$84 Find Cheap Flights from Washington Dulles Airport 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 Dulles Intl to Caribbean departing on 2/23. 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 Dulles Intl to Caribbean

Cheapest round-trip prices found by our users on KAYAK in the last 72 hours
Punta Cana
Punta Cana1 stop$334
Santo Domingo
Santo Domingo2 stops$419
Montego Bay
Montego Bay1 stop$392
Oranjestad
Oranjestad2 stops$351
Nassau
Nassau1 stop$370
Kingston
Kingston1 stop$398
Simpson Bay
Simpson Bay2 stops$468
Providenciales
Providenciales1 stop$397
Port of Spain
Port of Spain1 stop$448
Bridgetown
Bridgetown2 stops$394
George Town
George Townnonstop$317
Willemstad
Willemstad1 stop$319
St. John's
St. John's2 stops$469
Puerto Plata
Puerto Plata1 stop$451
Aguadilla
Aguadilla1 stop$182
Punta Cana
Punta Cana1 stop$334
Santo Domingo
Santo Domingo2 stops$419
Montego Bay
Montego Bay1 stop$392
Oranjestad
Oranjestad2 stops$351
Nassau
Nassau1 stop$370
Kingston
Kingston1 stop$398
Simpson Bay
Simpson Bay2 stops$468
Providenciales
Providenciales1 stop$397
Port of Spain
Port of Spain1 stop$448
Bridgetown
Bridgetown2 stops$394
George Town
George Townnonstop$317
Willemstad
Willemstad1 stop$319
St. John's
St. John's2 stops$469
Puerto Plata
Puerto Plata1 stop$451
Aguadilla
Aguadilla1 stop$182

Book Cheap Dulles Intl 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 Dulles Intl 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 Dulles Intl to Caribbean

Mon, Feb 9 - Sat, Feb 14
Multiple Airlines Logo
1:31 pm - 9:47 am
IAD
-
SJU
19h 16m
1 stop
Multiple Airlines Logo
4:17 pm - 7:25 pm
SJU
-
IAD
4h 08mnonstop
$177Multiple Airlines
Sat, Feb 14 - Sat, Feb 21
Frontier Logo
8:20 pm - 1:05 am
IAD
-
SJU
3h 45mnonstop
Frontier Logo
4:17 pm - 7:25 pm
SJU
-
IAD
4h 08mnonstop
$178Frontier
Sun, Feb 22 - Thu, Feb 26
United Airlines Logo
8:59 am - 1:56 pm
IAD
-
STT
3h 57mnonstop
United Airlines Logo
5:25 pm - 11:21 pm
STT
-
IAD
6h 56m
1 stop
$196United Airlines
Thu, Feb 19 - Thu, Feb 26
American Airlines Logo
6:00 am - 5:02 pm
IAD
-
STT
10h 02m
1 stop
American Airlines Logo
5:42 pm - 8:48 am
STT
-
IAD
16h 06m
1 stop
$200American Airlines
Tue, Feb 24 - Tue, Mar 3
Delta Logo
6:00 am - 4:22 pm
IAD
-
STT
9h 22m
1 stop
Delta Logo
4:15 pm - 12:21 am
STT
-
IAD
9h 06m
1 stop
$220Delta
Thu, Apr 16 - Sun, Apr 19
United Airlines Logo
6:15 am - 3:31 pm
IAD
-
STT
9h 16m
1 stop
United Airlines Logo
2:10 pm - 12:15 am
STT
-
IAD
10h 05m
1 stop
$221United Airlines
Mon, Feb 9 - Fri, Feb 13
American Airlines Logo
7:01 am - 3:06 pm
IAD
-
STT
7h 05m
1 stop
American Airlines Logo
1:00 pm - 8:30 pm
STT
-
IAD
8h 30m
1 stop
$242American Airlines
Sun, Feb 8 - Thu, Feb 12
Delta Logo
6:00 am - 4:20 pm
IAD
-
STT
9h 20m
1 stop
Delta Logo
1:50 pm - 12:21 am
STT
-
IAD
11h 31m
1 stop
$252Delta
Mon, Feb 9 - Thu, Feb 12
Copa Airlines Logo
3:35 pm - 11:35 am
IAD
-
PUJ
19h 00m
1 stop
Copa Airlines Logo
5:25 pm - 3:15 am
PUJ
-
IAD
10h 50m
1 stop
$347Copa Airlines
Sat, May 9 - Sun, May 17
Copa Airlines Logo
2:21 am - 2:42 pm
IAD
-
AUA
12h 21m
1 stop
Copa Airlines Logo
3:43 pm - 4:21 am
AUA
-
IAD
12h 38m
1 stop
$357Copa Airlines
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?

Data is based on round-trip flight searches on KAYAK over the past month.

The cheapest ticket to Caribbean from Washington, D.C. Dulles Intl Airport found in the last 72 hours was to San Juan, at $95 round-trip. The most popular route is from Washington, D.C. Dulles Intl Airport (IAD) to San Juan Luis Munoz Marin Intl Airport (SJU), and the cheapest round-trip airline ticket found on this route in the last 72 hours was $95.

Can I save money by flying with a layover from Washington, D.C. Dulles Intl Airport 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 $555, prices are generally cheapest when you fly direct.

What is the cheapest month to fly from Washington, D.C. Dulles Intl Airport 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. Dulles Intl Airport 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. Dulles Intl Airport to Caribbean is June, when tickets cost $298 (return) on average. On the other hand, the most expensive months are April and December, when the average cost of round-trip tickets is $526 and $495 respectively.

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

The average price of all round-trip flights from Washington, D.C. Dulles Intl Airport to Caribbean clicked on KAYAK for each day over the last 12 months.

If you are looking for a flight deal from Washington Dulles Airport 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. Dulles Intl Airport 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. Dulles Intl Airport 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. Dulles Intl Airport 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$84
Best time to beat the crowds with an average 5% drop in price.
Most popular time to fly with an average 13% increase in price.
Flight from Washington Dulles Airport to San Juan

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.

  • 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 $438.

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.
7.9
DeltaOverall score based on 8121 reviews
7.9Comfort
7.8Entertainment
8.1Boarding
8.5Crew
7.2Food
Airline reviews

The flight was comfortable and uneventful, which is what I desire

8.0 ExcellentLarry, Jan 2026
JFK - SJD
Read more Delta reviews

The flight was comfortable and uneventful, which is what I desire

The service from the flight attendants were of supreme quality. They greeted and treated everyone with a wide smile. This is totally absent nowadays. Kudos to them!!!!

Excellent flight and got us around tough weather. Only issue was seat TV did not work and crew tried to reboot.

Very large passenger too space from my own seat. Arm board couldn’t be lowered because of his size. It wads very uncomfortable trip, as the flight was full couldn’t move anywhere having back pain because of the position in which I was the entire flight.

was sitting in the jet bridge for 10 minutes in -20 degree weather waiting for my bag

Outdated equipment in disrepair, wifi inoperable. Broken seats, taped air vents, generally poor condition, the 717 showed its age and lack of upkeep.

My flight out of Baton Rouge to Atlanta was delayed by a half hour. This got us into Atlanta airport 30 minutes late. I ran through the airport to get to my connecting flight. As I approached the boarding gate, I saw the boarding door was still open and a passenger was being checked in. But when I got to the gate, the boarding agent told me they had already given away my seat and there were no empty seats on that flight. So I had to take a later flight. That has never happened to me before. Very frustrating.

Connection through Atlanta was difficult. Mechanical issue on plane caused a two hour delay. New gate was a mile away.

No WiFi. Comfort plus should have alcohol provided, crew only offered water or tea. Who the heck wants tea?

The flight was delayed and oversold. I volunteered to give up my seat for compensation. Thinking I could get a good night's sleep instead of arriving home at 2 am. It took over an hour to get the new reservation confirmed, three different gate attendants, and two red coats. It took even longer to confirm the overnight hotel, and when I arrived, the line was 45 minutes long, with two people checking in, and at least 15 people slowly, very slowly—no food except frozen convenience food, no coupon for food from airlines. Slept, headed back to the airport, and that flight had an equipment change and a gate change just as they were about to board. It took an additional hour to board as they cleaned the plane from storage.

Seats were awful. Media should have been included for such a long flight.

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.

They were super friendly bumped me up to exit row free of charge, All flight legs were on time

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

horrible service, food was an embarrassment, no charging for cellphones, stay away

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

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

Tell people to remain in their seats during the meal/beverage distribution. Enforce boarding by group numbers. No one was checking. Tell people to turn their electronics speakers off. Bigger cups for drinks.

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!

During booking, I kept trying submitting my payment from the Mexican website and it didn't work. After I had the idea to change it to the Canadian website, it worked but I had to be charged the equivalent of 50 CAD more. I received the clear instruction that I would only be able to check-in at the airport and that it was impossible to select a seat 24 hours before departure, that I had to pay 144 CAD to do so, although not only was I able to check-in 24 hours before departure, but I could have selected my seats for free then. All in all, I almost threw $200 out the window due to misleading information. Besides, the app kept crashing, the information to get to the gate on the app was inaccurate, my gate was switched and I was only informed once in the air (luckily I had noticed the departure pannel), I was not addressed in my language beforehand and even if I tried I was immediately answered in English (which meant the crew understood but didn't want to answer accordingly), there was only one snack & beverage service on my medium haul flight and no beverage service on my short haul flight. To be fair, the planes were comfortable, the crew apart from the language issue was helpful, dynamic and engaging, the plane was clean and the directions were clear and direct. United has a lot of potential to be one of my favourite airlines, but the devil is in the details and a lot of them missed the target.

The plane was experiencing problems with the HVAC system, it was very cold in the front of the plane and very hot in the back.

My flight to London from Philadelphia was cancelled due to weather.

The attendants were kind and helpful. A sugar-free drink would have been very welcome.

Pilot navigated severe weather/snow storm with skill. Described his intentions clearly

one crew said "he" didn't serve double alcohol drinks for travelers in exit rows. crew on prior flight did. Is this a AA rule, and the prior crew was being nice? Also, I think we deserve more than a 25% refund for losing first class seats when rescheduling a flight due to weather

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.

2 hour delay due to equipment failure. No updates via the app and airport screens (which continued to show a departure time in the past). AA eventually switched planes and the new plane was not catered or cleaned correctly.

I booked an aisle seat and was given a middle. At 6'4" 230lbs, it is not ideal to fly in the middle row for myself and passengers.

Trip delayed for 2 hours because of rain. We boarded and have to get down the flight and reboard again.

delayed due to weather. Could not communicate with family since the wifi was broken

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.

Plane and crew on board were fine. Everything else was terrible.

The third party booking with cheapflightsfares was awful. Kayak should NOT partner with them. They sold me a bundle including seat selection and carry-on, but did not book the carry-ons with Frontier, so I’m out of pocket for $414 more while I await resolution.

Everything you need to know for your flight to Caribbean

Information on your arrival and departure airports