Usually means: Metropolitan area surrounding Chicago, Illinois.
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We found 6 dictionaries that define the word Chicagoland:

General (5 matching dictionaries)
  1. Chicagoland: Merriam-Webster
  2. Chicagoland: Oxford Learner's Dictionaries
  3. Chicagoland: Wordnik
  4. Chicagoland: Wiktionary
  5. Chicagoland (TV series), Chicagoland (disambiguation), Chicagoland: Wikipedia, the Free Encyclopedia

Slang (1 matching dictionary)
  1. Chicagoland: Urban Dictionary

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Definitions from Wiktionary (Chicagoland)

▸ noun:  The metropolitan area of Chicago, including parts of Illinois, Indiana, and Wisconsin.

Similar:
Chicago, South Chicago, calumet, East Chicago, North Shore, Windy City, Second City, South Side, West Town, Plano, more...

Phrases:
Chicagoland Speedway, Chicagoland Television, Chicagoland Collegiate Athletic Conference, more...

▸ Words similar to Chicagoland

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▸ Popular adjectives describing Chicagoland

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▸ Rhymes of Chicagoland

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Similar:
Chicago, South Chicago, calumet, East Chicago, North Shore, Windy City, Second City, South Side, West Town, Plano, more...

Phrases:
Chicagoland Speedway, Chicagoland Television, Chicagoland Collegiate Athletic Conference, more...



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