$58 Find Cheap Flights from Washington, D.C. to Caribbean

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 departing on 5/27. 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

KAYAK searches hundreds of travel sites at once for deals on flights to Caribbean

Travelers love KAYAK
41,299,237 searches in the past 7 days on KAYAK

Save 22% or moreCompare multiple travel sites with one search.

Track pricesNot ready to book? Create a price alert for when prices drop.

Free to useThere are no hidden charges or fees.

Filter your dealsChoose cabin class, free Wi-Fi and more.

Flights Deals
Useful Info
Flights Deals

Best Caribbean Flight Deals from Washington, D.C.

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

Punta Cana
Punta Cananonstop$212
Santo Domingo
Santo Domingo1 stop$260
Montego Bay
Montego Bay1 stop$266
Oranjestad
Oranjestad1 stop$317
Nassau
Nassau1 stop$339
Kingston
Kingston1 stop$344
Simpson Bay
Simpson Bay1 stop$337
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
Castries
Castries2 stops$793
St. John's
St. John's1 stop$530
Puerto Plata
Puerto Plata1 stop$291
Aguadilla
Aguadilla1 stop$308
Punta Cana
Punta Cananonstop$212
Santo Domingo
Santo Domingo1 stop$260
Montego Bay
Montego Bay1 stop$266
Oranjestad
Oranjestad1 stop$317
Nassau
Nassau1 stop$339
Kingston
Kingston1 stop$344
Simpson Bay
Simpson Bay1 stop$337
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
Castries
Castries2 stops$793
St. John's
St. John's1 stop$530
Puerto Plata
Puerto Plata1 stop$291
Aguadilla
Aguadilla1 stop$308

Cheap Flights from Washington, D.C. to Caribbean

 
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 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 Washington, D.C. to Caribbean

Recommended round-trip deals departing in the coming months from the most popular airlines that fly from Washington, D.C. to Caribbean.
Discover the best prices for you by selecting your travel dates on KAYAK.
Spirit Airlines Logo
5:30 pm - 9:17 pmBWI-SJU
3h 47mnonstop
Spirit Airlines Logo
1:39 pm - 5:40 pmSJU-BWI
4h 01mnonstop
$107Spirit Airlines
Find Deal
Tue, May 27 - Wed, Jun 4
Spirit Airlines Logo
6:51 pm - 10:38 pmBWI-SJU
3h 47mnonstop
Spirit Airlines Logo
1:39 pm - 5:40 pmSJU-BWI
4h 01mnonstop
$116Spirit Airlines
Find Deal
Wed, May 28 - Thu, May 29
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
3:54 pm - 11:59 pmDCA-SJU
8h 05m1 stop
American Airlines Logo
6:10 am - 2:24 pmSJU-DCA
8h 14m1 stop
$250American Airlines
Find Deal
Sat, May 24 - Thu, May 29
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
JetBlue Logo
5:15 pm - 1:45 amDCA-SJU
8h 30m1 stop
JetBlue Logo
11:30 am - 6:44 pmSJU-DCA
7h 14m1 stop
$317JetBlue
Find Deal
Wed, Oct 8 - Tue, Oct 14
JetBlue Logo
6:30 am - 12:34 pmDCA-SJU
6h 04m1 stop
JetBlue Logo
1:55 pm - 10:47 pmSJU-DCA
9h 52m1 stop
$321JetBlue
Find Deal
Mon, Oct 27 - Mon, Nov 3
Useful Info

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

Get data-powered insights and trends into flights from Washington, D.C. to Caribbean to help you find the cheapest flights, the best time to fly and much more.

What is the cheapest Washington, D.C. to Caribbean 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. to Caribbean.

The cheapest ticket to Caribbean from Washington, D.C. found in the last 72 hours was to San Juan, at $120 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 $120.

Can I save money by flying with a layover from Washington, D.C. to Caribbean?

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 $792, prices are generally cheapest when you fly direct.

What is the cheapest month to fly from Washington, D.C. to Caribbean?

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, 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 is March, when tickets cost $293 (return) on average. On the other hand, the most expensive months are December and April, when the average cost of round-trip tickets is $475 and $384 respectively.

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

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

If you are looking for a flight deal from Washington, D.C. to Caribbean, look for departures on Tuesdays and avoid leaving on a Friday, as it's usually the priciest day. When flying back from Caribbean, Friday is the cheapest day to fly and Sunday is the most expensive.

How far in advance should I book a flight from Washington, D.C. to Caribbean?

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, 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, 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 seasonDecember
Cheapest flight$58
Best time to beat the crowds with an average 19% drop in price.
Most popular time to fly with an average 32% increase in price.
Flight from Baltimore to San Juan

FAQs - booking Caribbean flights

  • Which airport in Washington, DC, should I fly out of to get to the Caribbean?

    Washington, DC, is served by three main airports: IAD, DCA, and BWI. When flying to the Caribbean from downtown Washington, DC, consider flying from DCA. IAD is a major international gateway for Washington, DC, and it’s the airport with the most flights to Caribbean destinations. BWI serves most of the low-cost airlines in the area. IAD is a Southern Airways Express and United Airlines hub, while DCA is a hub for American Airlines. You can connect to various Caribbean destinations from these airports for more flight options.

  • Which airport in Washington, DC, is more accessible by public transportation?

    DCA is the airport in Washington, DC, with a good connection to public transport systems. You can access the airport via Metrorail, Metrobus, and taxis. You can use the yellow and blue lines of the Metrorail system to connect to the station in DCA from downtown Washington, DC, and other parts of the city. You can also use a Metrobus to get to DCA.

  • Which airport in Washington, DC, has lounges?

    When flying from Wahington, DC, to the Caribbean, you should be at the airport at least two hours early. When waiting for your flight, you can visit one of the lounges at the airport. IAD has more lounges to select from, including United Club, Lufthansa Senator, British Airways Galleries, Air France-KLM, Turkish Airlines, and Virgin Atlantic Clubhouse lounges. The lounges offer comfortable space and seating, complimentary refreshments, business facilities, children's play areas, and flight assistance services.

  • Which route in the Caribbean from Washington, DC, is flown most often?

    Most air travel from IAD and DCA airports in Washington, DC, arrives at San Juan Airport. Several airlines, including Delta, JetBlue, United, and American Airlines, offer multiple daily flights between Washington, DC, and San Juan, ensuring passengers have numerous flight options along the route. San Juan is a major hub for flights in the Caribbean, making it a great connecting point to other Caribbean destinations.

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

    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.

  • 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?

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight from Washington, D.C. to Caribbean 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?

    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 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?

    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 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?

    The cheapest time of day to fly to Caribbean 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 is generally in the morning, which is peak travel time and where the average cost of a ticket is $497.

Top tips for finding cheap flights to Caribbean

  • Washington Dulles International Airport (IAD) and Reagan National Airport (DCA) in Washington, DC, offer direct flights from Washington to different Caribbean airports. A direct flight from Washington, DC, to the Caribbean will minimize your travel time and any inconveniences encountered through changing planes.
  • If you want to fly to the Caribbean from Washington, DC, on a budget-friendly airline, consider flying Southwest or Spirit Airlines. You can fly from Washington International Thurgood Marshall Airport (BWI), serving the Baltimore-Washington, DC area, which is a major hub for these low-cost airlines.
  • If you want to travel to the Caribbean from Washington, DC, at night, consider flying Delta, JetBlue, American, or United Airlines, which offer red-eye travel from IAD and arrive at various Caribbean airports the next morning.
  • If you want to access multiple islands in the Caribbean on a single trip, consider flying into a major international hub airport, including Luis Muñoz Marín International Airport (SJU) in Puerto Rico. This airport connects to multiple Caribbean destinations, including Aruba, Saint Lucia, Dominica, Saint Vincent and the Grenadines, Barbados, and Curaçao.
  • Consider flying Delta, United, or American Airlines from Washington, DC, to the Caribbean, as the airlines offer special meals to passengers with special dietary requirements. They offer vegetarian, vegan, gluten-free, lactose-free, diabetic, and child meals based on your needs.

Top 5 airlines serving from Washington, D.C. to Caribbean

Need help choosing which airline to fly with from Washington, D.C. to Caribbean? 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.
7.4
United AirlinesOverall score based on 8696 reviews
6.6Food
8.1Crew
7.3Comfort
7.7Boarding
7.1Entertainment
Airline reviews

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. 👍👍

10.0 ExcellentAnonymous, Apr 2025SFO - HKG
Read more United Airlines reviews

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.

Excellent from start to finish. All staff members were amazing!

Excellent. Although they used to greet me as a mosaic member and provide a free drink, early boarding helps me to keep coming back to JetBlue.

Cancelled flight with no specific instructions to get a boarding pass for another flight. The whole flight of people were in line for an hour because there was only 1 person to help at the desk. This was unusual for JetBlue.

It was too hot in the cabin. The AC did not help.

Except for the 28 minute delay leaving and the earlier reschedule to a later takeoff time the flight was good.

Loved the leg room and tvs screens on the seats and free WiFi. Wish the price was lower and could save by rebooking

No music app working: no economy meal on five hour flight; hour on tarmac at the end waiting for a gate. Flight itself was smooth and easy.

It took 1-1/2 hours to get our luggage after we landed. That to me is unacceptable

The flight was delayed for 4 hours. Once onboard the crew was wonderful.

Overall was excellent. Will definitely us JetBlue in the future.

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 mean, it’s Spirit. But it was frustrating to have our flight canceled, get bumped to a later flight, and then Spirit was unwilling to check our bag until 4 hours before our flight… tell us we could not sit in the waiting area’s chairs… and really negative experience getting checked in and dropping the bag.

Not having it be changed after we bought the flight tickets from a direct flight getting in at a reasonable time to a connecting flight red eye of 9 hours, so that we would lose our 35 dollars in nonrefundable insurance would've been great! Our country really does need low-cost carrier options, but this type of "service" ain't it. Fortunately, had a little better success with them flying to and from San Juan PR last month at least.

All was good expecting the seats need a bit of cushion. Besides that I can’t complain.

You get what you pay for, and the flights went smoothly. There’s no reclining chairs, no screens, And there isn’t always wifi, but the plane was clean and staff was friendly and the takeoff/landing were smooth.

The only positive is that the flight made it both ways. Getting charged for every little thing after the cost of the ticket itself is comical, considering how the plane and services are as bottom-tier as possible. The self check-in kiosks are useless. It’s nice to think that you can print your boarding pass, tag your checked bag, and then just drop it off. But no, they still make you go through the line once you finish- what’s the point of the self check-in then? Any questions for the staff seem like the biggest inconvenience and were met with condescending responses. This was my first and now last time ever flying with Spirit. After all the extra costs, subpar plane and staff, I see no value. I’d rather drive the 13 hours than give Spirit another dime.

The flight was fine however what started as a reasonable priced ticket could have become an overpriced ticket with additional charge for carry on as well as checked bag $79 per bag per person each way. Additional charge for choosing one’s seat, additional charge for beverage and snack, we were on what was described as a new plane yet there were no audio/visual on the jet. A bare bones service but not at a bare bones price. Will think twice before flying Spirit again. 😕

Flight was delayed a bit, but that was expected (and updated), so really not bad at all for the price. Could’ve used one less email asking me to upgrade my seat; otherwise no significant complaints

I love Spirit. New aircraft, great cabin service, the airfares are low cost which helps me visit my hospitalized daughter anytime I can without paying a fortune.

Flight was 2hours late they had no crew or the pilot.

I paid for streaming wifi and the connection was poor.

The reps working at the airport counter were dumber than a second coat of paint.

My costume jewelry was stolen out of my bag. Got to airport and my bag weighed 45 pounds- 5 pounds over cost me $100 Long lines in tier one. No entertainment No WiFi no free drinks or snacks

Not very good. Paid in excess of $400 for assigned seating for my family and that was not provided. I want that money back.

The seats were hard molded plastic covered in plastic vinyl. And the scam to charge people extra to sit together. Don’t they know we can just ask someone to trade seats. And watching the staff separate young children from parents… super classy. We had to guilt them into offering up our seats. This companies policies suck. Don’t give them your money.

The seats were awful, hard plastic covered in sheet vinyl. The airline tries to scam you into paying extra to get seat together when the flight wasn’t full. They were going to separate a family with young children but my wife who had a row to herself gave up her seat so the young mom could be with her young boys. I’m never giving this airline my money again.

It was a short flight so no food or entertainment….

Seats are uncomfortable but price is good. Guess I can put up with misery for four hours.

I’ve never traveled on Frontier before. If you want basic, no frills, friendly service at great prices then give them a fly!

Cancelled and declined to find alternatives Earlier flight is 2 days later Sent the cancellation notification very late, wish I knew earlier would have stayed to watch the Miami open final game Very disappointing service

The worst flight of my life. Never will I fly frontier again

Everything you need to know for your flight to Caribbean

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.

Not what you’re looking for? Find thousands of other hotels, flights, car rentals and package deals with KAYAK.