$99 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 5/20. 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.
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Best Caribbean 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$440
Santo Domingo
Santo Domingo1 stop$437
Montego Bay
Montego Bay1 stop$373
Oranjestad
Oranjestad1 stop$403
Nassau
Nassaunonstop$315
Kingston
Kingston1 stop$461
Simpson Bay
Simpson Bay1 stop$427
Providenciales
Providenciales1 stop$304
Bridgetown
Bridgetown2 stops$392
Port of Spain
Port of Spain1 stop$368
George Town
George Town1 stop$508
Willemstad
Willemstad1 stop$442
St. John's
St. John's1 stop$549
Puerto Plata
Puerto Plata1 stop$513
Aguadilla
Aguadilla1 stop$264

Cheap Flight Deals from Reagan-National to Caribbean (DCA-0CB)

 
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.

Recent round-trip flight deals from Reagan-National to Caribbean

Recommended round-trip deals departing in the coming months from the most popular airlines that fly from Reagan-National to Caribbean.
Discover the best prices for you by selecting your travel dates on KAYAK.
Choose your dates
Delta Logo
9:00 am - 7:44 pmDCA-SJU
10h 44m1 stop
Delta Logo
12:43 pm - 11:30 pmSJU-DCA
10h 47m1 stop
$225Delta
Find Deal
Wed, Jul 16 - Wed, Jul 23
American Airlines Logo
5:00 am - 3:00 pmDCA-SJU
10h 00m1 stop
American Airlines Logo
6:10 am - 12:22 pmSJU-DCA
6h 12m1 stop
$231American Airlines
Find Deal
Mon, May 26 - Wed, May 28
United Airlines Logo
7:00 am - 1:45 pmDCA-SJU
6h 45m1 stop
United Airlines Logo
1:05 am - 10:27 amSJU-DCA
9h 22m1 stop
$235United Airlines
Find Deal
Sun, Jun 1 - Wed, Jun 4
American Airlines Logo
5:00 am - 3:00 pmDCA-SJU
10h 00m1 stop
American Airlines Logo
1:10 pm - 10:20 pmSJU-DCA
9h 10m1 stop
$245American Airlines
Find Deal
Mon, May 26 - Fri, May 30
Delta Logo
9:00 am - 7:44 pmDCA-SJU
10h 44m1 stop
Delta Logo
12:43 pm - 11:30 pmSJU-DCA
10h 47m1 stop
$285Delta
Find Deal
Wed, Jul 16 - Thu, Jul 24
JetBlue Logo
6:09 am - 4:15 pmDCA-SJU
10h 06m1 stop
JetBlue Logo
1:58 pm - 10:58 pmSJU-DCA
9h 00m1 stop
$297JetBlue
Find Deal
Wed, May 14 - Wed, May 21
United Airlines Logo
6:00 am - 1:45 pmDCA-SJU
7h 45m1 stop
United Airlines Logo
1:05 am - 12:58 pmSJU-DCA
11h 53m2 stops
$304United Airlines
Find Deal
Tue, Jun 10 - Wed, Jun 11
JetBlue Logo
7:00 am - 1:50 pmDCA-SJU
6h 50m1 stop
JetBlue Logo
1:58 pm - 10:58 pmSJU-DCA
9h 00m1 stop
$311JetBlue
Find Deal
Sun, May 11 - Wed, May 28
Southwest Logo
6:55 am - 3:10 pmDCA-PLS
8h 15m1 stop
Southwest Logo
4:05 pm - 10:55 pmPLS-DCA
6h 50m1 stop
$329Southwest
Find Deal
Fri, May 16 - Wed, May 21
Southwest Logo
2:55 pm - 11:55 pmDCA-SJU
9h 00m2 stops
Southwest Logo
7:00 am - 6:00 pmSJU-DCA
11h 00m2 stops
$405Southwest
Find Deal
Tue, Jun 10 - Tue, Jun 17

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?

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.
The cheapest ticket to Caribbean from Washington, D.C. Reagan-National Airport found in the last 72 hours was to San Juan, at $246 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 $246.

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

The average price for all round-trip flights from Washington, D.C. Reagan-National Airport to Caribbean depending on the time of departure, clicked by users on KAYAK in the last 2 weeks.
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 13% more expensive than evening flights, on average. The most expensive time of day to fly to Caribbean is generally in the afternoon, which is peak travel time and where the average cost of a ticket is $418.

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 September, when tickets cost $340 (return) on average. On the other hand, the most expensive months are December and June, when the average cost of round-trip tickets is $648 and $471 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 Tuesday and avoid Saturdays if you are looking for the best rates. For your return to Reagan Washington National Airport, you’ll find the best rates on Thursdays 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 2 weeks before departure. For the absolute cheapest price, our data suggests you should book 5 weeks before departure.

Good to know

Low season

September

High season

August

Cheapest flight

$99
Best time to beat the crowds with an average 20% drop in price.
Most popular time to fly and prices are also 6% lower on average.
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.

See more FAQs

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 4286 reviews
7.1Food
8.6Crew
8.2Boarding
8.0Comfort
7.6Entertainment
Airline reviews

I’ve always loved Southwest. No issues at all. I was flying standby and the gate agent was extremely friendly and helpful. Boarding was smooth and I was able to get a window seat in the emergency exit row. Crew was fantastic! They were very professional and accommodating. We had to divert from our destination due to weather but the flight crew kept everyone at ease and informed us of all pertinent information. Excellent flight

8.0 ExcellentJonathan, Apr 2025AUS - MSY
Read more Southwest reviews

I’ve always loved Southwest. No issues at all. I was flying standby and the gate agent was extremely friendly and helpful. Boarding was smooth and I was able to get a window seat in the emergency exit row. Crew was fantastic! They were very professional and accommodating. We had to divert from our destination due to weather but the flight crew kept everyone at ease and informed us of all pertinent information. Excellent flight

The price of the tickets isn't matching the flight experience. No matter how long the flight is, you're only getting pretzels. The flight attendants looked unkept and over it.

Plz don't take away free bags and free seating

The seats were a bit cramped and worn, but otherwise okay.

I would have liked to arrive on time - not 5 hours late!

After a 3 hour layover in Denver my flight was delayed over 5 hours! No explanation; no assistance; no offer to provide compensation; no one at Southwest was willing to offer any assistance. 8 hours in the Denver airport - ridiculous!

It was a perfect flight in all aspects! Both legs!

Only one drink pass through the cabin for a 4 hour flight. Quite rough and bumpy landing.

Boarding process, crew were good. But the seats were so uncomfortable that was all I could focus on. I literally had to sit forward so that all 3 of us could fit in row. I will try to avoid Southwest in the future for any flights over 60 minutes.

1.5 hour delay, poor service, no compassion from the crew. Terrible experience

Delta flight was on time, seats were comfortable, and crew was nice.

This had nothing to do with Delta… The flights were on time and flawless. The service was excellent. We purchased seats in (aisle/middle) comfort plus since this was a cross country flight. Unfortunately, the woman seated at the window was 300+ pounds and, as might be expected, covered up about a third of the middle seat also. there was absolutely nothing that Delta could have done about that… I just don’t know what the answer should be. If you purchase a seat, you should should be able to use the entire seat and not just the portion that someone else is not sitting/oozing in. Disappointing…there should be something that could be done….I'm just not sure what solution could be.

Delayed take-off. Very small plane so very scary with lots of bumps during the flight. Would never fly Delta on short flights in small 80 seaters plane again! Felt relieved when landed.

The worst part was I was NOT allowed in the lounge even though I was holding a first class ticket and have a premium American Express card. I have flown Business or First Class with many airlines. Delta is the ONLY one who does not extend this courtesy to anyone except people who hold the very expensive American Express card. As a result, I won’t fly Delta if I have any other choice.

It was an overnight flight and I desperately needed coffee before we landed, but Delta does only one beverage service, and that is shortly after takeoff, not before landing at 5 am.

A little bumpy ride . No food was being provided due the the turbulence. That was ok it was a short flight to my standards.

Simply outstanding. Their new lounge for Delta One customers is a cut above the rest.

The Dekta Rep that checked us in was great. She's very personable, pleasant, and can tell she enjoys her job.

After a 5 hour delay waiting at the gate (3 delays adding up) with no clear reason provided, we finally boarded flew 3/4 of the way to Toronto then were turned back to New York. As we neared New York, the pilot declared that it was his fault, something to do with timing and him not being allowed into the country???? How could the airline let his happen? They had hours to prepare and make sure they had a crew available for the flight! We ended up in Toronto a day late with no sleep.

The plane was old with small storage areas that had problems closing/latching and not enough storage for everyone, and worn, damaged seats. Service was great but feel a little unsafe on such well used planes.

Multiple delays and not straight answer from the United team

For economy, it was very good. Staff was great, they even let some of us change seats for more leg room... Put an empty seat between us which was fantastic for a 12hr flight. Onboard entertainment was excellent, I think over 200 choices of movies/tv/etc The bad was the barely/nonfunctional wifi that cost either $16.99 or 1700 miles (full flight). It was atrocious... Definitely the worst of the last 3 long haul major airlines I was on the last few months.

Stewardess spilled orange juice on my clothes/seat no help no apology just threw napkins at me to clean the mess up. Not Happy.

Smooth flight. Boarding was chaotic. Could not hear the gate agent over the intercom. People were lined up in the wrong lines. Groups one and two were told to board through line one and group 3 through line 2. All very confusing. Once in the air, the flight was smooth. There was no entertainment option on this aircraft, even though it was a larger aircraft.

The plane pushed back from the gate on time. However, it stopped on the ramp, and we waited for over 20 minutes before the aircraft pulled back to the gate. Apparently, something of importance had to be removed from the aircraft by the gate agent. I found this to be odd. The delay was not significant, but I felt that whatever was on the aircraft that had to be taken off, should’ve been done before we pushed back from the gate.

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.

Electric plugs didn't work. Entertainment system wasn't working

The design of the light switch on the arm rest is ridiculous.

Smooth boarding process. Early departure, smooth flight, early arrival. The entertainment package has very good recent movie options. The flight crew were friendly and professional.

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.

Excellent. Although they used to greet me as a mosaic member and provide a free drink, early boarding helps me to keep coming back to JetBlue.

Cancelled flight with no specific instructions to get a boarding pass for another flight. The whole flight of people were in line for an hour because there was only 1 person to help at the desk. This was unusual for JetBlue.

It was too hot in the cabin. The AC did not help.

Except for the 28 minute delay leaving and the earlier reschedule to a later takeoff time the flight was good.

Loved the leg room and tvs screens on the seats and free WiFi. Wish the price was lower and could save by rebooking

No music app working: no economy meal on five hour flight; hour on tarmac at the end waiting for a gate. Flight itself was smooth and easy.

It took 1-1/2 hours to get our luggage after we landed. That to me is unacceptable

The flight was delayed for 4 hours. Once onboard the crew was wonderful.

Overall was excellent. Will definitely us JetBlue in the future.

Very well organized both boarding and deplaning. Very satisfied with the service I received.

First world problems, but still… We were seated in first class and asked for a cocktail on a very short, 50 minute flight. After our drink order was taken, a half hour went by, and we noticed that every other person in the small plane had been served except for us. We got up to ask about it, the drinks finally came, then were taken away three minutes later since the flight was so short. Really strange situation, on the other hand, we were in Utah.

We missed our flight. The boarding pass had the wrong gate and by the time we received the text from Kayak, our flight was already gone. I’ll never use Kayak again and will go direct to the airlines in the future.

Boarding took forever, the plane was cramped and cold, and the seatbelt song came on constantly throughout the red eye flight with a loud pre-recorded message playing each time

Cabin felt crammed Snacks are lame But crew was super efficient getting us out on time despite delay

Took off on time and successfully avoided weather that looked to be a problem along the way

There were five broken seats on the plane. The crew was very rude in telling people they had to get off the plane and get a flight the next day. No call for volunteers, but telling people they had to get off. One woman was flying with her elderly mother and daughter and was told she had to leave or all three had to leave. Fortunately, a volunteer offered to stay. The situation was handled poorly.

The flight to Tokyo AA61 took off about two hours late, but then had to turn back. By that time the crew had to be replaced. Then they kept promising to take off in an hour, then in 3, then switch to the next day.

British Airways staff are very polite and willing to help.

Any sort of gluten free snack option would be nice

They lost my luggage and it didn’t get delivered until the next day.

Everything you need to know for your flight to Caribbean

Information on your arrival and departure airports

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