As I've currently seen other questions/clarifications to other's requests for information, I will add to my question that I am driving a van (probably filled with personal posessions), I have not been to anything in the midwest other than one short trip to Chicago and I currently have no time restrictions.

I am only familiar with I 90, west of Minnesota. If this is your first trip this way the corn palace in MItchell, SD. and Wall Drug are worth a stop. It would be a shame not to explore the Black Hills (MT. Rushmore, Crazy Horse, Custer Park) at a minimum. Devils Tower is a little east of there and Yellowstone is a must if you have not been there, even if its mostly a drive through. There are many sites that are just off of the road, literally park and see. Stay one night at the Old Faithful Inn and you will never forget it. Good luck and enjoy your trip, ziggypop

With a vanfull, make up a list of good motels along your route that have 24 hour security and front desk. Then park as close as you can to the office. You'll sleep better at night.

Here's a trip report I did on Flyertalk a couple of years ago, for what it's worth. Maybe some guidance.

http://www.flyertalk.com/forum/trip-reports/685006-sea-ewr-f-then-back-ford.html

tracys2cents is a good 2 cents. If this is your own van, make sure it has a good security system and that you park it with the back doors toward the hotel in view of the entrance. Not paranoia, just caution since you are bringing your life with you.

Second, prepare for distances beyond your wildest imagining, some of them quite boring unless you are in a "Big Sky" frame of mind. Don't leave a town hungry or with less than half a tank of gas. Prepare for wind. You will be driving a high profile vehicle. April should be okay, but you could have a spring storm that puts you in a motel for a couple of days. Have plenty to read.

Go to your public library and find some Road Food and other travel guides. Buy the best or copy the critical pages.

What a great adventure to undertake. I/we have driven all over the West and love the wide open spaces and finding out how big our country really is. Suggest you buy a good styrofoam cooler and keep some ice in it for cold drinks, and also you can pick up food items to have with you for snacks, quick meals when needed - and even for possible emergencies. Just put a little fresh ice in it from the hotel/motel each time you head out.

And get GOOD maps, ask about the roads at the front desk - and check weather reports ahead of time. If you could do one "detour" - suggest you consider driving the Beartooth pass down from 90 into Yellowstone, or up from 80. Either way would be just beautiful as is Yellowstone and the Grant Tetons. Sun Valley is also very beautiful.