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Find cheap flights from Washington, D.C. to Caribbean Islands from $67

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 5/20. 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
0 bags
Wed 6/5
Wed 6/12

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Best Caribbean Islands Flight Deals

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

Punta Cana
Punta Cana1 stop$191
Montego Bay
Montego Bay1 stop$295
Santo Domingo
Santo Domingo1 stop$248
Oranjestad
Oranjestad1 stop$276
Nassau
Nassau1 stop$264
Kingston
Kingston1 stop$319
Simpson Bay
Simpson Bay1 stop$217
Providenciales
Providenciales1 stop$437
Port of Spain
Port of Spain2 stops$321
Bridgetown
Bridgetown1 stop$309
George Town
George Town1 stop$405
Aguadilla
Aguadilla1 stop$264
Castries
Castries3 stops$977
Willemstad
Willemstad1 stop$393
St. John's
St. John's1 stop$518

Good to know

Low season

September

High season

March

Cheapest flight

$67
Best time to beat the crowds with an average 16% drop in price.
Most popular time to fly with an average 13% 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 to Caribbean Islands from Washington, D.C. 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 to Caribbean Islands with an airline and back to Washington, D.C. 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 to Caribbean Islands from Washington, D.C. up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

See more FAQs

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

 
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
DeltaOverall score based on 10818 reviews
8.2Boarding
7.9Comfort
7.4Food
8.6Crew
8.0Entertainment
Airline reviews

The gate area was incredibly short staffed, with one representative manning 4-5 flights, which caused a 3 hr delay in boarding even though the plane was all ready to leave. Other flights also were delayed because of this. The flight crew was awesome and I feel bad for the only gate worker on call, but Delta needs to hire more employees.

2.0 MediocreAnonymous, May 2024AVL - LGA
Read more about Delta reviews

The gate area was incredibly short staffed, with one representative manning 4-5 flights, which caused a 3 hr delay in boarding even though the plane was all ready to leave. Other flights also were delayed because of this. The flight crew was awesome and I feel bad for the only gate worker on call, but Delta needs to hire more employees.

Very frustrated with boarding gate crew. She announced the plane was small and they would be limiting us to one item to carry on. Not a problem for me as I understand the tiny planes have limited space!! Not the case here! It was a rather large plane and had plenty of room for bags! So because I don’t want to be one of “those people” who ignores the request to check a carry on I did so asking if I would be able to pick it up at the bottom of the ramp on arrival in Knoxville to which she responded “yes”! Then I watched as every other passenger held onto their 2 items and boarded!! Then when we arrived in Knoxville our 2 carry ons had been put with all the other luggage and we had to go to baggage pick up and wait for all the big checked bags to come off the carousel! So she lied!! Frustrating. Next time I won’t be so nice!

It was a good experience except when boarding a female flight attendant did not go out of her way to assist my teenage daughters in finding space for their carry-ons after their compartments were full.

On time departure, smooth trip, flight attendant told through passengers the gate we would arrive at and the gate our outbound flight was departing from. Early arrival

Checking in at the airport the agent only booked the first keg of my trip and had my checked luggage going to the airport with a layover! Never was issued a boarding pass for the second leg or received sticker fir my checked bag. All was well in the end! Delta agents helped to resolve the situation!!!

Delayed due to an ill passenger after loading. Not preventable on Delta's part. Was in first class. The seats are becoming worn and detaching from their velcro attachments. Only got snacks on flight. The attendant was not the friendliest.

I would fly again the whole experience was great. The only feed back I can give that they don't do that American Airlines does is the crew there is more humorous with boarding and thank their passengers. It makes it more fun to fly with them. I would however fly Delta again.

Big plane, long flight, absolutely no leg room and basically non existent air! I am 5”4’ and always travel Main Cabin, I was miserable on this plane and could barely move when we arrived in Cabo due to the cramped leg area!

From Atlanta to Cabo I would have hoped on a plane that size I would have been able to breathe and wiggle my feet a little! The leg room in that plane is non existent and I am only 5”4’. And the air vent either wasn’t working very well or just could not blow air from the ceiling to the seat area as I was suffocating through the entire flight! And please don’t say I would have been more comfortable in first class because I cannot afford those rates and have always travelled Main Cabin without issues !

The pilots were good. Disappointing when planes don't have electrical ports

Great. Loved that there was WiFi on flight to keep in touch and excellent service of beverages and snacks.

Business class is great. New airplane, very comfortable, better than some of the major airlines I am used to

Terrible. Flight was cancelled due to the weather in the east and sout east(florida). Did not get any compesation of any kind. According to them, it was not under their control so I lost all the money paid for the 2 fairs from Raleigh, NC to Orlando, Fl.

great flight. Pilot was communicative, flight attendants were excellent. Really nice experience except my tv didn’t work.

Overall, the flight was better than the flight I took to go to Florida, which had a bunch of problems. The crew is really nice and the plane was new so it had a small problem when we were on the runway, but the flight itself was great. They even made some time back up, which is always a good thing.

at the time for boarding the lady just call Group A and no other goups and everybody from A to F go inside without the right turn,and when we get in theres no more spsce for carry on , the ones that get in at not correct group from the back occupy our space !!!!! a mess !!!!

There were multiple delays but JetBlue tried to make the boarding and departure process as quick and efficient as possible. The crew was as detached from reality as could be, meaning: not very friendly and just doing things by the numbers.

I had back trouble prior to my flight and everyone was great about helping me.

Jetblue needs to improve on Onboarding as it seems to always be behind on departing. It never leaves on time. I would recommend to have an earlier Onboarding in order to leave on time and respect your customers time as well.

40 minute delay before take off after boarding flight. Bright lights throughout night flight due Issues with light panels. In flight Entertainment nonfunctional

Should have video screens Plane audio was poor and without wired connection hard to understand crew. Should serve more than just cups of water and pretzels on six hour flight. Did not see crew rest of flight. Fix charging sockets to retain charging blocks.

Food was terrible Not many options Stewards dont care Delay

The ride was good but no food ot entertainment hence, it was just over an hour flight.

they made me check my carryon. There was space in the overhead bins.

The plane was delayed 2 hours. The wifi did not work. The seat in first class was not comfortable because the bottom felt like it lost all of its padding. And I did not like when the flight attendant made me wait at my seat to use the bathroom and didn't tell me why. If there were too many people using the 1st Class bathroom, she should have told me to go in the back, coach bathrooms. I guess I have to feel fortunate that they found 2 local pilots to still fly the plane tonight after the original pilots ended up at an airport 60 miles away due to high winds.

The crew were really great, but the 4 hour delay in small chunks was the worst.

Every experience was good except for the lack of comfort in those economy seats. I never had knee pain until that flight. Those seats are uncomfortable.

I bought internet for the flight. Don’t waste your money. I wasn’t able to download a 1 Mb file from Google Docs during a 3-4 hr period. You can only use WhatsApp and email if you are willing to wait.

Just a crappy airline. The same every time. You feel you are a cow on a farm. You are being being whipped and pulled.

Wasn’t very crowded. Seamless processes. No issues traveling with two little kids.

Overall the flights pretty good. The snacks we’re good and they were plenty of them. Both boarding and deplaning went quickly.

Delayed abs delayed Gate crew giving poor info - we are definitely leaving at —- Ultimately to cancel flight after 4+ hours of delays Just cancel it earlier

The flight was scheduled to depart DCA at 12:30 pm but was delayed twice on the ground so that we were finally scheduled to depart at around 4:00 pm. Once we boarded, it was announced that takeoff would be delayed again to fix a hydraulic problem which delayed our eventual takeoff until around 5:00 pm. Once we departed, it was a smooth flight back to ORD. We did not get any explanation about what caused the original significant delay. In my experience, this happens frequently with AA.

Lots of weather delays that were poorly communicated and managed. I get there are weather delays but they didn’t make it clear what was happening or comfortable on the plane

Everything was on time; the flight attendants and the gate personnel were very pleasant and helpful.

Our second leg to Jackson WY was unable to land due to weather. We were flown back to Dallas after stopping in SLC. We were given hotel rooms and vouchers. We were told that we would be back on the same plane in the morning. Instead we were given a different flight with different seats. Not a good experience. No one knew what was going on.

Perfect flight. On time departure and early arrival. Smooth flight.

Awful! The flight was delayed and we sat on the plane in DCA for an hour because fuel was out in the wrong part of the plane and would not be accessible during flight. So the plane had to be refueled in correct tank. They also allowed someone to get off of the plane. This delayed my six hour flight by an hour and made me miss my connecting flight. I ran to new gate and American Airlines agents new about the delay and even knew that I was trying to make the connection. They knew thru communication with my friend while in flight that I was in the airport and running to the new gate and they still closed the gate and refused to let me on the new flight despite plane still being at the gate. It was horrible and I had to be rebooked on a flight for 24 hours later. This has been a nightmare and if American Airlines can cause customers to be delayed and then have zero empathy as having an on time flight was more important to them than helping a customer who was delayed by no fault of her own, then it's seems that it's not a company that I want to continue to give my loyalty to. I'm so disgusted.

Help was available but timing was bad in my case

It was a horrible snow storm, but updates were inconsistent and the app never displayed a remotely accurate time or gate until very close to boarding.

Terrible… missed our flight due to ridiculously long time to go thru baggage check-in!

The crew was not great or professional. It seemed like they didn't really want to be there. A true lack of effort for accommodating customers.

Everything was really good but the seats are not very comfortable.

I paid for WiFi, but it (WiFi) was very very slow, will never take again! Impossible open Utube 😤😤😤

I had no legroom, although I paid for extra legroom. I could barely put my bag in front of my feet and under the seat. The Wi-Fi was horrible. In fact the flight attendant said that they had to reboot it and see if it was going to work and never did.

The guy with severe body odor sat next to me. For the whole duration of the flight it was a torture. The airline should have better policy on limiting people with bad body odor to board the flight. Passengers should not be the ones to endure bad odor for the whole duration of the flight. The airline should be e the one to ensure decent air quality for ever passenger.

Overall it was a miserable experience... I will never fly spirit for more than a 3 hour flight or overnight.

The boarding attendant was slightly rude when I asked about checking our stroller. Made me feel like I was bothering her.

My wife and I are both handicapped and at boarding they upgraded us to a seat closer to the front rather than all the way towards the back. Much appreciated.

Not much seat room, but that was unexpected. But the seat headrest was very uncomfortable.

Book cheap flights from Washington, D.C. to Caribbean Islands

Recent round-trip flight deals

5/14Tue
nonstop
3h 46mBWI-SJU
5/15Wed
nonstop
4h 18mSJU-BWI
$129
6/4Tue
1 stopSpirit Airlines
15h 26mBWI-SJU
6/11Tue
1 stopSpirit Airlines
16h 56mSJU-BWI
$130
5/29Wed
nonstopJetBlue
3h 51mDCA-SJU
5/29Wed
nonstopJetBlue
4h 08mSJU-DCA
$257
5/29Wed
nonstopJetBlue
3h 51mDCA-SJU
6/12Wed
nonstopJetBlue
4h 05mSJU-DCA
$263
5/26Sun
nonstopAmerican Airlines
2h 40mDCA-NAS
5/29Wed
nonstopAmerican Airlines
2h 35mNAS-DCA
$268
8/17Sat
1 stopAmerican Airlines
13h 37mDCA-NAS
8/21Wed
nonstopAmerican Airlines
2h 38mNAS-DCA
$271
6/2Sun
nonstopUnited Airlines
3h 54mIAD-SJU
6/7Fri
nonstopUnited Airlines
3h 59mSJU-IAD
$273
5/29Wed
1 stopDelta
7h 29mDCA-NAS
6/6Thu
1 stopDelta
4h 55mNAS-DCA
$274
6/2Sun
1 stopUnited Airlines
7h 31mIAD-SJU
6/7Fri
nonstopUnited Airlines
3h 59mSJU-IAD
$278
6/11Tue
1 stopDelta
7h 13mIAD-SJU
6/14Fri
1 stopDelta
10h 27mSJU-IAD
$282

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Recent one-way flight deals

5/20Mon
1 stopSpirit Airlines
13h 20mBWI-SJU
$67
5/13Mon
1 stopSpirit Airlines
24h 18mBWI-SJU
$68
5/28Tue
nonstopAmerican Airlines
2h 40mDCA-NAS
$84
5/28Tue
1 stopAmerican Airlines
5h 15mDCA-NAS
$88
6/4Tue
1 stopUnited Airlines
6h 24mIAD-SJU
$141
6/3Mon
1 stopDelta
7h 49mDCA-SJU
$141
5/20Mon
1 stopJetBlue
8h 40mDCA-SJU
$150
6/1Sat
nonstopUnited Airlines
3h 54mIAD-SJU
$151
6/4Tue
nonstopJetBlue
3h 51mDCA-SJU
$158
6/3Mon
1 stopDelta
7h 25mIAD-AUA
$161

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Last minute flights from Washington, D.C. to Caribbean Islands

Last minute flight, train and bus deals

5/10Fri
nonstopSpirit Airlines
3h 46mBWI-SJU
5/14Tue
multi-stopSpirit Airlines
12h 45mSJU-BWI
$166
5/10Fri
nonstopSpirit Airlines
3h 46mBWI-SJU
5/14Tue
multi-stopSpirit Airlines
12h 45mSJU-BWI
$184
5/8Wed
multi-stopDelta
6h 13mDCA-NAS
5/9Thu
multi-stopDelta
5h 43mNAS-DCA
$313
5/9Thu
nonstopAmerican Airlines
2h 40mDCA-NAS
5/16Thu
nonstopAmerican Airlines
2h 35mNAS-DCA
$328
5/9Thu
multi-stopAmerican Airlines
5h 15mDCA-NAS
5/16Thu
nonstopAmerican Airlines
2h 35mNAS-DCA
$333
5/10Fri
multi-stopUnited Airlines
18h 15mDCA-NAS
5/12Sun
multi-stopUnited Airlines
28h 55mNAS-DCA
$426
5/11Sat
multi-stopJetBlue
10h 20mDCA-SJU
5/31Fri
nonstopJetBlue
4h 08mSJU-DCA
$442
5/10Fri
nonstopJetBlue
3h 51mDCA-SJU
6/14Fri
nonstopJetBlue
4h 02mSJU-DCA
$459
5/10Fri
multi-stopDelta
9h 20mDCA-SJU
6/14Fri
multi-stopDelta
11h 10mSJU-DCA
$518
5/10Fri
nonstopUnited Airlines
3h 54mIAD-SJU
5/31Fri
nonstopUnited Airlines
3h 59mSJU-IAD
$554

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Flights to Caribbean Islands

Return flight deals:

Caribbean Islands - Washington, D.C.

Cabin classes:

$220
$315
$284
$38

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