$68 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 1/2. 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.
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.
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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$259
Santo Domingo
Santo Domingo1 stop$265
Montego Bay
Montego Bay2 stops$323
Oranjestad
Oranjestad1 stop$197
Nassau
Nassau1 stop$341
Kingston
Kingston1 stop$344
Simpson Bay
Simpson Bay1 stop$256
Providenciales
Providenciales1 stop$369
Port of Spain
Port of Spain1 stop$353
Bridgetown
Bridgetown1 stop$443
George Town
George Town1 stop$273
Willemstad
Willemstad1 stop$354
Castries
Castries2 stops$897
St. John's
St. John's1 stop$436
Puerto Plata
Puerto Plata1 stop$382
Aguadilla
Aguadilla1 stop$168
Punta Cana
Punta Cana1 stop$259
Santo Domingo
Santo Domingo1 stop$265
Montego Bay
Montego Bay2 stops$323
Oranjestad
Oranjestad1 stop$197
Nassau
Nassau1 stop$341
Kingston
Kingston1 stop$344
Simpson Bay
Simpson Bay1 stop$256
Providenciales
Providenciales1 stop$369
Port of Spain
Port of Spain1 stop$353
Bridgetown
Bridgetown1 stop$443
George Town
George Town1 stop$273
Willemstad
Willemstad1 stop$354
Castries
Castries2 stops$897
St. John's
St. John's1 stop$436
Puerto Plata
Puerto Plata1 stop$382
Aguadilla
Aguadilla1 stop$168

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, Dec 1 - Sun, Dec 7
Frontier Logo
8:06 pm - 12:53 amIAD-SJU
3h 47mnonstop
Frontier Logo
6:30 am - 9:43 amSJU-IAD
4h 13mnonstop
$184Frontier
Find Deal
Sat, Nov 29 - Fri, Dec 12
Frontier Logo
7:56 pm - 12:43 amIAD-SJU
3h 47mnonstop
Frontier Logo
3:55 am - 8:24 pmSJU-IAD
17h 29m1 stop
$185Frontier
Find Deal
Wed, Jan 28 - Wed, Feb 4
JetBlue Logo
10:45 am - 8:02 pmDCA-SJU
8h 17m1 stop
JetBlue Logo
5:25 pm - 10:31 pmSJU-DCA
6h 06m1 stop
$209JetBlue
Find Deal
Sun, Jan 25 - Thu, Jan 29
American Airlines Logo
5:55 am - 2:59 pmDCA-SJU
8h 04m1 stop
American Airlines Logo
1:24 pm - 6:59 pmSJU-DCA
6h 35m1 stop
$215American Airlines
Find Deal
Mon, Feb 2 - Fri, Feb 6
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
Wed, Feb 18 - Thu, Feb 19
Spirit Airlines Logo
6:20 am - 3:31 pmBWI-SJU
8h 11m1 stop
Spirit Airlines Logo
4:36 pm - 11:31 pmSJU-BWI
7h 55m1 stop
$216Spirit Airlines
Find Deal
Thu, Dec 4 - Fri, Dec 12
Spirit Airlines Logo
8:00 pm - 10:33 amBWI-SJU
13h 33m1 stop
Spirit Airlines Logo
4:10 am - 9:35 amSJU-BWI
6h 25m1 stop
$219Spirit Airlines
Find Deal
Sun, Dec 7 - Wed, Dec 10
American Airlines Logo
6:45 am - 2:15 pmDCA-SJU
6h 30m1 stop
American Airlines Logo
11:00 am - 4:59 pmSJU-DCA
6h 59m1 stop
$235American Airlines
Find Deal
Mon, Dec 1 - Fri, Dec 5
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
Mon, Dec 1 - Fri, Dec 5
United Airlines Logo
6:00 am - 4:25 pmIAD-AUA
9h 25m1 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 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 $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 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 $418, 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 $446 and $396 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, Tuesday 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 16 weeks before departure.

Good to know

Low seasonSeptember
Cheapest flight$68
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 Oranjestad

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 8% cheaper than evening flights, on average. The most expensive time of day to fly to Caribbean Islands is generally at night, which is peak travel time and where the average cost of a ticket is $489.

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 4249 reviews
8.6Crew
7.0Food
8.0Comfort
8.1Boarding
7.5Entertainment
Airline reviews

No delays and arrived to destination 30 min early. Staff was super friendly.

10.0 ExcellentIlevba, Nov 2025DCA - DAL
Read more Southwest reviews

No delays and arrived to destination 30 min early. Staff was super friendly.

San Diego airport is brand new, spacious, airy and very smooth checkin at SW baggage drop.

It was rough. The staff was unprofessional, the choice of on board drinks terrible, it was cramped in space at every airport, they always ran out of overhead bin space so they pressured people to check bags for free or we couldn’t leave on the plane— so I did check my bag to help, and they nearly lost my bag. My bag did not arrive on the luggage belt, another man on my flight and I had to waste our time going to the baggage office to search for our bags. I would only fly southwest again if it was my last choice. Also, my flights were consistently delayed over and over again— at one point they straight up told us we were waiting for the pilot to arrive.

Crew could have been friendlier, maybe I'm spoiled by SW crews. In flight wifi was good. Would be nice to have more food offerings on a 4 plus hour flight

Had to get off plane from prior flight even though I had to reboard same plane to continue to my final destination.

Everything a cheap airline should be at normal airline rates.

Plane crashed into a bus or some other vehicle on the ground while pulling out of the gate. No injuries, but wing tip was damaged and returned to gate for “maintenance issues” and we departed 5 hours later because the plane went out of service and new plane was flown in from a nearby airport, Midway.

Ever since Southwest starting charging for bags, passengers don't want to pay to check their bags, so the gate agents have to beg people to check their roller bags now because there's "not enough space". This was a terrible business move by Southwest.

Full cans of soda would be nice. A choice between two snacks would be appreciated.

Tried watching free movie and it kept freezing so I couldn’t finish.

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.

We were told the flight was delayed 5 times, then it was moved to the next day.

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.

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

Endless, trip oof my life, we still are in in plane waiting for getting off.after 3 hours delay. Not even a glass of water.

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!

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.