I’d selfishly suggest Chicago, but since you’ve already been here, let me steer you towards our good friends to the north. A tour of southeastern Wisconsin, including Kenosha, Racine, and Milwaukee would fit your requirements on all counts. Kringles, frozen custard, fish fries, and a bunch of great burger drive-ins could make for a fine tour.
Plus, SE Wisconsin in the fall? Are we talkin’ beautiful foliage or what?
And if you get there early enough in the season, maybe buffetbuster could finally experience The Nite Owl…