$105 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 10/15. 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.
Travelers love KAYAK
41,299,237 searches in the past 7 days on KAYAK

Save 22% 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 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$337
Santo Domingo
Santo Domingo1 stop$340
Montego Bay
Montego Bay1 stop$355
Oranjestad
Oranjestad1 stop$406
Nassau
Nassau2 stops$405
Simpson Bay
Simpson Bay1 stop$411
Kingston
Kingston1 stop$393
Providenciales
Providenciales1 stop$341
Port of Spain
Port of Spain1 stop$378
Bridgetown
Bridgetown2 stops$362
George Town
George Town1 stop$360
Willemstad
Willemstad1 stop$282
St. John's
St. John's1 stop$510
Puerto Plata
Puerto Plata1 stop$389
Aguadilla
Aguadilla1 stop$280
Punta Cana
Punta Cana1 stop$337
Santo Domingo
Santo Domingo1 stop$340
Montego Bay
Montego Bay1 stop$355
Oranjestad
Oranjestad1 stop$406
Nassau
Nassau2 stops$405
Simpson Bay
Simpson Bay1 stop$411
Kingston
Kingston1 stop$393
Providenciales
Providenciales1 stop$341
Port of Spain
Port of Spain1 stop$378
Bridgetown
Bridgetown2 stops$362
George Town
George Town1 stop$360
Willemstad
Willemstad1 stop$282
St. John's
St. John's1 stop$510
Puerto Plata
Puerto Plata1 stop$389
Aguadilla
Aguadilla1 stop$280

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

Thu, Oct 30 - Fri, Oct 31
JetBlue Logo
8:00 am - 11:51 amDCA-SJU
3h 51mnonstop
JetBlue Logo
6:02 pm - 9:59 pmSJU-DCA
3h 57mnonstop
$217JetBlue
Find Deal
Fri, Oct 3 - Fri, Oct 3
JetBlue Logo
8:30 am - 12:19 pmDCA-SJU
3h 49mnonstop
JetBlue Logo
6:05 pm - 9:55 pmSJU-DCA
3h 50mnonstop
$218JetBlue
Find Deal
Tue, Jan 20 - Fri, Jan 23
United Airlines Logo
3:00 pm - 12:36 amDCA-SJU
8h 36m1 stop
United Airlines Logo
2:05 am - 9:19 amSJU-DCA
8h 14m1 stop
$243United Airlines
Find Deal
Sat, Nov 15 - Tue, Nov 18
Delta Logo
6:06 am - 5:20 pmDCA-SJU
10h 14m1 stop
Delta Logo
3:20 pm - 11:04 pmSJU-DCA
8h 44m1 stop
$245Delta
Find Deal
Sun, Feb 8 - Wed, Feb 11
United Airlines Logo
7:00 am - 2:40 pmDCA-SJU
6h 40m1 stop
United Airlines Logo
2:05 am - 12:42 pmSJU-DCA
11h 37m2 stops
$247United Airlines
Find Deal
Sun, Dec 7 - Wed, Dec 10
Delta Logo
6:07 am - 5:19 pmDCA-SJU
10h 12m1 stop
Delta Logo
2:10 pm - 10:52 pmSJU-DCA
9h 42m1 stop
$265Delta
Find Deal
Wed, Oct 22 - Thu, Nov 6
Southwest Logo
7:30 am - 5:15 pmDCA-SJU
9h 45m1 stop
Southwest Logo
6:40 am - 12:20 pmSJU-DCA
6h 40m1 stop
$271Southwest
Find Deal
Thu, Oct 30 - Tue, Nov 4
American Airlines Logo
11:59 am - 10:10 pmDCA-SJU
10h 11m1 stop
American Airlines Logo
6:42 pm - 12:24 amSJU-DCA
6h 42m1 stop
$282American Airlines
Find Deal
Sat, Nov 15 - Wed, Nov 19
American Airlines Logo
7:00 am - 12:11 pmDCA-NAS
5h 11m1 stop
American Airlines Logo
12:13 pm - 2:54 pmNAS-DCA
2h 41mnonstop
$410American Airlines
Find Deal
Mon, Nov 10 - Fri, Nov 14
Southwest Logo
9:35 pm - 12:15 pmDCA-NAS
14h 40m2 stops
Southwest Logo
1:10 pm - 10:45 pmNAS-DCA
9h 35m1 stop
$419Southwest
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 $179 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 $179.

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 $367, 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 $348 (return) on average. On the other hand, the most expensive months are December and August, when the average cost of round-trip tickets is $625 and $466 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 9% compared to booking last minute. For the absolute cheapest price, our data suggests you should book 12 weeks before departure.

Good to know

Low seasonOctober
Cheapest flight$105
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 $202 one-way - $269 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 4248 reviews
8.0Comfort
7.5Entertainment
7.0Food
8.6Crew
8.1Boarding
Airline reviews

I wish they had movie screens in the headrests. The seats are much improved, more legroom and recently renovated. Bathroom was clean. Staff was outstanding!!

10.0 ExcellentG, Sep 2025LAS - ATL
Read more Southwest reviews

I wish they had movie screens in the headrests. The seats are much improved, more legroom and recently renovated. Bathroom was clean. Staff was outstanding!!

As always, the entire Southwest experience was wonderful, from online booking to flight to baggage retrieval. Very grateful.

The weather could have been better. There was a 40 minute ATC delay in SFO because of marine fog and a micro cell storm delayed landing and take-off at Nashville. The gate was changed 5 minutes from boarding from gate B3 to gate C23 at Nashville airport.

After being assaulted by a flight attendant I was then brushed off as oh well because he long braids didn’t mean to whip me in the eye. I have filed complaints and will see. But like any other issue I’ve had with kayak involved it’s been trash. Last time I’ll be using your app

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.

Perfect flight both ways. On time, courteous staff, plane comfortable and cool. Best domestic flights I’ve had in awhile.

The food was terrible especially for a 15 hour international flight. The crew was unpleasant as well.

Really low quality food especially for an international flight. The crew also was surprisingly unpleasant except couple of ladies. I know we were not in first class but that’s no reason to treat customers as less.

Flight delayed for two and half hours and then canceled altogether due to mechanical issues. No mechanic onsite to fix so had to send one from LAX.

Quick check in. Everything went smooth. I don't know what can be done about airline food.

Crew was good. The reservation got mixed up and they didn't have my TSA number. I am also a Silver Medallion and wasn't able to use Sky Priority.

Delta made it easy, comfortable and timely. The crew was fantastic.

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

We had to deboard 2 times due to maintenance issues. They changed the plane, and then we got deviated to LAX due to maibtenance issues on the other plane, had to sleep at LAX and los a full day.

Everything was good, except the seats in economy were so close together, you could barely get out when the seat in front of your was reclined. If the airlines keep jamming in more and more seats, it will become intolerable. I will look for another airline that considers customer comfort and does not keep adding more rows of seats for more profit.

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

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.

Given it’s a red-eye into Charolotte, we didn’t get any food. The survey does not include “N/A” so the rating will be skewed.

Great. Quick and quiet and east. The breakfast choices were a welcome surprise!

American airlines suck they delay the flights all the time made me sleep in an airport because my flight was delayed and I miss my connecting flight

There's nothing I liked about it. For first off I scheduled this trip two weeks in advance then they delayed my flight which messed up my whole trip. So I scheduled it for the following weekend thinking there won't be a delay and guess what as soon as I got to the airport we said in the airplane on the tarmac for an hour and a half. Not only was it delayed I missed my connecting flight meaning I had to stay the night at Dallas-Fort Worth airport sleeping on the floor. I will tell you this I will never fly American airlines ever again I have had nothing but horrible experience with them and I just throw money at them

The stewardess hit me with the food kart twice on the head and didn't say I'm sorry once. The same stewardess gave me a warm Apple Juice with No ice. The Flight was delayed for Departure 6 times, starting from 2:36pm, finally taking off 7:50pm. I was late picking up my child from the sitter by 3 hours.

Don’t know they cancelled the flight day before I was to leave. They sent a email at 9:00 pm at night saying they cancelled. That is the smooth way to say we don’t want your business! I think they didn’t have enough people booking so they cancelled the flight! It’s all about the money anymore there is no honesty in business.

Having to reschedule flights a day later, they loaded by luggage on the wrong plane from Little rock now I have to HOPE they deliver it to where im staying like they said would. International flight crew was very disgruntled and not very friendly.

It took way too long to diagnose and solve the problem of a broken crew member cabin seat. Though compensation for the volunteer who left the flight was very kind.

We fly American Airlines quite a bit. And we always fly business class when traveling internationally. We were a bit disappointed with the comfort of this particular plane as well as the entertainment options.

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.

very difficult boarding process - aggressive passengers not the friendliest crew

WiFi was not eorkig (again) And the plane was from 1990 with the screens which were.not touch and most didn’t even work and if lucky could tune in tv

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…

Everything you need to know for your flight to Caribbean Islands

Information on your arrival and departure airports

Not what you’re looking for? Find thousands of other hotels, flights, car rentals and package deals with KAYAK.