$98 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$528
Santo Domingo
Santo Domingo3 stops$447
Montego Bay
Montego Bay1 stop$385
Oranjestad
Oranjestad1 stop$461
Nassau
Nassau1 stop$399
Kingston
Kingston2 stops$554
Simpson Bay
Simpson Bay1 stop$299
Providenciales
Providenciales1 stop$465
Port of Spain
Port of Spain1 stop$504
Bridgetown
Bridgetown1 stop$626
George Town
George Town1 stop$342
Willemstad
Willemstad1 stop$397
Aguadilla
Aguadilla1 stop$180
Puerto Plata
Puerto Plata1 stop$553
St. John's
St. John's1 stop$499
Punta Cana
Punta Cana2 stops$528
Santo Domingo
Santo Domingo3 stops$447
Montego Bay
Montego Bay1 stop$385
Oranjestad
Oranjestad1 stop$461
Nassau
Nassau1 stop$399
Kingston
Kingston2 stops$554
Simpson Bay
Simpson Bay1 stop$299
Providenciales
Providenciales1 stop$465
Port of Spain
Port of Spain1 stop$504
Bridgetown
Bridgetown1 stop$626
George Town
George Town1 stop$342
Willemstad
Willemstad1 stop$397
Aguadilla
Aguadilla1 stop$180
Puerto Plata
Puerto Plata1 stop$553
St. John's
St. John's1 stop$499
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 $326 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 $503.

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 $697, 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 $656 and $632 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

$98
Best time to beat the crowds with an average 5% drop in price.
Most popular time to fly with an average 22% 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 8681 reviews
7.8Entertainment
7.8Comfort
8.5Crew
7.2Food
8.1Boarding
Airline reviews

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.

2.0 MediocreKEVIN, Oct 2026
Read more Delta reviews

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.

2 of the seats in row 31 the entertainment system was not working, and one seat the tray table did not go all the way down. Flight arrived early and departed on time which was great.

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.

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 was great. Seats are cramped and uncomfortable and I’m a small person.

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.

Business Class layout was excellent. The seats were not nearly as comfortable as UA, Delta or Air New Zealand (the best). Nor were the controls as flexible. Food was okay but not great. Breakfast pancakes were like cardboard.

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.

I booked tickets from San Diego to Cincinnati months in advance to attend my sister’s wedding, a wedding where I was serving as the officiant. At 10:00 PM the night before my 6:00 AM flight (just 8 hours before departure), I received an alert that my first leg to Denver was delayed, causing me to miss my connecting flight to Cincinnati. When I called Frontier customer service, they informed me that they couldn't get me on any other flight that would get me there in time for the Saturday wedding, let alone the rehearsal dinner. Because I had a critical role in the wedding, I was forced to buy a last-minute ticket on another airline for three times the original price, costing me well over $1,000 extra. Even with the emergency flight, I still missed the rehearsal dinner entirely. When I spoke with Frontier, they agreed to refund my original ticket, but showed zero care or accountability for the massive financial burden and distress they caused. Their "compensation" for causing me to spend an extra $1,000+ and miss an irreplaceable family event? A $75 Frontier voucher. Frontier completely dropped the ball. Their customer service showed zero empathy, and their reliability is non-existent. I will never fly Frontier again, and no one else should either if they actually need to get where they want to go. Tip for anyone flying from Denver to Cincinnati: Avoid Frontier connecting flights or layovers at all costs, especially for time-sensitive events. Book direct flights with an airline that actually offers reliable customer support and rebooking options when delays occur.

I booked tickets from San Diego to Cincinnati months in advance to attend my sister’s wedding, a wedding where I was serving as the officiant. At 10:00 PM the night before my 6:00 AM flight (just 8 hours before departure), I received an alert that my first leg to Denver was delayed, causing me to miss my connecting flight to Cincinnati. When I called Frontier customer service, they informed me that they couldn't get me on any other flight that would get me there in time for the Saturday wedding, let alone the rehearsal dinner. Because I had a critical role in the wedding, I was forced to buy a last-minute ticket on another airline for three times the original price, it costing me well over $1,000 extra. Even with the emergency flight, I still missed the rehearsal dinner entirely. When I spoke with Frontier, they agreed to refund my original ticket, but showed zero care or accountability for the massive financial burden and distress they caused. Their "compensation” for causing me to spend an extra $1,000+ and miss an irreplaceable family event? A $75 Frontier voucher. Frontier completely dropped the ball. Their customer service showed zero empathy letting me know that it was Frontier who was the real victim by refunding my ticket price, and their reliability is non-existent. I will never fly Frontier again, and I strongly advise anyone who actually needs to arrive at their destination on time for an important event to book with literally any other airline.

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