Madison is a great place to live: beautiful scenery, low stress, low traffic, great for outdoorsy stuff, and full of laid back Wisconsinites. Chicago, while okay for a big city has its problems. Even driving through Chicago is like asking for an aneurysm. Madison's politicians might have a horrible ideology but at least most of them aren't crooks. Also Madison is way better for crime.
Lol I'd love to hear why
It takes like three hours to drive from one side of the city to another, you should expect to be randomly cut off like six times, and no one bothers with traffic laws whatsoever. Whatever it is, it certainly isn't an enjoyable experience.
Also, the tolls are excessive.