$102 Find Cheap Flights from Washington Dulles Airport to Caribbean - Compare and Save

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Cheap Flights from Dulles Intl 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 Domingo2 stops$450
Montego Bay
Montego Bay2 stops$392
Oranjestad
Oranjestad1 stop$466
Nassau
Nassau1 stop$395
Kingston
Kingston1 stop$592
Simpson Bay
Simpson Bay2 stops$305
Providenciales
Providenciales1 stop$470
Port of Spain
Port of Spain1 stop$568
Bridgetown
Bridgetown2 stops$596
George Town
George Town1 stop$413
Willemstad
Willemstad1 stop$450
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 Domingo2 stops$450
Montego Bay
Montego Bay2 stops$392
Oranjestad
Oranjestad1 stop$466
Nassau
Nassau1 stop$395
Kingston
Kingston1 stop$592
Simpson Bay
Simpson Bay2 stops$305
Providenciales
Providenciales1 stop$470
Port of Spain
Port of Spain1 stop$568
Bridgetown
Bridgetown2 stops$596
George Town
George Town1 stop$413
Willemstad
Willemstad1 stop$450
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 Dulles Intl to Caribbean flights

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

What is the cheapest Washington, D.C. Dulles Intl Airport to Caribbean flight route?

The cheapest ticket to Caribbean from Washington, D.C. Dulles Intl Airport found in the last 5 days was to San Juan, at $264 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 5 days was $264.

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. Dulles Intl Airport to Caribbean?

No, with an average price for the route of $709, prices are generally cheapest when you fly direct.

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

The cheapest month for flights from Washington, D.C. Dulles Intl Airport to Caribbean is January, when tickets cost $492 (return) on average. On the other hand, the most expensive months are July and June, when the average cost of round-trip tickets is $657 and $631 respectively.

What’s the cheapest day of the week to fly from Washington Dulles Airport to Caribbean?

If you are looking for a flight deal from Washington Dulles Airport 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. Dulles Intl Airport to Caribbean?

To get a below average price on the flight from Washington, D.C. Dulles Intl Airport 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

$102
Best time to beat the crowds with an average 8% drop in price.
Most popular time to fly with an average 44% increase in price.
Flight from Washington Dulles Airport to Simpson Bay

FAQs - booking Caribbean flights

  • What are some of the layover airports for flights from Washington Dulles Airport to the Caribbean?

    Some of the popular layover airports include Miami International Airport (MIA) used by American Airlines, and Hartsfield-Jackson Atlanta International Airport (ATL) by Delta Air Lines. Other airlines may use additional layover airports like Fort Lauderdale-Hollywood International Airport (FLL) or Charlotte Douglas International Airport (CLT).

  • Which airline(s) should I book when flying with kids from Washington Dulles Airport to the Caribbean?

    When flying with kids from Washington Dulles Airport to the Caribbean, consider booking with JetBlue Airways. They offer kid-friendly amenities like complimentary snacks and drinks, in-flight entertainment with kids' channels, and extra legroom options for more comfort. Additionally, JetBlue's friendly crew and accommodating services cater well to young travelers.

  • How convenient is it for people with reduced mobility flying from Washington Dulles Airport to Caribbean?

    Persons with reduced mobility have nothing to worry about when flying from IAD to the Caribbean. However, two airlines with outstanding services for persons with reduced mobility on flights from Washington Dulles Airport to the Caribbean are Delta Air Lines and United Airlines. They offer priority boarding and assistance, dedicated personnel for disabled passengers, and well-equipped cabins with spacious aisles for easy maneuverability, making travel more accessible and comfortable.

  • Which airline is more suitable to book when traveling with pet(s) from Washington Dulles Airport to the Caribbean?

    Traveling with pets from Washington Dulles Airport to the Caribbean is convenient, since all airlines along this route have pet-friendly policies. However, United Airlines is a better option, with a lower pet charge and a weight limit of 20 lb (9 kg) for pets to fly in-cabin. It's essential to comply with specific regulations and book in advance, ensuring a smooth and safe journey for your pet.

  • How does KAYAK find such low prices on flights from Washington Dulles Airport 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 Dulles Airport to Caribbean.

  • How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from Washington Dulles Airport to Caribbean?

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight from Washington Dulles Airport 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 Dulles Airport 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 Dulles Airport 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 Dulles Airport 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 Dulles Airport 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

  • Travelers seeking to fly to the Caribbean from Washington Dulles Airport (IAD) have several transport options from downtown to the airport. The common option is to take the Silver Line Express Bus (Bus 5A) from Rosslyn Metro Station. The bus provides direct service to the airport, offering a convenient and affordable transportation option for travelers.
  • Booking United Airlines for your Caribbean flight from Washington Dulles Airport (IAD) offers various benefits. As a hub for United Airlines, you can expect extensive flight options, convenient connections, and potential cost savings. Additionally, United's loyalty program and reputable service enhance the overall travel experience.
  • The majority of flights departing from Washington Dulles Airport and heading to the Caribbean have San Juan Luis Muñoz Marín International Airport (SJU) in Puerto Rico as their primary arrival point. This is particularly advantageous for those planning to explore the eastern Caribbean. Alternatively, travelers can opt for Nassau Lynden Pindling International Airport (NAS) in the Bahamas, providing an excellent gateway to the northern Caribbean, or Queen Beatrix International Airport (AUA) in Aruba, which serves as a convenient entry point to the southern Caribbean.
  • When flying from Washington Dulles Airport to the Caribbean, passengers often have the option to upgrade their tickets to higher classes like Business or First. American Airlines and United Airlines are particularly popular for offering such upgrading options, providing travelers with enhanced comfort and amenities during their journey.
  • Consider booking JetBlue Airways or Alaska Airlines if you want to enjoy one of the eco-friendly flights from Washington Dulles Airport to the Caribbean. The two airlines are recognized for their efforts in sustainability and eco-friendly practices. These include increased use of fuel-efficient engines in its aircraft and use of sustainable aviation fuels.

Reviews of the top 5 airlines serving from Dulles Intl to Caribbean

 
Need help choosing which airline to fly with from Dulles Intl 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.
7.8
DeltaOverall score based on 8697 reviews
7.8Comfort
7.2Food
8.5Crew
8.1Boarding
7.8Entertainment
Airline reviews

We experienced delays in small increments that added up to more than an hour. At the gate, staff showed little concern and compared our delay with the inbound flight’s two-hour tarmac wait, which didn’t address our situation. Once onboard, the flight attendants seemed tired and unfriendly. I understand delays are frustrating for everyone, but passengers shouldn’t feel blamed for them. During the flight, a bright light above the emergency exit stayed on. It was concerning, and no one explained it or offered passengers the option to move. After landing, we waited about 30 minutes on the tarmac for a gate, then waited again for an agent to connect the plane to the terminal. From the Reagan gate staff to the cabin crew and RDU personnel, the service felt dismissive throughout. Overall, this was a stressful trip and a very disappointing customer-service experience

4.0 OkayRonald, Oct 2026
Read more Delta reviews

We experienced delays in small increments that added up to more than an hour. At the gate, staff showed little concern and compared our delay with the inbound flight’s two-hour tarmac wait, which didn’t address our situation. Once onboard, the flight attendants seemed tired and unfriendly. I understand delays are frustrating for everyone, but passengers shouldn’t feel blamed for them. During the flight, a bright light above the emergency exit stayed on. It was concerning, and no one explained it or offered passengers the option to move. After landing, we waited about 30 minutes on the tarmac for a gate, then waited again for an agent to connect the plane to the terminal. From the Reagan gate staff to the cabin crew and RDU personnel, the service felt dismissive throughout. Overall, this was a stressful trip and a very disappointing customer-service experience

delayed take-off, then had to circle in air for awhile, wi-fi did not work, then the cabin got extremely hot multiple times and the luggage was at wrong carousel at LGA. In addition, plenty of overhead space so they checked bags too early. Horrible flight.

WiFi only works on about 75% of my Delta flights. I rarely fly SW, but their WiFi works 100% of the time and is easy to connect. On my DL flight from DCA to BNA today, I try to connect to WiFi for about 30 minutes, but I gave up. I have a lot of work to do, and I lost two hours today. Very frustrating.

I don't know why the crew decided to board 15 minutes early without informing anyone not at the gate. Why would you have the app send a notification that we're boarding on time, instead board early, and then rush me to the gate. Then have me check my carry-on when I specifically packed my bag as to not do so.

Long delays at both DCA and MSP; Crew did not keep us informed (or very little). Airplane was showing signs of heavy use (not up to Delta standards). Food options for Business Class have dropped in quality. After landing we sat on tarmac for maybe 25 minutes with no provided chance to use the bathroom and crew did not tell us what was going on or give an estimated time to expect to be at a gate.

Flight was delayed for about an hour but overall good experience

The gentleman at the gate I think his name is RIE was exceptional

This flight was no comparison to our prior flight. I'm thinking it all has to do with the age of the aircraft.

Inexpensive, got an exit row aisle aeat with no middle passenger, bought a great breakfast sandwich, flight comfortable & arrived ahead of schedule.

I wouldn't say I liked being forced to check my small roller bag at the gate; too many people had bags and were in a higher boarding group.

It is not a good experience with Copa Airlines: flight delay, luggage delay, etc.

We where skipped for this flight will not head to Panama until tonight..

There should be a warning regarding the quality of the aircraft on the website as we reserve the tickets. There was no TV or any type of screen onboard. The wifi they offer is good for nothing. Traveling 9 hours straight with kids and no type of entetainment was horrible. I wish I had been informed prior so I could buy a ticket with another airline. The food was a joke too. A very tiny portion per passenger. They also charged $100 per checked bag. With United I used to pay $60. So, fair to say that I wont be flying Copa anymore. Their aircraft was super old, outdated, no entertainment, with nearly no onboard food.

Very strict carry on rules meant most of the plane had to gate check their luggage. As is often the case had things that were broken because of this, but I appreciated not being charged to gate check. Otherwise good flight and great crew once on the plane

I liked the meatloaf the chicken was awful but the plane was on time and got there and the staff was nice.

Boarding was quick & efficient; they gave boarding groups due priority; staff & air crew were very cordial and helpful, pleasant flight.

Very happy with my flight. I would definitely recommend it.

Did upgrade, travel in business it was great (more room I could sleep)

There was no individual at the front check in when I arrived. I waited for at least 15 minutes and walked around asking security/janitors if they could help and they did not have a solution. So I had to take my checked bag through security and they threw away some of my items. I ended up making it to the gate only a few minutes before it closed due to my waiting for an agent at check in.

Boarding groups were called up in Spanish only. Luckily I know some of the language. They gave out grilled cheese sandwiches and a cup of fruit. I was very disappointed. I could only eat the cup of fruit because the only other option was vanilla pudding. The entertainment system and seating were great though.

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

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.

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.

It was pretty good, they give a small blanket, neck pillow and earphones. The only bad thing was not big enough leg room for your bag and feet. They gave us a snack, dinner, and breakfast on flight and food was good considering it was on a plane

The crew was great. The food was typical, but decent. Everything else - mediocre to poor. The flight was late arriving - happily for us and our 49 minute connection (what idiot came up with that?)- in another concourse - that concourse changed before we arrived (ticket and app was showing the incorrect gate - when we boarded at the correct gate - known by the airport person pushing my assistance cart). Had I walked and read the screens or United app I would have missed the flight! May other people arrived late to the correct gate, having been victims of a last minute gate change, were also relieved the flight arrived late. The aircraft (Boeing 757) was a sardine-can due to an uncomfortable seat pitch distance. The material or seat was beyond not comfortable, but I'm sure they made a lot of money with that aircraft type. I spent a lot of time standing in the back (in the middle of the night/morning to rest my back). I learned my lesson - any trans-oceanic fight - avoid United or American Airlines - and look for Airbus or Boeing 737, 767, 777. Also, pay for business class or premium coach seating.

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

the flight is delayed, which is not uncommon but the communication was still getting hopes on reaching on time which didn't happen. When I boarded the flight it was so like unimaginably filthy. My seat belt had some sticky stuff to it like food or something from before and the space below the arm rest is accumulated dust and waste like from few months i have the pictures. Cheery on top, the airhostess was an old lady who was so bossy and mad for no reason and bossing around everyone!! worst experience ever!!

As always, most AA flights that we fly are almost ALWAYS delayed and that too multiple times. Very frustrating

The small flights with Valet Luggage has a poor service

Human interaction. Thought there would be more service-even a smile would have been nice.

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