Cheap Flights from Chicago to Caribbean

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  • $569 - Roundtrip Flights to Morocco from Chicago
  • $219 - Flights to LA from Chicago
  • $679 - Flights to Athens Greece from Chicago
  • $521 - Flights to Lima Peru from Chicago
  • $179 - Flights to Miami from Chicago
  • $544 - Roundtrip Direct Flights to Istanbul from Chicago
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  Africa Athens Bahamas California Canada Cancun Caribbean Casablanca Denver Dublin Europe Florida Greece Ireland Istanbul Italy LA Las Vegas Lima Mexico Miami Milan Morocco Nassau Orlando Peru South America Turkey

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  • $199 - Roundtrip Direct Flights to Austin from San Francisco
  • $2629 - Around the World Flight with Air New Zealand
  • $835 - Flights to Buenos Aires Argentina from San Francisco
  • $303 - Flights to Puerto Vallarta Mexico from San Francisco
  • $250 - Weekend Flight to Boston from San Francisco on Virgin America
  • $569 - Roundtrip Flights to Morocco from Chicago
  • $529 - Roundtrip Flights to Casablanca Morocco from Boston
  • Alaska Airlines Flight Deals to Canada
  • $219 - Flights to San Francisco on JetBlue
  • $606 - Flights to Quito Ecuador from San Francisco