$93 Find Cheap Flights from Reagan Washington National Airport 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 Reagan-National to Caribbean Islands departing on 2/18. 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 Washington, D.C. to Caribbean Islands, as well as popular online travel agencies
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Washington, D.C. to Caribbean Islands, as well as popular online travel agencies
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Flight Deals

Cheap Flights from Reagan-National to Caribbean Islands

Cheapest round-trip prices found by our users on KAYAK in the last 72 hours
Punta Cana
Punta Cana1 stop$352
Santo Domingo
Santo Domingo1 stop$381
Montego Bay
Montego Bay1 stop$368
Oranjestad
Oranjestad1 stop$362
Nassau
Nassaunonstop$338
Kingston
Kingston1 stop$401
Simpson Bay
Simpson Bay2 stops$437
Providenciales
Providenciales1 stop$396
Port of Spain
Port of Spain2 stops$395
Bridgetown
Bridgetown1 stop$386
George Town
George Town1 stop$299
Willemstad
Willemstad2 stops$415
St. John's
St. John's1 stop$401
Puerto Plata
Puerto Plata1 stop$420
Aguadilla
Aguadilla2 stops$251
Punta Cana
Punta Cana1 stop$352
Santo Domingo
Santo Domingo1 stop$381
Montego Bay
Montego Bay1 stop$368
Oranjestad
Oranjestad1 stop$362
Nassau
Nassaunonstop$338
Kingston
Kingston1 stop$401
Simpson Bay
Simpson Bay2 stops$437
Providenciales
Providenciales1 stop$396
Port of Spain
Port of Spain2 stops$395
Bridgetown
Bridgetown1 stop$386
George Town
George Town1 stop$299
Willemstad
Willemstad2 stops$415
St. John's
St. John's1 stop$401
Puerto Plata
Puerto Plata1 stop$420
Aguadilla
Aguadilla2 stops$251

Book Cheap Reagan-National 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 Reagan-National 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 Reagan-National to Caribbean Islands

Mon, Feb 23 - Thu, Feb 26
JetBlue Logo
8:00 am - 12:42 pm
DCA
-
SJU
3h 42mnonstop
JetBlue Logo
6:59 pm - 9:59 pm
SJU
-
DCA
4h 00mnonstop
$216JetBlue
Tue, Mar 10 - Wed, Mar 11
American Airlines Logo
6:50 am - 7:39 pm
DCA
-
SJU
12h 49m1 stop
American Airlines Logo
6:00 am - 12:34 pm
SJU
-
DCA
6h 34m1 stop
$220American Airlines
Tue, Apr 7 - Sat, Apr 11
JetBlue Logo
8:00 am - 11:45 am
DCA
-
SJU
3h 45mnonstop
JetBlue Logo
6:05 pm - 9:59 pm
SJU
-
DCA
3h 54mnonstop
$221JetBlue
Mon, Feb 23 - Wed, Feb 25
American Airlines Logo
1:42 pm - 9:33 pm
DCA
-
SJU
6h 51m1 stop
American Airlines Logo
8:15 am - 1:44 pm
SJU
-
DCA
6h 29m1 stop
$225American Airlines
Fri, Jan 30 - Wed, Feb 4
Delta Logo
6:59 am - 3:05 pm
DCA
-
STT
7h 06m1 stop
Delta Logo
4:15 pm - 10:33 pm
STT
-
DCA
7h 18m1 stop
$278Delta
Thu, Jan 29 - Mon, Feb 2
United Airlines Logo
7:30 am - 4:18 pm
DCA
-
STT
7h 48m1 stop
United Airlines Logo
3:05 pm - 11:59 pm
STT
-
DCA
9h 54m1 stop
$289United Airlines
Mon, Jan 12 - Thu, Jan 29
Delta Logo
6:59 am - 3:20 pm
DCA
-
AUA
7h 21m1 stop
Delta Logo
3:10 pm - 10:48 pm
AUA
-
DCA
8h 38m1 stop
$364Delta
Mon, Jun 1 - Fri, Jun 5
United Airlines Logo
8:00 am - 4:40 pm
DCA
-
AUA
8h 40m1 stop
United Airlines Logo
1:50 pm - 10:16 pm
AUA
-
DCA
8h 26m1 stop
$383United Airlines
Sat, Jun 13 - Wed, Jun 17
Air Canada Logo
11:00 am - 11:20 am
DCA
-
MBJ
25h 20m1 stop
Air Canada Logo
12:15 pm - 12:00 pm
MBJ
-
DCA
22h 45m2 stops
$392Air Canada
Wed, Jan 28 - Sun, Feb 1
Air Canada Logo
4:15 pm - 2:40 pm
DCA
-
SXM
21h 25m1 stop
Air Canada Logo
3:40 pm - 10:23 am
SXM
-
DCA
19h 43m1 stop
$443Air Canada
Booking Insights

KAYAK's insights & trends for Reagan-National to Caribbean Islands flights

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

What is the cheapest Washington, D.C. Reagan-National Airport 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 Washington, D.C. Reagan-National Airport found in the last 72 hours was to San Juan, at $216 round-trip. The most popular route is from Washington, D.C. Reagan-National Airport (DCA) 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 $216.

Can I save money by flying with a layover from Washington, D.C. Reagan-National Airport 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 $384, prices are generally cheapest when you fly direct.

What is the cheapest month to fly from Washington, D.C. Reagan-National Airport to Caribbean Islands?

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for round-trip flights from Washington, D.C. Reagan-National Airport 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 Washington, D.C. Reagan-National Airport to Caribbean Islands is October, when tickets cost $301 (return) on average. On the other hand, the most expensive months are December and August, when the average cost of round-trip tickets is $514 and $487 respectively.

What’s the cheapest day of the week to fly from Reagan Washington National Airport to Caribbean Islands?

The average price of all round-trip flights from Washington, D.C. Reagan-National Airport to Caribbean Islands clicked on KAYAK for each day over the last 12 months.

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

How far in advance should I book a flight from Washington, D.C. Reagan-National Airport 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 Washington, D.C. Reagan-National Airport 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 Washington, D.C. Reagan-National Airport to Caribbean Islands, you should book around 3 weeks before departure, which saves you about 16% compared to booking last minute. For the absolute cheapest price, our data suggests you should book 14 weeks before departure.

Good to know

Low seasonSeptember
Cheapest flight$93
Best time to beat the crowds with an average 11% drop in price.
Most popular time to fly with an average 15% increase in price.
Flight from Reagan Washington National Airport to Saint Thomas Island

FAQs - booking Caribbean Islands flights

  • How does KAYAK find such low prices on flights from Reagan Washington National Airport 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 Reagan Washington National Airport to Caribbean Islands.

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

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight from Reagan Washington National Airport 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 Reagan Washington National Airport 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 Reagan Washington National Airport 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 Reagan Washington National Airport 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 Reagan Washington National Airport to Caribbean Islands up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

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

    The cheapest time of day to fly to Caribbean Islands is generally at night, when round-trip flights cost $292 on average. Morning departures are around 13% more expensive than evening flights, on average. The most expensive time of day to fly to Caribbean Islands is generally in the afternoon, which is peak travel time and where the average cost of a ticket is $418.

Top tips for finding cheap flights to Caribbean Islands

  • Looking for a cheap flight? 25% of our users found tickets from Reagan Washington National Airport to the following destinations at these prices or less: San Juan $169 one-way - $311 round-trip

Reviews of the top 5 airlines serving from Reagan-National to Caribbean Islands

 
See real verified KAYAK customer reviews for airlines flying from Washington, D.C. 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 Reagan-National 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
DeltaOverall score based on 8011 reviews
7.9Entertainment
7.3Food
8.5Crew
8.1Boarding
7.9Comfort
Airline reviews

Wasn't a Delta issue I don't think, but seems there was a Delta flight at each of the 2 Dallas airports at the same exact time, both to Atlanta. I was evidently booked on the one at Love Airport, but the Carey transport shuttle took me to DFW instead and I ended up missing the flight by just a few minutes. Was able to book a Southwest flight from Love Airport, but was a big loss of time and an inconvenience.

2.0 MediocreWilliam, Dec 2025
DAL - ATL
Read more Delta reviews

Wasn't a Delta issue I don't think, but seems there was a Delta flight at each of the 2 Dallas airports at the same exact time, both to Atlanta. I was evidently booked on the one at Love Airport, but the Carey transport shuttle took me to DFW instead and I ended up missing the flight by just a few minutes. Was able to book a Southwest flight from Love Airport, but was a big loss of time and an inconvenience.

Great. I had to modify a flight. That was easy and free. Thank You

I noticed that the planes seem to be outdated. There was no entertainment per se. Also, the waiting area did not have any working electrical outlets

None of the airplane features were available during the flight.

Original flight was cancelled and when i was rebooked by the airline, they couldn't seat me in the same type of seat as I had originally booked (went from window/aisle to middle/middle and one was a bulkhead seat, and other wasn't in the same class)

Lady Pilot was perfect in every way wheels up to wheels down communication, professionalism, excellent on time departure and on time arrival, excellent communication! Fantastic job with Superb attitude!!

The food is terrible. The staff is wonderful. Comfort is good.

Left on time, a bit delayed due to headwinds most of the trip.

I fly Delta all the time, have Platinum Medallion status. But this route seems to have major problems with delays and seems to never leave on time! Have only taken it twice in the last two weeks, and each time it had delays of more than 1 hour... very disappointed!!!!

Getting to the flight was arduous and lengthy. The flight itself was good but the food option wasn’t a good selection. I need to do a Kosher option on my return. Flight crew were nice

Not great experience - we were super late boarding due to issues with aircraft. Then when we finally all got onboard and seated and they started taxiing out to the runway they just stopped then turned around and went back to the airport. Apparently the crew “ran out of time” to legally fly us. They mentioned that they were about 2 minutes away from taking off. I understand the rules and safety but kinda wonder why they would have bothered boarding us in the first place? Had to go all the way back and de plane and then wait in a HUGE line to get a hotel (this is somewhere around 2:30am) finally got to hotel by Uber (no shuttle after 20min so gave up) and they ended up putting us all back on the same aircraft at 10am next morning so got about 2.5 hours sleep. They did give us. $250 credit, but it was a São Paulo Brazil flight out of Dulles. The flight and everything was fine.

Starlink wifi on the Embraer E175 is an excellent experience. I was able to connect and work from IAD all the way to approach into BTV.

7 hours delayed due to operational issues on United’s end. Basically laziness.

Short flight but an "eager to help" crew made the journey more enjoyable!

During booking, I kept trying submitting my payment from the Mexican website and it didn't work. After I had the idea to change it to the Canadian website, it worked but I had to be charged the equivalent of 50 CAD more. I received the clear instruction that I would only be able to check-in at the airport and that it was impossible to select a seat 24 hours before departure, that I had to pay 144 CAD to do so, although not only was I able to check-in 24 hours before departure, but I could have selected my seats for free then. All in all, I almost threw $200 out the window due to misleading information. Besides, the app kept crashing, the information to get to the gate on the app was inaccurate, my gate was switched and I was only informed once in the air (luckily I had noticed the departure pannel), I was not addressed in my language beforehand and even if I tried I was immediately answered in English (which meant the crew understood but didn't want to answer accordingly), there was only one snack & beverage service on my medium haul flight and no beverage service on my short haul flight. To be fair, the planes were comfortable, the crew apart from the language issue was helpful, dynamic and engaging, the plane was clean and the directions were clear and direct. United has a lot of potential to be one of my favourite airlines, but the devil is in the details and a lot of them missed the target.

Better WiFi. I cannot understand that in 2025, United is so behind on a technology that is now a necessity and still painfully unreliable, slow and keeps disconnecting.

Great service on board. Boarding a bit slow due to process. Food was pretty average.

Very small cramped plane for an international flight. Everything else was good, but it was maybe the smallest comfort-wise I've ever been on for longer than 3-4 hours and the trip was 7.5

Flight was delayed 3 hours. No food and drink vouchers was provided. They offered a mini pretzel bag and water .

Staff was rude. Didn’t give water for 2 hours. Worst service

Experience was good, however I had a delay due to weather happening and had to re purchase a seat on a new plane for a higher price (could be my own issue and misunderstanding) but other than that situation. First time flyer (by myself) was terrific!! The last from ORD to ALO didn't have wifi, but it was only 45 minutes so I'm sure that was part of the reason. Overall my experience was great! Next time I will remember to buy tickets with longer layovers. The delays really saved my overall anxiety. :)

Flight was delayed 17 hours due to aircraft issues. American did provide hotel, transportation and meals, 3 hours past boarding time, but it took us another hour to get the vouchers.

Flight was on time is the only good thing. Person loading the plane called 1-6 to board at the same time, made it chaotic. Plane was too small for even putting backpacks in overhead. Seat for normal sized people were too small. The WIFI didn't work. When we landed had to wait because not enough ground crew.

Did not understand a single word the attendant said on the pa system. I was glad it was not an emergency.

Flight was late and boarding was confusing because gate changed and I didn’t get a notification

Gate was overcrowded. Gate agents performed very well. Flight crew was top notch! Efficient & professional & courteous. Both meals not thermalized well. Dinner main dish was actually cold in the center. Almost inedible. Breakfast sandwich was lukewarm.

The boarding was as always, the crew tried their best but not enough. The food was a disaster I had dietary restrictions that were half met because the company did not loaded the food for the flight. The entertainment screen was fine but content was not and also they removed the free messaging option from the flight and they charged 30 dollars for that crappy bandwidth. This flight is not worth the cost and the company is going down on quality.

Not comparable to Qatar Airways services on flights to Doha. Flight attendants provided basic services; I was never recognized by name or as an Executive Platinum member. Restrooms were not kept clean during the flight.

Awful. They won’t help me with anything. I booked on American but they abdicated to Iberia. The ticket was overpriced. Everything negative

I got sick nothing contagious but distressing and the care I received by Kayla? Keighly the flight attendant will be memorable for ever. Thank You

The ride share experience in JFK is terrible. After traveling on a flight, then you need to take a subway to the last stop to get an uber or lyft. Unacceptable. Bad job JetBlue for permitting JFK and Port Authority to do this to your passengers.

Checking In on JetBlue site was impossible. It hung up on REAL ID. Even my Global Entry did not help. Luckily, on Kayak site it was a breeze. Entire flight the temperature was COLD! Otherwise the crew was great!

The flight was two hours late due to a computer fault and resulting maintenance. Nothing was offered as compensation beyond bottles of water during the time we were deplaned and waiting in the terminal.

Very pleasant flight attendants. Gate crew rather loud chatting with each other.

Four plus hour flight delay in New York caused us to take off after 11:30pm. We didn’t arrive at our hotel until five hours after check in. Started the trip off feeling exhausted.

Plane was in bad shape. TV’s and WiFi didn’t work. Plane need a refresh. Not enough room for bags.

There was a fowl odour coming from the lavatory the entire flight

Everything was great. I liked the text updates so that I never miss a gate change & I have all the latest info.

I don’t usually fly budget airlines or airlines in the United States. It was as good as any other airline. The seats are comfortable and the airline attendants are not rude & surly. Very nice flight (s).

No internet on a flight over three hours in this age is criminal. Staff inattentive and dismissive

Nothing specific. Cabin temperature was too high for some reason.

It was just fine. I managed to make all my connection too sbut had trouble in Munich with no wheel chair and trouble trying to get help from the airport people to get to the other terminal for my flight. Finally a wonderful lady Amelia, helped me to make my flight connection Timon with zero time to spare.

Over 40 years ago my AC return flight was canceled, during this last summer the same thing happened. AC denied everything Canadian like paying for accommodations and basic necessities. So why would I ever want to fly AC again? This last flight my wife took the return flight had problems and left late, so I guess they are getting better. However I have no faith in this airline so I drove to this last destination! I'll never fly AC again!!!

Great check in process in LA and good service The check in process as well as at the gate is way better in the US versus canada 🇨🇦

Super experience. Earlier than schedule departure and arrival. Baggage handling was very good

Allow me to book extra bag check in as free though I packed in 1 luggage but that was 7 LBS overweight so make another bag to free check in.

I would like to get my money back. I flight was 4 hours late on the way to detroit, And same on my way back to Brussels they cancelled my flight and give me an other ticket and i had to wait 5 hours.

All attendents were very efficient, pleasant and happy. Everything went smoothly. The seats could have been wider. There could have been more free food instead of just one small bar.

My seat was one of those that couldn't recline, but the problem was that it was abnormally upright, so the headrest actually made the seat concave, which was uncomfortable and hard on my lower back. I had to ball my jacket up and use it as lumbar support. goodness I had it with me.

Boarding was so so after zone 3 was called all other zones went in

Everything you need to know for your flight to Caribbean Islands

Information on your arrival and departure airports