I am going to be in Chicago for 4 or so days, not on a weekend, while a family member has some surgery. I'll be staying in the Medical District, near UIC.
What are the quintessential Chicago places I should not miss?
I will have a car, and will drive if necessary, but would prefer stay closer to the hotel for at least some of the meal.
Some meals might be by myself if my other family members choose not to go, so please keep that in mind. Will probably only be eating out for lunch or dinner.
I love local flavor, soul food, burgers/dogs, hole-in-the-wall joints, pizza (definitely want a deep dish recommendation), Italilan, and other stuff. Doesn't matter if it's cheap or expensive. Last trip I hit Frontera and Spiaggia and enjoyed both, but probably want to keep it a little more casual this time.
I shy away from Asian and Indian food.
Also, one night is a Sunday night, 830 PM or so at the earliest.
So, given all that... what do you experts recommend?