$88 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 11/25. 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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1 adult, Economy, 0 bags

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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$267
Santo Domingo
Santo Domingo1 stop$278
Montego Bay
Montego Bay1 stop$314
Oranjestad
Oranjestad1 stop$219
Nassau
Nassau1 stop$341
Kingston
Kingston1 stop$375
Simpson Bay
Simpson Bay1 stop$236
Providenciales
Providenciales1 stop$369
Port of Spain
Port of Spain1 stop$353
Bridgetown
Bridgetown1 stop$443
George Town
George Town2 stops$283
Willemstad
Willemstad1 stop$365
Castries
Castries2 stops$897
St. John's
St. John's1 stop$436
Puerto Plata
Puerto Plata1 stop$382
Aguadilla
Aguadilla1 stop$138
Punta Cana
Punta Cana1 stop$267
Santo Domingo
Santo Domingo1 stop$278
Montego Bay
Montego Bay1 stop$314
Oranjestad
Oranjestad1 stop$219
Nassau
Nassau1 stop$341
Kingston
Kingston1 stop$375
Simpson Bay
Simpson Bay1 stop$236
Providenciales
Providenciales1 stop$369
Port of Spain
Port of Spain1 stop$353
Bridgetown
Bridgetown1 stop$443
George Town
George Town2 stops$283
Willemstad
Willemstad1 stop$365
Castries
Castries2 stops$897
St. John's
St. John's1 stop$436
Puerto Plata
Puerto Plata1 stop$382
Aguadilla
Aguadilla1 stop$138

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

Sun, Dec 7 - Sat, Dec 13
Frontier Logo
12:04 pm - 9:37 amIAD-SJU
20h 33m1 stop
Frontier Logo
11:05 am - 8:24 pmSJU-IAD
10h 19m1 stop
$188Frontier
Find Deal
Thu, Dec 11 - Fri, Dec 19
Multiple Airlines Logo
5:45 am - 7:50 pmIAD-SJU
13h 05m2 stops
Multiple Airlines Logo
4:18 pm - 7:31 pmSJU-IAD
4h 13mnonstop
$189Multiple Airlines
Find Deal
Sun, Jan 25 - Tue, Feb 3
American Airlines Logo
4:43 pm - 11:56 pmDCA-SJU
6h 13m1 stop
American Airlines Logo
4:49 pm - 12:34 amSJU-DCA
8h 45m1 stop
$215American Airlines
Find Deal
Wed, Jan 28 - Wed, Feb 4
JetBlue Logo
8:00 am - 12:42 pmDCA-SJU
3h 42mnonstop
JetBlue Logo
6:45 pm - 9:46 pmSJU-DCA
4h 01mnonstop
$216JetBlue
Find Deal
Sat, Dec 13 - Sat, Dec 20
Spirit Airlines Logo
7:06 pm - 12:32 pmBWI-SJU
16h 26m1 stop
Spirit Airlines Logo
4:10 am - 9:35 amSJU-BWI
6h 25m1 stop
$217Spirit Airlines
Find Deal
Mon, Jan 19 - Thu, Jan 22
JetBlue Logo
7:00 am - 6:02 pmDCA-SJU
10h 02m1 stop
JetBlue Logo
6:45 pm - 9:46 pmSJU-DCA
4h 01mnonstop
$218JetBlue
Find Deal
Sat, Dec 6 - Sun, Dec 14
Spirit Airlines Logo
7:06 pm - 12:32 pmBWI-SJU
16h 26m1 stop
Spirit Airlines Logo
5:00 pm - 12:23 amSJU-BWI
8h 23m1 stop
$221Spirit Airlines
Find Deal
Thu, Dec 4 - Sat, Dec 6
American Airlines Logo
1:41 pm - 11:52 pmDCA-SJU
9h 11m1 stop
American Airlines Logo
6:42 pm - 12:38 amSJU-DCA
6h 56m1 stop
$235American Airlines
Find Deal
Sun, Dec 7 - Thu, Dec 11
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
Sun, Dec 7 - Thu, Dec 11
United Airlines Logo
6:00 am - 3:00 pmIAD-AUA
8h 00m1 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 $122 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 $122.

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 $564, 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 $446 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$84
Best time to beat the crowds with an average 12% drop in price.
Most popular time to fly with an average 23% 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 at night, which is peak travel time and where the average cost of a ticket is $489.

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 9014 reviews
8.1Crew
7.1Entertainment
7.7Boarding
6.6Food
7.3Comfort
Airline reviews

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.

10.0 ExcellentDavid, Nov 2025IAD - BTV
Read more United Airlines reviews

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

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.

More choices on snacks. Built-in video screen to enjoy entertainment choices.

we landed at cmh ten minutes early but had to sit on tarmac for twenty minutes because a plane was at our gate despite the fact that 3 other gates were open.

The experience with American Airlines was good, although the Philippines Airlines flight was much better (better seats, better food, better entertainment options, overall better). Again, the MIA to LAX flight was fine, but nothing in comparison to the comfort and accommodations of the Philippines Airlines flight from LAX to MNL.

I have a gluten allergy so did have any food

I have a gluten allergy so didn't have any food

Loved the crew . Absolutely no complaints. Except for luggage lost

Everything was good The connects, with no blame to crew. Or pilots. I understand they are short staffed. Everything went well for me. I'll be using you guys again in May if not sooner.

this plane was really old, had exit row seats and tray was in arm of seat so super uncomfortable to use. another seat they could t even use the tray it was broke. seat i. front of me had duct tape on it cause seat was ripped open... this plane should either be updated or retired.

Flight delay was communicated before leaving for airport which caused it to be a non-event. Great flight and crew!

The flight attendant, a black woman with curly hair who sat near Row 21, was wonderful and kind.

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.

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

It was cheap. Spirit is what it is. I got to my destination and home safely. There was no food or entertainment without paying extra, which is fine. That’s why the flight was inexpensive.

Like: seats that don't move; fast boarding; engaging crew; low-prices; individual gate at LGA; access to restrooms at the gate Dislike: no water on the flight

No leg room. My knee was sore for a day.

It was better than expected. But there were two delays in taking off.

To be Honest they canceled my flight and didn't have other options. Until 4 says later and I have a 2yr old very disappointed.

The whole thing everything was poorly managed poorly handled spirit doent deserve to be in business period.

Nothing. It was delayed three times and then canceled and we had to drive 15 hours to get home and rent a car.

Flight was delayed. (To be excepted because of TSA shortage) I’m super short and still struggled with leg room, there was no screen, and the seat didn’t recline at all.

The pilot would speak it was painfully load a d the crew had to know this! Maybe the were hesitant to tell him. It was just a mediocre experience and I was in Spirit first class!

My flight was cancelled last minute and I had to pay $1600 for flights, when my original flights were $300. It was a terrible experience.

When I wanted to check in 3 hours prior to boarding time, the employees mentioned “a little over an hour delay” so I waited for an hour then I went to go look for food in the terminal and most people from that flight were in the same area looking for food. Finally I decided after food to check to see if it’s anytime closer and now it’s 2 mins until boarding closes?! What are you kidding me? I didn’t receive anything via sms about boarding now nor via email or on the intercom. I luckily made it through, barely, and then there’s no room for my carry on mind you I’m in the very first row so I had to place my purse in one further row back and my carry on sections down. Not sure who pays for better seats to get your stuff placed all over the plane but that was the worst experience I’ve ever had flying with anyone.

Better than expected. Staff were friendly and nice on both flights.

There was no one at the counter to assist with our check in. The app didn’t work, so I arrived at the airport with time to check in and I couldn’t because no employees were there. When I finally got someone on the phone, it was inside the 60min rule and they said I could no longer check in and they could sell me another ticket. We had to scramble and pay an additional $800 for tickets and THEN AFTER (about 60 min from my original convo with customer service and 10min after original departure time) I had boarded my new flight, there was email saying my original flight from Frontier was delayed and leaving 2hr 50min later, but I STILL wouldn’t have been able to check in. Which means customer service should have been able to see it and let me check in because I was well within my check in time. When I call Frontier, they hang up on me. So their app didn’t work and they employees left and they take zero responsibility or assistance with their “customer service”

Terrible. Flight cancelled with no reasoning and no flights to rebook. Employees were useless and did nothing to help. Did not even know where to retrieve luggage from the cancelled flight. Flyers beware.

No fault of Frontier staff: plane was very late, reached Orlando at 1 am, took a while to get luggage. Weather, gov financial shutdown impact on TSA, air controllers seemed to have multiple flights backed up. Frontier staff seemed to cope as gracefully as possible. It did reassure me that I and my new hip could adapt to travel challenges. Food/entertainment were irrelevant to my trip.

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

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.