$82 Find Cheap Flights from Washington Dulles Airport to Caribbean Islands

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 Islands departing on 11/25. 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

KAYAK searches hundreds of travel sites at once for deals on flights to Caribbean Islands

 
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Washington, D.C. to Caribbean Islands.
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Washington, D.C. to Caribbean Islands.
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Flight Deals

Cheap Flights from Dulles Intl to Caribbean Islands

Cheapest round-trip prices found by our users on KAYAK in the last 72 hours
Punta Cana
Punta Cana1 stop$361
Santo Domingo
Santo Domingo1 stop$394
Montego Bay
Montego Bay2 stops$395
Oranjestad
Oranjestadnonstop$349
Nassau
Nassau1 stop$366
Kingston
Kingston2 stops$394
Simpson Bay
Simpson Bay2 stops$420
Providenciales
Providenciales1 stop$467
Port of Spain
Port of Spain1 stop$379
Bridgetown
Bridgetown1 stop$414
George Town
George Town1 stop$411
Willemstad
Willemstad1 stop$339
St. John's
St. John's1 stop$512
Puerto Plata
Puerto Plata1 stop$424
Aguadilla
Aguadilla1 stop$168
Punta Cana
Punta Cana1 stop$361
Santo Domingo
Santo Domingo1 stop$394
Montego Bay
Montego Bay2 stops$395
Oranjestad
Oranjestadnonstop$349
Nassau
Nassau1 stop$366
Kingston
Kingston2 stops$394
Simpson Bay
Simpson Bay2 stops$420
Providenciales
Providenciales1 stop$467
Port of Spain
Port of Spain1 stop$379
Bridgetown
Bridgetown1 stop$414
George Town
George Town1 stop$411
Willemstad
Willemstad1 stop$339
St. John's
St. John's1 stop$512
Puerto Plata
Puerto Plata1 stop$424
Aguadilla
Aguadilla1 stop$168

Book Cheap Dulles Intl to Caribbean Islands 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 Islands 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 Islands

Mon, Feb 2 - Mon, Feb 9
Frontier Logo
3:42 pm - 8:36 pmIAD-SJU
3h 54mnonstop
Frontier Logo
11:29 am - 2:42 pmSJU-IAD
4h 13mnonstop
$197Frontier
Find Deal
Thu, Dec 11 - Mon, Dec 22
Frontier Logo
10:38 am - 3:32 pmIAD-SJU
3h 54mnonstop
Frontier Logo
9:37 pm - 9:03 pmSJU-IAD
24h 26m1 stop
$199Frontier
Find Deal
Sun, Jan 25 - Thu, Jan 29
American Airlines Logo
7:04 am - 5:03 pmIAD-SJU
8h 59m1 stop
American Airlines Logo
5:55 pm - 11:12 pmSJU-IAD
6h 17m1 stop
$215American Airlines
Find Deal
Mon, Dec 8 - Fri, Dec 19
United Airlines Logo
5:32 pm - 10:22 pmIAD-SJU
3h 50mnonstop
United Airlines Logo
8:30 am - 11:35 amSJU-IAD
4h 05mnonstop
$229United Airlines
Find Deal
Mon, Dec 8 - Wed, Dec 17
Delta Logo
3:38 pm - 11:20 pmIAD-SJU
6h 42m1 stop
Delta Logo
6:38 pm - 12:12 amSJU-IAD
6h 34m1 stop
$235Delta
Find Deal
Mon, Nov 10 - Fri, Nov 14
United Airlines Logo
8:15 am - 1:40 pmIAD-AUA
4h 25mnonstop
United Airlines Logo
5:35 pm - 9:10 pmAUA-IAD
4h 35mnonstop
$349United Airlines
Find Deal
Thu, Nov 13 - Thu, Nov 20
Copa Airlines Logo
3:24 pm - 2:45 pmIAD-AUA
22h 21m1 stop
Copa Airlines Logo
3:47 pm - 3:22 amAUA-IAD
12h 35m1 stop
$353Copa Airlines
Find Deal
Sat, Nov 8 - Sun, Nov 16
Copa Airlines Logo
1:13 am - 11:09 amIAD-PUJ
8h 56m1 stop
Copa Airlines Logo
1:53 pm - 3:22 amPUJ-IAD
14h 29m1 stop
$361Copa Airlines
Find Deal
Mon, Nov 10 - Thu, Nov 13
Delta Logo
7:49 pm - 1:55 pmIAD-AUA
17h 06m1 stop
Delta Logo
4:35 pm - 12:16 amAUA-IAD
8h 41m1 stop
$364Delta
Find Deal
Wed, Jan 21 - Sun, Jan 25
American Airlines Logo
11:34 am - 12:13 pmIAD-NAS
24h 39m1 stop
American Airlines Logo
6:45 pm - 10:58 amNAS-IAD
16h 13m2 stops
$372American Airlines
Find Deal
Booking Insights

KAYAK's insights & trends for Dulles Intl to Caribbean Islands flights

Get data-powered insights and trends into flights from Dulles Intl to Caribbean Islands 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 Islands flight route?

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

The cheapest ticket to Caribbean Islands from Washington, D.C. Dulles Intl Airport found in the last 72 hours was to San Juan, at $129 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 $129.

Can I save money by flying with a layover from Washington, D.C. Dulles Intl Airport to Caribbean Islands?

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 $458, prices are generally cheapest when you fly direct.

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

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 Islands, 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 Islands is June, when tickets cost $304 (return) on average. On the other hand, the most expensive months are April and December, when the average cost of round-trip tickets is $561 and $516 respectively.

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

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

For Washington Dulles Airport to Caribbean Islands, Tuesday is the cheapest day to fly on average and Friday is the most expensive. Flying from Caribbean Islands back to Washington Dulles Airport, the best deals are generally found on Thursday, with Monday being the most expensive.

How far in advance should I book a flight from Washington, D.C. Dulles Intl Airport to Caribbean Islands?

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 Islands, 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 Islands, you should book around 1 week before departure. For the absolute cheapest price, our data suggests you should book 16 weeks before departure.

Good to know

Low seasonSeptember
Cheapest flight$82
Best time to beat the crowds with an average 9% drop in price.
Most popular time to fly with an average 22% increase in price.
Flight from Washington Dulles Airport to San Juan

FAQs - booking Caribbean Islands flights

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

    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 Islands.

  • 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 Islands?

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

    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 Islands 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 Islands?

    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 Islands 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 Islands?

    The cheapest time of day to fly to Caribbean Islands is generally in the afternoon, when round-trip flights cost $238 on average. Morning departures are around 8% cheaper than evening flights, on average. The most expensive time of day to fly to Caribbean Islands is generally at night, which is peak travel time and where the average cost of a ticket is $494.

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

 
See real verified KAYAK customer reviews for airlines flying from Washington, D.C. to Caribbean Islands. Airline scores are aggregated from all reviews left by passengers on KAYAK after flying with an airline. KAYAK doesn’t show reviews that are older than 5 years. Learn how KAYAK collects reviews.
Need help choosing which airline to fly with from Dulles Intl to Caribbean Islands? 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 7996 reviews
8.2Boarding
7.9Entertainment
7.3Food
8.5Crew
7.9Comfort
Airline reviews

Everything went well and was good. Nothing exceptional, but no complaints either. Cheap seats are pretty comfortable.

8.0 ExcellentPAULINA, Oct 2025LAS - ATL
Read more Delta reviews

Everything went well and was good. Nothing exceptional, but no complaints either. Cheap seats are pretty comfortable.

Staff were friendly and happy. Delta could make sure passengers that don't have the app know of changes. Without Kayak I would not have known about the change of gate or the delay. Kayak was faster to notify me.

They ended up paying for the bag twice, but the counter wouldn't take my baggage receipt. Left it to me to resolve. Not sure how to resolve the issue.

The customer service before board was very rude and when I expressed my concerns about making the connecting flight she laughed and told me I bought the wrong ticket. I explained once it showed the flight was delayed it no longer let me change seats or anything. I was trying to upgrade to make sure I would get to the next gate on time.

Non stop on long haul is the way to go. Great experience

The aircraft interior is old and tired on this aircraft. The entertainment system never worked despite the crews attempt to reset the system.

The flight used a B767 with a very old interior from before 2014. The entertainment system did not work at all during the flight despite attempts to reset the system. It was like they flew this route just to be competitive.

Old plane and old configuration/seats but still comfortable for a morning flight

They changed planes and the new plane couldn’t carry enough fuel to fly across the country so we had to stop in Kansas City to refuel. Flight was delayed .

Flight was too crowded and seats are too small, especially since passengrs are getting larger. Having a middle seat is ALWAYS tough! Woman on my left was large & kept creeping in to my space. Flight personnel were great! Have more savory rather than sweet snacks please.

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.

It was ok. However, the food was quite poor since I don't eat pasta.

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.

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.

Better WiFi. I cannot understand that in 2025, United is so behind on a technology that is now a necessity and still painfully unreliable, slow and keeps disconnecting.

Great service on board. Boarding a bit slow due to process. Food was pretty average.

Very small cramped plane for an international flight. Everything else was good, but it was maybe the smallest comfort-wise I've ever been on for longer than 3-4 hours and the trip was 7.5

Flight was delayed 3 hours. No food and drink vouchers was provided. They offered a mini pretzel bag and water .

Staff was rude. Didn’t give water for 2 hours. Worst service

Was on time until within 1 hour of flight-how does that happen? Staff very friendly.

I liked the choice of lemon ginger tea. I think stewardesses can be more considerate of older people needs.

We were given vouchers we couldn’t use with a 5.5 hour delay

Wish some foods provided rather than just biscuit/cookie for flight more than 2 hours

Wish a flight with more than 2 hours with some snack rather than just cookie/biscuit.

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

It was good..clean, comfy seat. Friendly warm welcoming crew. Was able to check my cabin luggage at the gate which I was able to pickup in a decent time from baggage claim. The app gave all updates from delays to baggage claim info. Overall smooth flight.

Flight was delayed leaving Dallas. Arrived about 2 hours later than scheduled.

Flight delayed and missed connection. Rescheduled flight cancelled after 6 hrs wait. Rerouted thru ORD, flight cancelled, overnight stay in ORD. Still in the air on new flight!

We are too tired and frustrated to comment politely at this point

Terrible. Our luggage was delayed and couldn’t be delivered for several days. We got bad information from the airline agents at baggage claim. We had to pick up our car so we wouldn’t be charged for an extra day. We got lost in the maze of airport parking. The baggage claim agents didn’t offer us any compensation for our extra time and expense. We are tired, hungry and very frustrated.

The flight was flawless and we even arrived between 20 and 25 minutes early!

The only thing to like was that we eventually got to our destination

Terrible. Flight cancelled with no reasoning and no flights to rebook. Employees were useless and did nothing to help. Did not even know where to retrieve luggage from the cancelled flight. Flyers beware.

No fault of Frontier staff: plane was very late, reached Orlando at 1 am, took a while to get luggage. Weather, gov financial shutdown impact on TSA, air controllers seemed to have multiple flights backed up. Frontier staff seemed to cope as gracefully as possible. It did reassure me that I and my new hip could adapt to travel challenges. Food/entertainment were irrelevant to my trip.

Terrible. The canceled my entire flight when I requested a refund for a trip frontier canceled trip one way.

Boarding was on time and plane departed as scheduled. There are obviously no amenities (food, drink, entertainment) on Frontier, but there also didn't seem to be any issues with luggage space either.

Inbound plane was on time and flight departed on time with no issues while boarding.

I knew going into this that Frontier, being a low cost carrier, would be pretty bare bones and charge for most extras but this was made up for by the fact that the airplane was a reasonably new Airbus, every employee was great and best of all, Everett Washington is an amazing airport - thanks Frontier for flying there!!!

i was unable to check in the flight. refund requested

It was well done. It was my first time flying with them and I was nervous b/c I have heard of many cancelled and/or delray flights. Everything went smoothly.

Just know that everything, and I mean everything is “ala cart”. 60$ just to put something in the overhead bin. I will never fly Frontier again nor do I recommend them to anyone else.

The single worst check in experience I could imagine. I’ll never do any business with Frontier or any affiliated company

Everything you need to know for your flight to Caribbean Islands

Information on your arrival and departure airports

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