$89 Find Cheap Flights from Richmond to Caribbean Islands - Compare and Save

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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$471
Santo Domingo
Santo Domingo1 stop$400
Montego Bay
Montego Bay1 stop$414
Oranjestad
Oranjestad1 stop$353
Nassau
Nassau1 stop$306
Kingston
Kingston2 stops$477
Simpson Bay
Simpson Bay1 stop$311
Providenciales
Providenciales1 stop$625
Port of Spain
Port of Spain2 stops$620
Bridgetown
Bridgetown1 stop$707
George Town
George Town1 stop$431
Willemstad
Willemstad1 stop$625
Aguadilla
Aguadilla1 stop$302
St. John's
St. John's1 stop$768
Puerto Plata
Puerto Plata2 stops$691
Punta Cana
Punta Cana1 stop$471
Santo Domingo
Santo Domingo1 stop$400
Montego Bay
Montego Bay1 stop$414
Oranjestad
Oranjestad1 stop$353
Nassau
Nassau1 stop$306
Kingston
Kingston2 stops$477
Simpson Bay
Simpson Bay1 stop$311
Providenciales
Providenciales1 stop$625
Port of Spain
Port of Spain2 stops$620
Bridgetown
Bridgetown1 stop$707
George Town
George Town1 stop$431
Willemstad
Willemstad1 stop$625
Aguadilla
Aguadilla1 stop$302
St. John's
St. John's1 stop$768
Puerto Plata
Puerto Plata2 stops$691
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 $265 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 $265.

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 afternoon, when round-trip flights cost $366 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 $388, 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 $461 (return) on average. On the other hand, the most expensive months are June and March, when the average cost of round-trip tickets is $654 and $653 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 Thursday, 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 10% compared to booking last minute. For the absolute cheapest price, our data suggests you should book 5 weeks before departure.

Good to know

Low season

September

Cheapest flight

$89
Best time to beat the crowds with an average 3% drop in price.
Most popular time to fly with an average 12% increase in price.
Flight from Richmond to San Juan

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 39m. The most common departure time is 3:00 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.
8.0
SouthwestOverall score based on 4217 reviews
8.6Crew
7.5Entertainment
7.0Food
8.1Boarding
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.

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.

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.

We waited to takeoff for about 1 hour delay for a 20 min flight.

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

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.

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.

Very poor help no one answering a question regarding seating. Very rude staff. They don’t care, as if it’s not part of their job. Flight was delayed for no good reason and no apologies given.

It was my worse flying experience. It was my first time and last time flying with Jet Blue.

The wifi didn't work and I needed to do some work. This was a business trip.

It was my first time in Jetblue flight in 10+ years(?) and the experience was horrible. You were better before. There were ATC delays sitting/waiting in the tarmac for 2 hours, I understand that this isn't Jetblue's problem but how the matter was handled poorly is. Cabin was so warm and hot couldn't get it to cool down for the entire waiting period worse, even during cruise flight. Start, the passengers were spoken to and treated like a little children with no respect. Constant/multiple annoying tone/voice PA announcements of mentioning "... only big/large suitcases are for the bin and small ones need to be placed under the seat, etc,..." I see that flight was delayed and crew were trying to get the plane ready to board as soon as they can but the way they presented was lack of better word, condesending and scolding tone to cattle. It was definite unpleasant, unwelcoming flight experience I have ever had with Jetblue. Whatever happen to smiles and fun employees , pleasant/helpful gate agents, flight attendants, crews, where have they gone? It was dissapointing flight experience overall from everyone. Sorry for the direct transparency.

Flight was cancelled as JetBlue could not find a pilot. Communication was poor and they did nothing for stranded passengers. Flight they rebooked us on was 4 days out.

JetBlue cancelled the flight. We had to rebook on another airline.

JetBlue cancelled the flight along with hundreds of others, for no apparent reason. no recourse, no rebooking options. never booking with them again

Jet Blue cancelled my flight after I had boarded. They attempted to rebook me for a new flight two days later. I was able to rebook with a different airline, but not until the next morning. As such, I was forced to get an expensive hotel and missed important work meetings Monday morning. I am very disappointed with the customer service and will be pursuing full reimbursement for my hotel cost.

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

Everything you need to know for your flight to Caribbean Islands

Information on your arrival and departure airports