Roadtripping from Canada: Destinations and Iconic Cuisine?

Hi! My girlfriend and I are from northern Canada and are travelling through Chicago on our way south. We're spending two days in your fine city and I was wondering if anyone could give some advice on:

• Most iconic Chicago foods/places to eat
• Destinations (Museums, Attractions)
• Best way to get to the White Sox stadium (been to Cubs)
• Affordable/Best Hotels

Thanks! We are looking forward to our time together in the Windy City.