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4: Indiana, Kentucky, Tennessee, Alabama. You would need to fly from Sturgeon Bay, WI (to miss Michigan) and fly to Pensacola, FL.

Of course, you could fly north and hit Michigan's upper peninsula while you almost completely circumnavigate the earth and hit Florida in Key West. That would be 1 State you would fly over. The definition of "state" comes into play on this answer, though. By one definition, a "state" is a country.

Another way to answer this is to say that you cannot fly in a straight line from Wisconsin to Florida because your plane cannot bore through the curvature of the earth and must follow an arc.

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