I will assume a New Yorker is asking this question. No, Chicago
does not have boroughs. But cluster areas of Chicago do have a
distinct NY borough like flavor. Just like NY, Chicago has
neighborhoods with names and often times with a certain "flavor". I
would compare areas of Chicago to NY like the following:
Manhattan = The Loop north to Uptown neighborhood
Brooklyn = south side
Bronx = west and near north west side
Queens = south west + north west + far north side