$77 Find Cheap Flights from Washington, D.C. 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 Washington, D.C. to Caribbean Islands departing on 1/24. 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

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 24% 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 Washington, D.C. to Caribbean Islands

Cheapest round-trip prices found by our users on KAYAK in the last 72 hours
Punta Cana
Punta Cana1 stop$294
Santo Domingo
Santo Domingo1 stop$310
Montego Bay
Montego Bay1 stop$313
Oranjestad
Oranjestad1 stop$241
Nassau
Nassau1 stop$262
Kingston
Kingston1 stop$365
Simpson Bay
Simpson Bay1 stop$247
Providenciales
Providenciales1 stop$246
Port of Spain
Port of Spain1 stop$354
Bridgetown
Bridgetown1 stop$410
George Town
George Townnonstop$296
Willemstad
Willemstad1 stop$313
Castries
Castries2 stops$1,466
St. John's
St. John's1 stop$406
Puerto Plata
Puerto Plata1 stop$410
Aguadilla
Aguadilla1 stop$172
Punta Cana
Punta Cana1 stop$294
Santo Domingo
Santo Domingo1 stop$310
Montego Bay
Montego Bay1 stop$313
Oranjestad
Oranjestad1 stop$241
Nassau
Nassau1 stop$262
Kingston
Kingston1 stop$365
Simpson Bay
Simpson Bay1 stop$247
Providenciales
Providenciales1 stop$246
Port of Spain
Port of Spain1 stop$354
Bridgetown
Bridgetown1 stop$410
George Town
George Townnonstop$296
Willemstad
Willemstad1 stop$313
Castries
Castries2 stops$1,466
St. John's
St. John's1 stop$406
Puerto Plata
Puerto Plata1 stop$410
Aguadilla
Aguadilla1 stop$172

Book Cheap Washington, D.C. 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 Washington, D.C. 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 Washington, D.C. to Caribbean Islands

Mon, Jan 19 - Sat, Jan 24
Frontier Logo
7:14 pm - 11:59 pm
IAD
-
SJU
3h 45mnonstop
Frontier Logo
7:00 pm - 12:36 pm
SJU
-
IAD
42h 36m2 stops
$175Frontier
Sat, Jan 17 - Sat, Jan 24
Frontier Logo
9:03 pm - 2:23 pm
IAD
-
SJU
16h 20m1 stop
Frontier Logo
4:36 pm - 8:33 am
SJU
-
IAD
16h 57m1 stop
$176Frontier
Wed, Jan 28 - Tue, Feb 3
JetBlue Logo
8:15 am - 1:08 pm
DCA
-
SJU
3h 53mnonstop
JetBlue Logo
6:30 pm - 9:32 pm
SJU
-
DCA
4h 02mnonstop
$181JetBlue
Wed, Jan 28 - Wed, Jan 28
JetBlue Logo
8:15 am - 1:08 pm
DCA
-
SJU
3h 53mnonstop
JetBlue Logo
6:30 pm - 9:32 pm
SJU
-
DCA
4h 02mnonstop
$193JetBlue
Sun, Jan 25 - Wed, Jan 28
United Airlines Logo
8:59 am - 1:56 pm
IAD
-
STT
3h 57mnonstop
United Airlines Logo
5:25 pm - 11:18 pm
STT
-
IAD
6h 53m1 stop
$196United Airlines
Tue, Jan 27 - Tue, Feb 10
American Airlines Logo
8:20 am - 8:50 pm
DCA
-
SJU
11h 30m1 stop
American Airlines Logo
6:00 am - 2:20 pm
SJU
-
DCA
9h 20m1 stop
$197American Airlines
Tue, Apr 21 - Tue, Apr 28
United Airlines Logo
6:15 am - 3:31 pm
IAD
-
STT
9h 16m1 stop
United Airlines Logo
2:10 pm - 12:15 am
STT
-
IAD
10h 05m1 stop
$200United Airlines
Sun, Feb 8 - Mon, Feb 16
Spirit Airlines Logo
6:00 am - 10:47 am
BWI
-
SJU
3h 47mnonstop
Spirit Airlines Logo
9:11 pm - 12:20 am
SJU
-
BWI
4h 09mnonstop
$200Spirit Airlines
Thu, Feb 5 - Tue, Feb 10
Spirit Airlines Logo
6:00 am - 10:47 am
BWI
-
SJU
3h 47mnonstop
Spirit Airlines Logo
9:29 pm - 12:41 am
SJU
-
BWI
4h 12mnonstop
$201Spirit Airlines
Mon, Feb 23 - Thu, Feb 26
American Airlines Logo
6:59 am - 9:34 pm
DCA
-
SJU
13h 35m1 stop
American Airlines Logo
7:01 pm - 12:36 am
SJU
-
DCA
6h 35m1 stop
$211American Airlines
Booking Insights

KAYAK's insights & trends for Washington, D.C. to Caribbean Islands flights

Get data-powered insights and trends into flights from Washington, D.C. 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. 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. found in the last 72 hours was to San Juan, at $119 round-trip. The most popular route is from Baltimore (BWI) 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. 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 $427, prices are generally cheapest when you fly direct.

What is the cheapest month to fly from Washington, D.C. 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. 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. to Caribbean Islands is July, when tickets cost $292 (return) on average. On the other hand, the most expensive months are December and April, when the average cost of round-trip tickets is $440 and $390 respectively.

What’s the cheapest day of the week to fly from Washington, D.C. to Caribbean Islands?

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

For Washington, D.C. to Caribbean Islands, Sunday is the cheapest day to fly on average and Friday is the most expensive. Flying from Caribbean Islands back to Washington, D.C., the best deals are generally found on Thursday, with Monday being the most expensive.

How far in advance should I book a flight from Washington, D.C. 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. 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. to Caribbean Islands, you should book around 2 weeks before departure, which saves you about 10% compared to booking last minute. For the absolute cheapest price, our data suggests you should book 20 weeks before departure.

Good to know

Low seasonSeptember
Cheapest flight$77
Best time to beat the crowds with an average 11% drop in price.
Most popular time to fly with an average 23% increase in price.
Flight from Washington Dulles Airport to Nassau

FAQs - booking Caribbean Islands flights

  • How does KAYAK find such low prices on flights from Washington, D.C. 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 Washington, D.C. to Caribbean Islands.

  • How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from Washington, D.C. to Caribbean Islands?

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight from Washington, D.C. 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 Washington, D.C. 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 Washington, D.C. 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 Washington, D.C. 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 Washington, D.C. 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 in the afternoon, when round-trip flights cost $238 on average. Morning departures are around 10% cheaper than evening flights, on average. The most expensive time of day to fly to Caribbean Islands is generally in the evening, which is peak travel time and where the average cost of a ticket is $428.

Reviews of the top 5 airlines serving from Washington, D.C. 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 Washington, D.C. 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 4255 reviews
7.0Food
8.0Comfort
7.5Entertainment
8.1Boarding
8.6Crew
Airline reviews

Flight was fine other than there was a gate change that I was not notified of. By chance I happened to check my phone and saw the change, otherwise, we would have missed our connecting flight.

8.0 ExcellentMaggie, Dec 2025
BWI - LAS
Read more Southwest reviews

Flight was fine other than there was a gate change that I was not notified of. By chance I happened to check my phone and saw the change, otherwise, we would have missed our connecting flight.

Haven’t flown on SW in years. Flight was on time departing and arriving. Served vegan butter onion flavored pretzels which were bad. Coke served was in a tiny paper cup. Crew was not engaging. Felt like they were going through the motions. Old plane, tight seats and no leg room.

Check-in, Boarding and flight were smooth. All the employees and crew was very nice and funny. They gave the kids crayons and workbooks to keep them occupied which was a big win. I’ve flown Southwest many times and that’s the first time I’ve seen that and it is a great addition.

Flight was on time. Wi-fi was a little spotty/slow. Boarding and exit were efficient.

Okay, not wonderful. Short flight. Wi-fi didn't work properly. Stuck waiting for a gate to open upon arrival for 20 or so minutes.

They sent a notice that they were boarding an hour early. We had to leave the club and run to the gate. They said sorry, that came from corporate and was a mistake. They did not have enough seating because the flight before it had not taken off on time. They moved our gate and delayed it for an hour.

The boarding and seat assignment system no longer works for me, but I know it is being replaced. Otherwise, I am good with the overall experience.

The lead steward kept singing about "San Francisco" and hotel California---more annoying than humorous....needs work. Flight was smooth and on time.

Still a fan of open seating. Flight was on schedule and arrived on time. The 737 MAX is very comfortable.

Airline travel is always too cramped to really be pleasant, but the cabin crew on this flight did a pretty good job of making up for it by putting on some music during boarding and sprinkling a few funny remarks into the safety briefing and announcements, and just generally being friendly and helpful. It definitely reminded me of why I prefer the in-flight experience on Southwest!

Sat next to a one year old. She crawled all over the place and made me laugh.

The Crew and the food was the worst I ever had in Business Class. First they told us there were no space for carry on. It was plenty of space over our 2 row seats, we had to ask to let us travel with it which was accepted. They were aware that we had to run for the connection due to the previous flight delay. Have us one hour waiting for more customers and not even offer a glass of water. Then started the service and they started to serve other passengers drinks in business and did not offer any drinks until they serve our pre ordered meal and I ask for something to drink. I had to wait until they finished to serve all passengers until Inget something. The crew was the worts I ever had for Business Class in my life.

Not great experience - we were super late boarding due to issues with aircraft. Then when we finally all got onboard and seated and they started taxiing out to the runway they just stopped then turned around and went back to the airport. Apparently the crew “ran out of time” to legally fly us. They mentioned that they were about 2 minutes away from taking off. I understand the rules and safety but kinda wonder why they would have bothered boarding us in the first place? Had to go all the way back and de plane and then wait in a HUGE line to get a hotel (this is somewhere around 2:30am) finally got to hotel by Uber (no shuttle after 20min so gave up) and they ended up putting us all back on the same aircraft at 10am next morning so got about 2.5 hours sleep. They did give us. $250 credit, but it was a São Paulo Brazil flight out of Dulles. The flight and everything was fine.

Starlink wifi on the Embraer E175 is an excellent experience. I was able to connect and work from IAD all the way to approach into BTV.

7 hours delayed due to operational issues on United’s end. Basically laziness.

Short flight but an "eager to help" crew made the journey more enjoyable!

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

Crew were all friendly and helpful. It was a short flight so just a beverage service with a cookie. After we were boarded the plane took about 45 minutes to leave the gate but it was New Year’s Eve so not shocking there was some delay. Overall good experience and very grateful.

After the door had been closed, the cockpit makes an announcement that catering is running late and it is not the airline's fault. It is their fault in the sense that we had to sit for 2 hours or more when we could have stayed in the terminal. Poor communications between catering and airline. This caused a young man to lose his temper and he went storming out hitting objects. He had complained to the gate agent that he had already waited at the gate 7 hours and when can the airplane leave? Airilnes do a poor job of explaining delays, maintenance issues, etc. whereas being truthful may gain more sympathy or understanding.

The flight was very smooth and the meal in business class was great.

The captain brought my 6 year old son into the cockpit and allowed him to ask questions, sit in the captain’s chair and talk about all the gears and levers. Made the trip very special for him.

I take this flight about 6-8 times per year. It is convenient and saves an hour or two by skipping PDX, SEA, PHX, or ORD (but it takes longer to get bags to the carousel than Alaska Airlines). I wish the food service were better (but they might cut back on it because it is a red-eye). The WifI seems to go down about an hour out of Anchorage, and then comes back about an hour later...so be warned if this is an issue for you.

Better service. No food options, but we did get drinks and a cookie.

Boarding was organized and timely. Food was mediocre, especially for first class travel.

We were 4+ hours delayed. AA is absolutely obnoxious. They just kept pushing back the time to the point where we did not get into Vegas until after midnight when we were supposed to arrive like 845pm.

My last flight on 25 Dec, it’s Christmas Day, everyone happy and very good mood. I really enjoy traveling with Americans Airlines from Miami to Minneapolis my home town after long flight from lhe to Doha then Miami. Thank you again to make my travels comfortable and relaxed. Best regards

The boarding process needs to be fixed. The zone don't work, especially when there is hardly anyone in zones 3, 4,and 5, leaving the majority of the passengers backed up in the aisle, especially because passengers seated near the front are blocking passengers who are seated in the rear of the plane. It would also help if the size of carry on bags was more strictly enforced.

1) No pilot available for 1 hour 2) no room for most passengers careyon in overhead—-> stowed below 3) when we landed we had to wait 45 min. Before docking at gate as gate was not ready

Good. No issues except a slight delay. Crew came in late.

Not a pleasant experience, service was poor. Didn't like it

It was good. I prefer JB over other airlines.I just wish we had headphones for the films, but other than that - good.

The ride share experience in JFK is terrible. After traveling on a flight, then you need to take a subway to the last stop to get an uber or lyft. Unacceptable. Bad job JetBlue for permitting JFK and Port Authority to do this to your passengers.

Checking In on JetBlue site was impossible. It hung up on REAL ID. Even my Global Entry did not help. Luckily, on Kayak site it was a breeze. Entire flight the temperature was COLD! Otherwise the crew was great!

The flight was two hours late due to a computer fault and resulting maintenance. Nothing was offered as compensation beyond bottles of water during the time we were deplaned and waiting in the terminal.

Very pleasant flight attendants. Gate crew rather loud chatting with each other.

Four plus hour flight delay in New York caused us to take off after 11:30pm. We didn’t arrive at our hotel until five hours after check in. Started the trip off feeling exhausted.

Plane was in bad shape. TV’s and WiFi didn’t work. Plane need a refresh. Not enough room for bags.

Worst every experience travelling with Family. So much delayed while going and returning both. All airlines were time except this. not sure Spirit operational issues. No recommend Spirit. It may spoil your entire trip. Rather spent extra $ and book better airlines.

Spirit cancelled my return flight the day before travel and so I had to book a last minute flight on American Airlines.

The traffic controllers had cancelled some flights, I wish they'd done it sooner so we didn't have to sit at the airport for 3 hours.

Horrible. They canceled the flight and didn’t offer much help

Late taking off. ATC sent us circling around Chicago for almost an hour, after landing taxied for 40 minutes.

I arrived two hours early, and at 9:20 I was still queuing for security.

We had too many delays for the crew not the plane

I liked that the crew looked well put together. I also liked that there were little turbulences.

The front desk personnel at ORF ticketing were the only good experience I had during my round trip. I encourage spirit to re-assess all aspects of their internal operations. This includes their website with constant issues connecting to their data base and questionable system practices. The employees of spirit airlines I will not comment on, as I believe primary issues had been a direct result of poor work conditions and expectations placed upon them. The holidays cause high emotions for everyone, this is an excellent time to take the opportunity to provide solutions for them, not take monetary advantage.

I knew what I was getting into, but never again. Hour long bag drop. 1.5 hour delay. 1 hr 45 mins sitting on the tarmac after landing. They lost a bunch of bags but luckily not mine. Awful experience.

Everything you need to know for your flight to Caribbean Islands

Cabin class types available on flights to Washington, D.C.

Cabin classes available on flights to Washington, D.C.. Prices are the lowest found on KAYAK over the last 7 days. Price and availability is not guaranteed.