$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 4% drop in price.
Most popular time to fly and prices are also 14% 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 Monday, where round-trip prices are $404 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 $344 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 $344.

  • 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 Richmond (RIC) and the cheapest round-trip airline ticket found on this route in the last 5 days was $274.

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

    The cheapest month for flights from Caribbean to Virginia is December, 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 $337 and $311 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 28% compared to booking last minute. For the absolute cheapest price, our data suggests you should book 21 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 7 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 7 direct flights from within Caribbean to Virginia. The most common day for departures is Monday, with 14% of flights taking off on this day.

  • How long is the flight to Virginia?

    An average nonstop flight from Caribbean to Virginia takes 7h 40m, covering a distance of 1489 miles. The shortest route is Nassau (NAS) to Washington, D.C. Reagan-National Airport (DCA) with an average flight time of 2h 45m.

  • 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 7 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. (74% of total searches to Virginia). The next most popular destinations are Raleigh (19%) and Norfolk (7%).

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 4205 reviews
7.5Entertainment
8.6Crew
8.1Boarding
7.0Food
8.0Comfort
Airline reviews

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.

4.0 OkayMather, Aug 2026
Read more Southwest reviews

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 would have been better if the flight was on time

Fairly good - the seats seemed more comfortable on this flight. The staff out of Detroit were quite friendly. But they directed us to the wrong carousel for luggage. :(

Just crazy with times being pushed and pushed and pushed and gate crew at Philly super rude and unprofessional with many under stress with delays.

I liked the new boarding process. I thought the buyup options (legroom, early boarding) to be easy to request and reasonably priced. All the Southwest team from gate to in-flight were so nice.

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

First time flying business class. Very comfortable for our long flight to Europe.

Not a United thing, but late afternoon departures from Denver with thunderstorms is always prone to delays.

Kayak booked this flight with only 1h 20min layover in Chicago. This made it impossible for me and several other passengers to reach this flight. Moreover, the gate closed boarding in spite of several passengers still on their way without waiting even one more minute. However, the plane departed with 20min (!) delay, i.e., there would have been at least 15 min time to let the delayed passengers board without causing any delays. I complained and as a "thank you" the attendent booked us on the last (!) flight to Indianapolis ~7h later! Thankfully, I caught the spitefulness and the United customer line rebooked the flight to an earlier flight. Although I can't grade this particular flight since I never had a chance to take it, Kayak made the mistake of a too short layover and the crew at the gate was awful.

Sitting in coach even in the larger leg space is extremely uncomfortable and the staff pay no attention.

Really delayed, no effort to support customers other than “sometimes we run late.”

It was serviceable, nothing special but nothing awful on this leg.

On boarding crew at the airport called in the boarding numbers too early meaning before the previous line was completed resulting in later numbers getting to board ahead. Also she asked those who boarded from number 3 to have the tags in their carry-on bags and leave it in the jet bridge. Most of the overhead bins were empty though. This is more work for the ground staff in addition to more inconvenience for passengers waiting to get their carry-ons from the jet bridge.

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.

The flight was delayed by about an hour due to a maintenance issue which later then required a change of planes. The crew was great and friendly. The in-flight entertainment did not play properly on Apple Vision Pro in a Safari browser. Although the movie trailers would play fine, the actual movies themselves just had a black screen with audio. There must be something with copy protection or something that isn’t compatible with the Safari browser on Apple Vision Pro. The free inflight Wi-Fi for American Airlines Advantage members is a nice bonus. and is great that they aren’t charging extra for things that have become basic utilities in 2026, like internet access.

DCA-LAX No screen on a 5 hour flight (almost) no food for sale on a 5 hour flight (practically) no wifi coverage or speed on a 5 hour flight I should have gotten my money back, shame on American

Delayed flight led to missed connection which led to new flight with 3 hours of delay so our family of 5 went from a 7pm arrival time to 1am Absolutely terrible yet again.

Flight was good, little delayed because of busy plane traffic

I had ridiculously long body search because I have knee and hip replacements

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

The series of delays were very unfortunately - first the captain timed out, then the new captain didn't show up when we were told he would, then the first officer timed out. Those delays were compounded by after boarding, weather came in - obviously that's out of JB's control but it was frustrating after all of the other delays that seemed avoidable.

3 hours late JetBlue flight made me miss my connecting flight to Nairobi Kenya, they did not even offer me hotel accommodation, I paid out of my pocket, they did not know where my luggage was, let say my experience with JetBlue was nightmare.

JFK is the worst airport and JetBlue is the worst airline

Crew at first tried to SELL snack boxes (for an hour-long flight?!?), and it was the only leg of four on which I was charged for a hard seltzer. 😕 Spent extra to select seats in Row 8 for quicker disembarking only to be seated in Row 25. Someone owes me $38 for that!

From Edinburgh to Boston was pretty good, actually! From Boston to DCA? Not so much. More food offerings for those w/gluten issues please! I don’t do well w/wheat OR legumes so neither the pasta nor the lentils would have been good for me (or pleasant for those around me on a 6+ hour flight!). Staff on the Boston to DCA leg were brusque compared to those on the other 3 legs of my trip. Also, I paid $19/seat to select 2 seats on the Boston to DC leg and we didn’t get those Row 8 seats but were sat in ROW TWENTY-FIVE😕 Someone owes me $38!

My screen didn’t work, my seat didn’t recline, the flight attendant was rude and completely dismissive, the airplane was freezing, the seats are way old, slanted and uncomfortable. I payed for a full ticket and got a horrific experience, with a flight attendant who dismissed me even though I was calm respectful and polite.

Check in and passport control were seamless and efficient. Plenty of room in overhead bins. Our original seats were separate but crew at the gate put us together in finer seats. I also had left my phone on board and the Jet Blue staff were so helpful in retrieving it after I had left the baggage area

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.

Everything you need to know for your flight to Virginia

Cabin class types available on flights to Caribbean