Cheap flights from Virginia to Caribbean from $95

In general, September is the cheapest month to fly from Virginia to Caribbean. Due to it being the ‘off-season’ during this time, you can expect flight prices to be around $290. If you don’t want to visit Caribbean in September, then you should wait until October to fly from Virginia, when ticket prices are also cheap, with an average price of $315.

The cheapest day to depart from Virginia to Caribbean is on a Tuesday when prices can be found for as low as $302. If your travel schedule is flexible, try to avoid departing on a Saturday because tickets tend to average around $472. These prices are subject to change though, so be sure to set up a Price Alert for flights to Caribbean.

At noon is the cheapest time of day to fly from Virginia to Caribbean when you can find flight prices for as low as $374. Flying to Caribbean at noon is an ideal time because this is during off-peak travel hours. Flights in the morning are often more expensive with an average ticket price of $1,627.

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

You are more likely to see cheaper flights to Caribbean from Virginia when booking weeks ahead of your departure date. In general, you can expect to find flights to Caribbean for around $407 when searching weeks out. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Caribbean from Virginia for as low as $316 on momondo.

There is only 1 cabin class available to choose from on Virginia to Caribbean flights. Cabin price and availability will vary by airline so perform a search above to find the right deals for you.

Southwest, Delta, and United Airlines are the most popular carriers operating from Virginia to Caribbean

American Airlines, Delta and JetBlue are the top three most popular airlines that fly to Caribbean from Virginia according to our data. American Airlines is the first choice among our users, with 54% of people opting to fly with this airline when traveling to Caribbean. Keep in mind that there are 7 different airlines that fly to Caribbean on a routine basis, so you have a few additional options to choose from.

As of March 2026, 29 flights take off from Virginia and land in Caribbean each week. The most common flight departure day for this route is Sat, with 66% of weekly flights taking off on this day.

If you’re flying from a popular airport in Virginia, such as Richmond or Norfolk, and flying into Caribbean, then you can expect flight times to average 14h 15m and 16h 41m, respectively.