$108 Find Cheap Flights from Washington Dulles Airport to Caribbean - Compare and Save

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 8/15. 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.
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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$472
Santo Domingo
Santo Domingo2 stops$498
Montego Bay
Montego Bay1 stop$452
Oranjestad
Oranjestad1 stop$476
Nassau
Nassau1 stop$383
Kingston
Kingston2 stops$499
Simpson Bay
Simpson Bay2 stops$369
Providenciales
Providenciales2 stops$499
Port of Spain
Port of Spain1 stop$521
Bridgetown
Bridgetown2 stops$448
George Town
George Town1 stop$329
Willemstad
Willemstad2 stops$456
Aguadilla
Aguadilla2 stops$268
Puerto Plata
Puerto Plata1 stop$470
St. John's
St. John's1 stop$620
Punta Cana
Punta Cana1 stop$472
Santo Domingo
Santo Domingo2 stops$498
Montego Bay
Montego Bay1 stop$452
Oranjestad
Oranjestad1 stop$476
Nassau
Nassau1 stop$383
Kingston
Kingston2 stops$499
Simpson Bay
Simpson Bay2 stops$369
Providenciales
Providenciales2 stops$499
Port of Spain
Port of Spain1 stop$521
Bridgetown
Bridgetown2 stops$448
George Town
George Town1 stop$329
Willemstad
Willemstad2 stops$456
Aguadilla
Aguadilla2 stops$268
Puerto Plata
Puerto Plata1 stop$470
St. John's
St. John's1 stop$620

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

Wed, Sep 2 - Tue, Sep 8
Frontier Logo
6:09 pm - 2:16 pm
IAD
-
SJU
20h 07m
2 stops
Frontier Logo
6:35 am - 7:44 pm
SJU
-
IAD
13h 09m
1 stop
$317Frontier
Sat, Aug 15 - Mon, Aug 17
Frontier Logo
1:21 pm - 7:57 am
IAD
-
SJU
18h 36m
1 stop
Frontier Logo
6:00 am - 7:38 pm
SJU
-
IAD
13h 38m
1 stop
$319Frontier
Sat, Aug 29 - Wed, Sep 2
American Airlines Logo
7:57 am - 11:43 pm
IAD
-
SJU
15h 46m
1 stop
American Airlines Logo
3:47 pm - 10:55 pm
SJU
-
IAD
7h 08m
1 stop
$321American Airlines
Wed, Jul 22 - Wed, Jul 29
American Airlines Logo
6:33 am - 10:59 pm
IAD
-
SJU
16h 26m
1 stop
American Airlines Logo
5:45 am - 10:52 pm
SJU
-
IAD
17h 07m
1 stop
$326American Airlines
Fri, Dec 11 - Tue, Dec 15
United Airlines Logo
8:56 am - 1:56 pm
IAD
-
STT
4h 00mnonstop
United Airlines Logo
2:15 pm - 8:33 pm
STT
-
IAD
7h 18m
1 stop
$412United Airlines
Tue, Aug 25 - Thu, Sep 3
Delta Logo
6:00 am - 1:34 pm
IAD
-
STT
7h 34m
1 stop
Delta Logo
2:49 pm - 12:34 am
STT
-
IAD
9h 45m
1 stop
$415Delta
Sat, Oct 24 - Fri, Oct 30
United Airlines Logo
9:00 am - 12:58 pm
IAD
-
STT
3h 58mnonstop
United Airlines Logo
12:07 pm - 4:30 pm
STT
-
IAD
4h 23mnonstop
$417United Airlines
Sun, Sep 27 - Sun, Oct 4
Delta Logo
6:00 am - 1:42 pm
IAD
-
STT
7h 42m
1 stop
Delta Logo
2:52 pm - 9:45 pm
STT
-
IAD
6h 53m
1 stop
$438Delta
Sat, Oct 3 - Wed, Oct 7
Copa Airlines Logo
4:34 pm - 11:33 am
IAD
-
SXM
18h 59m
1 stop
Copa Airlines Logo
12:32 pm - 4:20 am
SXM
-
IAD
15h 48m
1 stop
$439Copa Airlines
Thu, Oct 15 - Fri, Oct 23
Copa Airlines Logo
2:25 am - 11:33 am
IAD
-
SXM
9h 08m
1 stop
Copa Airlines Logo
12:32 pm - 3:04 pm
SXM
-
IAD
26h 32m
1 stop
$440Copa 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 5 days was to San Juan, at $313 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 $313.

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

The average price for all round-trip flights from Washington, D.C. Dulles Intl Airport to Caribbean depending on the time of departure, clicked by users on KAYAK in the last 2 weeks.

The cheapest time of day to fly to Caribbean is generally at night, when round-trip flights cost $344 on average. Morning departures are around 2% 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 $472.

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 $652, 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 October, when tickets cost $102 (return) on average. On the other hand, the most expensive months are August and July, when the average cost of round-trip tickets is $820 and $614 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 Friday, 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 5 weeks before departure.

Good to know

Low seasonSeptember
Cheapest flight$108
Best time to beat the crowds with an average 6% drop in price.
Most popular time to fly with an average 14% 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 8450 reviews
7.8Comfort
7.8Entertainment
8.1Boarding
8.5Crew
7.2Food
Airline reviews

The flight was mostly smooth and direct (although it was 2 hours late). The glow of the flight attendant’s phone was annoying as I tried to sleep on this midnight flight.

8.0 ExcellentAnonymous, Jul 2026
DTW - MBS
Read more Delta reviews

The flight was mostly smooth and direct (although it was 2 hours late). The glow of the flight attendant’s phone was annoying as I tried to sleep on this midnight flight.

The plane was not clean. Vomit was removed from seat-back pocket right in front of me. The flight attendants were rude to one another. 3 children were seated together with their parents across the aisle. The children fought physically with one slamming another’s head into the plane wall at one point. The parents were aware, but took no action to intervene. Delays occurred in Atlanta after boarding before takeoff, in the air, and in Detroit after landing (no ground crew assigned). Flight attendants offered no support for connecting flights. There were weather conditions on each end of the flight, but I didn’t mark down my ratings for these.

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.

Waited at the usual crowded gate at DCA where one ends up standing up because there aren't enough seats.

Delayed take-off. Very small plane so very scary with lots of bumps during the flight. Would never fly Delta on short flights in small 80 seaters plane again! Felt relieved when landed.

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.

715PM departure was 2.5 hours late. Received hotel & food voucher but after we already booked a room. Entire team just seemed like they were 2-3 steps behind in execution, and notifcations.

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)

Placed us in the last rear row of the plane so could not recline seats because of the rear wall, and also made it more of a tight space when the passenger in front reclined their seat. While understand seat assignments, every passenger should be afforded a reclining seat. The odor control scent from the restrooms was overwhelming strong. My wife and I could not deal with it, and she suffered a terrible headache as a result. I kept getting hit by the crew since I was on the ilse seat. No apologies, nothing. They made me feel like I was supposed to take the beating for a 3 hr flight.

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.

It would have been better if they don't separate families in seating. We were seated in the aile row in the middle of a family of four. It would have been better if they they seat the family of four together than separated.

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.

Staff could’ve been a little more cordial. The men were much more friendlier than the women. My daughter and I also missed the 2nd to last meal as we were sleeping but that is on us.

Like: departed and arrived on time. Unlike: Food options for purchase allways bad, 1 of 2 of the crew members not very friendly at all. Seats and leg room aweful. At this point I am thinking on switching to AA.

Our flight was canceled same day and we were never informed. Had to pay more and worse seating on another airline.

Did not like that we couldn't complete check in on-line without providing pictures of our passports. Worry about identity theft. We had no delays and boarding was handled In an efficient manner.

Excellent! I got to Munich and was transferred to my Lufthansa flight quickly, in 15 to 20 minutes, so I did not miss my flight. However, I had checked my overhead bag at the boarding gate in Tampa. That got to Tunis the next day. That is to be expected.

WiFi didn’t exist , seats were super cramped, lights stayed on near my seat for a long time while others were dimmed, the food/trash/drink cart hit my shoulder at least a couple of times while moving, food options were down to just one option by the time it got to my row, the utensils were garbage (knife bent at a couple of places by the time I was done eating) the spoon was very flimsy plastic

Vegetarian selection could be better. Bread was too hard to chew.

Crew was friendly and competent. Food, wine, and entertainment were excellent except the raw tuna on the flight to Split. Recommend against serving that - at least as the only option. Many medical conditions do not allow people to eat raw fish.

United didn’t even try to hold the flight for me. They knew I had a tight connection and when I arrived at the gate less than 10 mins after final boarding the flight had already gone. The gate agent wasn’t even notified that I was on my way. She was told I wasn’t at the airport

Good quick flight on a small but comfortable plane. I'm 6'3 and had plenty of space.

The seats were extremely cramped, with very little legroom or personal space. There was no room left in the overhead bins for a backpack, and the space under the seat in front was so limited that I could barely fit my bag underneath. Overall, the seating arrangement felt very uncomfortable and overcrowded.

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

Overall a good experience, however Wifi was not working on the flight.

THe flight was an hour late. You got us on the plan and we sat on the ground for 45 minutes with no information from the pilot whatsoever. Worst flight this year.

Going non stop to lax like I paid for. Not stopping in MCI for gas. Too long of delays

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

Incoming flight was delayed, delaying boarding. It then took 30 mins to take off. Took 20 mins to get to a gate because they changed the gate last minute, crew weren’t ready so there was no one staffed to work the jet bridge. Boarding was so disorganized as is usual with American because everyone just stands around the gate regardless of boarding group.

Delays with no explanation. It could have been handled better.

Flight delay for mechanical. Inbound arrived on time. No one said why mechanical delay.

I paid for the upgraded bundle. Was worth it! Great experience round trip!

It was awful everything about it terrible I will never ever ever ride it again

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.

Everything you need to know for your flight to Caribbean

Information on your arrival and departure airports