Are there any direct flights from Chicago to caribbean? Escape the Windy City and embark on a seamless tropical getaway with direct flights from Chicago to the Caribbean. Experience the convenience and allure of non-stop air travel as you journey from the bustling metropolis of Chicago to the sun-kissed beaches and vibrant cultures of the Caribbean. This direct connection ensures a swift and comfortable transition from the Midwest to paradise, making your dream Caribbean vacation just a flight away from the heart of Chicago