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

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight from Richmond to Caribbean Islands departing on 9/26. Fares are subject to change and may not be available on all flights or dates of travel. Click the price to replicate the search for this deal.
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Cheap Flights from Richmond to Caribbean Islands

Cheapest round-trip prices found by our users on KAYAK in the last 72 hours
Punta Cana
Punta Cana1 stop$471
Santo Domingo
Santo Domingo1 stop$426
Montego Bay
Montego Bay1 stop$412
Oranjestad
Oranjestad1 stop$381
Nassau
Nassau1 stop$308
Kingston
Kingston1 stop$470
Simpson Bay
Simpson Bay1 stop$337
Providenciales
Providenciales1 stop$660
Port of Spain
Port of Spain1 stop$584
Bridgetown
Bridgetown1 stop$672
George Town
George Town1 stop$411
Willemstad
Willemstad1 stop$625
Aguadilla
Aguadilla1 stop$280
St. John's
St. John's2 stops$813
Puerto Plata
Puerto Plata1 stop$720
Punta Cana
Punta Cana1 stop$471
Santo Domingo
Santo Domingo1 stop$426
Montego Bay
Montego Bay1 stop$412
Oranjestad
Oranjestad1 stop$381
Nassau
Nassau1 stop$308
Kingston
Kingston1 stop$470
Simpson Bay
Simpson Bay1 stop$337
Providenciales
Providenciales1 stop$660
Port of Spain
Port of Spain1 stop$584
Bridgetown
Bridgetown1 stop$672
George Town
George Town1 stop$411
Willemstad
Willemstad1 stop$625
Aguadilla
Aguadilla1 stop$280
St. John's
St. John's2 stops$813
Puerto Plata
Puerto Plata1 stop$720

Book Cheap Richmond to Caribbean Islands Plane Tickets

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Richmond to Caribbean Islands that are departing in the next months. While these flights were available on KAYAK in the last 72 hours, prices and availability are subject to change and deals may expire.
Discover the best prices for you by selecting your travel dates on KAYAK.

Recent round-trip flight deals from Richmond to Caribbean Islands

Tue, Sep 1 - Sat, Sep 5
JetBlue Logo
3:30 pm - 7:09 pmRIC  Richmond Byrd Intl-SJU San Juan Luis Munoz Marin Intl
3h 39mnonstop
JetBlue Logo
12:43 pm - 4:29 pmSJU  San Juan Luis Munoz Marin Intl-RIC Richmond Byrd Intl
3h 46mnonstop
$263JetBlue
Thu, Oct 1 - Thu, Oct 8
JetBlue Logo
1:40 pm - 5:20 pmRIC  Richmond Byrd Intl-SJU San Juan Luis Munoz Marin Intl
3h 40mnonstop
JetBlue Logo
9:00 am - 12:39 pmSJU  San Juan Luis Munoz Marin Intl-RIC Richmond Byrd Intl
3h 39mnonstop
$263JetBlue
Tue, Sep 1 - Sat, Sep 5
American Airlines Logo
6:10 am - 9:55 pmRIC  Richmond Byrd Intl-SJU San Juan Luis Munoz Marin Intl
15h 45m1 stop Miami
American Airlines Logo
6:45 am - 3:50 pmSJU  San Juan Luis Munoz Marin Intl-RIC Richmond Byrd Intl
9h 05m1 stop Charlotte Douglas
$263American Airlines
Tue, Sep 1 - Sat, Sep 5
American Airlines Logo
6:27 am - 2:51 pmRIC  Richmond Byrd Intl-SJU San Juan Luis Munoz Marin Intl
8h 24m2 stops Philadelphia Charlotte Douglas
American Airlines Logo
6:45 am - 4:40 pmSJU  San Juan Luis Munoz Marin Intl-RIC Richmond Byrd Intl
9h 55m2 stops Charlotte Douglas Philadelphia
$263American Airlines
Sat, Sep 26 - Tue, Sep 29
Multiple Airlines Logo
7:21 pm - 1:34 pmRIC  Richmond Byrd Intl-SJU San Juan Luis Munoz Marin Intl
18h 13m2 stops Tampa Fort Lauderdale
Multiple Airlines Logo
6:05 pm - 6:41 pmSJU  San Juan Luis Munoz Marin Intl-RIC Richmond Byrd Intl
24h 36m1 stop Tampa
$270Multiple Airlines
Fri, Sep 11 - Fri, Sep 18
Delta Logo
4:59 pm - 11:49 pmRIC  Richmond Byrd Intl-SJU San Juan Luis Munoz Marin Intl
6h 50m1 stop New York John F Kennedy Intl
Delta Logo
7:30 am - 4:19 pmSJU  San Juan Luis Munoz Marin Intl-RIC Richmond Byrd Intl
8h 49m1 stop New York John F Kennedy Intl
$276Delta
Tue, Sep 29 - Fri, Oct 2
Delta Logo
12:17 pm - 11:49 pmRIC  Richmond Byrd Intl-SJU San Juan Luis Munoz Marin Intl
11h 32m1 stop New York John F Kennedy Intl
Delta Logo
5:59 pm - 12:43 amSJU  San Juan Luis Munoz Marin Intl-RIC Richmond Byrd Intl
6h 44m1 stop Atlanta Hartsfield-Jackson
$276Delta
Fri, Sep 25 - Wed, Sep 30
Multiple Airlines Logo
5:51 pm - 8:48 pmRIC  Richmond Byrd Intl-SJU San Juan Luis Munoz Marin Intl
26h 57m1 stop Orlando
Multiple Airlines Logo
8:45 am - 6:41 pmSJU  San Juan Luis Munoz Marin Intl-RIC Richmond Byrd Intl
9h 56m2 stops Fort Lauderdale Tampa
$276Multiple Airlines
Wed, Sep 2 - Sat, Sep 5
United Airlines Logo
6:40 am - 8:38 pmRIC  Richmond Byrd Intl-SJU San Juan Luis Munoz Marin Intl
13h 58m2 stops Washington, D.C. Dulles Intl Houston George Bush Intcntl
United Airlines Logo
3:56 pm - 12:43 amSJU  San Juan Luis Munoz Marin Intl-RIC Richmond Byrd Intl
8h 47m1 stop Chicago O'Hare Intl
$278United Airlines
Sat, Sep 5 - Fri, Sep 11
United Airlines Logo
6:40 am - 8:38 pmRIC  Richmond Byrd Intl-SJU San Juan Luis Munoz Marin Intl
13h 58m2 stops Washington, D.C. Dulles Intl Houston George Bush Intcntl
United Airlines Logo
1:00 am - 2:50 pmSJU  San Juan Luis Munoz Marin Intl-RIC Richmond Byrd Intl
13h 50m2 stops Newark Chicago O'Hare Intl
$278United Airlines
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?

Data is based on round-trip flight searches on KAYAK over the past month.

The cheapest ticket to Caribbean Islands from Richmond found in the last 5 days was to San Juan, at $237 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 $237.

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

The average price for all round-trip flights from Richmond to Caribbean Islands depending on the time of departure, clicked by users on KAYAK in the last 2 weeks.

The cheapest time of day to fly to Caribbean Islands is generally in the evening, when round-trip flights cost $366 on average. Morning departures are around 55% 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?

The average round-trip price for all non-stop flights, flights with one layover, and flights with two layovers for the route found by users searching on KAYAK in the last 2 weeks.

No, with an average price for the route of $396, prices are generally cheapest when you fly direct.

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

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for round-trip flights from Richmond to Caribbean Islands, removes the top 0.1% to account for outliers, and then takes the median of all values for each month.

The cheapest month for flights from Richmond to Caribbean Islands is January, when tickets cost $462 (return) on average. On the other hand, the most expensive months are March and June, when the average cost of round-trip tickets is $656 and $654 respectively.

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

The average price of all round-trip flights from Richmond to Caribbean Islands clicked on KAYAK for each day over the last 12 months.

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 calculate weekly average prices, KAYAK takes all prices for each week before departure over the last year for round-trip flights from Richmond to Caribbean Islands, removes the top 0.1% to account for outliers, and then takes the average of all the values for each week.

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 12% 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

Cheapest flight

$100
Best time to beat the crowds with an average 4% drop in price.
Most popular time to fly with an average 12% increase in price.
Flight from Richmond to Nassau

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

 
See real verified KAYAK customer reviews for airlines flying from Richmond to Caribbean Islands. Airline scores are aggregated from all reviews left by passengers on KAYAK after flying with an airline. KAYAK doesn’t show reviews that are older than 5 years. Learn how KAYAK collects reviews.
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 4218 reviews
8.6Crew
8.1Boarding
7.5Entertainment
8.0Comfort
7.0Food
Airline reviews

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. :(

8.0 ExcellentDavid, Aug 2026
Read more Southwest reviews

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.

Flight time kept changing and so did the gate. It was very frustrating

Exceptional. The gate crew responded quickly and got me onto this earlier flight as the final passenger, saving me more than four hours of wait time for my reserved flight.

The flight was delayed due to earlier issues at other airports. The crew was excellent & made it a good trip.

Boarding process of asking for volunteers to check bags goes against the system you had before with 2 bags checked free. This process is more of a guilt trip than a caring attitude toward the customer. In addition bag-size scrutiny has increased which also slows down the process of boarding. My wife said she will not fly on your airline again unless there is no other option.

Eveeyrime I fly they are begging for bags due to cabin overhead space. What they should so ia take the bags that are clearly too big to fit wheels first on their side. And those of us who give up the bag should really get their bags first. When boarding, nobody wants stupid jokes about how hot it is on board. Give us some cool air. Im usually sick from the heat by the time we take off.

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

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.

Cut off carry ons, had to check, got on and there was plenty of bin space. Disappointing.

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.

You did a great job rescheduling my cancelled flight. However, you made me pay for two seats for $118 even though the seats on the original flight were free. I think that was a very unfair thing to do.

They cancelled the flight after 5 hours at the airport and the only flight they offered was for the next day with a 7.5 layover in fll. This was not going to work for me as this was only a weekend trip and getting into providence at 10 pm a day later caused me to lose Mo ey on hotels money on airport parking a dog sitter etc. they wouldn’t offer any type of a voucher or anything else. All they did was refund the flight which didn’t help me with all the money in time I lost. I was going to see my very sick father

The flight was on time the crew was courteous that makes for a good flight.

A more comfortable seat. Padding would be really helpful but I've read the airlines don't want customers to be satisfied with economy seats.

When I booked, I included my checked luggage and when the bill was sent there was no record of this. Its was costly since I am from Trinidad amd Tobago. Exchange rate over seven dollars to one US dollar.

Everything was good except checking bags . I had paid for two bags but it didn’t show so we had to do it again while people waited and we were struggling to get to our flight

Flight delayed 4 times on a non-stop from BOS to SFO. Then when landed in SFO had to wait for 30 mins for a gate AT 3:30AM.

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