$89 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 12/9. 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

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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.
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.
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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$371
Santo Domingo
Santo Domingo1 stop$374
Montego Bay
Montego Bay1 stop$361
Oranjestad
Oranjestad2 stops$406
Nassau
Nassau1 stop$405
Simpson Bay
Simpson Bay2 stops$407
Kingston
Kingston1 stop$413
Providenciales
Providenciales1 stop$363
Port of Spain
Port of Spain1 stop$378
Bridgetown
Bridgetown1 stop$388
George Town
George Town1 stop$428
Willemstad
Willemstad1 stop$308
St. John's
St. John's1 stop$441
Puerto Plata
Puerto Plata1 stop$457
Aguadilla
Aguadilla1 stop$292
Punta Cana
Punta Cana1 stop$371
Santo Domingo
Santo Domingo1 stop$374
Montego Bay
Montego Bay1 stop$361
Oranjestad
Oranjestad2 stops$406
Nassau
Nassau1 stop$405
Simpson Bay
Simpson Bay2 stops$407
Kingston
Kingston1 stop$413
Providenciales
Providenciales1 stop$363
Port of Spain
Port of Spain1 stop$378
Bridgetown
Bridgetown1 stop$388
George Town
George Town1 stop$428
Willemstad
Willemstad1 stop$308
St. John's
St. John's1 stop$441
Puerto Plata
Puerto Plata1 stop$457
Aguadilla
Aguadilla1 stop$292

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

Sun, Oct 19 - Sat, Oct 25
American Airlines Logo
12:22 pm - 11:59 pmDCA-SJU
11h 37m1 stop
American Airlines Logo
5:25 am - 5:59 pmSJU-DCA
12h 34m1 stop
$185American Airlines
Find Deal
Tue, Oct 14 - Tue, Oct 28
JetBlue Logo
8:30 am - 12:15 pmDCA-SJU
3h 45mnonstop
JetBlue Logo
6:02 pm - 9:59 pmSJU-DCA
3h 57mnonstop
$198JetBlue
Find Deal
Sun, Oct 26 - Thu, Oct 30
JetBlue Logo
8:00 am - 11:51 amDCA-SJU
3h 51mnonstop
JetBlue Logo
6:02 pm - 9:59 pmSJU-DCA
3h 57mnonstop
$199JetBlue
Find Deal
Tue, Oct 21 - Thu, Oct 23
American Airlines Logo
12:54 pm - 11:59 pmDCA-SJU
11h 05m1 stop
American Airlines Logo
3:50 pm - 10:16 pmSJU-DCA
6h 26m1 stop
$210American Airlines
Find Deal
Sat, Nov 15 - Wed, Nov 19
Delta Logo
1:44 pm - 11:13 pmDCA-SJU
8h 29m1 stop
Delta Logo
1:57 pm - 9:43 pmSJU-DCA
8h 46m1 stop
$225Delta
Find Deal
Thu, Oct 30 - Sun, Nov 2
Southwest Logo
7:25 am - 2:45 pmDCA-SJU
7h 20m1 stop
Southwest Logo
5:40 am - 11:00 amSJU-DCA
6h 20m1 stop
$255Southwest
Find Deal
Fri, Oct 31 - Mon, Nov 3
Delta Logo
6:05 am - 4:25 pmDCA-SJU
10h 20m1 stop
Delta Logo
3:22 pm - 10:59 pmSJU-DCA
8h 37m1 stop
$260Delta
Find Deal
Sat, Dec 13 - Sat, Dec 20
Southwest Logo
7:00 am - 6:40 pmDCA-SJU
10h 40m1 stop
Southwest Logo
6:35 am - 6:10 pmSJU-DCA
12h 35m1 stop
$265Southwest
Find Deal
Mon, Oct 6 - Wed, Oct 8
United Airlines Logo
6:00 am - 3:42 pmDCA-SJU
9h 42m1 stop
United Airlines Logo
1:05 am - 9:58 amSJU-DCA
8h 53m1 stop
$296United Airlines
Find Deal
Sat, Jan 3 - Wed, Jan 7
United Airlines Logo
7:00 am - 1:48 pmDCA-NAS
6h 48m1 stop
United Airlines Logo
12:55 pm - 7:33 pmNAS-DCA
6h 38m1 stop
$414United Airlines
Find Deal
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 $226 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 $226.

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 $618, 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 $351 (return) on average. On the other hand, the most expensive months are December and August, when the average cost of round-trip tickets is $627 and $465 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 Thursday, 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 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 seasonOctober
Cheapest flight$89
Best time to beat the crowds with an average 4% drop in price.
Most popular time to fly with an average 32% increase in price.
Flight from Reagan Washington National Airport to San Juan

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 15% 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 $423.

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 $168 one-way - $276 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.
8.0
SouthwestOverall score based on 4241 reviews
8.6Crew
8.1Boarding
8.0Comfort
7.0Food
7.5Entertainment
Airline reviews

AC sub par. WiFi not working correctly. Ac sucked. Seats very narrow.

2.0 MediocreMike, Aug 2025AUS - BWI
Read more Southwest reviews

AC sub par. WiFi not working correctly. Ac sucked. Seats very narrow.

Near 4 hour flight with only 1 service. Had to use call button to request water. Internet and power not working until into flight. Internet would stop working during flight.

Southwest's seats are the least comfortable I have ever sat in.

The cabin was quiet for the redeye flight. The area was clean. The staff was great. The 787 Max was in good condition. Drawbacks were that the seat widths were tight for some passengers. The seat padding was at best average and for a long flight uncomfortable.

Southwest like most American domestic airlines, is a mediocre airline. But it is among the cheapest. Oh well.

My flight was delayed 50 minutes and we were rushed to board to then sit for 15 minutes until the pilot arrived. Unacceptable since we could have waited to board. Also the delayed flight was updated AFTER we boarded to more than the 10 minutes as originally stated.

Other than a bit of a delay, everything was good. Again, the boarding process and picking seats is the only thing I don't enjoy.

If we are going to have to pay for luggage, make it easier to do. Put something on the app during check-in so I don't need to do it at the kiosk. I've done it twice recently and I ended up having to pay at the desk because something went wrong at the kiosk in Tampa.

Better and more food and drinks. Put msnbc and free speech tv on the news channel selection list.

southwest just starting charging for luggage. hadnt realized it until it was too late. now out $70 when i couldve bought a carry on if i wouldve known. free bags was one of the only reasons i chose southwest over another airline (the other being no assigned seats, which is apparently also being changed). stupid business decision. wont be flying southwest anymore.

This route with Delta always has delays or is cancelled. Aircrafts seem smaller and older. I fly Delta quite a bit - haven’t had issues with the international flights. But this route has always been the troublesome one

Nothing special. The crew never went out of their way for anything.

Three seats in first class were broken and while they were able to still acommodate us it was looking very touch and go and they had others they could not acommodate

Mechanic delay in addition to a 2 hour change in takeoff time was frustrating.

Delayed due to thunderstorms and no in-flight service due to rough weather — both of which are out of Delta’s control. Flight was good overall.

The flight attendants in SLC were rude. I arrived 40 minutes early to gate. Ticket said I needed check in for seat assignments and tried check in and attendants said they weren’t doing it. And proceeded to never call me to give me a ticket so when time to board I received the very last seat. Please relay to employees to do their job better..,

On this flight I felt the food offering was not as complete as on previous flights. The tomato salad was a bit off and there was nothing additional such a bread or butter. The breakfast was only one option, so you either ate what they had or ate nothing. The crew was efficient, but most seemed frustrated throughout the flight. The flight arrived early and was obstacle-free, so I’m overall quite happy, but the shine in the rest of the experience just wasn’t there.

The seats got pretty uncomfortable pretty fast. The armrests are bigger than on other planes, so I had less room in the actual seat. My butt hurt by the end of the flight. :/ comfort was the primary issue. The crew were fantastic!

I believe that a four-hour trip should have a meal. Delta had none.

Great flight with Delta! Boarding was quick and easy, the amenities were solid, and the plane was in great shape. The flight attendants had a fun, lively energy while staying professional. All in all, a smooth trip — even managed to catch up on some rest. Thanks, Delta!

I had no checked baggage but was required to hand over carry on baggage at the door of the plane. There was a lot of overboard space in the plane and I was one of the last ones. I ran to get my carry on but it was gone. I was given back at the plane door in Toronto, so the wait was not as long as it would have been at the carousel.

Armrest controller on my seat 35D and nextbooennseat 35E did not work right. Hard to press buttons to recognize and 35D had constantnpressure either upmost down somit was nearly impossible to make selections. .

I flew with my dog and had already purchased my dog’s ticket. Even that morning I had called costumer service to insure that my husband and I had seats together since the website was giving me an error when choosing our seats and the representative mentioned our dog. I showed up early to the airport and when I got to the gate and we started boarding I was help back and told that I was supposed to have a yellow tag and that I should have checked in at the counter for them to give me that tag. I was not aware of this, the representative on the phone did not say anything. Nor did I see it anywhere in the checking process online, so if you travel with a pet and are not checking in luggage, just know that you still have to go to the check in counter when arriving at the airport unless you want to be the last one to board and not have room for your carry on in the overhead bins. Other than that, I had a great experience.

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

Was on time until within 1 hour of flight-how does that happen? Staff very friendly.

I liked the choice of lemon ginger tea. I think stewardesses can be more considerate of older people needs.

We were given vouchers we couldn’t use with a 5.5 hour delay

I fly UAL 7-8 times per year. This flight was not up to snuff because it boarded very late "due to unexpected delays in restocking the plane" and yet Flight Aware showed the plane had landed some 10 hours earlier--so I think they could have planned accordingly. The FA's were nice but harried. The video system had to be rebooted 3-4 times. The food service was rather abrupt; they forgot my row and when I asked for my meal, they brought it with some impatience. Overall, the flight was fine, but the little details made it feel somewhat mundane and hurried.

The flight was canceled 3 hours after original take off time

My flight was delayed for several hours. Sitting at gate 16 for several hours, I got a text from Kayak the gate changed to 9 before it was announced. Very bad communication at each gate from American Airlines employees. I received 10 notifications of delay from Kayak. My vacation started off horrible! I will write to American Airlines corporate office also.

The AA staff person who checked our bags was curt and almost rude. The FA also seemed unhappy doing her job. Overall it was like riding the school bus back in grade school.

Internet was a bit expensive and did not work ask that week otherwise a good flight

Ring in first class for an overnight flight, there was no blankets nor pillows for first class customers.

My Internet did not work for Outlook email or basically anything. I paid for one hour of in-flight usage and it was terrible. I spent a lot of time on different sites and browsers with no luck and a lot of frustration. Other than that, the flight was on time, crew was nice, service was fine. Seat was OK even though I paid for the extra 6 inches. I cannot imagine how tight the seats in the back must be.

Delayed flight that lead to a missed connection and a 5-hour trip became a 12-hour flight 🙄

Any flight to ORD after about 2pm this summer has been challenging. Flight was delayed getting in (coming from ORD) and that led to it not leaving before a ground stop due to lightening before they could fuel the plane, and so forth. They made up some time but we were still late in arriving at ORD, and that led to missed connections.

Food was ok, but not as good as I have had before on AA.

No issues. They did change our gate FOUR times in about 30 minutes which was mildly annoying but the flight was fine.

I paid extra for a seat closer to the front. The TV didn’t work at all for the entire flight. Would have been nice to know before I purchased an “upgraded “ seat

It was great. I had never flown on JetBlue before, but would be very happy to fly with them in the future.

Worst flight experience ever flights canceled. JetBlue told us just did not even bother standing in line to come back in one and a half hours then without any information we had to go pick up all of our luggage and spend over $2000 in accommodation just to get home. JetBlue said that the next flight available for us to get home would be three days later. Absolutely absurd hasn’t offered to give us any compensation do not fly JetBlue horrible company. They said it was based on the weather and the weather is great in all locations that we would’ve been flying to total hoax. I think it’s a conspiracy theory.

The captain gave good announcements and the flight attendants were friendly. The WiFi was pretty good. The plane itself looked very old inside and the seats were very uncomfortable. The screens in the seat backs were the smallest I’ve ever seen. There were so many loud and obnoxious kids on this flight and the parents didn’t do much to try to quiet them down. Some had videos and games on tablets with higher than necessary volume going the whole time.

Too many long delays with JetBlue. Worst major airline that serves JFK but unfortunately I keep going back because of the prices.

My JetBlue experience was nice. The flights ran on time, the aircraft was clean and comfortable, and the flight attendants were attentive. My only issue, which is isolated to the low-cost (budget) option at JetBlue, is that the check in process makes the user feel that they have to buy their seats. The seats offered for purchase are upgrades from the budget seats you get (which are essentially the last seats remaining). The interface should not make it feel like you must purchase a seat.

The plane was late to leave.. Internet was lousy. TV was not working. when we arrived, We stayed on the plane for a long time before we got to the gate. It took us a long time to retrieve our luggage because they didn’t know what carousel to send them to. It was a bad experience.

I especially liked the lead crew officer. His boarding and safety announcements were made with a bit of novelty and humor. The flight also left the gate 10 minutes early and we landed about 20 minutes early… It was a delightful flight…

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

flight was delayed for hours with no explanation. The plane was a very old aircraft.

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