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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 5 days
Punta Cana
Punta Cana2 stops$523
Santo Domingo
Santo Domingo1 stop$440
Montego Bay
Montego Bay1 stop$387
Oranjestad
Oranjestad1 stop$466
Nassau
Nassau1 stop$392
Kingston
Kingston1 stop$581
Providenciales
Providenciales1 stop$468
Port of Spain
Port of Spain1 stop$568
Bridgetown
Bridgetown1 stop$596
George Town
George Town1 stop$377
Willemstad
Willemstad1 stop$390
Aguadilla
Aguadilla1 stop$288
Puerto Plata
Puerto Plata1 stop$456
St. John's
St. John's2 stops$528
Punta Cana
Punta Cana2 stops$523
Santo Domingo
Santo Domingo1 stop$440
Montego Bay
Montego Bay1 stop$387
Oranjestad
Oranjestad1 stop$466
Nassau
Nassau1 stop$392
Kingston
Kingston1 stop$581
Providenciales
Providenciales1 stop$468
Port of Spain
Port of Spain1 stop$568
Bridgetown
Bridgetown1 stop$596
George Town
George Town1 stop$377
Willemstad
Willemstad1 stop$390
Aguadilla
Aguadilla1 stop$288
Puerto Plata
Puerto Plata1 stop$456
St. John's
St. John's2 stops$528
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?

The cheapest ticket to Caribbean from Washington, D.C. found in the last 5 days was to San Juan, at $95 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 5 days was $95.

What is the cheapest time of day to fly to Caribbean?

The cheapest time of day to fly to Caribbean is generally at night, when round-trip flights cost $301 on average. Morning departures are around 4% more expensive than evening flights, on average. The most expensive time of day to fly to Caribbean is generally in the morning, which is peak travel time and where the average cost of a ticket is $505.

Can I save money by flying with a layover from Washington, D.C. to Caribbean?

No, with an average price for the route of $647, prices are generally cheapest when you fly direct.

What is the cheapest month to fly from Washington, D.C. to Caribbean?

The cheapest month for flights from Washington, D.C. to Caribbean is January, when tickets cost $476 (return) on average. On the other hand, the most expensive months are December and July, when the average cost of round-trip tickets is $611 and $599 respectively.

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

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

How far in advance should I book a flight from Washington, D.C. to Caribbean?

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 14 weeks before departure.

Good to know

Low season

September

Cheapest flight

$133
Best time to beat the crowds but there is an average 2% increase in price.
Most popular time to fly with an average 20% 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.

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.
8.0
SouthwestOverall score based on 4212 reviews
8.0Comfort
7.0Food
8.6Crew
8.1Boarding
7.5Entertainment
Airline reviews

When I made my reservation it would have been nice if kayak would have included my luggage. Unaware that I had to pay $45 each way. Should have asked at reservation time if luggage was being checked

8.0 ExcellentJeremy, Nov 2026
Read more Southwest reviews

When I made my reservation it would have been nice if kayak would have included my luggage. Unaware that I had to pay $45 each way. Should have asked at reservation time if luggage was being checked

Crew was a little surly. But plane left on time and arrived early. All one can ask for. New 737 Max was nice.

Flight was delayed about 50 minutes and completely full. they did the usual demand for people to check carry-ons. they called all groups to board very fast only to stand in the gangway after having boarding passes scanned. Why don't airlines board from the back to front - since they now have assigned seats? our stewardess got drink orders confused, so she just called out "cranberry". etc.,.. I wish they wouldn't serve pretzels snacks with a powdered coating, as it sticks to your hands and they don't have wet wipes. don't want to lick my fingers after hanging out in the terminal for over an hour.

Delayed over 3 hours, extremely rough landing on all four flights. Would not recommend

It's a shame that SW was previously my preferred carrier until they started imposing all these fees (luggage, seats,etc) and pulling back on other perks. I only flew with them this time due to time frame I needed to be at destination. Wasn't provided gate info during check-in, Gate info wasn't displayed at airport until last minute, gate info didn't match what SW personnel announced at fate. Kind of a mess.

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

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

Pretty standard flight. We left late, but arrived early. The wifi entertainment is always nice. The free snacks and beverages are simple, but appreciated. I'm tall and the seats are an issue. I can deal with a short flight, but any longer, I have to find another airline where I know beforehand I have extra legroom.

Awesome experience. No in-flight video or meal. Still do not like the boarding process.

On time, good crew, easy flight. Just like the old days!

Terrible boarding - 4 flights boarded from the same gate. Chaos there; long ramps to the plane.

The couple in front of me were constantly talking over the announcement from the captain and this was annoying me.

Short. Nice quick flight, appreciated after Munich to DC leg.

The flight from Frankfurt to Pisa was cancelled and we were rebooked to route through London. The flight to London was delayed for maintenance issues and we missed our connection flight. Lufthansa automatically rebooked my wife on the next flight but I was not rebooked. I spent over an hour trying to get onto the flight. Ultimately my wife’s gate checked bag from Washington did not arrive in Pisa and remained in London. Very bad experience overall.

This was a small aircraft (relatively) and we were delayed half an hour on takeoff, which is not the airlines fault.

Flight delayed over an hour with plane on runway because of weather in an area of the country we were not in or flying to.

Flight attendant incredibly rude. Stuck her finger in my drink and didn’t even have the courtesy to apologize.

The very best airline service I have experienced. Better than domestic airlines first class and I flew Economy Plus!

The food was horrible. There was no. Wifi, and it was just terrible from bangkok to d. C

Boarding was 2 hours late and then we were delayed another 5 hours on the tarmac. I'm sure the crew were also tired, but some of them were rather snappy. The special dinner I ordered was not served, and they only served a tapas box on takeoff and breakfast before landing. That was disappointing in premium economy. However United was good at rebooking my connecting flight.

Good experience with this flight. Boarding was smooth with no issues. The short flight was good with quick drink & snack service. Nice easy way to get back from DC.

Flight is delayed by more than an hour without any reason, the jet blue gates kept changing every 20 mins and there is no proper communication. No ear phones provided in flight, there is a screen with entertainment but what is the use, I have earphones but the console has outdated audio connections, no usb C or bluetooth, they are living 15 years behind

A nightmare. Scheduled flight delayed 2 hours then cancelled because pilot timed out . Unable to find another pilot. Really?! Weather certainly a factor, but JetBlue seemed totally unprepared for the chaos that ensued when flight routes were cancelled. More cancelled flights, finally many of us who had been bumped from other flights were allowed to board a Boston bound plane around 3:00am, delay after delay, sat on tarmac for another half hour while pilot dealt with weight distribution issues (?), arrived in Boston 4:30. Crew were wonderful- same attendants all day and night and they were exhausted. Fortunately for me and my son that Boston was our final destination, not so lucky for many who missed connecting flights.

The flight was delayed 14 hours and communication was very poor. No one seemed to know what was happening and the gate agent was trying to help people for several flights. She was by herself trying to help 100s of people.

JetBlue worker, Blythe, was so amazing at the DCA counter. If it wasn’t for her, I’m not sure we would’ve made it through. Please thank her!

On time, friendly attendants, quick wheelchair assistance and help checking in bags. Also appreciated change in seats, more forward to make it easier for my 97 year old mother to board and exit the plane. Thank you, JetBlue!

Flight was on time and smooth. Customer service was decent

They forced me to check my hand luggage at the gate.

Still hasn’t left. Why are you asking how it was?

My flight got delayed and eventually canceled, then rescheduled. I and several others had a connection from Boston to Paris and asked several times if we would make it. They assured us we would and then rebooked us mid flight without our consent and closed doors early even though they said they communicated we were a bit delayed. We got stranded in Boston and I opted with being rebooked for a different connection to France since they refused to pay for a Hotel. I've now been in Europe for 5 days and still haven't recieved my bags. There was absolutely no urgency for the fact that I'm in a foreign country with absolutely no change of clothes or any of my medication. Such an overwhelming and frustrating experience.

Crew tried to accommodate late arrival due to late departure

I injured myself during my trip. The staff of American Airlines were very compassionate and empathic. They took additional steps to make my experience easier. Thank you!!

There was no ground crew at HSV gate when we arrived. The were busy with another arrival. We had to wait 20 mins for them to arrive and direct the plane to the gate. It took almost 45 mins to get my luggage. The luggage belt had 3 flights bags on it and the other 2 luggage belts were not being used. It looked like there was only 1 crew serving .3 arriving flights.

Liked: staff, no delays, Could use some improvement: Food, comfort, cleanliness, lack of chargers on the DCA -> DSM flight

It was close to its perfect the flake could be took off early, landed early, didn’t have to wait for my daughter stroller luggage came out quick, very efficient, very good flight

comfy and spacious seats for premium economy, nice flight attendants. only problem was the wifi did not work, and my entertainment screen was locked in Arabic language and all kids shows with no way of seemingly changing it. but the flight was fine and I arrived with no issues

Limited service due to turbulence, N/A Food and Drink. No entertainment

Flight was delayed which isn’t the airline’s fault, but the communication around it was terrible. I left the lounge to show up at the gate to board at the time in my app, and the flight in front of mine was still boarding and the inbound plane hadn’t even taken off yet. Delays were slow to show up in my app. Improved communication could have let me have a more pleasant experience in the lounge vs waiting 1.5 hours at the gate.

Wifi was good on the flight from DCA to Dallas and terrible on the flight from Dallas to Tucson. The forward head in the flight from Dallas to Tucson was putrid smelling entirely urine soaked. The flight from DCA to Dallas was delayed by almost 30 min with a plane change.

Sat on tarmac at arrival at DFw for more than 30 min waiting for a gate.

THE BARE METAL SEATS AT THE FRONTIER GATE IN CLEVELAND HOPKINS AIRPORT ARE DISGUSTING...BUT JUST A LITTLE BETTER THAN THE SEAT MATERIALS ON THE PLANE! THE "COMMERCIAL" ANNOUNCMENT PUSHING THE CREDIT CARD DEAL IS OBNOXIOUS AND UNWELCOME! THE VOLUME OF THE OFFER ANNOUNCMENET BLARES LOUDLY AND IS FILLED WITH A HYPED UP, CANNED SCRIPT. BOTTOM LINE IS THE FLIGHT AND THE CREW WERE VERY GOOD EXCEPT FOR THE ABOVE.

Maximizing profits is one way to a healthy bottom line, the other is repeat business and referrals from satisfied customers. Frontier has clearly chosen the former. One of many examples: Family emergency required me to cut trip short. Headed to the airport to fly standby for the return trip I had already paid for (yes I understand prices vary with demand etc). Was told there is no standby and that I would need to pay for, despite what it's called by the company, what amounts to a new ticket. And surprise surprise, there turned out to be dozens of empty seats on that flight. To say nothing of the sleazy third and fourth party resellers, the flight/ticket insurance I elected and thought I had paid for that mysteriously wasn't there when I needed it before I left, and on and on with third world sleazy management decisions. The inflight coffee (that I had to pay for) was very good though.

More inflight connection. And leg space is horrible. And the paying for baggage I'd ridiculous!!!

Frontier Airlines was AWFUL. I was an hour early for my flight and the lady refused to check me in. I had to purchase a whole new ticket with a different airline.

I missed a flight because of a delay. I had to buy a new ticket through Southwest.

Bag should not be so much money. This is how Frontier takes advantage of customers

Frontier is definitely a good option for people traveling light or on a budget - just remember to bring your own entertainment and your own headphones if you need them.

Never offer anything to drink ☹️ Flight delayed gate moved poor communication

It’s a cheap airline. I wish they had better seats.

Seats are cramped and very uncomfortable. You have to pay for everything and it is too expensive.

More options for your flight to Caribbean

Complete your trip to Caribbean with a hotel stay or car rental