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Chicago Illinois USA here:
The two foods that scream “This is Chicago” to me are deep dish pizza and a Chicago style hotdog (poppy seed bun and a dog with mustard, chopped onions, tomato wedges, sweet relish, a pickle spear, and peppers, then sprinkled with celery salt).
As to which is my favorite, deep dish is definitely more unique and probably the better answer here, but man can I do love when the dogs are just right.
In terms of popular and well known local dishes, the deep dish pizza and Chicago dog are great. I agree with you there.
The one that people outside of Chicago don't know a lot about, that is still a delicious representation of the city, is Italian Beef.
And the one that is uniquely Chicago but isn't going to be winning over people in a blind tasting, is shots of Malort.
Oh yeah, I could smash an Italian beef just about any day.
And Malort. I mean, it’s awful, but I never say no when offered a shot. I kinda love that our local drink comes with language of “this is will taste terrible, but you have to try it.”
I found Malort to be not all that bad. Not something I'd choose as my liquor of choice but not the concentrated hell I expected from descriptions and reactions.