Great quiz! My only suggestion is to disallow "South" as an answer for "South Chicago" since there are multiple other community areas with "South" as part of their names.
Well done. I love the concept. I do find as a lifelong Chicagoan so many areas we locals recognize are excluded from lists like these: Roscoe Village, Streeterville, the Gold Coast, Old Town, Sauganash, Wrigleyville, River North, South Loop, etc.