$118 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 5/27. 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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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, as well as popular online travel agencies
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, as well as popular online travel agencies
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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$387
Santo Domingo
Santo Domingo1 stop$422
Montego Bay
Montego Bay1 stop$415
Oranjestad
Oranjestad1 stop$403
Nassau
Nassaunonstop$340
Kingston
Kingston1 stop$451
Simpson Bay
Simpson Bay1 stop$427
Providenciales
Providenciales1 stop$436
Bridgetown
Bridgetown2 stops$421
Port of Spain
Port of Spain1 stop$368
George Town
George Town1 stop$434
Willemstad
Willemstad1 stop$434
St. John's
St. John's1 stop$549
Puerto Plata
Puerto Plata1 stop$513
Aguadilla
Aguadilla2 stops$435
Punta Cana
Punta Cana1 stop$387
Santo Domingo
Santo Domingo1 stop$422
Montego Bay
Montego Bay1 stop$415
Oranjestad
Oranjestad1 stop$403
Nassau
Nassaunonstop$340
Kingston
Kingston1 stop$451
Simpson Bay
Simpson Bay1 stop$427
Providenciales
Providenciales1 stop$436
Bridgetown
Bridgetown2 stops$421
Port of Spain
Port of Spain1 stop$368
George Town
George Town1 stop$434
Willemstad
Willemstad1 stop$434
St. John's
St. John's1 stop$549
Puerto Plata
Puerto Plata1 stop$513
Aguadilla
Aguadilla2 stops$435

Cheap Flight Deals from Reagan-National to Caribbean Islands (DCA-zzEPX)

 
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.

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

Recommended round-trip deals departing in the coming months from the most popular airlines that fly from Reagan-National to Caribbean Islands.
Discover the best prices for you by selecting your travel dates on KAYAK.
Delta Logo
6:05 am - 1:25 pmDCA-SJU
7h 20m1 stop
Delta Logo
7:00 am - 6:13 pmSJU-DCA
11h 13m1 stop
$235Delta
Find Deal
Tue, Jun 24 - Thu, Jun 26
American Airlines Logo
5:00 am - 11:04 amDCA-SJU
6h 04m1 stop
American Airlines Logo
1:30 pm - 11:12 pmSJU-DCA
9h 42m1 stop
$255American Airlines
Find Deal
Sun, May 25 - Wed, May 28
American Airlines Logo
10:21 am - 8:33 pmDCA-SJU
10h 12m1 stop
American Airlines Logo
1:10 pm - 10:20 pmSJU-DCA
9h 10m1 stop
$260American Airlines
Find Deal
Sat, May 24 - Thu, May 29
United Airlines Logo
1:00 pm - 11:54 pmDCA-SJU
10h 54m1 stop
United Airlines Logo
1:25 pm - 9:39 pmSJU-DCA
8h 14m1 stop
$289United Airlines
Find Deal
Tue, Jun 3 - Thu, Jun 5
Delta Logo
6:05 am - 4:19 pmDCA-SJU
10h 14m1 stop
Delta Logo
12:43 pm - 11:30 pmSJU-DCA
10h 47m1 stop
$295Delta
Find Deal
Mon, Aug 11 - Wed, Aug 20
United Airlines Logo
6:00 am - 1:45 pmDCA-SJU
7h 45m1 stop
United Airlines Logo
1:05 am - 8:57 amSJU-DCA
7h 52m1 stop
$310United Airlines
Find Deal
Wed, May 21 - Wed, May 21
JetBlue Logo
9:55 am - 4:02 pmDCA-SJU
6h 07m1 stop
JetBlue Logo
9:00 am - 3:57 pmSJU-DCA
6h 57m1 stop
$316JetBlue
Find Deal
Tue, Aug 12 - Sat, Aug 16
JetBlue Logo
5:15 pm - 1:45 amDCA-SJU
8h 30m1 stop
JetBlue Logo
11:30 am - 6:44 pmSJU-DCA
7h 14m1 stop
$321JetBlue
Find Deal
Tue, Sep 9 - Wed, Sep 10
Southwest Logo
9:40 am - 9:50 pmDCA-SJU
12h 10m1 stop
Southwest Logo
11:50 am - 9:00 pmSJU-DCA
9h 10m2 stops
$385Southwest
Find Deal
Sat, Sep 27 - Wed, Oct 1
Southwest Logo
6:55 am - 4:00 pmDCA-SJU
9h 05m1 stop
Southwest Logo
5:30 am - 4:15 pmSJU-DCA
10h 45m2 stops
$410Southwest
Find Deal
Tue, Jul 15 - Wed, Jul 23
Useful Info

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 $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 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 September, when tickets cost $345 (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 $475 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 Tuesdays 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$118
Best time to beat the crowds with an average 19% drop in price.
Most popular time to fly with an average 4% 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 13% more expensive than evening flights, on average. The most expensive time of day to fly to Caribbean Islands is generally in the afternoon, which is peak travel time and where the average cost of a ticket is $418.

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 4292 reviews
8.6Crew
8.2Boarding
8.0Comfort
7.6Entertainment
7.1Food
Airline reviews

Bring back peanuts Take our drink orders when were all seated, especially after you switch to assigned seating.

10.0 ExcellentKurt V, May 2025AUS - ABQ
Read more Southwest reviews

Bring back peanuts Take our drink orders when were all seated, especially after you switch to assigned seating.

Staff was far less than helpful at all times. Departure and arrival times mean nothing to Southwest. Extremely disappointed, will never fly with them again, and I’ll be sure to share my experience with all.

It is southwest seat was ok. Not the most comfortable seat

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!

Food from the flight from Atlanta to Santiago was very poor..

Flight was delayed due to weather. Crew did a nice job of making us comfortable. No complain complaints.

Our bag was lost so that made unnecessary chaos On our trip

Delta is my preferred airline. I've traveled with them for years. On time in most cases, good communication, easy to use app. Most planes are pretty nice. I was on a CRJ 700/900 however, which was pretty badly aged inside and needed a refresh. No infotainment, unreliable wifi, best to download before boarding or bring a book. Food choices are really just snacks on this flight, nice variety but about what you'd expect. Great staff and prompt in departure and early arrival too. Overall quite satisfied.

Crew was friendly Love the entertainment in the seat head rest.

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.

Liked fold flat bed. Didn’t like having no window. Didn’t like poor choice of food and being served dinner very late, hours after take off of a 7:40pm flight. Servers not friendly. Food horrible in business class.

Everything is good except the dinner and breakfast. The sandwich is very delicious. Toilet is clean, I only use one of them. Flight attendants are very nice. 👍👍

A bit rush for transit. Food and entertainment are not available

Boarding was a little difficult. The gate area at O'Hare was very small and crowded due to multiple gates in the area. Could not hear the intercom, so had to rely on signage to see when my group was boarding and the signage was blocked by passengers standing in the gate. Flight was great and we arrived in Montreal on time.

Multiple delays and not straight answer from the United team

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.

We were delayed in Toronto on the tarmac for THREE hours with no clear indication as to why except that it was not a safety hazard. Pilot did apologize more than once but even he was unable to explain why exactly we were delayed. I overheard the stewards saying that the captain was very frustrated with the situation as well because he was not able to explain why except it had something to do with water supply or system on the aircraft and now we needed to wait for an engineer to approve the aircraft for flight. It was very frustrating and distressing as a passenger and we should have been given complimentary meals at the very least.

Flight was cramped with every seat taken. The food was fine, nothing crazy to write home about. The plane felt dated and needing some TLC, the button for the window shade didn't work and there were no AC outlets to use. When communicating with staff all except one nice lady never seemed happy to help me almost like I was bothering them when asked for things like a glass of water or a snack. The flight was overall fine. It did what was needed which is get me from point A to point B. But it certainly was not special. I don't expect much in economy but I believe economy on a host of other airlines is more memorable and better experience.

The flight was heavily booked so boarding was a lengthy process. The FA’s were rather abrupt during this process but became more gracious as the flight went on. Breakfast (puffed pastry and chewy sausage) was pretty horrible but there was fruit and yogurt which they didn’t mess up. Overall it was fine.

Excellent from start to finish. All staff members were amazing!

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.

Was a normal flight but it was delayed, and there wasn't an explanation.

In flight connectivity (via T-Mobile) was often not working.

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

really bad they refused to check in luggages that I had purchased, even showing them the transaction receipt from british airways app the staff in miami was MEDIOCRE

Several delays. Next flight was worse. Did not arrive home until 2am PT

Very helpful ground crew after an earlier flight delay and being rebooked on a different flight.

Everything about the flight was lovely…We left early, arrived early, cabin crew were efficient and helpful. Flight was easy and most pleasant.

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

Everything you need to know for your flight to Caribbean Islands

Information on your arrival and departure airports

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