$68 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 9/2. 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

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.
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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Best Caribbean Islands Flight Deals from Reagan-National

Cheapest round-trip prices found by our users on KAYAK in the last 72 hours
Punta Cana
Punta Cana1 stop$289
Santo Domingo
Santo Domingo1 stop$345
Montego Bay
Montego Bay1 stop$338
Oranjestad
Oranjestad1 stop$378
Nassau
Nassau1 stop$321
Kingston
Kingston1 stop$397
Simpson Bay
Simpson Bay1 stop$403
Providenciales
Providenciales1 stop$439
Port of Spain
Port of Spain1 stop$378
Bridgetown
Bridgetown2 stops$418
George Town
George Town1 stop$379
Willemstad
Willemstad1 stop$394
St. John's
St. John's2 stops$386
Puerto Plata
Puerto Plata1 stop$433
Aguadilla
Aguadilla1 stop$316
Punta Cana
Punta Cana1 stop$289
Santo Domingo
Santo Domingo1 stop$345
Montego Bay
Montego Bay1 stop$338
Oranjestad
Oranjestad1 stop$378
Nassau
Nassau1 stop$321
Kingston
Kingston1 stop$397
Simpson Bay
Simpson Bay1 stop$403
Providenciales
Providenciales1 stop$439
Port of Spain
Port of Spain1 stop$378
Bridgetown
Bridgetown2 stops$418
George Town
George Town1 stop$379
Willemstad
Willemstad1 stop$394
St. John's
St. John's2 stops$386
Puerto Plata
Puerto Plata1 stop$433
Aguadilla
Aguadilla1 stop$316

Cheap Flights from Reagan-National to Caribbean Islands

 
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

Tue, Sep 23 - Tue, Sep 23
JetBlue Logo
8:00 am - 11:45 amDCA-SJU
3h 45mnonstop
JetBlue Logo
6:05 pm - 9:56 pmSJU-DCA
3h 51mnonstop
$131JetBlue
Find Deal
Tue, Sep 2 - Sat, Sep 20
JetBlue Logo
8:00 am - 11:58 amDCA-SJU
3h 58mnonstop
JetBlue Logo
6:05 pm - 9:56 pmSJU-DCA
3h 51mnonstop
$136JetBlue
Find Deal
Fri, Sep 19 - Tue, Sep 23
Southwest Logo
12:55 pm - 8:45 pmDCA-SJU
7h 50m1 stop
Southwest Logo
3:45 pm - 10:00 pmSJU-DCA
6h 15m1 stop
$145Southwest
Find Deal
Mon, Jul 28 - Fri, Aug 1
Southwest Logo
4:45 pm - 11:15 pmDCA-SJU
6h 30m1 stop
Southwest Logo
6:30 am - 3:55 pmSJU-DCA
9h 25m1 stop
$150Southwest
Find Deal
Tue, Sep 23 - Tue, Sep 23
American Airlines Logo
5:05 am - 11:11 amDCA-SJU
6h 06m1 stop
American Airlines Logo
4:43 pm - 11:01 pmSJU-DCA
6h 18m1 stop
$160American Airlines
Find Deal
Wed, Aug 20 - Wed, Aug 27
American Airlines Logo
8:59 am - 3:00 pmDCA-SJU
6h 01m1 stop
American Airlines Logo
5:15 pm - 11:59 pmSJU-DCA
6h 44m1 stop
$165American Airlines
Find Deal
Tue, Sep 2 - Sat, Sep 20
Delta Logo
6:05 am - 12:18 pmDCA-SJU
6h 13m1 stop
Delta Logo
2:15 pm - 10:57 pmSJU-DCA
8h 42m1 stop
$215Delta
Find Deal
Sat, Nov 1 - Wed, Nov 5
United Airlines Logo
3:00 pm - 11:36 pmDCA-SJU
8h 36m1 stop
United Airlines Logo
2:05 am - 10:29 amSJU-DCA
9h 24m1 stop
$235United Airlines
Find Deal
Tue, Aug 19 - Mon, Aug 25
United Airlines Logo
8:20 am - 11:23 pmDCA-POS
15h 03m1 stop
United Airlines Logo
12:30 am - 11:36 amPOS-DCA
11h 06m1 stop
$380United Airlines
Find Deal
Mon, Sep 1 - Thu, Sep 4
Delta Logo
8:45 pm - 2:10 pmDCA-AUA
17h 25m1 stop
Delta Logo
3:25 pm - 11:46 pmAUA-DCA
8h 21m1 stop
$393Delta
Find Deal
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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?

The cheapest price for flight routes found by users searching on KAYAK in the last 2 weeks for round-trip flights from Washington, D.C. Reagan-National Airport to Caribbean Islands.

The cheapest ticket to Caribbean Islands from Washington, D.C. Reagan-National Airport found in the last 72 hours was to San Juan, at $146 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 $146.

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 $621, 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 November, when the average cost of round-trip tickets is $648 and $463 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 2 weeks before departure. For the absolute cheapest price, our data suggests you should book 5 weeks before departure.


Good to know

Low seasonSeptember
High seasonJuly
Cheapest flight$68
Best time to beat the crowds with an average 20% drop in price.
Most popular time to fly with an average 1% 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 14% 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 $419.

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 $123 one-way - $336 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 4250 reviews
7.0Food
8.0Comfort
8.1Boarding
7.6Entertainment
8.6Crew
Airline reviews

It was one and half hour late... Not sure if any other experience matters.

4.0 OkaySudhir, Jul 2025LGA - MCI
Read more Southwest reviews

It was one and half hour late... Not sure if any other experience matters.

Delayed flight. Nicest crew member was a SW pilot flying seated next to me who kindly move to seat the final passenger. Flight extra delayed. My cup of refreshment of ginger ale was so packed with ice it was literally 2 sips.

For my birthday trip this was my second time ever flying, this trip was the best.

after landing, we stay 2 hours on the taxi way before reaching the gate The airline and the crew were good though

No trays in our seats, we sat in first row, purchased a business class fare. Had to hold our drinks and snack in our hands. No plugs for our cell phones. Had to pay for it a drink cocktail each. Seats so uncomfortable.

Flight wasn’t even full, but too many carry-ons caused us to run out of bin space. New bag fee has folks who would usually check their bags carrying on. Watching Southwest morph into Spirit/Frontier is so sad to watch

Sat on tarmac for 2 hours and then missed my connecting flight

First time traveling on Southwest since bag fees were implemented. Usual good service. Just more expensive now.

Everything was on time. I was disappointed by the front section female, African American flight attendant. I did not see her name tag or would have identified by name not race. As passengers moved to the bathroom early in flight, she would say with a disdainful tone “I have to say the seat belt light is on” then go back to her book. Better trained flight attendants say something like be careful the seat belt light is on.

Cluster mess boarding. Can't wait for SWA reserved seating. Internet didn't seem to work on the plane.

Everything was fine except the entertainment was not working for half of the flight.

Easy boarding with an extremely kind attendant. Seats were spacious and we had 3 seats for 2 people so we could stretch out. Comfortable air flow and very attentive and hospital attendants. Bathrooms and food were the only negative. Bathrooms were so small you could hardly get in and close the door. I don’t think an obese person would fit or a person with a movement disability. Food was the trending food for flights, nonexistent. We spent $40 getting sandwich and snack at airport for our 6 hour flught.

At first, we were on the runway for about an hour, literally. The Captain did explain that the Control Tower just had a change shift (sounds like an unrealistic excuse) and then that we had to change a runway. A regular economy seat is made for 12 yo twiggy. I understand Delta wants to push for an upgrade, but after sitting in a Comfort seat and in First class. I would say First class is not worthy of my money. The landing was delayed because of the weather in NYC, I don't hold that against Delta, of course. The Captain did alert us to that upon takeoff in Vegas and again as we reached NY.

No one fussed at me about my pap machine as a 3rd pice on the plane. Boarding was pleasant and smooth. The boarding agent in Anchorage was a fun character- he could be in a movie. :~) The on-board crew were downright pleasant. No militant attitudes on Delta. Like all planes these days the seats are too narrow for standard Americans and at 5’2” there is barely enough leg room. I don’t know how tall people fold themselves into the seats. But that’s nothing specific to Delta

Great. Very smooth. Plenty of information. However, wish they would give out a menu in advance of making a dinner choice like other international airlines. The flight attendant says chicken or pasta and there are details about ingredients or spices requiring the passenger to ask which requires the flight attendant to answer many times. So easy to solve this problem. P

I'm a tall guy and even the seats with more leg room were not as comfortable as I had hoped.

My husband upgraded our seats and I don't know if it was due to the type of planet was or if they didn't upgrade our seats. We were supposed to be in I believe comfort seats and they were just as tight as any other seat- no leg room and we are very tall people but at least it wasn't extremely cold. My husband did put in a complaint about our seating because he paid extra and if we would have known that the space and the tightness would have been the same, we just would have gotten the emergency row emergency row seats that we normally get. We love Delta but both our flights coming home we're not good. Oh I forgot to mention that on our flight to Hawaii our luggage wheels got broke and we had to purse new luggage on vacation then we never had this problem so we didn't know protocol and reported it after we got home only for them to tell is we only had 24hrs to report the damage. Not sure what was going on with Delta this vacation trip.

My flight was extremely cold. I had a jacket and a cover was left in each seat. The cover was extremely thin and I have a disability, fibromyalgia and arthrithis and AC air is the worst. I closed my vent and my husbands vent and it still was frigid. I asked the attendant if I could get another cover and she quickly almost dismissively and totally unconcerned stating, (I quote) (one per chair) and walked off so quickly that I didn't get a chance to explain to her that I literally have adisability. I didnt want to make a seen so I set on that flight for over 5 hours in pain, joints locking up and extremely uncomfortable. When my fibromyalgia flares up my joints not only ache but they will lock up also and it takes me days to get back to my regular self even though I take medication for it. I felt like it would not have hurt anyone at all for her to just give me an extra cover because I'm sure they have all types of medical issues in people that fly every day.

After all the weather issues at least they got me to my destination the next day

My flight was canceled after being rescheduled for four days canceling my trip. Kayak and everyone affiliated with it I.e the airlines, and just fly have been excruciating to deal with. My trip to visit family had to be canceled as there was no way to make it. I am furious at all of you.

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

The food should improve! And The flight should leave on time and not make the traveler wait.

It was great, I’m very grateful for the pilots and crew flight attendants for everything.

Everything was great. Only thing that could’ve made it better was buy on board options for hot food, but the snacks were decent. The flight attendants were great. I had no complaints. I was able to make it to my destination safely

A little bit more leg room in premium economy. I am 6’4”.

Overall it was good. I missed my connection but I was put on another flight.

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.

I didn’t get on plane. Passport being processed by consulate with visa application. Tried to cancel through underpricer after purchasing cacelling for any reason. No dice, they are thieves.

When I booked it on Kayak it aaid that I wasn't allowed hamd luggage. I called United Airlines and it took them 6 minutes to figure out if I was allowed free hand luggage. Surely something that simple they should be able to tell me instantly.

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.

Spend hours delayed with no food, water anything sitting on the aieplane with no ability to eat or use the restroom. My entire experience was the absolute worst. I will never fly jet Blue again.

It would have been nice if they had offered more than one set of snacks

Seats were not too comfortable; it was impossible to locate the underseat power outlet.

You get what you pay for with JetBlue. Every little thing costs more, you are nickel and dimed until the end. Entertainment doesn’t function. Flight attendants do the bare minimum.

The check in and boarding process was a bit of a cluster. Two people at the counter to check in, three random lines that nobody knew which was for what, and people kept getting shuffled from one line to another for no apparent reason because then they’d get shuffled back and end up getting out further back in the line than they were originally. I only had to hand my already checked bag over and it took 45 minutes. I was never assigned a seat so when I tried to board I was pulled out of line again while someone had to try to manually assign me a seat. During the flight I got up to go to the bathroom, and there was an attendant in the aisle offering pillows etc and it was a 30 min wait unbuckled standing by the bathrooms because she said I couldn’t go past her. First and last time flying jet blue to be honest.

Communication since no reason or explanation was given for 3 hrs delay

The flight departed more than 1 hour late. Leg room is bigger than most airlines

Flight was delayed several 3 hours - no reason was given and no communication what so ever.

The AA app really sucks ... Every flight & connecting flights were delayed over 30 mins. One connecting flight on American Eagle said it was delayed in its arrival ... when it was actually parked across from the gate for over 1 hr before they pulled it to the gate. Seats in the economy/ main cabin are packed together like sardines ... no leg room.

Initial flight was cancelled at the time of arrival to the airport, flight alternative requires switching from direct to flight with a layover, and the plane felt like it would split apart, it was so rattle-y.

Amazing food, great staff, with one noticable detail missing ...but no seat entertainment in any of aircraft ...I am not a fan

Flight was delayed again and again ultimately almost three hours getting us to our location at close to midnight by the time we got in and out of airport to destination. I had taken time off work to enjoy an evening at destination and that was now wasted

AA re-routed flight from HNL to LAX due to delay. My group of 3 with reserved seats in row 9 was broken up, with one assigned to a middle seat, another in the last row of the plane. Not happy. No explanation to the delay. No apologies. No compensation. Would have been nice to be offered an Admiral Club admission or a voucher for the extra 3 hours of layover in LAX. Could not hear the boarding gate announcements in LAX. Adjacent gate was boarding at the same time. Loud speakers were competing against each other. Barely made my boarding group.

Boarding gate in Honolulu was staffed with a great clerk with a soothing voice despite the flight delay of over an hour. Flight attendants in the plane were all grumpy, not pleasant looking bunch. Their sour attitude showed throughout the flight. Inly able to get a select few movies started. Most of the movie links in the “free entertainment” did not work.

Above and beyond effort from this crew in a tough situation. So helpful and understanding. Thank you!

They are still charging me after taking 466 and 833 for round trip from AR to to Bradley airport from 19 to 21. Then poor experience. Am hurt and I will say it on social media. Please stay away from this airline. I see in my bank account they are still taking 644. Am trying to stop it. I used to fly United airlines and I suggest that if you don't want extra charges and good service you go back there. American airlines delayed my flight again and I was late for my meeting, no recompensation but charging me over and over.

They changed our Gate 5 times, and concourse twice. Changed our seats twice.

Pitch was very small. Knees were on the seat back in front of me.

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