If you are into chili dogs, you can have a pretty epic trip as some posters have mentioned.
Starting in Detroit get a Coney Dog, you can anywhere actually. I've been to several different spots as well as American and Lafeyette (the only real difference is the decor of each interior) Most Coneys are basically the same. Just find a spot that looks busy and go there.
Toledo has got to be the only town in the world with two local chili joints to be visited by Presidents: Tony Packo's and Rudy's.
Cincy chili is famous (in Cincy at least) and worth trying at least once. Skyline is the standard bearer, with a few other spots as well.
Coming from Toronto with it's very diverse and vibrant ethnic communities, you will likely be disappointed with any ethnic food you may try here. The midwestern palate doesn't go for really authentic foods and most places have severely dumbed down their menus to accommodate the local sensibilities.
Probably the most unique item you could eat that is staple food of the region would be the spaghetti chili.
Who knows where the best Tripas tacos are around here? Or just of any place that has them on the menu?
went there for the first time a few days ago and walked away completely disappointed. Me and my wife tried a few little things to share and could barely finish small items between two people.
Los Ocampa served up two of the blandest asada tacos I've ever had, between the meat, salsa, and the cilantro/onion...the only flavor that stood out was the cilantro/onion. La Loma Tamales were overcooked and greasy it somehow took them 15 minutes to take two tamales out of a steamer and put them on a plate. Phams Deli also provided one of the worst Bahn Mi sandwiches (more bland meats with huge buns and skimpy fillings, you get a 2:1 bun to filling ratio in every bite...and the bun sucks too).
On a positive note, the food at Holy Land looked good and that burger spot smelled the best!