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There are many living in Cook County, IL, including in Chicago. They have been there for a long time. Interactions with humans are very rare.
Dupage County too; I have seen them within a few blocks of home. They're pretty skittish though.
I see a few deer when I'm on my bike after work. Deer are active around dusk and they like to step right out of the brush when you're almost right on top of them. I'd sure hate to T-bone one; I am sure it would be only a little better than hitting a parked car!