I don't know ______ in Chicago.

• A. Anyone
• B. Someone
• C. No one
• D. Everyone

Answer: (A)

When you make a negative statement about knowing people, the natural choice is anyone to mean “not a single person.” So, I don’t know anyone in Chicago means you don’t know any person there at all, which sounds natural and correct.

Using someone after a negative sounds off because it points to a specific person, which clashes with the idea of not knowing anyone. No one would require a different sentence structure (I know no one in Chicago) and isn’t the natural fill for the given construction. Everyone would imply you know every person there, which doesn’t match the negation.

So the best completion expresses the intended meaning with a general, non-specific person: anyone.