to skyways and basically never go outside. I guess -40' weather really pushes people to become moles in a sense. I think a lot of big cities also have huge tunnel systems for heating fuel (coal delivery and the like) and other utilities
