Usually means: Most risky or uncertain situation.
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We found 10 dictionaries that define the word chanciest:

General (9 matching dictionaries)
  1. chanciest: Merriam-Webster
  2. chanciest: Oxford Learner's Dictionaries
  3. chanciest: Collins English Dictionary
  4. chanciest: Vocabulary.com
  5. chanciest: Cambridge Advanced Learner's Dictionary
  6. chanciest: Wiktionary
  7. chanciest: Dictionary.com
  8. chanciest: Cambridge Essential American English Dictionary
  9. chanciest: TheFreeDictionary.com

Business (1 matching dictionary)
  1. chanciest: Legal dictionary

(Note: See chancy as well.)

Definitions from Wiktionary (Chancy)

adjective:  Uncertain; risky; hazardous.
adjective:  Subject to chance; random.
adjective:  (dated, colloquial) Lucky; bringing good luck.
noun:  An English surname from Old French.
noun:  A male given name transferred from the surname.
▸ Also see chancy


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