$111 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 5/28. 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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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 Cananonstop$437
Santo Domingo
Santo Domingo1 stop$466
Montego Bay
Montego Bay2 stops$434
Oranjestad
Oranjestad1 stop$399
Nassau
Nassau1 stop$430
Kingston
Kingston1 stop$416
Simpson Bay
Simpson Bay2 stops$390
Providenciales
Providenciales1 stop$418
Port of Spain
Port of Spain1 stop$446
Bridgetown
Bridgetown1 stop$387
George Town
George Town1 stop$321
Willemstad
Willemstad1 stop$390
Aguadilla
Aguadilla1 stop$194
Puerto Plata
Puerto Plata1 stop$512
St. John's
St. John's1 stop$526
Punta Cana
Punta Cananonstop$437
Santo Domingo
Santo Domingo1 stop$466
Montego Bay
Montego Bay2 stops$434
Oranjestad
Oranjestad1 stop$399
Nassau
Nassau1 stop$430
Kingston
Kingston1 stop$416
Simpson Bay
Simpson Bay2 stops$390
Providenciales
Providenciales1 stop$418
Port of Spain
Port of Spain1 stop$446
Bridgetown
Bridgetown1 stop$387
George Town
George Town1 stop$321
Willemstad
Willemstad1 stop$390
Aguadilla
Aguadilla1 stop$194
Puerto Plata
Puerto Plata1 stop$512
St. John's
St. John's1 stop$526

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

Sat, May 30 - Mon, Jun 1
Frontier Logo
6:49 am - 2:07 pm
IAD
-
SJU
7h 18m
1 stop
Frontier Logo
6:00 am - 6:42 pm
SJU
-
IAD
12h 42m
1 stop
$214Frontier
Tue, May 19 - Tue, Jun 16
Frontier Logo
6:37 pm - 2:08 am
IAD
-
SJU
7h 31m
1 stop
Frontier Logo
6:00 am - 12:53 pm
SJU
-
IAD
6h 53m
1 stop
$216Frontier
Sun, May 17 - Wed, May 20
United Airlines Logo
8:15 am - 12:20 pm
IAD
-
STT
4h 05mnonstop
United Airlines Logo
4:45 pm - 8:58 pm
STT
-
IAD
4h 13mnonstop
$281United Airlines
Sun, May 17 - Wed, May 20
United Airlines Logo
8:15 am - 12:20 pm
IAD
-
STT
4h 05mnonstop
United Airlines Logo
1:22 pm - 11:59 pm
STT
-
IAD
10h 37m
1 stop
$286United Airlines
Wed, May 13 - Wed, May 20
American Airlines Logo
8:11 pm - 10:47 am
IAD
-
STT
14h 36m
1 stop
American Airlines Logo
1:15 pm - 7:25 pm
STT
-
IAD
6h 10m
1 stop
$316American Airlines
Sun, Aug 30 - Fri, Sep 11
Air Canada Logo
4:20 pm - 3:25 pm
IAD
-
BGI
23h 05m
1 stop
Air Canada Logo
4:20 pm - 9:14 pm
BGI
-
IAD
28h 54m
2 stops
$387Air Canada
Mon, May 25 - Wed, Jun 3
American Airlines Logo
8:22 pm - 1:22 pm
IAD
-
SXM
17h 00m
2 stops
American Airlines Logo
4:43 pm - 8:50 am
SXM
-
IAD
16h 07m
2 stops
$390American Airlines
Sat, Sep 5 - Fri, Sep 11
Air Canada Logo
4:20 pm - 3:25 pm
IAD
-
BGI
23h 05m
1 stop
Air Canada Logo
4:20 pm - 8:25 pm
BGI
-
IAD
28h 05m
1 stop
$398Air Canada
Wed, Jun 3 - Sun, Jun 7
Copa Airlines Logo
6:25 am - 10:00 pm
IAD
-
AUA
15h 35m
1 stop
Copa Airlines Logo
7:10 am - 12:33 am
AUA
-
IAD
17h 23m
1 stop
$411Copa Airlines
Thu, May 28 - Wed, Jun 3
Copa Airlines Logo
4:38 pm - 11:27 am
IAD
-
SXM
18h 49m
1 stop
Copa Airlines Logo
12:25 pm - 12:33 am
SXM
-
IAD
12h 08m
1 stop
$421Copa Airlines
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 $271 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 $271.

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

The average price for all round-trip flights from Washington, D.C. Dulles Intl Airport to Caribbean Islands 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 Islands is generally at night, when round-trip flights cost $344 on average. Morning departures are around 9% cheaper than evening flights, on average. The most expensive time of day to fly to Caribbean Islands is generally in the evening, which is peak travel time and where the average cost of a ticket is $452.

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 $512, 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 August, when tickets cost $137 (return) on average. On the other hand, the most expensive months are November and December, when the average cost of round-trip tickets is $1,589 and $1,046 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, Sunday is the cheapest day to fly on average and Wednesday 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 20 weeks before departure.

Good to know

Low seasonSeptember
Cheapest flight$111
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 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.

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 8465 reviews
8.1Boarding
7.2Food
7.8Entertainment
8.5Crew
7.9Comfort
Airline reviews

The flight was operated by Latam. The aircraft had a technical issue and the flight was delayed for the next day. They grounded other passengers to get their airplane assigned to my flight. Most of he ground staff don't speak English (Orlando Airport), but were very polite.The crew on the other hand could speak English and Portuguese. On board service was good.

6.0 GoodSilvestre, Apr 2026
MCO - GRU
Read more Delta reviews

The flight was operated by Latam. The aircraft had a technical issue and the flight was delayed for the next day. They grounded other passengers to get their airplane assigned to my flight. Most of he ground staff don't speak English (Orlando Airport), but were very polite.The crew on the other hand could speak English and Portuguese. On board service was good.

The agent at check in and at the gate were less than thrilled to be at work. I'm not a fan of Kayak's placement on the plane. I got put in the middle seat and none of my preferences were used.

In ATL they have two sets of departure screens. Follow what is on your airline's departure board - the ATL Airport Authority departure board had completely incorrect details about the gate assignment for my flight, which would have made me miss boarding.

Flight was delayed it was hot while sitting on the plane, one engine was working on the plane until they had to do some jimmy rigging down the runway in order for the other engine to charge up. It was ridiculous

The flight was very good and the staff was very friendly and helpful!

The only thing I would say is we tried to get on a standby earlier flight, but with our fair we couldn’t. That seems senseless to leave with open seats..

Very easy to use and convenient, you can perform any action within the same portal

In a world of delays, Delta was on time both ways! Boarding was fast and efficient. Staff was friendly. AND wifi worked.

WiFi didn’t work. Flight delayed 3 hours Crew members were illiterate Seat lean back did not work.

Flight was delayed, we could have been notified earlier and in a consistent manner. App was not refreshing for another passenger to get the latest flight status. We could have stayed and waited at the hotel instead of waiting at the airport had we known the flight was going to delayed for more than 5 hours. The toilet is too tight, and needs to be cleaned more frequently (every hour). The entertainment screen froze, the touch screen not responding to touch. We were upgraded to comfort, it is more comfortable than regular economy seats.

I was flying business class, and the French fellow passengers were super noisy. It was not a comfortable flight. And the crew was not helpful.

Boarding was a mess, they call all priority members without distinction so gold, platinum, silver were all mixed together in a long line which defeats the purpose

Entire experience from check in to landing was amazing the flight crew was excellent and friendly. Seats were comfortable.

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.

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.

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 flight was delayed so we were dead tired, and after that the turbulence was horrible. I was very scared.

Wifi took a while to kick in and we had a maintenance issue that took over 40 mins at the gate in Washington before pulling back

Very good. Because of the delays with my previous flight, I missed my connection, but I was able to book another flight through the United app easily.

Was happy we finally got upgraded in 1st class. The seat getting old. The cushiness need some improvement.

Ineffective communication with United resulted in lost baggage. Their Baggage Tracing counter at MUC was shut down from 11:00-14:15 on my arrival. Undertrained, underinformed staff had me Running all over MUC to find someone to help me to no avail. Staff was rude, unhelpful, and unable to effectively use the systems they did have operational. They refused to contact United in any way or provide any accommodation or other resources while I waited for my luggage. This has destroyed my downstream itinerary. If they had even the slightest visibility I may have been able to reschedule/plan, but again, their staff provided nothing, and did nothing more than their website, which doesn’t even work on a standard phone browser. Miserable failure at all levels that weren’t associated with the operation of the aircraft.

Sat next to a one year old. She crawled all over the place and made me laugh.

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.

Flight boarded, departed and landed on time. Excellent service from flight attendant in FIRST

This was one of the most frustrating travel experiences I've had to date. I had changed my flight day of to this one as it was slated to depart on time. It ended up being so delayed that my original flight took off before this one did. The boarding process began but eventually stopped and everyone had to get off the plane as a problem was identified. The person at the front desk just tried to laugh it off as if this wasn't already a huge inconvenience. From there, we eventually got to board only to sit at the gate for an additional hour because of some additional issue. This was extremely frustrating and caused a lot of stress.

It was a little concerning to hear the ground crew arguing with the flight crew over baggage space. Instead of taking them and checking them, they started checking for space in the first class cabin moving items around like the flight crew didn't know what they were doing. I was embarrassed for them.

The bag check, flight check-in, and onboard experience convinced my wife and me that we will actively go out of our way to avoid flying Frontier Airlines in the future. At bag check, we were informed that check-in could only be completed via the Frontier mobile app. Unfortunately, the app was extremely frustrating—sending us through repetitive, confusing loops that repeatedly forced us to decline add-on services with nearly every click. While most airline apps upsell, this one felt intentionally exhausting. As the process dragged on, we became genuinely concerned that my phone battery would die before check-in could be completed. We approached the bag check staff—who were standing together talking—and explained both our frustration and our predicament. They laughed. Later, my wife described the interaction as “gaslighting,” which felt accurate. We were then informed it would cost $25 per person simply to have our boarding passes printed. From that point forward, the tone of the experience was consistently hostile. The bag check employees were condescending and combative, behaving more like bullies than customer service staff. Unfortunately, that same attitude continued onboard. One flight attendant argued with me when I attempted to stow my backpack in the overhead bin. I explained that we had each paid $75 to check our bags specifically so we would not need to use carry-on space and could have adequate legroom. She demanded to see my ticket, pointed out that it said “no carry-on”—which I acknowledged—and I reiterated that this was precisely why we paid to check our bags. Her response was, “I don’t make the rules.” She then walked away, but not before asking if I “truly wanted to fly back to Chicago today?”—an unnecessary and unmistakable threat. It is also worth noting that despite booking our tickets together in the same transaction, we were not seated together. Upon our return to Chicago—where we could once again sit together—we compared onboard experiences. We both remarked on how unhappy the flight attendants appeared and how each of us was separately asked whether we would like to purchase a beverage. We declined. At no point was water mentioned as an option, leaving us with the clear impression that even water came at a cost—or that complimentary water, if available at all, was deliberately left unmentioned. Overall, the experience was shocking and deeply disappointing, but it was also a profound learning experience—one we will not forget and will not repeat. -Steve

Plane was hot and miserable and the crew was rude!

12 hour delay required getting on and off plane 3 times - would have at least liked to have been offered a snack or drink

They didn’t offer a water, even after I asked

They switched our terminal 3 times and we were delayed for four plus hours!!!

It was an early flight and most people napped/slept and the crew let us which was nice.

The crew acted like they had never done this and kept barking passive aggressive orders at people. + the security line + the delay + sitting on the tarmac for 2 hours + none of the apps or signage updating with correct times

More inflight connection. And leg space is horrible. And the paying for baggage I'd ridiculous!!!

My flight was originally from SAT to MCO connecting from MCO to ORD. We got diverted to ATL and than Frontier staff there was sooo un helpful first they said they couldn’t give us any accommodation since our flight first got delayed that cancelled and now it’s 221am and I am still in ATL since they said they need to create a new flight my final destination is ORD and I have been delayed twice and cancelled. With no real help the frontier app didn’t work no email updates over all such a horrible experience

There's no seats that lean back with little leg space i wad uncomfortable the entire flight. Your charges for extra baggage is despicable and costly!!

Everything you need to know for your flight to Caribbean Islands

Information on your arrival and departure airports