$102 Find Cheap Flights from Reagan Washington National Airport 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 Reagan-National to Caribbean departing on 3/11. 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.
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Best Caribbean Flight Deals from Reagan-National

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

Punta Cana
Punta Cana1 stop$332
Santo Domingo
Santo Domingo1 stop$382
Montego Bay
Montego Bay1 stop$352
Oranjestad
Oranjestad1 stop$343
Nassau
Nassaunonstop$306
Kingston
Kingston1 stop$380
Simpson Bay
Simpson Bay1 stop$453
Providenciales
Providenciales1 stop$392
Bridgetown
Bridgetown1 stop$534
Port of Spain
Port of Spain1 stop$368
George Town
George Town1 stop$420
Willemstad
Willemstad1 stop$504
St. John's
St. John's2 stops$486
Puerto Plata
Puerto Plata1 stop$493
Aguadilla
Aguadilla1 stop$264

Good to know

Low season

September

High season

July

Cheapest flight

$102
Best time to beat the crowds with an average 16% drop in price.
Most popular time to fly with an average 7% increase in price.
Flight from Reagan Washington National Airport to Nassau

FAQs - booking Caribbean flights

  • How does KAYAK find such low prices on flights from Reagan Washington National Airport 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 Reagan Washington National Airport to Caribbean.

  • How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from Reagan Washington National Airport to Caribbean?

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight from Reagan Washington National Airport 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 Reagan Washington National Airport 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 Reagan Washington National Airport 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 Reagan Washington National Airport 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 Reagan Washington National Airport to Caribbean up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

See more FAQs

Top tips for finding cheap flights to Caribbean

  • Looking for a cheap flight? 25% of our users found tickets from Reagan Washington National Airport to the following destinations at these prices or less: San Juan $178 one-way - $364 round-trip
  • Book at least 1 week before departure in order to get a below-average price.
  • High season is considered to be January, November and December. The cheapest month to fly from Washington, D.C. is September.
  • Morning departure is around 3% cheaper than an evening flight, on average*.
See more tips
*Average of the lowest prices shown in KAYAK’s search results for departures within the next 30 days

Top 5 airlines serving from Reagan-National to Caribbean

Need help choosing which airline to fly with from Reagan-National 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.
8.1
SouthwestOverall score based on 4411 reviews
7.6Entertainment
8.2Boarding
8.1Comfort
7.1Food
8.7Crew
Airline reviews

Gate agents were informative and friendly… flight attendants were as well. Had a fun time chatting about their legacy AirTran experiences as a former fan of the airline that Southwest acquired.

10.0 ExcellentAnonymous, Jan 2025ATL - LGA
Read more Southwest reviews

Gate agents were informative and friendly… flight attendants were as well. Had a fun time chatting about their legacy AirTran experiences as a former fan of the airline that Southwest acquired.

Flight was awfully bumpy and landing was a bit jolting. I was in the restroom when snacks and drinks were served and was not asked if i wanted any. I had to ask for water finally.

Wi Fi was horrible kept cutting out the whole time and too expensive

I really like open seating. I hate that I've heard this is going away. This is one of the unique things that makes Southwest my goto choice.

Boarding was a little late, but made up for it. It was quick to taxi to the runway, since it's a smallish airport.

Excellent! Only question is how we check in at exactly 24 hours in advance and end up at the end of the B boarding group

Multiple delays and gate changes. Arrived at final destination 6 hours late. All rental cars had been taken.

Employees were kind and funny, as always! Flight was late but no announcements were made for people with tight connections to help them transition quickly. No service due to turbulence.

It was 2 hours 45 minutes late, for no apparently clear reason.

I recently flew Southwest from San Jose to Honolulu. I was very impressed with the flight crew, especially the flight attendant in charge of the front of the plane. She came through the aisle at least five times for drinks and water, and two times for snacks. I have not seen such service since I flew first class. Also, for the first time, they gave us the correct baggage claim number, and the luggage came out quickly. I can't wait for Southwest to have assigned seating! I absolutely hate the Cattle Call boarding procedure and the mad dash to get seats and overhead bins. However, the boarding was efficient.

Boarding is, as it always is… horrible. Gate lice. Slow moving zones. Too many people with carry ons

I loved having a most black flight crew during Black History Month; rather by design or accident I appreciated the representation. ❤️

This was the second flight this week with flight attendant Marcus I’m not sure if his last name is Lane or Lang but this guy is awesome. He funny, attentive and his service is 5 stars. Marcus makes business travel more enjoyable !

Although the flight left late, we arrived early. It was one of the quickest boarding and off boarding experiences I’ve had. It was kind of annoying the only drinks they had were water, coffee, and tea. The flight was very smooth, temperature was just right, and flight attendants were friendly.

Rode in a smaller plane and short trip meant no snacks, no free wifi or tv. It was only 30min flight so honestly wasn’t a big deal to lack these items.

Lower number on this flight so spaced out passengers. Able to enjoy more room to relax during flight. It was lovely.

Kind staff. Snacks are small but that’s the new normal.

Overall, terrible. Flight from SFO was delayed due to “air traffic control issues”, and we were all mislead about connecting flights. Told “you have 20 minutes to catch your connection”. Reality was 5. We got to watch the plane sit at the bridge. Won’t fly Delta with a connection again.

The young man who was our flight attendant in first class was lazy and did not do his job well at all. Never offered drinks upon boarding - actually I take that back... said "are you okay with water" as if I do not want to get you anything else, only passed the snacks around once, got my drink order wrong and then never offered a second round of drinks. He was the worst I have ever seen on Delta and we fly a lot.

Great service. Great staff. Boarding was a little slow, but I think there was a service dog slowing things down.

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.

Very well organized both boarding and deplaning. Very satisfied with the service I received.

I rate it is good we had a 4-hour travel delay at one point but JetBlue gave out food vouchers and travel points credits for another flight so they try to make up for it

Smooth boarding and friendly crew. Unfortunately as soon as we boarded the unit that provides air circulation failed. The pilot informed us and requested maintenance technicians to check it out. The plane became uncomfortably warm without any fresh air coming in. Plus the repair delayed our departure. I am glad the maintenance crew were able to fix the problem. I also was without use of my tv monitor for the first 1/3rd of the trip.

Flight was on time arrived at the destination 10min early they kept in touch via email

I don’t understand the purpose of the orange “priority” tag on my bag. This tagged, my bag is last or near to the last bag to come down the carousel at IAH.

The tv monitor in front of my seat was not responding. The flight crew reset it and it still didn’t work.

The agents was very rude and they charged me $50 for a carry-on bag saying that it was too big and then I saw someone going on a plane with the same size bag as me

Liked nothing. As per previous segment it was delay delay delay.

Terrible. First of all we were delayed 4 3/4 hours departing Honolulu. As we had to leave our condo and the rental car had to be returned we had to go to the airport. Even though we had a business class boarding pass to Washington, since we did not have business class to Montreal we could not access the lounge without paying a $59 fee each. This does not make sense to us. Since we could not meet our original connection United booked us to Montreal via New York LaGuardia on Air Canada. In Washington a further delay got us into LaGuardia too late to make our connection to Montreal so we were booked on another Air Canada flight 3 hours later. We were originally scheduled to arrive in Montreal at 10:40 and arrived at 19:55. A totally exhausting day, United did not offer a meal voucher or any type of compensation. Air Canada did give us a digital meal voucher. The food in United business class is poor among all meals offered. The pods look nice but are not that confortable. Overall would not fly on United again.

Plenty of room for me and the cat in Premium Economy. Seat was comfortable. Boarding was a breeze. The lady at the special check-in desk was great, super helpful and professional.

I completely missed my flight because the first leg was longer than planned. I had to sleep overnight in the airport because no accommodation was provided and then sent to Trinidad in the morning with an anticipated 7 hour layover before my flight to Georgetown which was now with Caribbean Airlines. I tried twice with customer service to see if they could put me on an earlier flight which had seats available but was told it wasn’t possible.

First class felt like economy, seats were horrible, food was horrible, staff inattentive

EVen warmer in the plane it think it was 24+ degrees

The flying experience was great. The flight was on time with no boarding issues during a peak travel period. The short cut baggage drop and process was not smooth and efficient at Dulles.

Delays on all NY flights. There was no communication on why but they didn’t say it was weather. Other carriers were not delayed.

The flights were terribly delayed and then cancelled which forced us booking another night at the hotel. Very poor management from American Airlines

Extraordinary service in business class, and very good breakfast and snacks. A really lovely flight.

Same as before being upgraded to business class made it perfect

I flew out of Reagan National. My flight was delayed, delayed, delayed, and then canceled ...THREE TIMES over TWO DAYS. Staff were seemingly not empowered to provide information on why the flights were screwed up. A real nightmare.

They cancelled our flight without warning OR a refund. Never doing business with American Airlines again! This is the second AA booked trip in a row that we've had challenges with.

Crew was late. Baggage was late. 2hs inside the plane waiting fro de-icing and traffic. A 3:30hs flight ended up being almost 6hs inside the airplane.

Flight delayed on both ends - have a gate ready at DCA, don't make us sit for 30min after being late to take off as well.

The seats were crammed and the guy in front of me wouldn't stop reclining. If AA is cramming extra rows in, they need to take away the reclining in coach. My knees were smashed for 4 1/2 hours and I was very close to confronting the passenger in front of me.

This flight didn’t happen because AA agents didn’t let us board the flight

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

Recent round-trip flight deals

4/1Tue
2 stopsUnited Airlines
14h 18mDCA-SJU
4/4Fri
1 stopUnited Airlines
7h 48mSJU-DCA
$169
3/5Wed
1 stopUnited Airlines
9h 46mDCA-SJU
3/18Tue
1 stopUnited Airlines
9h 26mSJU-DCA
$193
3/4Tue
1 stopJetBlue
6h 19mDCA-SJU
3/5Wed
1 stopJetBlue
8h 03mSJU-DCA
$213
3/3Mon
1 stopJetBlue
8h 14mDCA-SJU
3/25Tue
1 stopJetBlue
7h 47mSJU-DCA
$219
3/11Tue
1 stopDelta
6h 50mDCA-SJU
3/18Tue
1 stopDelta
10h 15mSJU-DCA
$247
3/3Mon
nonstopAmerican Airlines
2h 45mDCA-NAS
3/6Thu
nonstopAmerican Airlines
2h 40mNAS-DCA
$306
4/28Mon
1 stopAmerican Airlines
8h 58mDCA-SJU
5/2Fri
1 stopAmerican Airlines
9h 36mSJU-DCA
$307
3/5Wed
1 stopSouthwest
7h 00mDCA-SJU
3/12Wed
2 stopsSouthwest
9h 20mSJU-DCA
$318
3/16Sun
1 stopDelta
7h 03mDCA-SJU
3/25Tue
1 stopDelta
10h 15mSJU-DCA
$326
3/4Tue
2 stopsSouthwest
10h 25mDCA-SJU
3/11Tue
2 stopsSouthwest
9h 20mSJU-DCA
$331

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Recent one-way flight deals

3/11Tue
nonstopAmerican Airlines
3h 00mDCA-NAS
$102
3/11Tue
1 stopJetBlue
12h 32mDCA-NAS
$105
3/6Thu
1 stopUnited Airlines
7h 48mDCA-NAS
$107
4/1Tue
1 stopJetBlue
9h 11mDCA-SJU
$110
3/19Wed
1 stopDelta
7h 01mDCA-NAS
$112
5/19Mon
nonstopAmerican Airlines
2h 40mDCA-NAS
$119
3/1Sat
1 stopDelta
6h 34mDCA-SJU
$124
3/1Sat
2 stopsUnited Airlines
14h 26mDCA-SJU
$161
3/6Thu
1 stopSouthwest
9h 45mDCA-SJU
$220
3/10Mon
2 stopsSouthwest
17h 05mDCA-MBJ
$228

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Last minute flights from Reagan-National to Caribbean

Last minute flight, train and bus deals

2/24Mon
nonstopJetBlue
3h 40mDCA-SJU
2/26Wed
multi-stopJetBlue
8h 03mSJU-DCA
$278
2/24Mon
nonstopJetBlue
3h 40mDCA-SJU
2/27Thu
nonstopJetBlue
4h 04mSJU-DCA
$287
2/22Sat
multi-stopDelta
10h 46mDCA-SJU
2/26Wed
multi-stopDelta
6h 38mSJU-DCA
$296
2/22Sat
multi-stopDelta
9h 48mDCA-SJU
2/25Tue
multi-stopDelta
8h 33mSJU-DCA
$307
2/25Tue
multi-stopUnited Airlines
6h 36mDCA-SJU
3/2Sun
multi-stopUnited Airlines
8h 49mSJU-DCA
$316
2/22Sat
nonstopAmerican Airlines
2h 45mDCA-NAS
2/27Thu
nonstopAmerican Airlines
2h 40mNAS-DCA
$326
2/21Fri
multi-stopUnited Airlines
7h 36mDCA-SJU
2/27Thu
multi-stopUnited Airlines
12h 12mSJU-DCA
$326
2/22Sat
multi-stopAmerican Airlines
11h 25mDCA-NAS
2/26Wed
nonstopAmerican Airlines
2h 40mNAS-DCA
$331
2/22Sat
multi-stopSouthwest
8h 15mDCA-SJU
2/26Wed
multi-stopSouthwest
11h 35mSJU-DCA
$392
2/22Sat
multi-stopSouthwest
8h 15mDCA-SJU
2/28Fri
multi-stopSouthwest
11h 15mSJU-DCA
$410

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Everything you need to know for your flight to Caribbean

Information on your arrival and departure airports

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