How long is the flight from Chicago to the caribbean? The duration of a flight from Chicago to the Caribbean varies depending on the specific destination within the Caribbean. On average, non-stop flights from Chicago to popular Caribbean destinations take around 4 to 6 hours. However, the exact time can be influenced by factors such as the specific departure and arrival airports, weather conditions, and the airline chosen for the journey. Travelers should check with airlines for the most accurate and up-to-date information on flight durations and schedules.