$88 Find Cheap Flights from Reagan Washington National Airport to Caribbean

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 departing on 11/12. 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

Travelers love KAYAK
41,299,237 searches in the past 7 days on KAYAK

Save 23% or moreCompare multiple travel sites with one search.

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

Free to useThere are no hidden charges or fees.

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

Flight Deals
Booking Insights
Flight Deals

Cheap Flights from Reagan-National to Caribbean

Cheapest round-trip prices found by our users on KAYAK in the last 72 hours
Punta Cana
Punta Cana1 stop$362
Santo Domingo
Santo Domingo1 stop$373
Montego Bay
Montego Bay1 stop$371
Oranjestad
Oranjestad1 stop$356
Nassau
Nassau1 stop$377
Simpson Bay
Simpson Bay1 stop$365
Kingston
Kingston1 stop$382
Providenciales
Providenciales2 stops$348
Port of Spain
Port of Spain1 stop$379
Bridgetown
Bridgetown2 stops$395
George Town
George Town1 stop$325
Willemstad
Willemstad1 stop$279
St. John's
St. John's1 stop$399
Puerto Plata
Puerto Plata1 stop$383
Aguadilla
Aguadilla1 stop$250
Punta Cana
Punta Cana1 stop$362
Santo Domingo
Santo Domingo1 stop$373
Montego Bay
Montego Bay1 stop$371
Oranjestad
Oranjestad1 stop$356
Nassau
Nassau1 stop$377
Simpson Bay
Simpson Bay1 stop$365
Kingston
Kingston1 stop$382
Providenciales
Providenciales2 stops$348
Port of Spain
Port of Spain1 stop$379
Bridgetown
Bridgetown2 stops$395
George Town
George Town1 stop$325
Willemstad
Willemstad1 stop$279
St. John's
St. John's1 stop$399
Puerto Plata
Puerto Plata1 stop$383
Aguadilla
Aguadilla1 stop$250

Book Cheap Reagan-National to Caribbean 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 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

Wed, Nov 12 - Tue, Nov 18
JetBlue Logo
8:00 am - 12:50 pmDCA-SJU
3h 50mnonstop
JetBlue Logo
6:51 pm - 9:48 pmSJU-DCA
3h 57mnonstop
$219JetBlue
Find Deal
Sun, Nov 16 - Sat, Nov 22
JetBlue Logo
8:00 am - 12:50 pmDCA-SJU
3h 50mnonstop
JetBlue Logo
6:10 pm - 9:08 pmSJU-DCA
3h 58mnonstop
$229JetBlue
Find Deal
Mon, Nov 10 - Thu, Nov 13
Delta Logo
6:07 am - 5:20 pmDCA-SJU
10h 13m1 stop
Delta Logo
3:20 pm - 11:04 pmSJU-DCA
8h 44m1 stop
$245Delta
Find Deal
Sun, Nov 2 - Thu, Nov 13
Delta Logo
5:05 am - 4:25 pmDCA-SJU
10h 20m1 stop
Delta Logo
7:00 am - 3:00 pmSJU-DCA
9h 00m1 stop
$265Delta
Find Deal
Tue, Nov 18 - Tue, Nov 18
American Airlines Logo
5:00 am - 12:05 pmDCA-SJU
6h 05m1 stop
American Airlines Logo
2:47 pm - 12:24 amSJU-DCA
10h 37m1 stop
$277American Airlines
Find Deal
Wed, Oct 22 - Wed, Oct 22
American Airlines Logo
5:00 am - 11:06 amDCA-SJU
6h 06m1 stop
American Airlines Logo
4:45 pm - 11:59 pmSJU-DCA
7h 14m1 stop
$280American Airlines
Find Deal
Fri, Nov 7 - Mon, Nov 10
United Airlines Logo
6:00 am - 1:33 pmDCA-NAS
7h 33m1 stop
United Airlines Logo
2:35 pm - 11:44 pmNAS-DCA
9h 09m1 stop
$377United Airlines
Find Deal
Fri, Oct 31 - Mon, Nov 3
United Airlines Logo
6:00 am - 1:33 pmDCA-NAS
7h 33m1 stop
United Airlines Logo
2:35 pm - 10:09 pmNAS-DCA
7h 34m1 stop
$378United Airlines
Find Deal
Tue, Mar 10 - Fri, Mar 13
Southwest Logo
12:40 pm - 6:30 pmDCA-NAS
5h 50m1 stop
Southwest Logo
1:25 pm - 10:55 pmNAS-DCA
9h 30m2 stops
$415Southwest
Find Deal
Mon, Nov 10 - Thu, Nov 13
Southwest Logo
9:35 pm - 12:35 pmDCA-GCM
15h 00m2 stops
Southwest Logo
1:30 pm - 8:45 amGCM-DCA
19h 15m2 stops
$489Southwest
Find Deal
Booking Insights

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

Get data-powered insights and trends into flights from Reagan-National to Caribbean 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 flight route?

Data is based on round-trip flight searches on KAYAK over the past month.

The cheapest ticket to Caribbean from Washington, D.C. Reagan-National Airport found in the last 72 hours was to San Juan, at $219 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 $219.

Can I save money by flying with a layover from Washington, D.C. Reagan-National Airport to Caribbean?

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 $443, prices are generally cheapest when you fly direct.

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

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, 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 is October, when tickets cost $327 (return) on average. On the other hand, the most expensive months are December and August, when the average cost of round-trip tickets is $600 and $485 respectively.

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

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

When flying from Reagan Washington National Airport to Caribbean, you should consider leaving on a Monday and avoid Thursdays if you are looking for the best rates. For your return to Reagan Washington National Airport, you’ll find the best rates on Saturdays and the most expensive ones on Sundays.

How far in advance should I book a flight from Washington, D.C. Reagan-National Airport to Caribbean?

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, 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, you should book around 3 weeks before departure, which saves you about 15% compared to booking last minute. For the absolute cheapest price, our data suggests you should book 7 weeks before departure.

Good to know

Low seasonSeptember
Cheapest flight$88
Best time to beat the crowds with an average 12% drop in price.
Most popular time to fly with an average 22% increase in price.
Flight from Reagan Washington National Airport to Nassau

FAQs - booking Caribbean flights

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

    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.

  • 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?

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight from Reagan Washington National Airport to Caribbean 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?

    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 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?

    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 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?

    The cheapest time of day to fly to Caribbean 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 is generally in the morning, which is peak travel time and where the average cost of a ticket is $421.

Top tips for finding cheap flights to Caribbean

  • 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 $142 one-way - $305 round-trip

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

 
Need help choosing which airline to fly with from Reagan-National to Caribbean? 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 4240 reviews
8.1Boarding
7.0Food
8.6Crew
7.5Entertainment
8.0Comfort
Airline reviews

I was re-booked onto another flight because my original flight was delayed and I would have missed my connector. I ended up in the “C” group after paying extra to be in the “A “ group on the original flight. At least if you’re going to re-book people, re-book them into the same group.

2.0 MediocrePrincess, Oct 2025MSY - DAL
Read more Southwest reviews

I was re-booked onto another flight because my original flight was delayed and I would have missed my connector. I ended up in the “C” group after paying extra to be in the “A “ group on the original flight. At least if you’re going to re-book people, re-book them into the same group.

Flight was delayed due to plane not passing inspection And one of the crew had to time out and we had to wait for another one A 3 hour delay

mandatory demand customer to check their carry on because not enough people check bags.

Connecting flight is on time and boarding was a breeze!

Excellent. Would encourage Southwest to keep current boarding procedures with free style seating. Makes for a fantastic experience

As always, the entire Southwest experience was perfect. Purchasing the tickets on the Southwest web site was effortless, departure and arrival gates were spotless and comfortable, plane was clean and comfortable, crew was excellent and flight was on time. Wheelchair service in Las Vegas at departure was somewhat chaotic and disjointed, but I am not sure if that was Southwest problem, airport problem or combination.

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

Delayed flight (1hour) plus a long layover after an overnight flight with no backup plane available.

We were delayed, which I think had to do with air traffic control. Otherwise, everything was great.

The boarding process needs to be refined. Sometimes the gate crew calls out the zones and then flip to showing the.zones boarding on the gate monitor display. So, unless you are huddled around the gate lanes watching the monitor, you could miss your boarding zone. Suggest the zones be announced each time a new zone is allowed to board.

The boarding process needs to be refined. Sometimes the gate crew call out the boarding zone, and then flip to the monitor to show which zones are boarding. So unless everyone is gathered around to see the monitor there is usually confusion as wi which zones are boarding.

On time flight. Seat comfort could be better in the Comfort section.

My issue was with TSA agents for delta airlines. My luggage got flagged. The agent was going thru another persons first. He took 20 min to go thru hers. I asked them to bring mine closer so I could sit down . They said you can go sit it will be fine. I said I am supposed to keep my eyes on my bags at all times. The agent was meticulously unwrapping 2 gifts that the lady had and then tried to re warp it. He was trying to be kind i get it but 20 min for me to stand watching him do that was ridiculous. It was 6 am and there were a ton of travelers. Mine was flagged for some air packed tea that I bought in Turkey. My previous delta flight and 2 others before didn’t flag it. Consistency would be nice. Also on the flight the window shades were down for take off and landing - I thought that was very odd I thought they had to remain open for take off and landing.

The flight was an hour and a half late departing which was inconvenient

Delay in SLC jammed us up in Chicago. Got caught up in rush hour traffic

The crew took good care of us. The flight from ATL to SFO is a longer one, and there were multiple beverage offerings. I like the 757's that Delta uses. Good airplane that is comfortable. I do wish Delta would separate Priority boarding from the better seats. I would gladly take a smaller seat in an open row than be jammed into Comfort just to get priority boarding, just to make sure I don't have to check a bag.

The flight was great. The gate location was way to far away!!!

Flight was good but there are way to many announcements for credit cards etc.

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

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

Poor seat in rear of aircraft Food at Admiral’s Club Terminal D at DFW inedible

Always seated jammed in rear of aircraft Admirals Club food at DFW terminal D was absolute worst food experience and I pay $600/year to eat this dried out junk

Flight was delayed because of a bird strike. They had another plane available within 45 minutes.

Mostly good. Flight was crowded but Airline personnel were very friendly & accommodating. It would be good to have savory snacks rather than just sweet Biscoff cookies.

It was a typical flight. We had a delay which seems to be the normality now. And we had no in flight service due to conditions.

Flight attendants on this flight were very attentive and friendly

After we landed we sat on the tarmac for 1.5 hours waiting to get to our gate. Ridiculous.

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.

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

They have the most inexperienced / rude flight staff I’ve encountered

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.

Everything you need to know for your flight to Caribbean

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.