Some quicky suggestions:
If you're in the Twin Cities, you have to try a Juicy Lucy (it's a burger stuffed with cheese in the middle). I had mine at the Nook in St.Paul and it was one of the best burgers I've ever had. It's amazing that places outside of the twin cities haven't caught on to this magical dish.
Chicago is a fantastic place to visit. I would recommend doing one of those architectural boat tours, it's a great way to see the city. Some of, if not the, best architecture in America. Seeing the city from on top of the Hancock is awesome as well. And of course, you have to get yourself some deep-dish....
If you're going to Detroit, I'd recommend the Henry Ford museum, some fantastic cars and trains in that place.
I'd definitely do Montreal if you can. That place is worth a couple days alone. Rent yourself a Bixi bike and ride around the Plateau. Get the Duck in a Can at Au Pied de Cochon.
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