$100 Find Cheap Flights from Richmond to Caribbean Islands

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 6/30. 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.
1 adult
1 adult, Economy, 0 bags

KAYAK searches hundreds of travel sites at once for deals on flights to Caribbean Islands

 
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Richmond to Caribbean Islands.
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Richmond to Caribbean Islands.
Travelers love KAYAK
41,299,237 searches in the past 7 days on KAYAK

Save 24% or moreCompare multiple travel sites with one search.

Track pricesNot ready to book? Create a price alert for when prices drop.

Bundle and saveSave money when you bundle your flight + hotel.

Filter your dealsChoose cabin class, free Wi-Fi and more.

Flight Deals
Booking Insights
Flight Deals

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$391
Santo Domingo
Santo Domingo1 stop$368
Montego Bay
Montego Bay1 stop$324
Oranjestad
Oranjestad1 stop$316
Nassau
Nassau1 stop$309
Kingston
Kingston1 stop$449
Simpson Bay
Simpson Bay1 stop$305
Providenciales
Providenciales1 stop$611
Port of Spain
Port of Spain2 stops$679
Bridgetown
Bridgetown1 stop$652
George Town
George Town1 stop$359
Willemstad
Willemstad1 stop$594
Aguadilla
Aguadilla1 stop$376
Puerto Plata
Puerto Plata1 stop$610
St. John's
St. John's2 stops$715
Punta Cana
Punta Cana1 stop$391
Santo Domingo
Santo Domingo1 stop$368
Montego Bay
Montego Bay1 stop$324
Oranjestad
Oranjestad1 stop$316
Nassau
Nassau1 stop$309
Kingston
Kingston1 stop$449
Simpson Bay
Simpson Bay1 stop$305
Providenciales
Providenciales1 stop$611
Port of Spain
Port of Spain2 stops$679
Bridgetown
Bridgetown1 stop$652
George Town
George Town1 stop$359
Willemstad
Willemstad1 stop$594
Aguadilla
Aguadilla1 stop$376
Puerto Plata
Puerto Plata1 stop$610
St. John's
St. John's2 stops$715

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, May 5 - Sat, May 9
JetBlue Logo
1:50 pm - 6:04 pm
RIC
-
SJU
4h 14mnonstop
JetBlue Logo
8:44 am - 12:39 pm
SJU
-
RIC
3h 55mnonstop
$240JetBlue
Tue, May 5 - Sat, May 9
Delta Logo
1:29 pm - 11:13 pm
RIC
-
SJU
9h 44m
1 stop
Delta Logo
5:43 pm - 12:43 am
SJU
-
RIC
7h 00m
1 stop
$254Delta
Sat, May 9 - Fri, May 15
American Airlines Logo
6:21 pm - 10:47 am
RIC
-
STT
16h 26m
1 stop
American Airlines Logo
5:05 pm - 11:57 pm
STT
-
RIC
6h 52m
1 stop
$260American Airlines
Wed, May 6 - Thu, May 14
American Airlines Logo
5:05 am - 2:49 pm
RIC
-
STT
9h 44m
1 stop
American Airlines Logo
1:15 pm - 12:23 am
STT
-
RIC
11h 08m
1 stop
$265American Airlines
Sat, May 2 - Tue, May 5
United Airlines Logo
10:25 am - 9:24 pm
RIC
-
SJU
10h 59m
2 stops
United Airlines Logo
7:00 am - 4:01 pm
SJU
-
RIC
9h 01m
1 stop
$275United Airlines
Sun, May 3 - Fri, May 8
United Airlines Logo
6:00 am - 3:42 pm
RIC
-
SJU
9h 42m
1 stop
United Airlines Logo
1:00 am - 9:37 am
SJU
-
RIC
8h 37m
2 stops
$279United Airlines
Sat, May 9 - Sat, May 16
JetBlue Logo
1:34 pm - 5:48 pm
RIC
-
SJU
4h 14mnonstop
JetBlue Logo
12:50 pm - 10:38 pm
SJU
-
RIC
9h 48m
1 stop
$291JetBlue
Tue, May 5 - Wed, May 13
Delta Logo
6:35 am - 2:48 pm
RIC
-
STT
8h 13m
1 stop
Delta Logo
3:01 pm - 12:48 am
STT
-
RIC
9h 47m
1 stop
$301Delta
Sat, May 16 - Sat, May 23
Southwest Logo
6:05 am - 11:35 am
RIC
-
PLS
5h 30m
1 stop
Southwest Logo
4:35 pm - 10:50 pm
PLS
-
RIC
6h 15m
1 stop
$611Southwest
Sat, May 16 - Sat, May 23
Southwest Logo
6:05 am - 3:35 pm
RIC
-
PLS
9h 30m
2 stops
Southwest Logo
4:35 pm - 10:50 pm
PLS
-
RIC
6h 15m
1 stop
$616Southwest
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 72 hours was to San Juan, at $225 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 72 hours was $225.

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 afternoon, when round-trip flights cost $373 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 $1,161.

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 $363, 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 October, when tickets cost $334 (return) on average. On the other hand, the most expensive months are March and December, when the average cost of round-trip tickets is $494 and $491 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 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 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 6% compared to booking last minute. For the absolute cheapest price, our data suggests you should book 21 weeks before departure.

Good to know

Low seasonSeptember
Cheapest flight$100
Best time to beat the crowds with an average 7% drop in price.
Most popular time to fly with an average 16% 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.

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 4331 reviews
8.1Boarding
7.5Entertainment
8.0Comfort
8.6Crew
7.0Food
Airline reviews

Southwest is kind of a slum airline. It’s gotten more expensive over the years for less and less service. I am a Southwest Chase Visa card holder and was forced to choose a seat in the 26th row in the middle seat. However my wife who is a rewards member but doesn’t hold a card or anything else, gets randomly assigned a normally paid seat in row 6! How does that work?

4.0 OkayDavid, Apr 2026
COS - DAL
Read more Southwest reviews

Southwest is kind of a slum airline. It’s gotten more expensive over the years for less and less service. I am a Southwest Chase Visa card holder and was forced to choose a seat in the 26th row in the middle seat. However my wife who is a rewards member but doesn’t hold a card or anything else, gets randomly assigned a normally paid seat in row 6! How does that work?

For the first time in a long time, the Wi-Fi actually worked the entire flight! The flight crew was amazing as usual.

The seat was not comfortable. 1D. My back was sore all night and the next day.

Great flight. I didn't get a drink because I was asleep whole on the flight.

Great flight from Seattle to Phoenix and to Chicago-Midway from Phoenix

The new boarding process was easy and straightforward. Very pleasant.

The flight was okay. The pilots did an amazing job and kept us updated on the flight. The flight attendants were okay. They found time to be chatty with each other rather than focus on the guests. One of the attendants was a little less warm when asking about my bag I had on my lap that I was using during latter part of the mid- flight. Mind you, it was not the departure descent. I’m respectful to each and every attendant, it was the tone in her voice reminding me to place my carryon bag on the floor. I hope to have a better experience next time.

The entire travel day was a disaster from beginning to end. Woke up at two in the morning to make it to San Juan airport in time for a 5:30 am flight to Milwaukee which connected in Baltimore. Massive delays lead to me missing original connection out of Baltimore. Sixteen hours of delays/rebooking/layover time later, arrived in Milwaukee to find that only one of two checked bags made it there (despite the fact that Southwest brought another 737 jet to San Juan to fly us out to our original Baltimore connection—-not squeezed into another booked flight). The flight from Baltimore to Milwaukee was barely half full, so there was no logical reason to ship my bags out of Baltimore on a different flight to Chicago to then ship to Milwaukee. Southwest decided that my bags should not have been on the same connecting flight I WAS ON to Milwaukee, and then proceeded to accidentally leave my larger bag with the important items in Chicago. Terrible logic and support all around. Extremely angered and disappointed with SW. What a clownish operation your company has become!

It was as expected and I was grateful for the wheel chair help and ease of use.

One of the best airlines for fast boarding, on time arrivals, and top notch service!

The baggage belt was not updated on the Delta App and was displayed on the wrong belt board. Was not expecting this to happen.

The plan was delayed and left DC 90 minutes late. However, it showed a 20 minute delay on the delta app, then a 12 min delay. It turned out to be an hour delay. I found out where the plane was with flightaware. Stop keeping customers in the dark about what is going on.

Everything went smoothly, although the usual gripes about airline travel were still present: the boarding process is inefficient, the snack selection is limited, and so on. Since there was extra space on the flight, the gate agent rearranged many people's seats to put people on the aisles and windows, leaving the middle seats empty, as much as possible, which was pretty great.

Landed without a gate ready. Plane is extremely old and dirty.

All the amenities was wonderful, if they could keep their prices that low. I'd fly with them all the time.

Very old plane with no inflight entertainment. I purchased the internet pass and it was nearly unusable.

My tray was broken so i had no place to work or eat except my lap. Flight attendant said I would get an email with some credit or miles, it was a complete waste of time as I could only function at about 20% of normal. I have not received anything yet.

Short trip, no food and therefore no expectation for much interaction with staff who were pleasant and professional. My critique is on comfort of the seats. Exit rows and comfort seats do not provide enough personal space for 3 side-by-side seats, especially when in the middle row. Some passengers are not considerate of the middle seat and there should be signs that state something to the effect of: "please consider giving middle seats use of the armrests."

My flight yesterday evening was delayed 3.5 hours with no water or food service. Poor experience

Transparency from pilots, quick boarding and exiting the plane, staff greeted to each and everyone,

The flight was significantly delayed. The inbound flight from EWR was delayed departing because of mechanical problems. My original departure from CLT was 5:28 pm but due to the delay of the inbound flight, after arrival, deplaning, cleaning, boarding, we did not push back from the gate until 9:00 pm. Once in the air, the flight was smooth and what was originally supposed to be an arrival in ORD at 7:30 pm local time turned out to be 9:35 pm.

Putting people that close to the bathroom, where you have to look into the bathroom as people are exiting and entering was not great and the smell was also not great. I know the airlines are desperate for more chairs, but that seat is a crime.

My bags were misplaced!!! Im in a foreign country with no bags

The entertainment options on the seat back video boards were nice.

The flight I was supposed to be on was supposed to take off at 1:50 from State College. It was delayed over and over and over again until somehow I had to rebook on a flight that was supposed to have left State College at 8 am that morning but didn't end up taking off until almost 6 pm. Not only was this completely unacceptable, the "token from United" was a 15 dollar meal voucher that has to be used by today. I would personally like some miles added to my account for this inconvenience. I was in transit for 8 hours from the time I arrive at State College Aiport to when I got home. I was supposed to be home at 3 pm and I returned at 8 pm. Unacceptable. I have not been on an on Time united flight in nearly 5 years.

Crew was friendly. Seats are too narrow, particularly when a big person is in the adjacent seat, but I understand this is due to smaller planes usually flight into Lincoln. I have experienced several flight delays going out and coming into Lincoln airport, I say maybe 50% or higher of the flights I've taken out of this airport have been delayed.

newer aircraft, ability to connect my headset via blue tooth for entertainment.

Great flight. Boarded efficiently. Arrived early at CLT. There was no in flight entertainment on this aircraft. Great crew.

Due to cancellation of connecting flight (Lufthansa) I didn’t fly with United

The seat was comfortable. There was a lot of turbulence. If it weren't for that,it would have been okay.

The flight was delayed 4 hours and the JetBlue people at the counter kept lying to us and telling us it was due to weather however all other flights were going in and out of NY and FL. Then they lied that the plane had to stop to refuel. Then they lied and said the plane needed a tire change. JetBlue is the worst. Then they gave a lot of people meal vouchers however I didn’t know they did that and they didn’t offer anything to me.

My experience with Jet Blue was wonderful. My experience with Kayak sucked and will never use again.

Jet Blue has excellent everything, Friendly customer service and staff, clean aircraft’s and is always on time.

Entertainment and wifi were very sub-par - audio issues and no wifi

We were delayed and had to circle due to weather and had to divert for fuel. While I understand that you can’t control the weather I would have appreciated knowing that the crew wasn’t going to run out of hours and then having to spend the night in the Raleigh airport.

Messy plane that was falling apart Small screens that didn't work

I was traveling with two small kids and our TV s were the only ones not working. Informed the flight attendant who did nothing about them.

They forced me to check my hand luggage at the gate.

I specifically choose not to check bags to ensure I can proceed directly to ground transportation upon arrival. However, due to a recurring lack of cabin space, I was again forced to gate-check my rolling luggage after going through my luggage to take out electronics and batteries. This practice unilaterally changes the service agreement made at the time of purchase. JetBlue needs to find a better way to manage overhead space that honors the carry-on baggage allowance.

Still hasn’t left. Why are you asking how it was?

The crew was very kind, but no in-flight entertainment monitors and a 2 hour and 30 minute delay was extremely frustrating.

Everything was delayed and the staff sent me to the wrong gate, causing me to miss one of my flights. I arrived at my destination 6 hours later than I was supposed to.

Got home at 3am after deboarding the plane. No compensation offered by American

Delayed flight. Missed connection, AA put us on a later connecting flight. The connection flight was delayed 4 times and we had to deplane. Didnt get home until 3am, when I was supposed to be home at 8:30p. Zero compensation offered from American. I would not fly them again.

The seats need better cushioning for a nearly 5-hour flight, it was a bit uncomfortable. I'm glad American has free wi-fi but there were was a bout 30 minutes in the middle of the flight when there was no connection which was frustrating.

My original flight got delayed day of so I had to rebook it from one layover to two layovers. The flight also left earlier which was a slight inconvenience but manageable. Then my first connection flight got delayed 3 separate times for a total of 2 hours delayed, causing me to miss my second connection flight back to Santa Barbara. Now, because of this missed flight, I am missing my college classes that I pay for.

Flight: Started on time. Comfortable flight. Arrived on time. Crew: Very cordial and helpful. Drinks and snack was served with a smile. Overall enjoyed the trip. Regards, Hari Doss Chanchala Doss

It was good, the staff was great, and the food, was as usual, tea and biscuit. Bathroom was clean, and the plane was clean as well.

Early departure meant on time arrival. Only real problem was free internet had issues, although chatting with the internet help desk (you can do this via aainflight.com) got the issue resolved.

It was really a terrific experience both going and returning on AA. Staff and crew were professional.

Everything you need to know for your flight to Caribbean Islands

Information on your arrival and departure airports