Anywhere in the country can have bad weather in winter. But the poster above is right … this isn’t Siberia. People drive between Chicago and Michigan every single day of the year. There’s no reason to assume you can’t or to act all scared about it, until / unless a storm hits. I got stranded at the Philly airport for 5 days in 2010 and I got stranded in NY last year and had to take Amtrak back to Chicago because the flights were down, but I don’t have to act as though traveling to the East Coast is such a big scary deal.