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Clue:
Downtown Chicago
Answer:
2 possible answers to Downtown Chicago. From 4 to 7 leters.
Downtown Chicago answers with 4 characters:
LOOP
Downtown Chicago answers with 7 characters:
THELOOP
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Downtown Chicago area
(THELOOP with 7 letters)
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(HOPACAB with 7 letters)
One-time Chicago slugger
(SOSA with 4 letters)
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Her talk show was based in Chicago
(OPRAH with 5 letters)