Yes, planes fly from the USA to Jamaica and back. Direct flights depart from the American cities of Orlando, Baltimore, Miami, Boston, Atlanta, New York and some others to Jamaican Montego Bay and Kingston. For cities from which there are no non-stop flights (for example, Las Vegas, Rochester, Pittsburgh), there are indirect flights. Airlines such as American Airlines, US Airways, Caribbean Airlines (operated by Air Jamaica), Continental Airlines, jetBlue, Delta, Sun Country Airlines, and many others are involved in organizing flights between these two countries.