$157 Find Cheap Flights from Caribbean Islands to Washington Dulles Airport - 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 to Dulles Intl 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

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Cheap Flights from Caribbean Islands to Dulles Intl

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Caribbean Islands to Dulles Intl 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 Caribbean Islands to Dulles Intl

Fri, Oct 2 - Sun, Oct 4
Frontier Logo
7:00 am - 8:09 pm
SJU
-
IAD
13h 09m
1 stop
Frontier Logo
6:13 pm - 1:34 pm
IAD
-
SJU
19h 21m
1 stop
$295Frontier
Thu, Aug 20 - Mon, Aug 24
Frontier Logo
6:35 am - 7:44 pm
SJU
-
IAD
13h 09m
1 stop
Frontier Logo
10:45 am - 7:52 pm
IAD
-
SJU
9h 07m
1 stop
$295Frontier
Fri, Oct 30 - Mon, Nov 2
American Airlines Logo
3:51 pm - 8:44 am
SJU
-
IAD
16h 53m
1 stop
American Airlines Logo
7:00 am - 9:13 pm
IAD
-
SJU
13h 13m
1 stop
$296American Airlines
Thu, Sep 17 - Tue, Sep 22
American Airlines Logo
3:41 pm - 10:51 pm
SJU
-
IAD
7h 10m
1 stop
American Airlines Logo
7:57 am - 2:50 pm
IAD
-
SJU
6h 53m
1 stop
$296American Airlines
Fri, Aug 28 - Mon, Aug 31
United Airlines Logo
4:55 pm - 8:47 pm
SJU
-
IAD
3h 52mnonstop
United Airlines Logo
9:00 am - 12:54 pm
IAD
-
SJU
3h 54mnonstop
$307United Airlines
Fri, Aug 28 - Tue, Sep 1
United Airlines Logo
4:55 pm - 8:47 pm
SJU
-
IAD
3h 52mnonstop
United Airlines Logo
9:00 am - 12:54 pm
IAD
-
SJU
3h 54mnonstop
$307United Airlines
Fri, Sep 4 - Mon, Sep 7
Delta Logo
2:49 pm - 12:34 am
STT
-
IAD
9h 45m
1 stop
Delta Logo
6:00 am - 1:34 pm
IAD
-
STT
7h 34m
1 stop
$340Delta
Thu, Jan 14 - Tue, Jan 19
Delta Logo
1:50 pm - 12:20 am
STT
-
IAD
11h 30m
1 stop
Delta Logo
6:00 am - 4:15 pm
IAD
-
STT
9h 15m
1 stop
$340Delta
Thu, Aug 27 - Sun, Aug 30
Air Canada Logo
6:30 pm - 3:24 pm
NAS
-
IAD
20h 54m
1 stop
Air Canada Logo
9:55 am - 5:30 pm
IAD
-
NAS
7h 35m
1 stop
$383Air Canada
Thu, Oct 15 - Mon, Oct 19
Air Canada Logo
2:20 pm - 3:00 pm
NAS
-
IAD
24h 40m
1 stop
Air Canada Logo
9:55 am - 5:30 pm
IAD
-
NAS
7h 35m
1 stop
$389Air Canada
Useful Info

Good to know

Low season

September

Cheapest flight

$157
Most popular time to fly and prices are also 15% lower on average.
Flight from San Juan to Washington Dulles Airport

FAQs for booking Caribbean Islands to Washington Dulles Airport flights

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

    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 Caribbean Islands to Washington Dulles Airport.

  • How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from Caribbean Islands to Washington Dulles Airport?

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

    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 to Washington Dulles Airport with an airline and back to Caribbean Islands with another airline.

  • What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from Caribbean Islands to Washington Dulles Airport?

    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 to Washington Dulles Airport from Caribbean Islands up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

Reviews of the top 4 airlines serving from Caribbean Islands to Dulles Intl

 
Need help choosing which airline to fly with from Caribbean Islands to Dulles Intl? 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 8494 reviews
8.5Crew
7.2Food
7.8Entertainment
8.1Boarding
7.8Comfort
Airline reviews

Comfortable seats. Nice service online. Short flight, so not a lot of time to enjoy.

8.0 ExcellentMichael, Jul 2026
SEA - SMF
Read more Delta reviews

Comfortable seats. Nice service online. Short flight, so not a lot of time to enjoy.

Awful. There was an unexpected delay of nearly three hours because there were not enough flight attendants. I understand this is likely due to FAA regulations; but in that case, Delta should coordinate with smaller airports such as RDU to have extra flight attendants on the ground and "on call". In addition, this was the second 2-hour+ delay to Boston on this route in one week.

It was strange that the flight attendant was so adamant about having phones turned to airplane mode that he was calling out names from networks shown and waiting until they were all gone. I've never experienced that before, and after already working through an hour+ delay, it felt tone deaf. I take dozens of flights per year and have never experienced anything similar.

Chaotic boarding at these gates, multiple gates squeezed in at the very end of a concourse, behind a restaurant. Agents gave up on boarding by individual zones. Flight itself was uneventful, which is all we hope for any more.

Flight delayed due to ground hold. Republic airways did a great job.

The flight was smooth, the crew was great but the plane was quite old

Flight was warm for first few hours and quite rough

Flight was delayed several times. At one point, they "pulled back" 15 minutes from the delayed boarding and sent a text saying we would board sooner than previously advised. The flight then was delayed again. And when we boarded, there was an unspecified technical issue which had us waiting in the plane for about an hour.

The Dekta Rep that checked us in was great. She's very personable, pleasant, and can tell she enjoys her job.

1st flight had mechanical issues after we boarded and almost took off. They tried to fix on runway but couldn’t do we went back to the gate. They couldn’t fix it there either. So we had to deplane and board another plane 2 hrs later. All in all our flight was delayed 4 hrs so we had to cancel some business meeting we had in London for the morning since we were supposed to arrive at 7am and did not arrive until 11:45am. Also, the 2nd plane had mechanical issues as well but fortunately they were able to fix on runway.

stood in line to check in luggage for nearly an hour. very poor service and not excusable

Same as the previous flight as far as comfort and food. Entertainment didn’t have a watchable screen so everything would need to be watched on your own device in which they didn’t have a charging port that accommodated my iPhone. Seats were very uncomfortable. Staff was very friendly.

Do not book it’s a scam! They stole $1200 from me

Some of the Air hostesses are not that friendly. Need improvement

horrible service, food was an embarrassment, no charging for cellphones, stay away

Great experience with a crew always thinking in the passenger

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.

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....

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

Copa crew is almost never great in terms of service.

Entertainment center did not work and no electric available at seat for 11 hour flight. Didn’t have access to overhead light or call button. Food was tasteless and had a high salt (27 %) of recommended daily salt intake

What would be infinitely better if for Kayak to not offer this flight as if it was completely different airlines rather than United and then filtering me through some creepy discount site.

Our flight was great with an unexpected upgrade. However, four days into our travel we are still without a piece of luggage. The bag tracker has not been accurate, the airline is not communicating with me or the luggage delivery service and no one is willing to take responsibility or guarantee any kind of support or reimbursement. Unfortunately, we do not have the option to easily shop to replace items as we are currently on a cruise. I have been very disappointed by United Airlines response.

The flight was canceled. I couldn't get on another flight. Meal voucher wouldn't work. The whole experience was a clusterfuck.

It was terribly delayed with zero support from united airlines. I reached at 1 am in the night. They did not provide any option to change the flights.

Flight was delayed 14 hours due to DC air show and weather. Missed connection to MUC.

Horrible I am at almost 2,000,000 miles on United. This was probably the worst flight ever. An hour and a half before takeoff I get a message that they’re changing the plane and I no longer have a seat in Polaris business Supposedly, there was a problem with the plane, but then there was no other plane Finally, they decided to bring a plane from Newark to Washington Dulles Of course the original flight was at 10:45 PM so by the time the plane got there it was 12:30 AM. It had not been cleaned. It had not been catered. They don’t really have people available to do those things when it’s not pre-programmed at 1 o’clock in the morning. The crew had to be changed And the new plane held 28 fewer people than the scheduled plane There is no way you can hate United Airlines enough The people at the gate were actually just fine, but it was management who was completely useless And did they send extra help to the people at the gate? Did they send supervisors? Of course not. Just don’t take United find somebody else or buy a boat

Flight attendants were great. Food mediocre. Bamboo utensils not Great especially if you have to cut something. Seating a bit crowded.

The crew was the worst ive ever had in my life flying with United Airlines, letting another person move my bag without asking and then the staff saying would the floor be better after I kept begging saying dont move my bag it has fragile things inside. This incident truly makes me they favor other customers more and I dont want to worry about being on the tail end. Especially if they dont listen any input, no care for what I asked but accommodated those who are reckless and disturb others more...

Our flight was delayed 2.5 hours from Lisbon to DC so we missed our connection to Seattle that would have arrived at about 9 PM. The agent initially said we had to stay overnight in DC and there were no other options to put us on to get us to Seattle. While on board I discovered a flight via American he could have put us in but by the time we arrived in DC that was sold out. We were then put on a flight to San Francisco that was also delayed then arrived in San Francisco and our flight to Seattle was also delayed so we ended up not arriving until 2:15 am. Our son could not pick us up so we ended up having to pay over $100 to Uber home. This is the second trip with United that the flight has been delayed causing us to miss an evening in Las Vegas and we were given nothing.

On time departure & early arrival. Made a long day much better.

Like all planes recently, entertainment is achieved by giving the patron free WiFi and letting them stream shows via the screen on a phone or tablet.

Crew and agents misguiding on tight connections, and lack of connecting crew looking for inbound planes. A very avoidable missed connection as a result.

My flight was 4 hours delayed on departure at 6a causing me to miss my connection at DCA. I had to scramble to find a seat home on a later flight and instead of an exit seat, I was in row 30 on a flight getting me home 5 hours later than planned. The AA team on the ground did a fine job. AA continues to run the airline like the passengers are cargo.

American Airlines changed are gate no fewer than four times. Walking back and forth from one concourse to another was exhausting, especially after all the flight delays.

Hydraulic leak caused the flight to be cancelled. Auto system scheduled us on a 3 am flight. Wevhsedvrebook on the app and hit schedules later in the afternoon. Our luggage per gate and ticket agent would be rescanned and put in our new flight. Did not happen. Our luggage stayed in hsv. Baggage claim in wash dc unable to help. We filed a claim. Several emails about our luggage were in conflict with one another. Called as baggage and was on hold 30 minutes. Oscar said one of 2 was out fir delivery then cancelled. About 45 minutes later both pieces were delivered. Their system is suspect

The airplane was an old model, the overhead didn’t have enough room for people’s items and made boarding and boarding disappointing and stressful. Crew allowed passengers to bring more than the permitted baggage sizes.

It was great. Smooth flight, comfortable, left on time and landed on time.

Horrible experience upon landing. Probably more due to DCA utter incompetence than AA.

Concern Regarding Significant Gate Delay and Jet Bridge Issue Dear Customer Relations Team, I am writing to express my disappointment with the experience I had on my recent flight AA 2414 on Sunday January 18, 2026. What should have been a routine departure turned into a frustrating and avoidable delay due to an issue with the jet bridge at the gate. As a result, the flight was delayed by approximately 90 minutes while multiple gate changes were attempted. The lack of clear communication during this period made the situation even more challenging. Passengers were left uncertain about the cause of the delay, the expected timeline, and the next steps. This not only disrupted travel plans but also created unnecessary stress for everyone on board. I understand that operational issues can arise, but a malfunctioning jet bridge and the resulting extended delay suggest an area where procedures or equipment maintenance may need attention. I hope you will review this incident to prevent similar disruptions in the future. I would appreciate acknowledgment of this concern and consideration of appropriate compensation for the inconvenience and lost time caused by this delay. Thank you for taking the time to review my experience. I look forward to hearing from you. Sincerely, Dion Dillard

Traveling to a place near Dulles Intl?

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Winchester
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Hanover
Springfield
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Owings Mills
Charles Town
Greenbelt
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Edgewood
Camp Springs
Ellicott City
Chesapeake Beach
Pikesville
Colonial Beach
Hunt Valley
Lutherville Timonium

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