Direct flights from Chicago to the Caribbean provide a seamless journey from the vibrant cityscape of Chicago to the sun-soaked, idyllic islands of the Caribbean. Major airlines like American, United, Delta, and Southwest offer convenient non-stop options to popular destinations such as Cancun, Montego Bay, Punta Cana, San Juan, and Nassau. Whether you're seeking the laid-back charm of the Bahamas or the lively rhythms of Jamaica, these direct flights make it easy to trade the urban hustle for the warm hospitality and tropical allure of the Caribbean.

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