Embark on an effortless escape from Chicago to Caribbean direct flights. Leading airlines such as American, United, Delta, and Southwest whisk you away to tropical havens like Cancun, Montego Bay, Punta Cana, San Juan, and Nassau without the inconvenience of layovers. Enjoy a seamless transition from the urban energy of Chicago to the sun-soaked beaches and vibrant cultures of the Caribbean. These nonstop flights promise a swift and direct connection, allowing you to trade the cityscape for the warmth and allure of island life in no time.