$84 Find Cheap Flights from Washington, D.C. 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 Washington, D.C. to Caribbean departing on 11/2. 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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Cheap Flights from Washington, D.C. to Caribbean

Cheapest round-trip prices found by our users on KAYAK in the last 72 hours
Punta Cana
Punta Cana1 stop$259
Santo Domingo
Santo Domingo1 stop$295
Montego Bay
Montego Bay1 stop$303
Oranjestad
Oranjestad1 stop$280
Nassau
Nassau1 stop$357
Kingston
Kingston1 stop$351
Simpson Bay
Simpson Bay1 stop$314
Providenciales
Providenciales2 stops$450
Port of Spain
Port of Spain2 stops$379
Bridgetown
Bridgetown2 stops$398
George Town
George Town1 stop$287
Willemstad
Willemstad1 stop$323
Castries
Castries3 stops$856
St. John's
St. John's1 stop$424
Puerto Plata
Puerto Plata1 stop$392
Aguadilla
Aguadilla1 stop$239
Punta Cana
Punta Cana1 stop$259
Santo Domingo
Santo Domingo1 stop$295
Montego Bay
Montego Bay1 stop$303
Oranjestad
Oranjestad1 stop$280
Nassau
Nassau1 stop$357
Kingston
Kingston1 stop$351
Simpson Bay
Simpson Bay1 stop$314
Providenciales
Providenciales2 stops$450
Port of Spain
Port of Spain2 stops$379
Bridgetown
Bridgetown2 stops$398
George Town
George Town1 stop$287
Willemstad
Willemstad1 stop$323
Castries
Castries3 stops$856
St. John's
St. John's1 stop$424
Puerto Plata
Puerto Plata1 stop$392
Aguadilla
Aguadilla1 stop$239

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

Thu, Jan 1 - Mon, Jan 12
Frontier Logo
8:18 pm - 1:06 amBWI-SJU
3h 48mnonstop
Frontier Logo
6:00 am - 9:14 amSJU-BWI
4h 14mnonstop
$170Frontier
Find Deal
Thu, Jan 1 - Wed, Jan 7
Frontier Logo
8:18 pm - 1:06 amBWI-SJU
3h 48mnonstop
Frontier Logo
6:00 am - 9:14 amSJU-BWI
4h 14mnonstop
$171Frontier
Find Deal
Sun, Nov 16 - Tue, Nov 25
JetBlue Logo
8:00 am - 12:50 pmDCA-SJU
3h 50mnonstop
JetBlue Logo
6:10 pm - 9:08 pmSJU-DCA
3h 58mnonstop
$197JetBlue
Find Deal
Mon, Dec 8 - Wed, Dec 10
JetBlue Logo
8:00 am - 12:51 pmDCA-SJU
3h 51mnonstop
JetBlue Logo
6:51 pm - 9:48 pmSJU-DCA
3h 57mnonstop
$198JetBlue
Find Deal
Tue, Nov 18 - Thu, Nov 20
American Airlines Logo
4:51 pm - 11:52 pmDCA-SJU
6h 01m1 stop
American Airlines Logo
2:50 pm - 12:24 amSJU-DCA
10h 34m1 stop
$215American Airlines
Find Deal
Tue, Nov 18 - Thu, Nov 20
American Airlines Logo
11:25 am - 8:48 pmIAD-SJU
8h 23m1 stop
American Airlines Logo
4:44 pm - 11:59 pmSJU-IAD
8h 15m1 stop
$225American Airlines
Find Deal
Sat, Dec 6 - Sat, Dec 13
Spirit Airlines Logo
11:09 am - 3:55 pmBWI-SJU
3h 46mnonstop
Spirit Airlines Logo
7:00 am - 10:04 amSJU-BWI
4h 04mnonstop
$226Spirit Airlines
Find Deal
Sun, Nov 9 - Thu, Nov 13
Spirit Airlines Logo
9:36 pm - 3:20 pmBWI-PUJ
16h 44m1 stop
Spirit Airlines Logo
4:25 pm - 11:49 pmPUJ-BWI
8h 24m1 stop
$259Spirit Airlines
Find Deal
Sun, Nov 16 - Wed, Nov 19
United Airlines Logo
8:15 am - 1:40 pmIAD-AUA
4h 25mnonstop
United Airlines Logo
5:35 pm - 9:10 pmAUA-IAD
4h 35mnonstop
$349United Airlines
Find Deal
Sat, Dec 6 - Wed, Dec 10
United Airlines Logo
6:30 am - 4:40 pmIAD-AUA
9h 10m1 stop
United Airlines Logo
5:35 pm - 9:10 pmAUA-IAD
4h 35mnonstop
$354United Airlines
Find Deal
Booking Insights

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

Get data-powered insights and trends into flights from Washington, D.C. to Caribbean to help you find the cheapest flights, the best time to fly and much more.

What is the cheapest Washington, D.C. 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. found in the last 72 hours was to San Juan, at $129 round-trip. The most popular route is from Washington, D.C. Dulles Intl Airport (IAD) 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 $129.

Can I save money by flying with a layover from Washington, D.C. 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 $557, prices are generally cheapest when you fly direct.

What is the cheapest month to fly from Washington, D.C. 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. 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. to Caribbean 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 $443 and $396 respectively.

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

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

If you are looking for a flight deal from Washington, D.C. to Caribbean, look for departures on Tuesdays and avoid leaving on a Friday, as it's usually the priciest day. When flying back from Caribbean, Thursday is the cheapest day to fly and Monday is the most expensive.

How far in advance should I book a flight from Washington, D.C. 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. 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. to Caribbean, 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 16 weeks before departure.

Good to know

Low seasonSeptember
Cheapest flight$83
Best time to beat the crowds with an average 12% drop in price.
Most popular time to fly with an average 25% increase in price.
Flight from Washington Dulles Airport to San Juan

FAQs - booking Caribbean flights

  • Which airport in Washington, DC, should I fly out of to get to the Caribbean?

    Washington, DC, is served by three main airports: IAD, DCA, and BWI. When flying to the Caribbean from downtown Washington, DC, consider flying from DCA. IAD is a major international gateway for Washington, DC, and it’s the airport with the most flights to Caribbean destinations. BWI serves most of the low-cost airlines in the area. IAD is a Southern Airways Express and United Airlines hub, while DCA is a hub for American Airlines. You can connect to various Caribbean destinations from these airports for more flight options.

  • Which airport in Washington, DC, is more accessible by public transportation?

    DCA is the airport in Washington, DC, with a good connection to public transport systems. You can access the airport via Metrorail, Metrobus, and taxis. You can use the yellow and blue lines of the Metrorail system to connect to the station in DCA from downtown Washington, DC, and other parts of the city. You can also use a Metrobus to get to DCA.

  • Which airport in Washington, DC, has lounges?

    When flying from Wahington, DC, to the Caribbean, you should be at the airport at least two hours early. When waiting for your flight, you can visit one of the lounges at the airport. IAD has more lounges to select from, including United Club, Lufthansa Senator, British Airways Galleries, Air France-KLM, Turkish Airlines, and Virgin Atlantic Clubhouse lounges. The lounges offer comfortable space and seating, complimentary refreshments, business facilities, children's play areas, and flight assistance services.

  • Which route in the Caribbean from Washington, DC, is flown most often?

    Most air travel from IAD and DCA airports in Washington, DC, arrives at San Juan Airport. Several airlines, including Delta, JetBlue, United, and American Airlines, offer multiple daily flights between Washington, DC, and San Juan, ensuring passengers have numerous flight options along the route. San Juan is a major hub for flights in the Caribbean, making it a great connecting point to other Caribbean destinations.

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

  • 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?

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight from Washington, D.C. 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 Washington, D.C. 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 Washington, D.C. 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 Washington, D.C. 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 Washington, D.C. 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 in the afternoon, when round-trip flights cost $238 on average. Morning departures are around 8% cheaper than evening flights, on average. The most expensive time of day to fly to Caribbean is generally in the evening, which is peak travel time and where the average cost of a ticket is $447.

Top tips for finding cheap flights to Caribbean

  • Washington Dulles International Airport (IAD) and Reagan National Airport (DCA) in Washington, DC, offer direct flights from Washington to different Caribbean airports. A direct flight from Washington, DC, to the Caribbean will minimize your travel time and any inconveniences encountered through changing planes.
  • If you want to fly to the Caribbean from Washington, DC, on a budget-friendly airline, consider flying Southwest or Spirit Airlines. You can fly from Washington International Thurgood Marshall Airport (BWI), serving the Baltimore-Washington, DC area, which is a major hub for these low-cost airlines.
  • If you want to travel to the Caribbean from Washington, DC, at night, consider flying Delta, JetBlue, American, or United Airlines, which offer red-eye travel from IAD and arrive at various Caribbean airports the next morning.
  • If you want to access multiple islands in the Caribbean on a single trip, consider flying into a major international hub airport, including Luis Muñoz Marín International Airport (SJU) in Puerto Rico. This airport connects to multiple Caribbean destinations, including Aruba, Saint Lucia, Dominica, Saint Vincent and the Grenadines, Barbados, and Curaçao.
  • Consider flying Delta, United, or American Airlines from Washington, DC, to the Caribbean, as the airlines offer special meals to passengers with special dietary requirements. They offer vegetarian, vegan, gluten-free, lactose-free, diabetic, and child meals based on your needs.

Reviews of the top 5 airlines serving from Washington, D.C. to Caribbean

 
Need help choosing which airline to fly with from Washington, D.C. 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.
7.4
United AirlinesOverall score based on 8997 reviews
8.1Crew
7.3Comfort
6.6Food
7.7Boarding
7.1Entertainment
Airline reviews

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.

8.0 ExcellentMonsieur, Oct 2025IAD - EWR
Read more United Airlines reviews

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

I fly UAL 7-8 times per year. This flight was not up to snuff because it boarded very late "due to unexpected delays in restocking the plane" and yet Flight Aware showed the plane had landed some 10 hours earlier--so I think they could have planned accordingly. The FA's were nice but harried. The video system had to be rebooted 3-4 times. The food service was rather abrupt; they forgot my row and when I asked for my meal, they brought it with some impatience. Overall, the flight was fine, but the little details made it feel somewhat mundane and hurried.

It was good..clean, comfy seat. Friendly warm welcoming crew. Was able to check my cabin luggage at the gate which I was able to pickup in a decent time from baggage claim. The app gave all updates from delays to baggage claim info. Overall smooth flight.

Flight was delayed leaving Dallas. Arrived about 2 hours later than scheduled.

Flight delayed and missed connection. Rescheduled flight cancelled after 6 hrs wait. Rerouted thru ORD, flight cancelled, overnight stay in ORD. Still in the air on new flight!

We are too tired and frustrated to comment politely at this point

Terrible. Our luggage was delayed and couldn’t be delivered for several days. We got bad information from the airline agents at baggage claim. We had to pick up our car so we wouldn’t be charged for an extra day. We got lost in the maze of airport parking. The baggage claim agents didn’t offer us any compensation for our extra time and expense. We are tired, hungry and very frustrated.

The flight was flawless and we even arrived between 20 and 25 minutes early!

The only thing to like was that we eventually got to our destination

Delayed delayed delayed and no offer for food or vouchers

Disliked having to wait a little longer to disembark from the plan when we landed in London

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.

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.

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

Excessive fees for flight delays. What a Scam. I was not able to attend the wedding I needed to go.

Waited at the airport for over 4 hours to board this flight. Terrible airline

Was supposed to take off 8:00 last night. Got delayed till 8:00 this morning

It was terrible, we had to board and unboard the flight with a hour delay that caused me to miss an appointment and a surprise for my wife

When the flight ticket is expensive and you have to purchase check in luggage and there is no snacks, no entertainment, tight seats stuffed in the back of the plane not such good experience. I would like some to reach out to me . I paid for check luggage when I bought the ticket they made me pay again on the return flight extra $70. Very frustrating.

Excellent experience when I am looking for a budget airline where the main expectation is getting me from point A to point B with no frills.

Great! I intend to use Spirit for future flights. No complaints .

Seats are not very comfortable, maybe a little more padding for a 2hr plus flight

Very sad about what Spirit has become, because the flights I had with them were delayed between an hour and a half and two, terrible service

Vegas is such a quick flight that amenities aren’t the important part, in my opinion. Just get me there efficiently and safely, and that’s exactly what they did!

Terrible. The canceled my entire flight when I requested a refund for a trip frontier canceled trip one way.

Boarding was on time and plane departed as scheduled. There are obviously no amenities (food, drink, entertainment) on Frontier, but there also didn't seem to be any issues with luggage space either.

Inbound plane was on time and flight departed on time with no issues while boarding.

I knew going into this that Frontier, being a low cost carrier, would be pretty bare bones and charge for most extras but this was made up for by the fact that the airplane was a reasonably new Airbus, every employee was great and best of all, Everett Washington is an amazing airport - thanks Frontier for flying there!!!

i was unable to check in the flight. refund requested

It was well done. It was my first time flying with them and I was nervous b/c I have heard of many cancelled and/or delray flights. Everything went smoothly.

Just know that everything, and I mean everything is “ala cart”. 60$ just to put something in the overhead bin. I will never fly Frontier again nor do I recommend them to anyone else.

The single worst check in experience I could imagine. I’ll never do any business with Frontier or any affiliated company

Too many extra fees, uncomfortable, little leg room. Will not recommend this airline.

Everyone seemed to be in zone 1 for boarding. Maybe break it up a little. Otherwise, smooth flight.

Everything you need to know for your flight to Caribbean

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.

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