$76 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 2/21. 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$374
Santo Domingo
Santo Domingo1 stop$394
Montego Bay
Montego Bay1 stop$395
Oranjestad
Oranjestad1 stop$354
Nassau
Nassau2 stops$370
Kingston
Kingston1 stop$430
Simpson Bay
Simpson Bay1 stop$444
Providenciales
Providencialesnonstop$399
Port of Spain
Port of Spain1 stop$336
Bridgetown
Bridgetown1 stop$370
George Town
George Townnonstop$317
Willemstad
Willemstad1 stop$330
St. John's
St. John's1 stop$445
Puerto Plata
Puerto Plata2 stops$437
Aguadilla
Aguadilla1 stop$192
Punta Cana
Punta Cana1 stop$374
Santo Domingo
Santo Domingo1 stop$394
Montego Bay
Montego Bay1 stop$395
Oranjestad
Oranjestad1 stop$354
Nassau
Nassau2 stops$370
Kingston
Kingston1 stop$430
Simpson Bay
Simpson Bay1 stop$444
Providenciales
Providencialesnonstop$399
Port of Spain
Port of Spain1 stop$336
Bridgetown
Bridgetown1 stop$370
George Town
George Townnonstop$317
Willemstad
Willemstad1 stop$330
St. John's
St. John's1 stop$445
Puerto Plata
Puerto Plata2 stops$437
Aguadilla
Aguadilla1 stop$192

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

Sat, Mar 21 - Tue, Mar 24
Frontier Logo
11:03 am - 2:48 pm
IAD
-
SJU
3h 45mnonstop
Frontier Logo
3:22 pm - 11:56 pm
SJU
-
IAD
8h 34m
1 stop
$165Frontier
Sat, Apr 11 - Wed, Apr 15
Frontier Logo
12:28 pm - 4:21 pm
IAD
-
SJU
3h 53mnonstop
Frontier Logo
6:30 am - 7:27 am
SJU
-
IAD
24h 57m
1 stop
$168Frontier
Sat, Feb 21 - Wed, Feb 25
Frontier Logo
8:20 pm - 1:05 am
IAD
-
SJU
3h 45mnonstop
Frontier Logo
5:25 pm - 9:25 am
SJU
-
IAD
17h 00m
1 stop
$169Frontier
Mon, Mar 16 - Thu, Mar 19
United Airlines Logo
8:59 am - 12:56 pm
IAD
-
STT
3h 57mnonstop
United Airlines Logo
4:25 pm - 11:19 pm
STT
-
IAD
6h 54m
1 stop
$196United Airlines
Thu, Mar 5 - Thu, Mar 19
American Airlines Logo
5:00 am - 3:53 pm
IAD
-
STT
9h 53m
1 stop
American Airlines Logo
4:42 pm - 8:48 am
STT
-
IAD
16h 06m
1 stop
$200American Airlines
Sun, Mar 22 - Wed, Mar 25
United Airlines Logo
8:59 am - 12:56 pm
IAD
-
STT
3h 57mnonstop
United Airlines Logo
12:02 pm - 4:25 pm
STT
-
IAD
4h 23mnonstop
$201United Airlines
Mon, Mar 9 - Tue, Mar 17
American Airlines Logo
6:00 am - 4:02 pm
IAD
-
STT
10h 02m
1 stop
American Airlines Logo
12:45 pm - 8:29 pm
STT
-
IAD
7h 44m
1 stop
$211American Airlines
Mon, Mar 2 - Wed, Mar 11
Delta Logo
6:00 am - 3:04 pm
IAD
-
STT
8h 04m
1 stop
Delta Logo
12:49 pm - 12:27 am
STT
-
IAD
11h 38m
1 stop
$220Delta
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
Tue, Mar 3 - Fri, Mar 13
Delta Logo
7:52 pm - 11:50 am
IAD
-
NAS
15h 58m
1 stop
Delta Logo
1:10 pm - 7:19 pm
NAS
-
IAD
6h 09m
1 stop
$371Delta
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 $108 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 $108.

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 $549, 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 $533 and $494 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$76
Best time to beat the crowds with an average 4% drop in price.
Most popular time to fly with an average 15% 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 $434.

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 8174 reviews
8.5Crew
7.9Comfort
8.1Boarding
7.8Entertainment
7.2Food
Airline reviews

Was forced to check in my small carry on, even though I informed the crew it has very fragile items inside

2.0 MediocreJaspreet, Feb 2026
SEA - SMF
Read more Delta reviews

Was forced to check in my small carry on, even though I informed the crew it has very fragile items inside

This was one of the worst flights I’ve been on in years. I upgraded to comfort and had such an uncomfortable experience. The person next to me was oversized - which I understand - however, they took up their space and mine. I could only use about 50% of my seat space to not be physically touching this person the entire flight and there was no spatial awareness. I also could not use the seat outlet because their body was obstructing it. It was very inconvenient. Their body kept touching me repeatedly during the flight and I felt very uncomfortable. To pay more for an upgraded space and then not even being able to use it was highly disappointing.

No wheel chair as requested at Atlanta arrival on first flight.

Only freetext wifi was available in flight; browsing WiFi required payment. Since the seats had no in flight entertainment, Delta should revisit this policy on this longer flight.

Only water, tea or coffee served midflight, even to comfort seating. Man next to me needed two seats and took up a portion of my seat and Delta did nothing.

The flight was great as well as the airline staff

First class and monitors weren’t working for mine & my husbands. Eventually fixed, but quite annoyed as we bought first class. Also, No foot rests.

Prior to takeoff, the pilot told us there was a possibility of not being able to land and going to Portland. Well that happened, we took off and then did 8 loops around Spokane before the pilot told us we ran out of fuel and had to go to Portland. So for a 35 minute flight we have now been on the plane for 3 hours (boarded at 6:50 am and landed in Portland at 10:30). Then, we just sat in Portland's airport with no updates of when we can start heading back. All of a sudden, our pilots and crew just left, leaving us stranded in a different city and state. We continued to sit in Portland until we finally got a new crew assigned and boarded the plane (This was from 10:30-2). We then sat on the plane for an additional hour before take off because they had to count us multiple times. We finally landed in Spokane at 3:55 PM. So a flight that should have taken at max an hour took us 10 hours and we missed the majority of the recruiting event we went for.

It was delayed but other than that it was great.

Got on the plane and sat there for an hour before departure.

Horrible. No TV or any type of entertainment on board. Passwnger listening to/watching stuff on their own phone with no headphones making it noise and uncomfortable for everyone else, little/tiny food portions, old seats, useless wifi (cant access anything). Horrible exlerience especially it was a lomg distance flight with kids.

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)

Had to go through security at the gate again. Had to take off shoes and go through the whole thing again even though we have global entry. They asked us to check in items bought at duty free during our layover and since we checked our luggage at the original departure airport, they forced us to check in a small backpack. None of this ever happened with other airlines. In addition, no vegetarian food option and no snacks during a 7 hr flight. Luggage limits are unusually small. This is unacceptable. Will NEVER fly Copa again and will tell friends and family to avoid this airline.

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

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

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

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

Sat next to a one year old. She crawled all over the place and made me laugh.

The Crew and the food was the worst I ever had in Business Class. First they told us there were no space for carry on. It was plenty of space over our 2 row seats, we had to ask to let us travel with it which was accepted. They were aware that we had to run for the connection due to the previous flight delay. Have us one hour waiting for more customers and not even offer a glass of water. Then started the service and they started to serve other passengers drinks in business and did not offer any drinks until they serve our pre ordered meal and I ask for something to drink. I had to wait until they finished to serve all passengers until Inget something. The crew was the worts I ever had for Business Class in my life.

Not great experience - we were super late boarding due to issues with aircraft. Then when we finally all got onboard and seated and they started taxiing out to the runway they just stopped then turned around and went back to the airport. Apparently the crew “ran out of time” to legally fly us. They mentioned that they were about 2 minutes away from taking off. I understand the rules and safety but kinda wonder why they would have bothered boarding us in the first place? Had to go all the way back and de plane and then wait in a HUGE line to get a hotel (this is somewhere around 2:30am) finally got to hotel by Uber (no shuttle after 20min so gave up) and they ended up putting us all back on the same aircraft at 10am next morning so got about 2.5 hours sleep. They did give us. $250 credit, but it was a São Paulo Brazil flight out of Dulles. The flight and everything was fine.

Starlink wifi on the Embraer E175 is an excellent experience. I was able to connect and work from IAD all the way to approach into BTV.

7 hours delayed due to operational issues on United’s end. Basically laziness.

Short flight but an "eager to help" crew made the journey more enjoyable!

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

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

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

This was one of the most frustrating travel experiences I've had to date. I had changed my flight day of to this one as it was slated to depart on time. It ended up being so delayed that my original flight took off before this one did. The boarding process began but eventually stopped and everyone had to get off the plane as a problem was identified. The person at the front desk just tried to laugh it off as if this wasn't already a huge inconvenience. From there, we eventually got to board only to sit at the gate for an additional hour because of some additional issue. This was extremely frustrating and caused a lot of stress.

It was a little concerning to hear the ground crew arguing with the flight crew over baggage space. Instead of taking them and checking them, they started checking for space in the first class cabin moving items around like the flight crew didn't know what they were doing. I was embarrassed for them.

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

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

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

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

The flight attendant, a black woman with curly hair who sat near Row 21, was wonderful and kind.

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

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

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

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

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

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

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

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

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

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

Everything you need to know for your flight to Caribbean

Information on your arrival and departure airports