$75 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 3/10. 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 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$345
Santo Domingo
Santo Domingo1 stop$317
Montego Bay
Montego Bay1 stop$309
Oranjestad
Oranjestad1 stop$251
Nassau
Nassaunonstop$307
Kingston
Kingston1 stop$362
Simpson Bay
Simpson Bay1 stop$226
Providenciales
Providenciales1 stop$363
Port of Spain
Port of Spain1 stop$336
Bridgetown
Bridgetown1 stop$370
George Town
George Town1 stop$275
Willemstad
Willemstad1 stop$330
Castries
Castries2 stops$799
St. John's
St. John's1 stop$414
Puerto Plata
Puerto Plata2 stops$437
Aguadilla
Aguadilla1 stop$192
Punta Cana
Punta Cana1 stop$345
Santo Domingo
Santo Domingo1 stop$317
Montego Bay
Montego Bay1 stop$309
Oranjestad
Oranjestad1 stop$251
Nassau
Nassaunonstop$307
Kingston
Kingston1 stop$362
Simpson Bay
Simpson Bay1 stop$226
Providenciales
Providenciales1 stop$363
Port of Spain
Port of Spain1 stop$336
Bridgetown
Bridgetown1 stop$370
George Town
George Town1 stop$275
Willemstad
Willemstad1 stop$330
Castries
Castries2 stops$799
St. John's
St. John's1 stop$414
Puerto Plata
Puerto Plata2 stops$437
Aguadilla
Aguadilla1 stop$192

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

Sat, Apr 25 - Thu, Apr 30
Frontier Logo
9:43 pm - 12:33 pm
BWI
-
SJU
14h 50m
1 stop
Frontier Logo
1:43 pm - 5:55 pm
SJU
-
BWI
4h 12mnonstop
$157Frontier
Wed, Apr 29 - Thu, Apr 30
Frontier Logo
5:35 pm - 2:01 am
BWI
-
SJU
8h 26m
1 stop
Frontier Logo
1:43 pm - 5:55 pm
SJU
-
BWI
4h 12mnonstop
$158Frontier
Mon, Feb 23 - Sat, Feb 28
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
$164Spirit Airlines
Mon, Mar 16 - Thu, Mar 19
United Airlines Logo
8:59 am - 12:56 pm
IAD
-
STT
3h 57mnonstop
United Airlines Logo
4:25 pm - 11:19 pm
STT
-
IAD
6h 54m
1 stop
$196United Airlines
Thu, Mar 5 - Thu, Mar 19
American Airlines Logo
5:00 am - 3:53 pm
IAD
-
STT
9h 53m
1 stop
American Airlines Logo
4:42 pm - 8:48 am
STT
-
IAD
16h 06m
1 stop
$200American Airlines
Sun, Mar 22 - Wed, Mar 25
United Airlines Logo
8:59 am - 12:56 pm
IAD
-
STT
3h 57mnonstop
United Airlines Logo
12:02 pm - 4:25 pm
STT
-
IAD
4h 23mnonstop
$201United Airlines
Mon, Mar 9 - Tue, Mar 17
American Airlines Logo
6:00 am - 4:02 pm
IAD
-
STT
10h 02m
1 stop
American Airlines Logo
12:45 pm - 8:29 pm
STT
-
IAD
7h 44m
1 stop
$211American Airlines
Sun, Feb 22 - Tue, Mar 3
JetBlue Logo
8:00 am - 12:46 pm
DCA
-
SJU
3h 46mnonstop
JetBlue Logo
6:10 am - 12:59 pm
SJU
-
DCA
7h 49m
1 stop
$225JetBlue
Wed, May 27 - Thu, May 28
JetBlue Logo
3:59 pm - 11:00 pm
DCA
-
SJU
7h 01m
1 stop
JetBlue Logo
6:00 am - 2:40 pm
SJU
-
DCA
8h 40m
1 stop
$241JetBlue
Tue, Mar 17 - Thu, Mar 26
Spirit Airlines Logo
6:25 am - 2:35 pm
BWI
-
AUA
8h 10m
1 stop
Spirit Airlines Logo
3:40 pm - 11:59 pm
AUA
-
BWI
8h 19m
1 stop
$251Spirit Airlines
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 $108 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 $138.

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 $532, 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 $290 (return) on average. On the other hand, the most expensive months are December and January, when the average cost of round-trip tickets is $438 and $349 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 Sundays and avoid leaving on a Wednesday, 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 1 week before departure. For the absolute cheapest price, our data suggests you should book 3 weeks before departure.

Good to know

Low seasonSeptember
Cheapest flight$75
Best time to beat the crowds with an average 9% drop in price.
Most popular time to fly with an average 19% increase in price.
Flight from Baltimore 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 9% 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 $434.

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 9273 reviews
7.3Comfort
8.1Crew
6.6Food
7.1Entertainment
7.7Boarding
Airline reviews

Wifi took a while to kick in and we had a maintenance issue that took over 40 mins at the gate in Washington before pulling back

6.0 Goodrob, Feb 2026
IAD - YYZ
Read more United Airlines reviews

Wifi took a while to kick in and we had a maintenance issue that took over 40 mins at the gate in Washington before pulling back

Very good. Because of the delays with my previous flight, I missed my connection, but I was able to book another flight through the United app easily.

Was happy we finally got upgraded in 1st class. The seat getting old. The cushiness need some improvement.

Ineffective communication with United resulted in lost baggage. Their Baggage Tracing counter at MUC was shut down from 11:00-14:15 on my arrival. Undertrained, underinformed staff had me Running all over MUC to find someone to help me to no avail. Staff was rude, unhelpful, and unable to effectively use the systems they did have operational. They refused to contact United in any way or provide any accommodation or other resources while I waited for my luggage. This has destroyed my downstream itinerary. If they had even the slightest visibility I may have been able to reschedule/plan, but again, their staff provided nothing, and did nothing more than their website, which doesn’t even work on a standard phone browser. Miserable failure at all levels that weren’t associated with the operation of the aircraft.

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!

The flight was on time/early, attentive crew, and everything overall went smoothly. Disappointed that WIFI was not working for the flight.

One day, I do so hope for a gluten free snack! Seems like with the rest of the world FINALLY figuring out what gluten free is, American Airlines would too. Fingers crossed!!

The flight was significantly delayed for 6.5 hours because of snow. There was no communication once the plane returned to the gate regarding when the flight would resume. Other flights were departing while our flight was being unloaded for reasons unknown. Our flight also seemed out of the queue regarding further deicing, refueling, and waiting to Taxi to the runway.

Flight was on time and the meal and service were good.

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

I got sick nothing contagious but distressing and the care I received by Kayla? Keighly the flight attendant will be memorable for ever. Thank You

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

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

The crew for the flight was A+ top notch. They were friendly and professional and made the flight a very relaxing and enjoable.

Rude crew member. She seemed annoyed at me without me saying a single word. Also loudly admonished me for having my bag next to my seat instead of tucked away before landing. Just telling me to put it away and guiding me without giving me a lecture would have been enough.

No included food for a 5 hour flight and the entertainment was only accessible if you had wired headphones (not provided). Otherwise though, great and smooth flying and customer service.

Crew were fantastic and so catering and wonderful! Full score for the entire crew!

Because of weather and mechanical issues our flight was 4 hours late. The only compensation offered to us was a meal voucher to be used only at Boston Airport and only on the day issued. But by the time it was offered to us all the restaurants were closed, so there was no way to use that offer.

Friendly crew, efficient boarding and flight arrived early. Couldn’t ask for a better experience

Terrible. They canceled our early morning flight after midnight on the day of and had no available flights to rebook my family on for the next 72 hours. Yet they still had other flights that were not cancelled from JFK so it couldn’t be based on the weather. It felt like they canceled the flight based on it not being profitable enough for them. I am not interested in traveling with the again. The absolute worse customer service and lack of accountability.

Horribly rude check in at airport, worst in 25 years of flying. All over a simple issue they could have googled to resolve.

First time flying with JetBlue and never again. I went to the counter to request meet and assist because I'm 74 and my wife is 79. I walk with a cane and my wife is handicapped and has her own wheel chair. I told the agent that my wife and luggage was at the entrance door. The ticketing agent said to me that they don't offer meet and assist. I need to bring them our luggage and then go back and get my wife in order to get my boarding pass. As I went back to get my luggage a Southwest agent along with a TSA agent recognized the situation and came over and took my wife and luggage to the JetBlue ticketing counter alongside the line and told the JetBlue agent to issue to take our luggage as soon as they could.

Flight was fine, price was good but food onboard was abysmal. I was on there for breakfast and lunch and dinner 845am EST to 845pm GMT and all I got was a yoghurt parfait, fruit and a piece of cake. Later snacks included an ice-cream brownie and a pizza twist. I was hungry by the time I landed and the airport amenities were closed. Not happy.

More comfortable seats, free snacks and soft drinks, some sort of entertainment or WiFi.

Delay at the gate without any communication such as announcement, sign, monitor, email or text. Found out later we were boarded with the knowledge of a significant delay, awaiting communication from Europe. Pilot was the only source of information regarding the delay after a long gate delay and sitting for more than 30 minutes after boarding. More than 2 hour delay, landing at 2 AM. Offered to deplane and reboard, but probably should have just waited rather than repeat the process. Not the first time experiencing the lack of communication with Spirit airlines. This morning was not as bad as showing up to a terminal without an agent (or aircraft) without any sort of communication. Much later an email was sent that stated our flight was rescheduled for a week later. Situations do arise, but simple communication can alleviate a lot of the frustration. Hard to believe a corporation doesn't understand that. But, you get what you pay for...

This was a horrible experience for both KAYAK and Spirit. My flight was canceled with no alternative flight option. I paid $600 for a last minute flight and didn't receive an email from KAYAK regarding the cancelled flight until hours after it was canceled. Never again for either.

No complaints with pricing so don’t expect a lot of extras.

Flight out was great but this flight was canceled and nothing was available for 2 days after this so I had to purchase an expensive ticket from another airline so I could go home. The flight cancellation was said to be a crew issue, it wasn’t weather or maintenance.

Flight got cancelled 1.5 hours prior to gate open and logistics of travel got delayed.

They cancelled the flight due to crew unavailability. The next day they cancelled the flight again.

They cancelled my flight last minute, forcing me to rebook with another airline.

the fligh was delay form 9am to 10, delayed again from 10 to 11, than delay and gate change to 12 and delay another gate change to 3;25 pm

Missed flight cause tsa took so long, overbooked flight, left terminal earlier than posted departure ridiculous upcharges stayed at airport additional 6 hours to catch next available flight. Had to make other arrangements to be picked up for later flight. Terrible experience!

First of all we hade waited 3 hours in the airplane waiting to leave. Second the return schedule was changed and it messed up my entire vaction. I won't buy never again another flight and recommend to nobody traveling with them.

There was no food and no entertainment, so I'm not sure why these are even in the survey, as my understanding is frontier does not ever offer food without a few, not even a snack, and there are no screens so unless the flight safety talk is our entertainment why ask how we liked it?. One of the flight attendants say in the back of the plane as people filed in to their seats, yelling orders about where to put baggage and telling people to hurry up. It was the least professional experience I've ever had on a flight.

Very well recently! Frontier is improving and less harrassing customer on luggages! Positive!

Good for a budget airline! It was easy to get on, staff was really nice. Can’t say anything about the food or entertainment because it wasn’t available, which is fine.

I am writing to express my disappointment with my recent Frontier Airlines flight. I was charged $99 at the gate because my bag was said to be too large, yet once onboard there was no available overhead bin space, and I was required to place the bag under the seat in front of me anyway. This made the charge feel unnecessary and unfair. Additionally, before the flight even took off, I was asked to move from the seat I paid for into a middle seat so another passenger and her cat could have my seat to themselves. I was not offered compensation or an explanation for being moved from a paid seat. Between the unexpected bag fee and being forced to give up my seat, this experience fell well below acceptable customer service standards. I would appreciate a review of this situation and appropriate compensation.

It was costly and difficult to check in. $85 to take a small suitcase with me, carry on or checked and $75 on the return trip, Plus $25 if I didn't check my self in check in $25, because I couldn't do it on the kiosk. Small very uncomfortable seats, waited on the runway for near an hour each way. It was my worst flight to date.

It was ok. It was expensive to check 2 bags ($75.00 per bag), and then it took a long time to wait for shuttle to take us from one terminal to the terminal where the plane was taking off at LAX. And all of this for a flight where we had to pay for any food or drink that was not water.

It didn’t happen. I booked it and then was told it wasn’t available and then forced to pay far higher prices for a worse option

A 630departure flight Delayed 6hours! They changed my gate, I moved to the new gate. Had our flight on the screen for 12noon departure. I go get above to eat, check screen again and the flight was gone, no notice no announcement, nothing!! They sent my bag on the flight I wasn’t on, got it back to me 3days later. Thank goodness they did refund my money but I will NEVER fly them again.

Due to weather, my flight was delayed, further delayed, then canceled. I eventually got through to a support person who helped me find a different route out of MSP, but to get to DIA, they didn't want to, but eventually did help with the connection ticket purchase. But even this replacement flight was delayed time and time again, and I would have missed my connecting flights and I didn't want to get stuck in a layover city, so after 12 hours at the airport with two young boys who were very tired, we just cancelled our plans and spent the week at home, instead of Nana's.

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.