Ah Yes, I just pretty much did that exact routing as part of my honeymoon a few weeks ago.

Here is what we accomplished:

Springfield, MA – White Hut for burgers w/Fried Onions
Rochester, NY – Nick Tahou for Garbage Plate
Northern Rochester, NY – LDR Char Pit for Steak Sandwich & Abbott’s Custard for Vanilla Frozen Custard
Buffalo, NY – Ted’s for Hotdogs
Canada = Roadfood Wasteland. Fill up beforehand.
Detroit, MI – Lafayette Coney Dogs for Coney Dogs and Chili Fries
Chicago, IL – Mr. Beef for Italian Spiced Beef & Garretts Popcorn for Caramel Crips
Racine, WI – Get Kringle anywhere
Milwaukee, WI – Kopp’s Custard for Butter Burger and Custard
Souix Falls, SD – Bob’s Cafe for Bacon, Broasted Chicken or Cheesteak
Wall, SD – Wall Drug for donuts
Hill City, SD (Near Mt. Rushmore) – Alpine Inn for Filet Mignon dinner (Only $8!)

You can find reviews for almost all of these places on the site.

Good luck and have fun!