$113 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 10/3. 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

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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$330
Santo Domingo
Santo Domingo1 stop$345
Montego Bay
Montego Bay1 stop$336
Oranjestad
Oranjestad2 stops$402
Nassau
Nassau1 stop$405
Simpson Bay
Simpson Bay1 stop$451
Kingston
Kingston1 stop$413
Providenciales
Providenciales1 stop$351
Port of Spain
Port of Spain1 stop$352
Bridgetown
Bridgetown1 stop$392
George Town
George Town1 stop$360
Willemstad
Willemstad1 stop$291
St. John's
St. John's1 stop$485
Puerto Plata
Puerto Plata1 stop$449
Aguadilla
Aguadilla1 stop$250
Punta Cana
Punta Cana1 stop$330
Santo Domingo
Santo Domingo1 stop$345
Montego Bay
Montego Bay1 stop$336
Oranjestad
Oranjestad2 stops$402
Nassau
Nassau1 stop$405
Simpson Bay
Simpson Bay1 stop$451
Kingston
Kingston1 stop$413
Providenciales
Providenciales1 stop$351
Port of Spain
Port of Spain1 stop$352
Bridgetown
Bridgetown1 stop$392
George Town
George Town1 stop$360
Willemstad
Willemstad1 stop$291
St. John's
St. John's1 stop$485
Puerto Plata
Puerto Plata1 stop$449
Aguadilla
Aguadilla1 stop$250

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

Sun, Nov 9 - Thu, Nov 13
Frontier Logo
7:26 pm - 12:18 amIAD-SJU
3h 52mnonstop
Frontier Logo
3:45 pm - 6:41 pmSJU-IAD
3h 56mnonstop
$164Frontier
Find Deal
Sun, Nov 9 - Thu, Nov 13
Frontier Logo
7:26 pm - 12:18 amIAD-SJU
3h 52mnonstop
Frontier Logo
3:45 pm - 6:41 pmSJU-IAD
3h 56mnonstop
$168Frontier
Find Deal
Mon, Nov 10 - Thu, Nov 13
United Airlines Logo
8:27 am - 1:17 pmIAD-SJU
3h 50mnonstop
United Airlines Logo
8:10 am - 5:30 pmSJU-IAD
10h 20m1 stop
$239United Airlines
Find Deal
Tue, Nov 11 - Tue, Nov 18
Delta Logo
6:00 am - 5:26 pmIAD-SJU
10h 26m1 stop
Delta Logo
3:20 pm - 11:03 pmSJU-IAD
8h 43m1 stop
$245Delta
Find Deal
Mon, Jan 12 - Wed, Jan 21
Delta Logo
6:45 am - 3:54 pmIAD-STT
8h 09m1 stop
Delta Logo
4:00 pm - 11:17 pmSTT-IAD
8h 17m1 stop
$327Delta
Find Deal
Sat, Oct 4 - Sun, Oct 12
Copa Airlines Logo
2:25 am - 10:56 amIAD-SDQ
8h 31m1 stop
Copa Airlines Logo
2:10 pm - 4:20 amSDQ-IAD
14h 10m1 stop
$387Copa Airlines
Find Deal
Mon, Oct 27 - Tue, Nov 11
Copa Airlines Logo
2:25 am - 10:58 amIAD-SDQ
8h 33m1 stop
Copa Airlines Logo
6:39 pm - 3:22 amSDQ-IAD
9h 43m1 stop
$388Copa Airlines
Find Deal
Sun, Oct 26 - Sun, Nov 2
United Airlines Logo
8:15 am - 12:40 pmIAD-AUA
4h 25mnonstop
United Airlines Logo
5:35 pm - 9:10 pmAUA-IAD
4h 35mnonstop
$405United Airlines
Find Deal
Sat, Nov 1 - Tue, Nov 4
American Airlines Logo
6:34 am - 10:43 amIAD-NAS
28h 09m2 stops
American Airlines Logo
3:02 pm - 11:07 pmNAS-IAD
8h 05m1 stop
$419American Airlines
Find Deal
Fri, Nov 7 - Tue, Nov 11
American Airlines Logo
5:35 pm - 11:23 amIAD-NAS
17h 48m2 stops
American Airlines Logo
7:49 am - 11:07 pmNAS-IAD
15h 18m2 stops
$424American 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 $155 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 $155.

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 $457, 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 $303 (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 $550 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 3 weeks before departure, which saves you about 15% compared to booking last minute. For the absolute cheapest price, our data suggests you should book 16 weeks before departure.

Good to know

Low seasonSeptember
Cheapest flight$113
Best time to beat the crowds with an average 11% drop in price.
Most popular time to fly with an average 27% 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 6% 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 $600.

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 7954 reviews
8.5Crew
7.9Comfort
7.9Entertainment
8.2Boarding
7.3Food
Airline reviews

Perfect flight both ways. On time, courteous staff, plane comfortable and cool. Best domestic flights I’ve had in awhile.

10.0 ExcellentAnonymous, Sep 2025CLT - BOS
Read more Delta reviews

Perfect flight both ways. On time, courteous staff, plane comfortable and cool. Best domestic flights I’ve had in awhile.

The food was terrible especially for a 15 hour international flight. The crew was unpleasant as well.

Really low quality food especially for an international flight. The crew also was surprisingly unpleasant except couple of ladies. I know we were not in first class but that’s no reason to treat customers as less.

Flight delayed for two and half hours and then canceled altogether due to mechanical issues. No mechanic onsite to fix so had to send one from LAX.

Quick check in. Everything went smooth. I don't know what can be done about airline food.

Crew was good. The reservation got mixed up and they didn't have my TSA number. I am also a Silver Medallion and wasn't able to use Sky Priority.

Delta made it easy, comfortable and timely. The crew was fantastic.

This route with Delta always has delays or is cancelled. Aircrafts seem smaller and older. I fly Delta quite a bit - haven’t had issues with the international flights. But this route has always been the troublesome one

Nothing special. The crew never went out of their way for anything.

Three seats in first class were broken and while they were able to still acommodate us it was looking very touch and go and they had others they could not acommodate

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.

We paid extra with copa for seats near one another The plane was changed and we lost our seats We were all Separated. We have not received a refund for our seats despite emailing and calling.

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.

Enforce the boarding process by group numbers. Tell people to stay seated during the meal/drink distribution. It took forever to get food and drinks because people would not stay out the isle and let the crew do their jobs. Everyone wanted to go to the bathroom forcing the crew to enter and leave the isle constantly so people can pass. Tell people to keep their electronics off speaker mode. No one wants to hear phone conversations and music playing.

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.

We had to deboard 2 times due to maintenance issues. They changed the plane, and then we got deviated to LAX due to maibtenance issues on the other plane, had to sleep at LAX and los a full day.

Everything was good, except the seats in economy were so close together, you could barely get out when the seat in front of your was reclined. If the airlines keep jamming in more and more seats, it will become intolerable. I will look for another airline that considers customer comfort and does not keep adding more rows of seats for more profit.

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

I fly UAL 7-8 times per year. This flight was not up to snuff because it boarded very late "due to unexpected delays in restocking the plane" and yet Flight Aware showed the plane had landed some 10 hours earlier--so I think they could have planned accordingly. The FA's were nice but harried. The video system had to be rebooted 3-4 times. The food service was rather abrupt; they forgot my row and when I asked for my meal, they brought it with some impatience. Overall, the flight was fine, but the little details made it feel somewhat mundane and hurried.

Given it’s a red-eye into Charolotte, we didn’t get any food. The survey does not include “N/A” so the rating will be skewed.

Great. Quick and quiet and east. The breakfast choices were a welcome surprise!

American airlines suck they delay the flights all the time made me sleep in an airport because my flight was delayed and I miss my connecting flight

There's nothing I liked about it. For first off I scheduled this trip two weeks in advance then they delayed my flight which messed up my whole trip. So I scheduled it for the following weekend thinking there won't be a delay and guess what as soon as I got to the airport we said in the airplane on the tarmac for an hour and a half. Not only was it delayed I missed my connecting flight meaning I had to stay the night at Dallas-Fort Worth airport sleeping on the floor. I will tell you this I will never fly American airlines ever again I have had nothing but horrible experience with them and I just throw money at them

The stewardess hit me with the food kart twice on the head and didn't say I'm sorry once. The same stewardess gave me a warm Apple Juice with No ice. The Flight was delayed for Departure 6 times, starting from 2:36pm, finally taking off 7:50pm. I was late picking up my child from the sitter by 3 hours.

Don’t know they cancelled the flight day before I was to leave. They sent a email at 9:00 pm at night saying they cancelled. That is the smooth way to say we don’t want your business! I think they didn’t have enough people booking so they cancelled the flight! It’s all about the money anymore there is no honesty in business.

Having to reschedule flights a day later, they loaded by luggage on the wrong plane from Little rock now I have to HOPE they deliver it to where im staying like they said would. International flight crew was very disgruntled and not very friendly.

It took way too long to diagnose and solve the problem of a broken crew member cabin seat. Though compensation for the volunteer who left the flight was very kind.

We fly American Airlines quite a bit. And we always fly business class when traveling internationally. We were a bit disappointed with the comfort of this particular plane as well as the entertainment options.

The AA staff person who checked our bags was curt and almost rude. The FA also seemed unhappy doing her job. Overall it was like riding the school bus back in grade school.

Seats were new and comfortable. Staff was fine. Missed my connection due to weather -which wasn’t their fault- but got no help at all. Gate staff sent me to customer service, which was and stayed unstaffed. Sign with QR code directed me to call or chat. Chat was useless. Call was returned after an hour. No itinerary offered by Frontier could get me home in less than 30 hours. Rebooked with another airline and got a partial refund that came to about 10 percent of what I paid to get home.

Finally a Frontier on time and efficient. I've had problems before with your airline, but this time everything went fine.

The experience was good. No frills but I got there safe and sound and on time.

Great for the price. No wifi or entertainment, but gate agents and crew were fantastic and we boarded quickly and left on time.

sluggish boarding and arrival procedures, fake nice flight attendants, and lots of delays.

Disaster. They lied every step of the way. We ended up being delayed due to crew and then allegedly abandoned the flight because of a curfew at LGA. No rebooking to LGA at any reasonable time. No hotel. No meal vouchers. Had to sleep in the airport and fly to Newark instead. Will never fly Frontier again.

What I expected, nickeled and dined and a frontier flight attendant loudly complained about her job and lack of communication as she headed to the gate on her cell phone. Not professional.

As every law enforcement agency I could imagine surrounded the plane and we didn’t disembark for 2 hours and then had to stick around for another hour to go get our personal belongings after leaving them behind and being bused away from the plane, it was scary and inconvenient. We were given no information as to why this was happening. Lack of communication with passengers was disappointing.

After boarding and un-boarding twice over 6+hours, the flight was canceled.

Severe turbulence. Captain never came on to reassure passengers after things settled down.

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