$85 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 10/19. 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

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 Cananonstop$270
Santo Domingo
Santo Domingo1 stop$296
Montego Bay
Montego Bay1 stop$303
Oranjestad
Oranjestad1 stop$308
Nassau
Nassau1 stop$353
Simpson Bay
Simpson Bay1 stop$332
Kingston
Kingston1 stop$351
Providenciales
Providenciales2 stops$322
Port of Spain
Port of Spain1 stop$352
Bridgetown
Bridgetown1 stop$378
George Town
George Town1 stop$341
Willemstad
Willemstad1 stop$290
Castries
Castries3 stops$755
St. John's
St. John's1 stop$429
Puerto Plata
Puerto Plata1 stop$389
Aguadilla
Aguadilla1 stop$250
Punta Cana
Punta Cananonstop$270
Santo Domingo
Santo Domingo1 stop$296
Montego Bay
Montego Bay1 stop$303
Oranjestad
Oranjestad1 stop$308
Nassau
Nassau1 stop$353
Simpson Bay
Simpson Bay1 stop$332
Kingston
Kingston1 stop$351
Providenciales
Providenciales2 stops$322
Port of Spain
Port of Spain1 stop$352
Bridgetown
Bridgetown1 stop$378
George Town
George Town1 stop$341
Willemstad
Willemstad1 stop$290
Castries
Castries3 stops$755
St. John's
St. John's1 stop$429
Puerto Plata
Puerto Plata1 stop$389
Aguadilla
Aguadilla1 stop$250

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

Sun, Nov 16 - Fri, Nov 21
Frontier Logo
7:26 pm - 12:18 amIAD-SJU
3h 52mnonstop
Frontier Logo
4:08 pm - 7:11 pmSJU-IAD
4h 03mnonstop
$168Frontier
Find Deal
Sat, Oct 18 - Sun, Oct 26
Spirit Airlines Logo
4:20 pm - 12:54 amBWI-SJU
8h 34m1 stop
Spirit Airlines Logo
7:05 am - 11:08 amSJU-BWI
4h 03mnonstop
$179Spirit Airlines
Find Deal
Wed, Oct 15 - Fri, Oct 17
JetBlue Logo
8:30 am - 12:15 pmDCA-SJU
3h 45mnonstop
JetBlue Logo
6:05 pm - 9:57 pmSJU-DCA
3h 52mnonstop
$219JetBlue
Find Deal
Wed, Nov 5 - Tue, Nov 11
JetBlue Logo
8:00 am - 12:50 pmDCA-SJU
3h 50mnonstop
JetBlue Logo
12:30 pm - 10:15 pmSJU-DCA
10h 45m1 stop
$229JetBlue
Find Deal
Mon, Dec 8 - Wed, Dec 10
Delta Logo
6:00 am - 2:10 pmIAD-SJU
7h 10m1 stop
Delta Logo
7:00 am - 5:01 pmSJU-IAD
11h 01m1 stop
$245Delta
Find Deal
Mon, Dec 8 - Wed, Dec 10
Delta Logo
6:06 am - 2:10 pmDCA-SJU
7h 04m1 stop
Delta Logo
3:32 pm - 11:39 pmSJU-DCA
9h 07m1 stop
$245Delta
Find Deal
Fri, Oct 31 - Tue, Nov 4
American Airlines Logo
3:25 pm - 10:10 pmDCA-SJU
6h 45m1 stop
American Airlines Logo
5:59 pm - 11:34 pmSJU-DCA
6h 35m1 stop
$272American Airlines
Find Deal
Sun, Nov 2 - Sat, Nov 8
American Airlines Logo
8:21 pm - 2:03 pmBWI-AUA
16h 42m1 stop
American Airlines Logo
5:45 pm - 12:30 amAUA-BWI
7h 45m1 stop
$363American Airlines
Find Deal
Sun, Feb 22 - Thu, Feb 26
United Airlines Logo
6:30 am - 4:40 pmBWI-AUA
9h 10m1 stop
United Airlines Logo
3:00 pm - 9:27 pmAUA-BWI
31h 27m1 stop
$370United Airlines
Find Deal
Sun, Oct 12 - Wed, Oct 15
United Airlines Logo
6:15 am - 3:25 pmIAD-AUA
9h 10m1 stop
United Airlines Logo
4:25 pm - 7:32 amAUA-IAD
15h 07m1 stop
$389United Airlines
Find Deal
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 $155 round-trip. The most popular route is from Washington, D.C. Reagan-National Airport (DCA) 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 $177.

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 $399, 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 $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 $466 and $400 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, Tuesday is the cheapest day to fly on average and Friday 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 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$85
Best time to beat the crowds with an average 10% drop in price.
Most popular time to fly with an average 26% 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.

  • 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 7% 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 $576.

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 4242 reviews
7.5Entertainment
7.0Food
8.0Comfort
8.6Crew
8.1Boarding
Airline reviews

I wish they had movie screens in the headrests. The seats are much improved, more legroom and recently renovated. Bathroom was clean. Staff was outstanding!!

10.0 ExcellentG, Sep 2025LAS - ATL
Read more Southwest reviews

I wish they had movie screens in the headrests. The seats are much improved, more legroom and recently renovated. Bathroom was clean. Staff was outstanding!!

As always, the entire Southwest experience was wonderful, from online booking to flight to baggage retrieval. Very grateful.

The weather could have been better. There was a 40 minute ATC delay in SFO because of marine fog and a micro cell storm delayed landing and take-off at Nashville. The gate was changed 5 minutes from boarding from gate B3 to gate C23 at Nashville airport.

After being assaulted by a flight attendant I was then brushed off as oh well because he long braids didn’t mean to whip me in the eye. I have filed complaints and will see. But like any other issue I’ve had with kayak involved it’s been trash. Last time I’ll be using your app

AC sub par. WiFi not working correctly. Ac sucked. Seats very narrow.

Near 4 hour flight with only 1 service. Had to use call button to request water. Internet and power not working until into flight. Internet would stop working during flight.

Southwest's seats are the least comfortable I have ever sat in.

The cabin was quiet for the redeye flight. The area was clean. The staff was great. The 787 Max was in good condition. Drawbacks were that the seat widths were tight for some passengers. The seat padding was at best average and for a long flight uncomfortable.

Southwest like most American domestic airlines, is a mediocre airline. But it is among the cheapest. Oh well.

My flight was delayed 50 minutes and we were rushed to board to then sit for 15 minutes until the pilot arrived. Unacceptable since we could have waited to board. Also the delayed flight was updated AFTER we boarded to more than the 10 minutes as originally stated.

Terrible. They wouldn't allow me on my flight on the 14th..

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

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.

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.

They are still charging me after taking 466 and 833 for round trip from AR to to Bradley airport from 19 to 21. Then poor experience. Am hurt and I will say it on social media. Please stay away from this airline. I see in my bank account they are still taking 644. Am trying to stop it. I used to fly United airlines and I suggest that if you don't want extra charges and good service you go back there. American airlines delayed my flight again and I was late for my meeting, no recompensation but charging me over and over.

No internet on a flight over three hours in this age is criminal. Staff inattentive and dismissive

They have the most inexperienced / rude flight staff I’ve encountered

very difficult boarding process - aggressive passengers not the friendliest crew

WiFi was not eorkig (again) And the plane was from 1990 with the screens which were.not touch and most didn’t even work and if lucky could tune in tv

I paid extra for a seat closer to the front. The TV didn’t work at all for the entire flight. Would have been nice to know before I purchased an “upgraded “ seat

It was great. I had never flown on JetBlue before, but would be very happy to fly with them in the future.

Worst flight experience ever flights canceled. JetBlue told us just did not even bother standing in line to come back in one and a half hours then without any information we had to go pick up all of our luggage and spend over $2000 in accommodation just to get home. JetBlue said that the next flight available for us to get home would be three days later. Absolutely absurd hasn’t offered to give us any compensation do not fly JetBlue horrible company. They said it was based on the weather and the weather is great in all locations that we would’ve been flying to total hoax. I think it’s a conspiracy theory.

The captain gave good announcements and the flight attendants were friendly. The WiFi was pretty good. The plane itself looked very old inside and the seats were very uncomfortable. The screens in the seat backs were the smallest I’ve ever seen. There were so many loud and obnoxious kids on this flight and the parents didn’t do much to try to quiet them down. Some had videos and games on tablets with higher than necessary volume going the whole time.

Too many long delays with JetBlue. Worst major airline that serves JFK but unfortunately I keep going back because of the prices.

My JetBlue experience was nice. The flights ran on time, the aircraft was clean and comfortable, and the flight attendants were attentive. My only issue, which is isolated to the low-cost (budget) option at JetBlue, is that the check in process makes the user feel that they have to buy their seats. The seats offered for purchase are upgrades from the budget seats you get (which are essentially the last seats remaining). The interface should not make it feel like you must purchase a seat.

Spirit rescheduled a 4:30 PM flight to 8:52 AM. That's ridiculous and borderline fraud.

Everything was fine. I'm average height and I pack light. I'm ready for my Spirit flight.

Changing the flight time to 6:15 am on the return flight is extremely inconvenient. The flight was okay. It was on time. The crew was friendly. The seats were uncomfortable. All the upsells are annoying, and I would prefer paying a single higher fee and not have to purchase so much extra.

Spirit Airlines was ok but TRAVELHELPDESK, the 3rd party travel agent IS A JOKE! VERY RUDE CUSTOMER AGENTS ont he phone. NO HELP AT ALL. But the airlines was ok.

No Tumberlence smooth flight. Try to change the menu on Snacks.

Cancelled my flight last minute and did not help me rebook. It was a horrible experience.

No frills - because you get what you pay for. The crew was amazing!! I had plenty of room to spread out because the flight was half full. Which made it easy to sleep.

The terminal crew is so rude cabin crew is extremely rude flight is very good

Spirit is low fare air line. Food also cost you. No free food.

The flight was delayed twice with minimal explanation. The terminal and airplane were filthy. The food voucher didn’t even cover a tiny pizza from a kiosk in the terminal. All in all, a pretty miserable experience for a flight to attend a funeral

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.

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