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Cheap Flights from Richmond to Caribbean Islands

Cheapest round-trip prices found by our users on KAYAK in the last 5 days
Punta Cana
Punta Cana1 stop$474
Santo Domingo
Santo Domingo2 stops$365
Montego Bay
Montego Bay1 stop$429
Oranjestad
Oranjestad1 stop$306
Nassau
Nassau1 stop$306
Kingston
Kingston2 stops$584
Simpson Bay
Simpson Bay1 stop$286
Providenciales
Providenciales2 stops$587
Port of Spain
Port of Spain2 stops$625
Bridgetown
Bridgetown2 stops$652
George Town
George Town2 stops$452
Willemstad
Willemstad1 stop$625
Aguadilla
Aguadilla1 stop$316
Puerto Plata
Puerto Plata2 stops$630
St. John's
St. John's1 stop$667
Punta Cana
Punta Cana1 stop$474
Santo Domingo
Santo Domingo2 stops$365
Montego Bay
Montego Bay1 stop$429
Oranjestad
Oranjestad1 stop$306
Nassau
Nassau1 stop$306
Kingston
Kingston2 stops$584
Simpson Bay
Simpson Bay1 stop$286
Providenciales
Providenciales2 stops$587
Port of Spain
Port of Spain2 stops$625
Bridgetown
Bridgetown2 stops$652
George Town
George Town2 stops$452
Willemstad
Willemstad1 stop$625
Aguadilla
Aguadilla1 stop$316
Puerto Plata
Puerto Plata2 stops$630
St. John's
St. John's1 stop$667
Booking Insights

KAYAK's insights & trends for Richmond to Caribbean Islands flights

Get data-powered insights and trends into flights from Richmond to Caribbean Islands to help you find the cheapest flights, the best time to fly and much more.

What is the cheapest Richmond to Caribbean Islands flight route?

The cheapest ticket to Caribbean Islands from Richmond found in the last 5 days was to San Juan, at $276 round-trip. The most popular route is from Richmond (RIC) to San Juan Luis Munoz Marin Intl Airport (SJU), and the cheapest round-trip airline ticket found on this route in the last 5 days was $276.

What is the cheapest time of day to fly to Caribbean Islands?

The cheapest time of day to fly to Caribbean Islands is generally in the evening, when round-trip flights cost $369 on average. Morning departures are around 53% more expensive than evening flights, on average. The most expensive time of day to fly to Caribbean Islands is generally in the morning, which is peak travel time and where the average cost of a ticket is $566.

Can I save money by flying with a layover from Richmond to Caribbean Islands?

No, with an average price for the route of $439, prices are generally cheapest when you fly direct.

What is the cheapest month to fly from Richmond to Caribbean Islands?

The cheapest month for flights from Richmond to Caribbean Islands is January, when tickets cost $467 (return) on average. On the other hand, the most expensive months are March and June, when the average cost of round-trip tickets is $653 and $647 respectively.

What’s the cheapest day of the week to fly from Richmond to Caribbean Islands?

If you are looking for a flight deal from Richmond to Caribbean Islands, look for departures on Mondays and avoid leaving on a Friday, as it's usually the priciest day. When flying back from Caribbean Islands, Tuesday is the cheapest day to fly and Saturday is the most expensive.

How far in advance should I book a flight from Richmond to Caribbean Islands?

To get a below average price on the flight from Richmond to Caribbean Islands, you should book around 2 weeks before departure, which saves you about 7% compared to booking last minute. For the absolute cheapest price, our data suggests you should book 4 weeks before departure.

Good to know

Low season

September
Best time to beat the crowds with an average 4% drop in price.
Most popular time to fly with an average 11% increase in price.

FAQs - booking Caribbean Islands flights

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

    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 Richmond to Caribbean Islands.

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

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight from Richmond to Caribbean Islands 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 Richmond to Caribbean Islands?

    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 Richmond to Caribbean Islands 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 Richmond to Caribbean Islands?

    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 Richmond to Caribbean Islands up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

  • How many flights are there between Richmond and Caribbean Islands per day?

    There is a maximum of 1 nonstop flight a day that takes off from Richmond and lands in Caribbean Islands, with an average flight time of 3h 40m. The most common departure time is 1:00 pm and most flights take off in the afternoon. Each week, there are 3 flights.

Reviews of the top 5 airlines serving from Richmond to Caribbean Islands

 
Need help choosing which airline to fly with from Richmond to Caribbean Islands? 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.
7.9
SouthwestOverall score based on 4215 reviews
7.5Entertainment
7.0Food
8.6Crew
8.0Comfort
8.1Boarding
Airline reviews

Flight boarded 2.5 hours late (my second southwest flight of the day with late departure), the gate agent was grumpy and unhelpful. Said she was "tired so we aren't going to follow normal boarding order". No complaints about the actual flight crew.

2.0 MediocreBrittney, Oct 2026
Read more Southwest reviews

Flight boarded 2.5 hours late (my second southwest flight of the day with late departure), the gate agent was grumpy and unhelpful. Said she was "tired so we aren't going to follow normal boarding order". No complaints about the actual flight crew.

Your computers were down and took a long time to check baggage

Southwest has lost most of what made it special. The flight attendants all used to seem fun and like they were having fun. Now they seem just miserable. They do NOT seem happy to give you your pretzels and drinks. They stick it in your hand or on your tray like it's an annoyance. They bark safety instructions at you. It's not just this flight but the last few SW flights I've had to SNA and SAN as well and it's not just me. I've informally surveyed my colleagues (business and leisure travelers) and these feelings are consistent. The tickets are similarly priced to other carriers and the seat assignments make boarding slower. The free luggage and free ability to change flights is still a differentiator. You lose that and there's virtually nothing special left.

Flight attendant skipped about 6 rows for drink service. I got a side eye when I asked for a drink - like it was an inconvenience or my mistake. He shouldn't be on a flight if he doesn't like his job and doesn't have customer service first attitude.

The entire crew were wonderful but 1 flight attendant stood out with his sense of humor on the microphone. I told him as much as I exited the plane.

They did not fix the wifi that they knew was an issue on an earlier flight. The flight was filled with business people that were clearly frustrated not being able to work. That can’t happen on a 3 1/2 hour flight. Would rather have been delayed a bit.

The WiFi did not work three hours of productivity lost. 15 people from the firm were on the flight. Loss of revenue

Like new plane. Great crew. Comfortable. Clean. On time. Happy employees. Good organization and control of passengers.

The trip was good. Short, uneventful, and can't ask for more than that My one complaint is that I had signed up for wheel chair assist between gates. I fractured my foot/ankle in two places and needed the help. Neither flight did the requested help appear. I ended up walking through both Atlanta and Nashville Airport and was a very unhappy traveler. While I know that it's the airport responsibility for the service, I wish that SW had at least verified that the assistance was there as requested.

I liked that we arrived safely. I did not like how Southwest personnel blamed the boarding delays on wheel chair passengers. If there is a national wheelchair basketball tournament occurring, be ready as a company to respond with appropriate resources to match your cudtomers needs.

Flight attendants were great. Cheerful, upbeat and friendly. Jet, in particular, was fantastic.

Would have been better if there was a nonstop flight from Tampa to Norfolk or Tampa to New Port News.

The boarding process doesn't make sense since some people that will sit behind your rows are boarded before you and then they take up the luggage space above your head. I then have to wait for people to get off the plane before I can go back to get my luggage.

Good seat comfort ORF to ATL. Bad seat ATL to SEA (terrible lumbar support, hard, ouch)..

They made us board and then deboard due to mechanical issue which delayed the departure by almost 2 hours and we barely made our connecting flight. These quality checks should've been done before boarding not after.

My Flight was cancelled and there was no other options available for me to Travel on that date and my options for the next day was all connecting flights that would have me in the airports all day before reaching my destination

Atlanta boarding crew at gate were filled with arrogance and were disrespectful. In flight crew showed indifference to the needs of passengers. This is about the flight from ATL to BDL.

They were 2 hours late departing with no explanation. I missed my connection, was rebooked not in correct seating that I paid for. Over all of was horrible. I now know why I've not flown Delta since 2018

I appreciate the crew and their hard work. In Atlanta, the ticket counter had 1 woman to do all the work. She was amazing. People weren’t happy they had to check their carry on roller bags, but she handled them well. She was cordial and worked quickly to get the passengers boarded.

I understand why there was a 40 minute delay, but we should have been offered snacks during that time. We weren’t offered it until later.

Awful!!!. I do not recommend United. The flight staff are unhappy and don't attempt to make the passengers feel comfortable or welcome. The food is not edible, and the seats are miserable. My expensive luggage was destroyed, and the ticket prices are too much for the experience.

Airline tickets are not cheap. You expect reliable competent service. Thanks to canceled flights and botched transfers we arrived at our destination two days late. This is not acceptable

We were a little disappointed to not be able to complete check in online without uploading pics of passports. Also we have KTN's and they weren't on our boarding passes when we got to security. Had to trek back to counter to have them fix.

They did the one thing that really matters - got to Chicago early.

The person I bought the ticket for didn’t make the flight.

Overall great. I was forced to check my carry-on backpack from EWR to BOS but it came out on the luggage carousel so fast I didn't even get delayed for my pickup.

Everything was perfect except the pad at the top of the seat back. It pushes my head forward into a very uncomfortable position and it is not removable.

The Check-in process at ORF for united is ABSOLUTELY TERRIBLE. I got there two hours early for a flight down the street and didn’t make it halfway to the register before I had to get out of line and remove my bags or miss my flight. This is every day thing and I’m clueless how this has gone on for years. This was the final straw. I’d rather pay a fortune more for a different airline than deal with this process

It is a modern tragedy that any airline expects you to travel for 14 hours in such discomfort and that the only way to add comfort is exorbitant prices. I was in pain by the time we landed. Shameful.

Planes were on time, we were offered opportunities to take seats in exit aisles that had better leg room, tasks offs and landings were smooth, we were kept informed of flight status

Our seats were moved for no reason. The plane was old and wifi and tv were slow. The flight was delayed over an hour for a paperwork issue. Only bright spot was the flight attendants good service.

Unacceptable pre-boarding ticket issues. Paid for and reserved Mint seat approximately a month in advance. Checked in to flight in Mint seat 24 hours before flight. Shortly before flight, was bumped out of Mint entirely, even though other Mint seats were still available and for sale. Was told it was "operational", however seats were still available/being sold. Got to gate and they could not explain it, but the gate agent was able to put me back into Mint (however to a different seat). Nothing proactive done by Jetblue, I would have been bumped had I not arrived at gate early enough to have a helpful gate agent rectify. No explanations from Jetblue.

The crew did not ensure the Evermore seats had their carry on space available. When my family and I boarded, we saw people putting their carry on suitcases in the overhead spaces above our seats and then proceed to the rear part of the plane. This resulted in us having to check our bags and being late to our meetings/events.

Crew was friendly. Free headphones would be nice. Free new movies would be better.

Diana at the gate was unhelpful which was fine, but she was also rude which I did not appreciate at all.

Multiple delays, poor communication, dismissive staff, chaotic boarding, broken seat back entertainment. Not really much to like.

The crew was friendly and helpful. The entertainment system in my row did not work for movies and TV shows and the Direct TV cut off in parts and stopped showing the baseball playoff game.

Non-stop commercials were frustrating when trying to view direct TV

Forced to check bag, even though plenty of space in overhead bins. Did not appreciate having to wait at baggage claim to retrieve suitcase.

There were mutliple delays. There was inconsistent, delayed, and poor communication regarding the delays.

Delays and cancellations. Mechanics weren’t on site. Replacement plane took hours to arrive although it should have arrived within 90 minutes. Flight back was cancelled. Ended up driving over 12 hours and wasting 3 days between everything.

They did not offer coffee on a 7am flight…awful!!

RIC Staff was not enough. Elderly passengers had to wait 30 minutes to deplane, so we could board and still had to walk as no chairs were provided. And, passenger in front of my seat assignment rammed seat against my legs entire flight time. Was mildly bruised and left thigh still sore.

The flight had a delay that made me being in a real rush to take the second flight. The delay was almost for 2 hours. They moved us from gate to gate in 4 times. Once I arrived to Philadelphia, I got to run thorough all the airport, as the train was already closed by that time. So I got sick with asthma for all the running I had to do. And I was the last one to board, when it was almost closed. So irresponsable with the people

5.5 hour delay with no explanation on why, along with no proactive effort to reaccomodate me.

Flight overall was good. Landing was a little rough, but could be attributed to the rainy weather.

The free internet access did not work, so we had to purchase 2 Internet packages. Flight attendants were not proactive in checking in with first class patrons

Equipment swap led to 2+ hour delay on international flight. And to top it off, boarding took forever.

Wretched scheduling - they got themselves into a critical crew situation and didn’t try to address it until 15 minutes before they had to cancel my flight

Terrible. I hate flying with AA. There is always a high level of stress felt when I fly with them.

More options for your flight to Caribbean Islands

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