I'm beginning to plan a tour around the perimeter of Lake Michigan next summer. However, I'm struggling with the reach from Madison to South Bend. I know that there is a ferry from Milwaukee to the eastern shore, but I would prefer to ride around the south side of the lake (to do a full circumnavigation). Anyone have any advice on routes through or around the Chicagoland area? Also, is Gary (IN) really as bad as I've heard?

Thanks folks