Traditionally, the Caribbean has always been a more cost-friendly destination to travelers who buy air-land package deals than to independent travelers. It's not uncommon, for example, to find hotel deals that include airfare cheaper than the published prices for airfare alone on airline websites.
American Airlines has long been the dominant airline in the region, and still is the only major U.S. carrier serving many destinations. The good news is that competition has increased to many of the most popular islands, notably from discount carriers like Jet Blue and USA 3000 Airlines. If you are flying to San Juan or Nassau, for example, you're likely to get a good deal thanks to increased competition, although of course prices are always higher in the high (winter) season.
The bad news is that if you are headed to one of the region's more off-the-beaten path destinations, you'll still end up paying dearly for air transportation. But even these destinations are sometimes served by charter airlines, which occasionally offer discounted airfares to fill up scheduled tourist flights.
