Cheap flights from Virginia to Caribbean Islands from $115

The month of January is, on average, the cheapest month to fly to Caribbean Islands from Virginia, with most prices found around $475. The month of October is another great option to travel to Caribbean Islands, with average flight prices from Virginia averaging around $548.

The cheapest day to depart from Virginia to Caribbean Islands is on a Monday. Travelers who choose to depart for Caribbean Islands on a Monday will often find tickets for as low as $245. If your travel schedule is flexible, try to avoid departing on a Thursday because tickets tend to average around $399. These prices are subject to change though, so be sure to set up a Price Alert for flights to Caribbean Islands.

According to our data, the cheapest time of day to fly to Caribbean Islands is at noon. momondo users have found flights departing from Virginia to Caribbean Islands at noon for as low as $368. Keep in mind that these prices may fluctuate based on what airline you choose and the time of year you plan to travel. Try not to purchase tickets in the morning because they tend to be around $566. Of course, these prices can vary depending on the time of year and what airport you fly to.

Fly from Richmond Byrd Intl to San Juan Luis Munoz Marin Intl for the best Virginia - Caribbean Islands flight prices

You are more likely to see cheaper flights to Caribbean Islands from Virginia when booking weeks ahead of your departure date. In general, you can expect to find flights to Caribbean Islands for around $389 when searching weeks out. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Caribbean Islands from Virginia for as low as $284 on momondo.

There are 2 cabin classes available to choose from on Virginia to Caribbean Islands flights. Cabin price and availability will vary by airline so perform a search above to find the right deals for you.

JetBlue, Air Canada, and United Airlines are the most popular carriers operating from Virginia to Caribbean Islands

American Airlines, JetBlue and Delta are the top three most popular airlines that fly to Caribbean Islands from Virginia according to our data. American Airlines is the first choice among our users, with 48% of people opting to fly with this airline when traveling to Caribbean Islands. Keep in mind that there are 7 different airlines that fly to Caribbean Islands on a routine basis, so you have a few additional options to choose from.

The number of flights available between Virginia and Caribbean Islands is 8 per day as of August 2026. The most frequent departure time is 4:00PM, with 100% of daily flights leaving in the afternoon.

59 flights are operational weekly from Virginia to Caribbean Islands as of August 2026. The most popular departure day for this route is Sun, with 20% of flights per week taking off on this day.