$81 Find Cheap Flights from Washington, D.C. 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 Washington, D.C. to Caribbean Islands departing on 4/28. 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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Flight Deals

Cheap Flights from Washington, D.C. to Caribbean Islands

Cheapest round-trip prices found by our users on KAYAK in the last 72 hours
Punta Cana
Punta Cana1 stop$401
Santo Domingo
Santo Domingo1 stop$304
Montego Bay
Montego Bay1 stop$264
Oranjestad
Oranjestad1 stop$256
Nassau
Nassau2 stops$377
Kingston
Kingston1 stop$358
Simpson Bay
Simpson Bay1 stop$262
Providenciales
Providenciales2 stops$402
Port of Spain
Port of Spain1 stop$384
Bridgetown
Bridgetown1 stop$410
George Town
George Townnonstop$313
Willemstad
Willemstad2 stops$331
Castries
Castries2 stops$856
Puerto Plata
Puerto Plata1 stop$471
St. John's
St. John's1 stop$482
Aguadilla
Aguadilla1 stop$194
Punta Cana
Punta Cana1 stop$401
Santo Domingo
Santo Domingo1 stop$304
Montego Bay
Montego Bay1 stop$264
Oranjestad
Oranjestad1 stop$256
Nassau
Nassau2 stops$377
Kingston
Kingston1 stop$358
Simpson Bay
Simpson Bay1 stop$262
Providenciales
Providenciales2 stops$402
Port of Spain
Port of Spain1 stop$384
Bridgetown
Bridgetown1 stop$410
George Town
George Townnonstop$313
Willemstad
Willemstad2 stops$331
Castries
Castries2 stops$856
Puerto Plata
Puerto Plata1 stop$471
St. John's
St. John's1 stop$482
Aguadilla
Aguadilla1 stop$194

Book Cheap Washington, D.C. 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 Washington, D.C. 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 Washington, D.C. to Caribbean Islands

Mon, Apr 13 - Fri, Apr 17
Frontier Logo
7:38 pm - 11:28 pm
BWI
-
SJU
3h 50mnonstop
Frontier Logo
11:30 am - 10:51 am
SJU
-
BWI
23h 21m
1 stop
$162Frontier
Fri, Apr 10 - Thu, Apr 16
Frontier Logo
7:38 pm - 11:28 pm
BWI
-
SJU
3h 50mnonstop
Frontier Logo
1:42 pm - 5:54 pm
SJU
-
BWI
4h 12mnonstop
$163Frontier
Sun, May 10 - Wed, May 13
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
$261United Airlines
Sat, May 9 - Wed, May 13
United Airlines Logo
6:15 am - 5:00 pm
IAD
-
STT
10h 45m
1 stop
United Airlines Logo
4:45 pm - 8:58 pm
STT
-
IAD
4h 13mnonstop
$266United Airlines
Mon, May 4 - Wed, May 13
Delta Logo
7:06 am - 2:48 pm
IAD
-
STT
7h 42m
1 stop
Delta Logo
1:16 pm - 12:51 am
STT
-
IAD
11h 35m
1 stop
$270Delta
Wed, Apr 15 - Wed, Apr 22
American Airlines Logo
8:11 pm - 10:47 am
IAD
-
STT
14h 36m
1 stop
American Airlines Logo
1:15 pm - 11:59 pm
STT
-
IAD
10h 44m
1 stop
$296American Airlines
Thu, Apr 9 - Wed, Apr 15
JetBlue Logo
8:00 am - 11:43 am
DCA
-
SJU
3h 43mnonstop
JetBlue Logo
6:00 pm - 9:56 pm
SJU
-
DCA
3h 56mnonstop
$320JetBlue
Tue, Apr 21 - Tue, Apr 21
JetBlue Logo
8:00 am - 11:43 am
DCA
-
SJU
3h 43mnonstop
JetBlue Logo
6:00 pm - 9:56 pm
SJU
-
DCA
3h 56mnonstop
$323JetBlue
Tue, Apr 28 - Mon, May 4
Delta Logo
9:00 am - 8:24 pm
DCA
-
SJU
11h 24m
1 stop
Delta Logo
1:25 pm - 10:41 pm
SJU
-
DCA
9h 16m
1 stop
$342Delta
Sun, May 3 - Mon, May 4
American Airlines Logo
6:25 am - 2:00 pm
IAD
-
AUA
7h 35m
1 stop
American Airlines Logo
4:20 pm - 11:59 pm
AUA
-
IAD
7h 39m
1 stop
$379American Airlines
Booking Insights

KAYAK's insights & trends for Washington, D.C. to Caribbean Islands flights

Get data-powered insights and trends into flights from Washington, D.C. 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. 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. found in the last 72 hours was to San Juan, at $188 round-trip. The most popular route is from Baltimore (BWI) 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 $188.

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

The average price for all round-trip flights from Washington, D.C. 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 10% 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 $444.

Can I save money by flying with a layover from Washington, D.C. 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. 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. 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. to Caribbean Islands is July, when tickets cost $296 (return) on average. On the other hand, the most expensive months are December and March, when the average cost of round-trip tickets is $435 and $373 respectively.

What’s the cheapest day of the week to fly from Washington, D.C. to Caribbean Islands?

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

For Washington, D.C. 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, D.C., 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. 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. 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. 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$81
Best time to beat the crowds with an average 9% drop in price.
Most popular time to fly with an average 20% increase in price.
Flight from Baltimore to San Juan

FAQs - booking Caribbean Islands flights

  • How does KAYAK find such low prices on flights from Washington, D.C. 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, D.C. to Caribbean Islands.

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

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight from Washington, D.C. 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, D.C. 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, D.C. 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, D.C. 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, D.C. 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 Washington, D.C. 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 Washington, D.C. 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
SouthwestOverall score based on 4339 reviews
8.0Comfort
8.1Boarding
8.6Crew
7.5Entertainment
7.0Food
Airline reviews

Plane was late. Zero service for 2+ hour flight and it was not that bumpy.

2.0 MediocreCourtenay, Apr 2026
DAL - CLT
Read more Southwest reviews

Plane was late. Zero service for 2+ hour flight and it was not that bumpy.

It was good from LAX to Phoenix, But the connection in Phoenix to Tulsa was not that great. The staff on both flights were great. The choice of free entertainment was ok nothing to brag about. The 45 min delay because of some electrical issue wasn't great from Phoenix to Tulsa. We sat there with hardly any air, The seat I had was between windows so the side of the plane pushed in on you. My being a bigger man it then made the seating area uncomfortable. The seats on the plane had no power to connect to recharge your phone or anything. I would recommend that they should look into a slot or clamp to hold your phone to enjoy while watching the entertainment choices hands-free. Also make it possible to raise the inner seat by the window be able to raise the arm rest up to make more room for larger people to set more comfortably. I would also say other then that stop price gouging the airfare or nickel and diming everything. Not fair for people having to fly for emergencies and be paying for higher prices due to the season or holidays. Your making your money either way and the cost of flying is still going to be the same regardless if there's 100 people or 200 people.

Had a great flight. Delayed takeoff, but comfortable. Snacks were good.

Love them will get a Southwest card to track my points and keep flying with them. My family and I were pleased with the services.

I have roller bag with food and medication told me I couldn't bring on my 2nd flight today. 15 years flying with SW never an issue with that bag.

Southwest continues to do less for more money. Flight attendants used to be fun and friendly. But now it’s like they don’t even see you. Such a shame.

Great flight. Good snacks and drinks. Grateful it was free. The flight from Nashville to louisville, i think her name was Tracy (not sure that's right) super awesome, nice and cheerful. She really enjoyed being at work today! She was the person who scanned the boarding pass on flight wn941. She should be recommended for a raise !

I liked it better when you were truer to your roots Am paying more for less fun

Southwest was greaat! The most expensive but the least upsetting for those we were flying to see.

I flew twice this week on Southwest, was delayed over 2 hours both ways. From Pittsburgh to Chicago it was due to weather but the gate agents, pilot etc were great at updating everyone. Today from Midway to Pittsburgh the plane had come from an international location, kept getting delayed, no information was given until we were delayed for the third time. It was ridiculous, whoever scheduled that plane to fly to Pittsburgh after didn’t consider a lot of things.

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.

Wonderful. Quick boarding. Early departure and we arrived 30 minutes early at our destination. Unfortunately, when you arrive early, there is still a departing aircraft at our gate. We had to park for 30 minutes until the gate was clear. So our early arrival was not really early at the gate. Otherwise it was a quick and smooth flight. Appreciated the efficiency.

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.

The Crew and the food was the worst I ever had in Business Class. First they told us there were no space for carry on. It was plenty of space over our 2 row seats, we had to ask to let us travel with it which was accepted. They were aware that we had to run for the connection due to the previous flight delay. Have us one hour waiting for more customers and not even offer a glass of water. Then started the service and they started to serve other passengers drinks in business and did not offer any drinks until they serve our pre ordered meal and I ask for something to drink. I had to wait until they finished to serve all passengers until Inget something. The crew was the worts I ever had for Business Class in my life.

Not great experience - we were super late boarding due to issues with aircraft. Then when we finally all got onboard and seated and they started taxiing out to the runway they just stopped then turned around and went back to the airport. Apparently the crew “ran out of time” to legally fly us. They mentioned that they were about 2 minutes away from taking off. I understand the rules and safety but kinda wonder why they would have bothered boarding us in the first place? Had to go all the way back and de plane and then wait in a HUGE line to get a hotel (this is somewhere around 2:30am) finally got to hotel by Uber (no shuttle after 20min so gave up) and they ended up putting us all back on the same aircraft at 10am next morning so got about 2.5 hours sleep. They did give us. $250 credit, but it was a São Paulo Brazil flight out of Dulles. The flight and everything was fine.

Flight was good wish there were more snacks options for such a long flight but stewardesses were very pleasant as was flight crew.

I was denied a plastic fork to eat my food and was told plastic forks are for paying customers who buy Jet Blue’s food. So I had to make a utensil out of a cup so nourish my body. Like a refugee. Because decency is dead.

I was especially impressed without efficiently the crew got passengers on and off. One of the stewards was slightly gruff, I thought. No big deal but that's what I noticed.

Absolutely horrible. Flight was delayed 4 hours and they had no clue what was going on.

Onboard functioning wide-variety entertainment on a budget and having an open pantry is nice. Seats are not comfortable but go provide plenty of legroom for a 6'2" 260lbs man.

Even though the weather made a lot of flights become cancelled Jet Blue made the flight that was supposed to leave at 9 pm and we left at 12:15 am and I was so grateful- Thanks to the Senior Jet Blue Staff who made those decisions

Worst customer service ever experienced on the planet, dirty plane, no communication, and severe delays

Flight cancelled 2 hours prior to boarding. No explanation. No refunds.

Delayed by 1.5 hours. Terrible apologies, half hearted at best. It will be a LONG time until i book w Jet Blue again. Very disappointed.

My check in was stressful. I somehow lost my seat from my original booking, the plane showed no availability/no seat when it was time to check-in. I called and was instructed to try to get a seat at the airport. I asked if it was a full flight and the travel agent said the site showed some seating but was not able to secure one for me. Why not? On my way to the airport the app finally revealed one available seat towards the back of the aircraft that I was able to book. It ended up being an overbooked flight, so glad I wasn't stuck.

I have never been assaulted they way I was today in Charlotte - shame on American

One of our group members was struggling to walk. In Charlotte we asked for a wheelchair and she was accompanied by Desmond. I was impressed by his patience and attention. In Boston she received the same service. I didn’t get the name of the helper but she went above and beyond in assisting us. A great AA service

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.

delayed due to weather. Could not communicate with family since the wifi was broken

I got sick nothing contagious but distressing and the care I received by Kayla? Keighly the flight attendant will be memorable for ever. Thank You

We were told the flight was delayed 5 times, then it was moved to the next day.

The ticket price are reasonable, however, they can do better with the price on the luggage. Overall, I will continue using spirit.

That this is my second time the they cancel flights and they always wait until the last minute to let people know

The flight was supposed to leave at 6:22pm we are just now leaving the gate after deplaning twice at 1:07am.

Spirit is always late. Every single time. Always a different reason

They keep delaying and cancel at last moment and height was for you to get refund need to be in chat line for two hours. I complained to DOT. Never recommend this airline on Kayak please

First flight in along time with spirit! I’m honored to say this flight was excellent 😊

Spirit is awful. Do not fly spirit. Nothing but delays, cancellations.

Every connection was late but that meant I was not running from one to the next so that was a good thing. No one wants to miss a connection

Food and entertainment see irrelevant to rate them as that’s not really an option anymore. The flight was fast and friendly. The plane was immaculately clean.

it was great except the extra charges. for carry on ,seat choice, and wifi. these should all be included in flight charge. The extra charges are redicuolouse and because of that I will not be flying spirit again

Everything you need to know for your flight to Caribbean Islands

Cabin class types available on flights to Washington, D.C.

Cabin classes available on flights to Washington, D.C.. Prices are the lowest found on KAYAK over the last 7 days. Price and availability is not guaranteed.