Usually means: Coldest, most relaxed or coolest.
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We found 10 dictionaries that define the word chilliest:

General (10 matching dictionaries)
  1. chilliest: Merriam-Webster
  2. chilliest: Oxford Learner's Dictionaries
  3. chilliest: Collins English Dictionary
  4. chilliest: Vocabulary.com
  5. chilliest: Wordnik
  6. chilliest: Cambridge Advanced Learner's Dictionary
  7. chilliest: Wiktionary
  8. chilliest: Dictionary.com
  9. chilliest: Cambridge Essential American English Dictionary
  10. chilliest: TheFreeDictionary.com

(Note: See chilly as well.)

Definitions from Wiktionary (chilly)

adjective:  Cold enough to cause discomfort.
adjective:  Feeling uncomfortably cold.
adjective:  (figuratively) Distant and cool; unfriendly.
noun:  Alternative spelling of chili. [(countable) The pungent, spicy fresh or dried fruit of any of several cultivated varieties of capsicum peppers, used in cooking.]
▸ Also see chilly

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