$64 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 7/8. 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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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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Flights Deals

Best Caribbean Islands Flight Deals from Dulles Intl

Cheapest round-trip prices found by our users on KAYAK in the last 72 hours

Punta Cana
Punta Cana1 stop$336
Santo Domingo
Santo Domingo1 stop$260
Montego Bay
Montego Bay1 stop$415
Oranjestad
Oranjestad1 stop$373
Nassau
Nassau1 stop$339
Kingston
Kingston1 stop$423
Simpson Bay
Simpson Bay1 stop$359
Providenciales
Providenciales1 stop$436
Bridgetown
Bridgetown1 stop$414
Port of Spain
Port of Spain1 stop$327
George Town
George Town1 stop$424
Willemstad
Willemstad1 stop$411
St. John's
St. John's2 stops$553
Puerto Plata
Puerto Plata2 stops$482
Aguadilla
Aguadilla1 stop$308
Punta Cana
Punta Cana1 stop$336
Santo Domingo
Santo Domingo1 stop$260
Montego Bay
Montego Bay1 stop$415
Oranjestad
Oranjestad1 stop$373
Nassau
Nassau1 stop$339
Kingston
Kingston1 stop$423
Simpson Bay
Simpson Bay1 stop$359
Providenciales
Providenciales1 stop$436
Bridgetown
Bridgetown1 stop$414
Port of Spain
Port of Spain1 stop$327
George Town
George Town1 stop$424
Willemstad
Willemstad1 stop$411
St. John's
St. John's2 stops$553
Puerto Plata
Puerto Plata2 stops$482
Aguadilla
Aguadilla1 stop$308

Cheap Flight Deals from Dulles Intl to Caribbean Islands (IAD-zzEPX)

 
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.

Recent round-trip flight deals from Dulles Intl to Caribbean Islands

Recommended round-trip deals departing in the coming months from the most popular airlines that fly from Dulles Intl to Caribbean Islands.
Discover the best prices for you by selecting your travel dates on KAYAK.
Frontier Logo
12:10 pm - 4:02 pmIAD-SJU
3h 52mnonstop
Frontier Logo
7:40 am - 11:33 amSJU-IAD
3h 53mnonstop
$148Frontier
Find Deal
Sun, May 25 - Sun, Jun 1
Frontier Logo
12:10 pm - 4:02 pmIAD-SJU
3h 52mnonstop
Frontier Logo
7:20 am - 11:15 amSJU-IAD
3h 55mnonstop
$153Frontier
Find Deal
Sun, May 25 - Thu, May 29
United Airlines Logo
6:48 am - 2:44 pmIAD-SJU
7h 56m1 stop
United Airlines Logo
7:25 am - 11:24 amSJU-IAD
3h 59mnonstop
$247United Airlines
Find Deal
Sun, May 25 - Sun, Jun 1
American Airlines Logo
8:02 pm - 11:10 amIAD-SJU
15h 08m1 stop
American Airlines Logo
7:15 am - 12:02 amSJU-IAD
16h 47m1 stop
$255American Airlines
Find Deal
Wed, May 28 - Wed, Jun 4
United Airlines Logo
8:40 am - 12:34 pmIAD-SJU
3h 54mnonstop
United Airlines Logo
1:05 am - 7:19 amSJU-IAD
6h 14m1 stop
$281United Airlines
Find Deal
Sun, Jun 1 - Wed, Jun 4
American Airlines Logo
8:02 pm - 11:10 amIAD-SJU
15h 08m1 stop
American Airlines Logo
7:15 am - 12:02 amSJU-IAD
16h 47m1 stop
$283American Airlines
Find Deal
Tue, May 27 - Wed, Jun 4
Delta Logo
1:20 pm - 10:47 pmIAD-SJU
9h 27m1 stop
Delta Logo
5:43 pm - 12:28 amSJU-IAD
6h 45m1 stop
$285Delta
Find Deal
Sat, May 24 - Thu, May 29
Copa Airlines Logo
2:21 am - 11:33 amIAD-NAS
9h 12m1 stop
Copa Airlines Logo
12:36 pm - 4:20 amNAS-IAD
15h 44m1 stop
$339Copa Airlines
Find Deal
Sat, May 31 - Sun, Jun 8
Delta Logo
12:30 pm - 11:46 pmIAD-SJU
11h 16m1 stop
Delta Logo
2:15 pm - 10:59 pmSJU-IAD
8h 44m1 stop
$345Delta
Find Deal
Sat, Aug 16 - Fri, Aug 22
Copa Airlines Logo
4:34 pm - 11:33 amIAD-NAS
18h 59m1 stop
Copa Airlines Logo
12:36 pm - 12:29 amNAS-IAD
11h 53m1 stop
$358Copa Airlines
Find Deal
Thu, Jun 5 - Sun, Jun 8
Useful Info

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?

The cheapest price for flight routes found by users searching on KAYAK in the last 2 weeks for round-trip flights from Washington, D.C. Dulles Intl Airport to Caribbean Islands.

The cheapest ticket to Caribbean Islands from Washington, D.C. Dulles Intl Airport found in the last 72 hours was to San Juan, at $127 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 $127.

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 $899, 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 October, when tickets cost $407 (return) on average. On the other hand, the most expensive months are December and April, when the average cost of round-trip tickets is $623 and $560 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 Friday, with Sunday 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 3 weeks before departure. For the absolute cheapest price, our data suggests you should book 16 weeks before departure.


Good to know

Low seasonSeptember
High seasonJune
Cheapest flight$64
Best time to beat the crowds with an average 15% drop in price.
Most popular time to fly with an average 8% 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 9% more expensive than evening flights, on average. The most expensive time of day to fly to Caribbean Islands is generally in the morning, which is peak travel time and where the average cost of a ticket is $497.

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.
8.0
DeltaOverall score based on 7936 reviews
7.9Comfort
8.2Boarding
7.9Entertainment
7.3Food
8.5Crew
Airline reviews

Our bag was lost so that made unnecessary chaos On our trip

6.0 GoodBarbara, Apr 2025JFK - FCO
Read more Delta reviews

Our bag was lost so that made unnecessary chaos On our trip

Delta is my preferred airline. I've traveled with them for years. On time in most cases, good communication, easy to use app. Most planes are pretty nice. I was on a CRJ 700/900 however, which was pretty badly aged inside and needed a refresh. No infotainment, unreliable wifi, best to download before boarding or bring a book. Food choices are really just snacks on this flight, nice variety but about what you'd expect. Great staff and prompt in departure and early arrival too. Overall quite satisfied.

Crew was friendly Love the entertainment in the seat head rest.

Delta flight was on time, seats were comfortable, and crew was nice.

This had nothing to do with Delta… The flights were on time and flawless. The service was excellent. We purchased seats in (aisle/middle) comfort plus since this was a cross country flight. Unfortunately, the woman seated at the window was 300+ pounds and, as might be expected, covered up about a third of the middle seat also. there was absolutely nothing that Delta could have done about that… I just don’t know what the answer should be. If you purchase a seat, you should should be able to use the entire seat and not just the portion that someone else is not sitting/oozing in. Disappointing…there should be something that could be done….I'm just not sure what solution could be.

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.

The worst part was I was NOT allowed in the lounge even though I was holding a first class ticket and have a premium American Express card. I have flown Business or First Class with many airlines. Delta is the ONLY one who does not extend this courtesy to anyone except people who hold the very expensive American Express card. As a result, I won’t fly Delta if I have any other choice.

It was an overnight flight and I desperately needed coffee before we landed, but Delta does only one beverage service, and that is shortly after takeoff, not before landing at 5 am.

A little bumpy ride . No food was being provided due the the turbulence. That was ok it was a short flight to my standards.

Simply outstanding. Their new lounge for Delta One customers is a cut above the rest.

We were in transit from Lima (flight at 1.10am) and we were in stand by in our flight from Panama to Washington. We wait from 4.30 am to 18.30pm in the Airport. The company give us 2 x 15 dollars for eat during the day and a personnal travel voucher of 400 dollars each. Do they buy food one time something in the Airport ??? And one of us live in France so the voucher is not usable. More than 24 hours travel !! And our place were near the toilets, with 8 children around us. The boy behind my seat stamped his feet on my back all the flight. Really Wonder full ! So we are totally unhappy with our travel. Thanks Copa Airlines....

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.

The flight was delayed about 4 hours without any explanation. No wifi or entertainment at all on planes. Had to pay for checked bags I was allowed according to reservations.

It was good, plane is a bit older so seats are somewhat flat

Great from check in all the way to the end. Very happy with Copa

Well the airline was fine. The only thing is I was charged for a checked in luggage. But when I reserved the ticket it showed a check in bag allowed. Who can I get in contact with for reimbursement.? The airline said I had to speak to whoever I booked ticket with.

Friendly flight team and seamless travel from one stop to next.

I loved my experience. Very safe, Very informative and very friendly.

At JFK the Security line was extremely long and few checkpoints open.

Check in person said there would be lunch. We were first class passengers and lunch was chips.

Everything is good except the dinner and breakfast. The sandwich is very delicious. Toilet is clean, I only use one of them. Flight attendants are very nice. 👍👍

A bit rush for transit. Food and entertainment are not available

Boarding was a little difficult. The gate area at O'Hare was very small and crowded due to multiple gates in the area. Could not hear the intercom, so had to rely on signage to see when my group was boarding and the signage was blocked by passengers standing in the gate. Flight was great and we arrived in Montreal on time.

Multiple delays and not straight answer from the United team

For economy, it was very good. Staff was great, they even let some of us change seats for more leg room... Put an empty seat between us which was fantastic for a 12hr flight. Onboard entertainment was excellent, I think over 200 choices of movies/tv/etc The bad was the barely/nonfunctional wifi that cost either $16.99 or 1700 miles (full flight). It was atrocious... Definitely the worst of the last 3 long haul major airlines I was on the last few months.

Stewardess spilled orange juice on my clothes/seat no help no apology just threw napkins at me to clean the mess up. Not Happy.

Smooth flight. Boarding was chaotic. Could not hear the gate agent over the intercom. People were lined up in the wrong lines. Groups one and two were told to board through line one and group 3 through line 2. All very confusing. Once in the air, the flight was smooth. There was no entertainment option on this aircraft, even though it was a larger aircraft.

The plane pushed back from the gate on time. However, it stopped on the ramp, and we waited for over 20 minutes before the aircraft pulled back to the gate. Apparently, something of importance had to be removed from the aircraft by the gate agent. I found this to be odd. The delay was not significant, but I felt that whatever was on the aircraft that had to be taken off, should’ve been done before we pushed back from the gate.

I didn’t get on plane. Passport being processed by consulate with visa application. Tried to cancel through underpricer after purchasing cacelling for any reason. No dice, they are thieves.

When I booked it on Kayak it aaid that I wasn't allowed hamd luggage. I called United Airlines and it took them 6 minutes to figure out if I was allowed free hand luggage. Surely something that simple they should be able to tell me instantly.

Several delays. Next flight was worse. Did not arrive home until 2am PT

Very helpful ground crew after an earlier flight delay and being rebooked on a different flight.

Everything about the flight was lovely…We left early, arrived early, cabin crew were efficient and helpful. Flight was easy and most pleasant.

First world problems, but still… We were seated in first class and asked for a cocktail on a very short, 50 minute flight. After our drink order was taken, a half hour went by, and we noticed that every other person in the small plane had been served except for us. We got up to ask about it, the drinks finally came, then were taken away three minutes later since the flight was so short. Really strange situation, on the other hand, we were in Utah.

We missed our flight. The boarding pass had the wrong gate and by the time we received the text from Kayak, our flight was already gone. I’ll never use Kayak again and will go direct to the airlines in the future.

Boarding took forever, the plane was cramped and cold, and the seatbelt song came on constantly throughout the red eye flight with a loud pre-recorded message playing each time

Cabin felt crammed Snacks are lame But crew was super efficient getting us out on time despite delay

Took off on time and successfully avoided weather that looked to be a problem along the way

There were five broken seats on the plane. The crew was very rude in telling people they had to get off the plane and get a flight the next day. No call for volunteers, but telling people they had to get off. One woman was flying with her elderly mother and daughter and was told she had to leave or all three had to leave. Fortunately, a volunteer offered to stay. The situation was handled poorly.

The flight to Tokyo AA61 took off about two hours late, but then had to turn back. By that time the crew had to be replaced. Then they kept promising to take off in an hour, then in 3, then switch to the next day.

I receive a service for what I pay, so it is fair.

There isn't much space in-between seats and even water needs to be paid for during the flight.

We did not know about the bag fees until check in. They are way too high. It’s insane. We also had a huge delay and everything costed extra which was very annoying.

Lounge for business was closed. Boarding was rush and stand by. Seat for business is just the middle seat blocked and some more leg room.

Flew with our two children. Paid $380 to check two bags (one was overweight). They then left the bags behind on Sunday, December 21st, with all our family’s clothes and family Christmas presents. When we arrived at our destination they told us the bags had not arrived, and they thought (but didn’t know) they were still in Boston, but that there’d be a flight the next day and the bags would arrive the next day. The next day we found out there was no flight, now we’re hoping we get our bags before we fly back out. Meanwhile, trying to get any engagement or accurate information is a waste of time. The folks at the call center are just gatekeepers, who can’t connect with any departments that actually do things to solve a problem. Getting information is made deliberately difficult. My biggest regret is that I’ve had a number of awful experiences with Avianca traveling between the US and Colombia, and still let myself get suckered into buying these tickets because the schedule was great. Never again.

We were not aware carry-on bags cost extra until we arrived at the airport so, we were charged $240.00 for two small carry- on bags! There was a substantial fee for drinks and snacks. No wifi, or other entertainment was available. Waiting areas were crowded and uncomfortable.

COP 7,000 for a cup of mediocre coffee. I thought I was on Spirit Airlines for a minute. Otherwise the flight was fine. Nothing exceptional to report.

please see previous response; it covers the whole travel trajectory.

I enjoyed it! In that case, I should have been offered this choice. On my first trip to Miami, I was asked to pay $320 for my luggage just for getting it totally broken. I cannot accept this situation at all!!!!

Overpriced checked bag price of $120 and they charge you for carryon if the size is not minimal of $120.

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