I've done this trip a few times and agree with everything Table said. From west to east, I'd do:
South Dakota: Mt. Rushmore, Crazy Horse Memorial, Black Hills and the Badlands
Chicago: Johnnie's Beef (Italian beef dipped with peppers, and a lemon ice), deep dish pizza (I like Giordano's, but Gino's and Lou Malnati's are good too), hot dogs, architectural boat tour, Wrigley Field and the Shedd Aquarium
Cleveland: Rock and Roll Museum, West Side Market (beef jerky at Czuchraj Meats)
Buffalo: Duff's wings
Niagara Falls
Toronto
Montreal
If you have time on the way back, you can swing through Detroit and Minneapolis, but I wouldn't cut out any of the other destinations to make time for them.
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