From where we live probably 3 hours, from my old place 2.5 hrs. I tend to have a lead foot and lead wrist when riding long distances. I went from Palatine to U of I in roughly two hours once, I then went from U of I to ISU in 30.. good time.
"Ho Chunk" would be the name of the casino.
Madison is about 3.5 hours from Minneapolis by cage. By bike it would be a little more. We would have to make this a two day event for it to make sense for me. There is some good riding in southern WI, we just need to dig in and plan some routes and a place to stay.