You're going to have a toll between Indiana and Chicago, I forget the amount its not terrible, not like Northeast turnpikes. Word of caution, if you hit Chicago at the wrong time it will eat up 2+ hours. Locals can give you more info but by wrong time I mean anytime between 7am and 8pm. Midday might be ok. I debated going the north route from VA on my way home for the scenery, I was exhausted on the way back and solo so I stayed south. I kind of wish I had done it as I will probably not have the opportunity again. Do not plan to buy ammo in Illinois. The route through Il, WI, MN, SD, ND seems to have a Cabelas or Rogers every 200 miles or so. If you plan to spend a night in Grand Forks, check the college hockey schedule, all hotels will be booked if it is a region match up, or maybe stop in for a game.