$107 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 6/15. 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, 0 bags

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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$428
Santo Domingo
Santo Domingo1 stop$479
Montego Bay
Montego Bay1 stop$444
Oranjestad
Oranjestad1 stop$397
Nassau
Nassau1 stop$429
Kingston
Kingston1 stop$395
Simpson Bay
Simpson Bay1 stop$367
Providenciales
Providenciales1 stop$493
Port of Spain
Port of Spain2 stops$538
Bridgetown
Bridgetown1 stop$421
George Town
George Town1 stop$317
Willemstad
Willemstad2 stops$482
Aguadilla
Aguadilla1 stop$314
Puerto Plata
Puerto Plata1 stop$600
St. John's
St. John's2 stops$554
Punta Cana
Punta Cana1 stop$428
Santo Domingo
Santo Domingo1 stop$479
Montego Bay
Montego Bay1 stop$444
Oranjestad
Oranjestad1 stop$397
Nassau
Nassau1 stop$429
Kingston
Kingston1 stop$395
Simpson Bay
Simpson Bay1 stop$367
Providenciales
Providenciales1 stop$493
Port of Spain
Port of Spain2 stops$538
Bridgetown
Bridgetown1 stop$421
George Town
George Town1 stop$317
Willemstad
Willemstad2 stops$482
Aguadilla
Aguadilla1 stop$314
Puerto Plata
Puerto Plata1 stop$600
St. John's
St. John's2 stops$554

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

Sat, Aug 22 - Sat, Aug 29
American Airlines Logo
5:26 pm - 12:15 am
DCA
-
SJU
6h 49m
1 stop
American Airlines Logo
10:33 am - 9:00 pm
SJU
-
DCA
10h 27m
1 stop
$276American Airlines
Wed, Aug 19 - Wed, Aug 26
American Airlines Logo
6:05 am - 4:03 pm
DCA
-
SJU
9h 58m
1 stop
American Airlines Logo
7:05 am - 3:59 pm
SJU
-
DCA
8h 54m
1 stop
$281American Airlines
Sun, Aug 30 - Sat, Sep 5
American Airlines Logo
3:17 pm - 12:15 am
DCA
-
SJU
8h 58m
1 stop
American Airlines Logo
10:33 am - 10:00 pm
SJU
-
DCA
11h 27m
1 stop
$301American Airlines
Sun, Aug 9 - Fri, Aug 14
Southwest Logo
4:35 pm - 10:45 pm
DCA
-
SJU
6h 10m
1 stop
Southwest Logo
5:45 pm - 11:55 pm
SJU
-
DCA
6h 10m
1 stop
$323Southwest
Tue, Aug 4 - Wed, Aug 12
Southwest Logo
12:55 pm - 9:05 pm
DCA
-
SJU
8h 10m
1 stop
Southwest Logo
8:20 am - 6:25 pm
SJU
-
DCA
10h 05m
2 stops
$326Southwest
Sun, Aug 16 - Thu, Aug 27
Delta Logo
6:00 am - 1:34 pm
DCA
-
STT
7h 34m
1 stop
Delta Logo
2:49 pm - 11:48 pm
STT
-
DCA
8h 59m
1 stop
$348Delta
Wed, Aug 19 - Fri, Aug 28
Delta Logo
6:59 am - 1:34 pm
DCA
-
STT
6h 35m
1 stop
Delta Logo
2:49 pm - 11:48 pm
STT
-
DCA
8h 59m
1 stop
$369Delta
Sat, Sep 5 - Sat, Sep 12
JetBlue Logo
6:00 am - 12:37 pm
DCA
-
SXM
6h 37m
1 stop
JetBlue Logo
1:45 pm - 9:05 pm
SXM
-
DCA
7h 20m
1 stop
$375JetBlue
Thu, Aug 27 - Tue, Sep 1
JetBlue Logo
6:00 am - 12:37 pm
DCA
-
SXM
6h 37m
1 stop
JetBlue Logo
1:42 pm - 9:16 pm
SXM
-
DCA
7h 34m
1 stop
$393JetBlue
Mon, Jul 6 - Sat, Jul 11
United Airlines Logo
8:25 am - 2:57 pm
DCA
-
NAS
6h 32m
1 stop
United Airlines Logo
2:53 pm - 10:15 pm
NAS
-
DCA
7h 22m
1 stop
$440United Airlines
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 3 days was to San Juan, at $277 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 3 days was $277.

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 in the morning, when round-trip flights cost $411 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 $411.

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 $536, 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 September, when tickets cost $108 (return) on average. On the other hand, the most expensive months are August and April, when the average cost of round-trip tickets is $1,379 and $849 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 Thursdays if you are looking for the best rates. For your return to Reagan Washington National Airport, you’ll find the best rates on Fridays 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 9% compared to booking last minute. For the absolute cheapest price, our data suggests you should book 26 weeks before departure.

Good to know

Low seasonSeptember
Cheapest flight$107
Best time to beat the crowds with an average 5% drop in price.
Most popular time to fly with an average 9% 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.

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 $207 one-way - $394 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.
7.9
SouthwestOverall score based on 4277 reviews
7.5Entertainment
8.0Comfort
8.1Boarding
7.0Food
8.6Crew
Airline reviews

The first time I flew in the extra legroom section. It was difficult to notice a difference. I had bad luck with my neighbors. The crew was okay. Southwest has reduced the live TV options.

4.0 OkayAnonymous, May 2026
MDW - LAX
Read more Southwest reviews

The first time I flew in the extra legroom section. It was difficult to notice a difference. I had bad luck with my neighbors. The crew was okay. Southwest has reduced the live TV options.

The flight was smooth. The Southwest experience has degraded overall, but this one was okay.

No gluten free snacks. Seats felt worn or bare bones even though it was a new 737 MAX 8.

One major problem that was very unprofessional and uncalled for. Plane landed and we had to wait 20 minutes to get off the plane since they were waiting for someone to come to the gate to drive the jetway. Southwest couldn't have someone available and waiting for the plane to land? Is there only one person in Hobby airport who knows to drive the jetway? Was he at lunch? In the bar? Uncomfortable and uncalled for!

The checking experience in Orlando was terrible, almost missed the flight. Too many travelers and Southwest completely understaffed.

I'm glad it wasn't only 75% full because I could get a good seat

if I was good. Not happy that I have to pay extra money to get the seat I need for lake room, but I guess that’s a sign of the times.

Seats were very comfortable. They tilted back. Drinks and snacks were free and served 3 times. Attendants were awesome.

Plane was clean and comfortable. Flight attendants and gate staff were professional, friendly and efficient. Boarding and deplaning were orderly and efficient. All in all, the typical excellent Southwest experience.

Truly terrible. Will never willingly fly southwest again. Seats are worse than before they switched to assigned seating. One flight attendant was the opposite of helpful (rude, unhelpful, dismissive, and as my stranger seatmate said unprompted: a total prick). This caused me, 15 minutes into the flight, to book an alternate return flight home on a competing airline (first class 1.2k purchase instead of my existing planned flight) just so I would not have to ever be on that aircraft, with that terrible service person, with those horrific seats ever again.

I continue to be satisfied with Delta’s excellent service out of LGA. The digit id works well and gets me through security in no time. Whenever possible, I choose Delta.

Was revoked with Jet Blue due to delay from Kenya Air

The Boarding process was great. Particularly since my wife and I require assistance. The flight attendants were amazing. We travel frequently; they honestly were a cut above. 😀

Enjoyed it very much. Especially liked the free WiFi that Delta offers.

Smooth flight. Left on time, and got in 15 minutes early. Onboard video was great

For some reason, TSA Atlanta didn’t have my bag on the flight on time and they don’t have to provide Delta a reason for that.

WiFi didn’t work on two of four planes. Flight attendants were not overly friendly or welcoming. Planes were extremely slow to board and deplane.

Delta does a great job with entertainment and free wifi. I can still be in touch with my colleagues while in the air.

Aside from a completely packed plane, I really have no complaints.

Bus to plane was delayed for no apparent reason and our luggage was still on the belt when they shut it off. Took about 20 minutes to turn it back on to get our luggage.

Our flight was canceled same day and we were never informed. Had to pay more and worse seating on another airline.

Did not like that we couldn't complete check in on-line without providing pictures of our passports. Worry about identity theft. We had no delays and boarding was handled In an efficient manner.

Excellent! I got to Munich and was transferred to my Lufthansa flight quickly, in 15 to 20 minutes, so I did not miss my flight. However, I had checked my overhead bag at the boarding gate in Tampa. That got to Tunis the next day. That is to be expected.

WiFi didn’t exist , seats were super cramped, lights stayed on near my seat for a long time while others were dimmed, the food/trash/drink cart hit my shoulder at least a couple of times while moving, food options were down to just one option by the time it got to my row, the utensils were garbage (knife bent at a couple of places by the time I was done eating) the spoon was very flimsy plastic

Vegetarian selection could be better. Bread was too hard to chew.

Crew was friendly and competent. Food, wine, and entertainment were excellent except the raw tuna on the flight to Split. Recommend against serving that - at least as the only option. Many medical conditions do not allow people to eat raw fish.

After arriving in Chicago, we were taxiing for 1.5 hours with infrequent and untruthful updates about the amount of time it would take to arrive at the gate. Minimally, the team could have provided timing expectations that were more truthful, especially one their original expectations were not met.

United didn’t even try to hold the flight for me. They knew I had a tight connection and when I arrived at the gate less than 10 mins after final boarding the flight had already gone. The gate agent wasn’t even notified that I was on my way. She was told I wasn’t at the airport

Good quick flight on a small but comfortable plane. I'm 6'3 and had plenty of space.

The flight was delayed so we were dead tired, and after that the turbulence was horrible. I was very scared.

It was good. I’m very disappointed that they don’t give commentary ear pods for the movie. I forgot mine at home

Great price, easy check in, love the free drinks and snacks, and nice crew. The only negative part was waiting for your seat assignment 5 minutes before boarding, and the seats are a bit uncomfortable.

What a great flight. Seats were more comfortable than other airlines. Flight was full but very easy to navigate. No stress no drama

Flight was quick, less time than expected, and the attendants all friendly and helpful. We had paid extra for more leg room and were very comfortable. Haven't flown JetBlue in quite a while. Glad to be back!

All airline travel outside of First or Business class is an ordeal to be endured. This trip was ok, small o, small k.

TV was broken and could not shut it off. The flicking was bother me and gave me a headache. The WiFi wouldn’t work correctly, I was able to text but not search the web or surf social media. The plane itself had a lot of wear and tear it is due for an update.

JetBlue not only has the most comfortable planes, but also used to have the best customer service. Lorie Wright, the lady at the gate was very rude not only to me, but to other passengers as well. Her colleague, the gentleman was also not very friendly. They both were acting like they were doing passengers a favor. The crew on board was very nice.

Flight was on time and smooth. Customer service was decent

The space between seat rows seemed to be larger than other airlines. I didn’t check their food or entertainment since I slept most of the way. They do seem to have a lot of options for purchase though.

Kayak sucked. You gave me a confirmation number that was not useable by the jet blue system. Nor did you send any check in emails. I’ll not be using your site again. Nice work.

Overall a good experience, however Wifi was not working on the flight.

THe flight was an hour late. You got us on the plan and we sat on the ground for 45 minutes with no information from the pilot whatsoever. Worst flight this year.

Going non stop to lax like I paid for. Not stopping in MCI for gas. Too long of delays

Incoming flight was delayed, delaying boarding. It then took 30 mins to take off. Took 20 mins to get to a gate because they changed the gate last minute, crew weren’t ready so there was no one staffed to work the jet bridge. Boarding was so disorganized as is usual with American because everyone just stands around the gate regardless of boarding group.

Delays with no explanation. It could have been handled better.

Flight delay for mechanical. Inbound arrived on time. No one said why mechanical delay.

Flight boarded, departed and landed on time. Excellent service from flight attendant in FIRST

This was one of the most frustrating travel experiences I've had to date. I had changed my flight day of to this one as it was slated to depart on time. It ended up being so delayed that my original flight took off before this one did. The boarding process began but eventually stopped and everyone had to get off the plane as a problem was identified. The person at the front desk just tried to laugh it off as if this wasn't already a huge inconvenience. From there, we eventually got to board only to sit at the gate for an additional hour because of some additional issue. This was extremely frustrating and caused a lot of stress.

It was a little concerning to hear the ground crew arguing with the flight crew over baggage space. Instead of taking them and checking them, they started checking for space in the first class cabin moving items around like the flight crew didn't know what they were doing. I was embarrassed for them.

delayed due to weather. Could not communicate with family since the wifi was broken

Everything you need to know for your flight to Caribbean

Information on your arrival and departure airports