$100 Find Cheap Flights from Caribbean to Virginia - Compare and Save

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Low season

September

Cheapest flight

$100
Best time to beat the crowds with an average 1% drop in price.
Most popular time to fly and prices are also 15% lower on average.
Flight from San Juan to Richmond

FAQs for booking flights from Caribbean to Virginia

  • How does KAYAK find such low prices on flights from Caribbean to Virginia?

    KAYAK is a travel search engine. That means we look across the web to find the best prices we can find for our users. With over 2 billion flight queries processed yearly, we are able to display a variety of prices and options on flights from Caribbean to Virginia.

  • How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from Caribbean to Virginia?

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight from Caribbean to Virginia is likely to change within 7 days, so travelers know whether to wait or book now.

  • What is the Hacker Fare option on flights from Caribbean to Virginia?

    Hacker Fares allow you to combine one-way tickets in order to save you money over a traditional round-trip ticket. You could then fly from Caribbean to Virginia with an airline and back with another airline.

  • What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from Caribbean to Virginia?

    Sometimes travel dates aren't set in stone. If your preferred travel dates have some wiggle room, flexible dates will show you all the options when flying from Caribbean to Virginia up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

  • How many airports are there in Virginia?

    There are 7 airports in Virginia. The busiest airport is Richmond Byrd Airport (RIC), with 41% of all flights arriving there.

  • Which is the cheapest airport to fly into in Virginia?

    Prices will differ depending on the departure airport, but generally, the cheapest airport to fly to in Virginia is Richmond Byrd Intl Airport (RIC), with an average flight price of $202.

  • What is the cheapest day to fly to Virginia?

    Based on KAYAK data, the cheapest day to fly to Virginia is Wednesday where round-trip tickets can be as cheap as $322. On the other hand, the most expensive day to fly is Sunday, where round-trip prices are $424 on average.

  • What is the cheapest time of day to fly to Virginia?

    The cheapest time of day to fly to Virginia is generally in the morning, when round-trip flights cost $345 on average. The most expensive time of day to fly to Virginia is generally in the morning, which is peak travel time and where the average cost of a ticket is $345.

  • What is the cheapest flight to Virginia?

    The cheapest ticket to Virginia from Caribbean found in the last 5 days was to Richmond, at $274 round-trip. The most popular route is San Juan Luis Munoz Marin Intl Airport (SJU) to Norfolk (ORF) and the cheapest round-trip airline ticket found on this route in the last 5 days was $275.

  • What is the cheapest month to fly from Caribbean to Virginia?

    The cheapest month for flights from Caribbean to Virginia is November, when tickets cost $204 (return) on average. On the other hand, the most expensive months are January and April, when the average cost of round-trip tickets is $347 and $319 respectively.

  • How far in advance should I book a flight from Caribbean to Virginia?

    To get a below average price on the flight from Caribbean to Virginia, you should book around 3 weeks before departure, which saves you about 29% compared to booking last minute. For the absolute cheapest price, our data suggests you should book 16 weeks before departure.

  • How many cities have direct flights to Virginia?

    From Caribbean, there are direct flights to Virginia from 1 city. This city is San Juan and there are 3 direct flights each week.

  • How many direct flights to Virginia are there each day?

    There are around 1 direct flights from within Caribbean to Virginia every day. All flights depart in the morning.

  • How many direct flights to Virginia are there each week?

    Each week there are around 3 direct flights from within Caribbean to Virginia. The most common day for departures is Monday, with 33% of flights taking off on this day.

  • How long is the flight to Virginia?

    An average nonstop flight from Caribbean to Virginia takes 7h 59m, covering a distance of 1529 miles. The shortest route is Nassau (NAS) to Washington, D.C. Reagan-National Airport (DCA) with an average flight time of 2h 46m.

  • How many long-haul flights are there to Virginia each week?

    There are not any long-haul (6-12 hour flight duration) or medium-haul (3-6 hour flight duration) flights to Virginia. Instead, there are 3 short-haul flights (up to 3 hour flight duration), with the most arriving from San Juan.

  • What are the most popular destinations in Virginia?

    Based on KAYAK flight searches, the most popular destination is Washington, D.C. (77% of total searches to Virginia). The next most popular destinations are Raleigh (19%) and Norfolk (5%).

Reviews of the top 5 airlines serving from Caribbean to Virginia

 
Need help choosing which airline to fly with from Caribbean to Virginia? KAYAK airline reviews give an overall score for each airline based on loads of factors, including comfort, boarding, in-flight entertainment and more, to make your decision easier. See airline scores according to verified KAYAK customer reviews.
8.0
SouthwestOverall score based on 4195 reviews
8.1Boarding
7.5Entertainment
8.6Crew
7.0Food
8.0Comfort
Airline reviews

Delayed and once landed waited very long for the luggage

6.0 GoodIngeborg, Sep 2026
Read more Southwest reviews

Delayed and once landed waited very long for the luggage

Nice managed … it was a smaller plane, so the seating wasn’t as comfortable.

The Southwest airline was ok. A big thank you to Kayak team (David), who worked with me on Sunday afternoon to rebook my travel from Burbank, CA, to CVG. My original flight on Sunday was delayed, so I had to cancel Sunday flight and rebook my travel to Monday. Could not have done it without help from David from Kayak team. Ante Soda GE Aerospace

Very poor service with connecting flight. I missed the connection because of a delayed flight and significant delay in getting my bags in order to make the connection. The ground staff where unhelpful and rude!

Seated at front bulkhead for a smidge extra leg room away from home and on flight back home. Away crew was very proactive about assuring our carryons had space close behind us (because no seat in front of us our personal items had to be in a small bin overhead). They actively required passengers place overhead luggage on its side so more items could fit in bins. Home crew made no such efforts. I had to struggle back rows to get overhead bags upon landing, no crew help then either, and some disgruntled passengers as I and others retrieved our bags. There was a system that worked pretty well. The home bound crew just didn't feel like working.

Southwest has inacted unfriendly customer policies like other airlines. Watch the fine print very carefully if you are having to alter flight arrangements. Rules are now complicated and very stilted to travelers sacrificing travel funds (unlike before where the simple, straight forward flight change policy was worth the extra premium for ticket price.) On the positive side, SW Flight crews are still wonderfully helpful.

Flight left on time and was early landing. Seats not comfortable and not enough space…

Flight left on time. Seat spacing is way too small…

It was great. The gate staff were very helpful in Portland when my son forgot his rolling bag and had to go back to get it just in time to make it on the plane. We really appreciate that. Great job!

WIFI was great. My selection for seating is an aisle, but during my trip, I never had an aisle seat. If we can get that corrected, I will be thrilled. No snack or drink on this flight.

The second half of terminal C at Hartsfield was 80 something degrees. I was sweating just sitting at the gate.

Seat was too small for someone as tall as I am. I was behind an exit row making my leg room even less. There flights were delayed by multiple hours. Some weather related and others staff related. The plane was hot. Horrible experience.

Missed the Flight from Atlanta to Roanoke due to initial flight from Houston being 2hr. late. Now waiting 17hrs. till my first available flight.

I was told that they needed to check my bag at the gate and to pick it up at the gate in Richmond. No big deal. I know they can't control the weather, but we flew around RIC for 45 minutes to avoid the storm and were 25 minutes late leaving as well. Once we landed, we were told to go to baggage claim to pick up our luggage. I went to bathroom, paid for parking, and went to the assigned baggage claim location. United flight people came down with us as well. They got their luggage immediately. Next, South West people came down about 10 minutes later. They got their luggage next. We finally got our luggage around 30 minutes in waiting. Was not a wonderful experience. No reflection on Delta, but the ground crew was lousy at best.

Never got on it. Was re-routed through Detroit and am still in airports 12 hours later waiting for my connecting plane to arrive.

Flight was delayed and no reasons provided. After the passengers were boarded, the crew made announcement that the captain has jot arrived and he would take another 15 mins. All passengers patiently sat until the captain came and started. Terrible experience!

Seats were really tight and the seat belts did not give enough slack.

Great flight. On-time, comfortable, clean aircraft, and offered snacks pre-flight to plan for a potentially turbulent route. I wish there was Wi-Fi an all Delta Aircrafts but for a short flight this is not much of a problem.

Flight was changed from departing from Boston to departing from Detroit.

cancel my non stop flight for no reason. And force me rebook 2stop flights automatically then get short time to catch my flight from Atlanta to Charlottesville. We missed the flight then ask me rebook again to another city Richmond which far away 90mile from Charlottesville. Spend all day for flight and spend Uber from Richmond to Charlottesville airport cause my luggage was sent to there earlier half day and my food was bad cause heat. Damn delta

Did not like the check in guy quibbling over a couple pounds at the luggage weigh in

Just having a little bit more legroom would've been nice.

This is related to my second leg of the flight, from Washington DC to SFO. I understand things happen, but I got home at 3 am for a 12:59 am landing. I live 10 min from the airport. Bridge breaks when a few rows of the plane are off? Maintenance didn’t catch that?

Boarding, time to take off, in flight offerings, and staff were all great. I recommend using UA for this short flight.

Good experience. Staff was friendly and helpful. Flight was slightly delayed due to airport construction, but they still arrived on time.

This is the worst airline I’ve ever been on in my life and I’ve been probably on 75% of them. I said 15 years ago I would never go on United again. I was an idiot. I booked a flight with them from Las Vegas to San Francisco and of course they screwed that up and cost me a day flying all over the world trying to get to Thailand. My luggage was gone for 35 hours all because they couldn’t make their route on time

This was an auto-rebook due to being delayed from an earlier UA connecting flight. The boarding was fine, but they sat me in a middle seat when my original booking was a window seat. Overall, the flight was fine as it still got me to my final destination.

Have not had a flight out or returning to Norfolk that has not required maintenance, and a gate delay. Properly staff the crew so maintenance can be performed without last minute emergencies on each flight and there is enough staff to have gates prepared for inbound flights. Staff to ensure the safety and on time service vs. profit.

I understand weather is an issue, but making us chase our plane down at five scheduled gates across three terminals in an airport the size of O'Hare was unfair. They'd have probably been better off to leave gates as TBD until the inbound plane is in final approach instead of running us all over the place. Also, props to the consistently-unprepared ground crew in Richmond for once again leaving my lane parked short of the gate because they couldn't have a crew in place on time with 2 hours notice...

cabin crew was OK, food was OK, the trip from the US to Munich was actually pretty bad comfort wise. Noisy aircraft, lights never dimmed even in Business class (night flight) barely sufficient amenities for the price. I have millions of miles with United but TBH American is gaining ground and Delta has always been marginally better then United although on paper United has more longes and cheaper upgrades.

Flying under Economy Class shouldn’t mean having to deal with such uncomfortable seats. For an overnight flight, it is expected that the seat would recline a decent amount. The food portion could have been more generous. There was an incident with someone by my side. They got sick and vomited. I hit the button for the crew but no one showed up. So I went to the back of the plane and explained what happened. They only brought clean tissues and coffee ground bags. There wasn’t any kind of disinfecting wipes nor any type of sprays. She cleaned as best as she could and poured the coffee ground around. The crew did not seem to care how she was doing. The coffee helped with the smell, but it should have been cleaned in a more efficient manner.

Old dirty plane but great lie flat seats in business class

Business Class layout was excellent. The seats were not nearly as comfortable as UA, Delta or Air New Zealand (the best). Nor were the controls as flexible. Food was okay but not great. Breakfast pancakes were like cardboard.

The average age of the flight crew had to be 58. With that said I just felt the flight crew was old and grumpy during meal service. The one male flight attendant was annoyed that Dr. pepper was the popular drink of choice during dinner service. He had to bend down multiple times and sort through popular sodas to get the Dr. Pepper. I overheard he complained under his breath. Another flight had no clue what they are serving for breakfast. She said we had American waffles and Japanese Cold soba noodles with dumplings. It turn out to be hot noodles with shu-mai. It the cold affected my choice.

Communication not good, too many changes. Three flights were cancelled due to weather and the options were not acceptable. I had to cancel my Canada portion of the trip.

3 hour weather delay followed by 1 hour (and counting) maintenance delay. UGH!

Flight was delayed , waited in the tarmac for 3 hours and then came back and was cancelled

Delayed almost 4 hours for a 45 minute flight with no explanation.

The flight was excellent, provided that we had inclement weather. We departed earlier than scheduled and arrived early. There was a little turbulence, but nothing to be worried about.

I disliked that I didn’t have a flight today, not entirely sure why I’m being asked

Very good flight that left on time and arrived earlier than anticipated, which was a plus! The crew members were very welcoming and helpful. However, the temperature on the flight was very cold - almost to the point of extreme discomfort. Additionally, requiring passengers to pay $8 for headphones to access the JetBlue entertainment was disappointing. Those earbud jacks are not used with most technology and would not be able to be used. There was no option to use Bluetooth for my own earbuds. Beyond those inconveniences, the flight was good.

My original flight was cancelled. My replacement flight was delayed over 2 hours. I lost my whole day in NY

Delays were crazy long (over an hour) both for boarding and baggage claim

awful expereince. boarding was a mess and not communicated, then we sat on a hot plane and were at risk of getting kicked off

2 hour delay and a lack of air conditioning on the plane. Not a good combination

It was so nice! I wish that we can have direct flights to El Salvador 😊😊

Fabulous! This was the first time we've flown with JetBlue and the entire experience was flawless!

Easy experience even with the outbound flight being delayed. The seating and space was comfortable and the crew seemed very nice and helpful.

It was great. I had never flown on JetBlue before, but would be very happy to fly with them in the future.

The captain gave good announcements and the flight attendants were friendly. The WiFi was pretty good. The plane itself looked very old inside and the seats were very uncomfortable. The screens in the seat backs were the smallest I’ve ever seen. There were so many loud and obnoxious kids on this flight and the parents didn’t do much to try to quiet them down. Some had videos and games on tablets with higher than necessary volume going the whole time.

More options for your flight to Virginia

Complete your trip to Virginia with a hotel stay or car rental