$114 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 3/19. 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

Search 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 23% 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.

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$433
Santo Domingo
Santo Domingo1 stop$437
Montego Bay
Montego Bay1 stop$425
Oranjestad
Oranjestad1 stop$423
Nassau
Nassaunonstop$330
Simpson Bay
Simpson Bay1 stop$454
Kingston
Kingston1 stop$471
Providenciales
Providenciales1 stop$416
Bridgetown
Bridgetown1 stop$601
Port of Spain
Port of Spain1 stop$323
George Town
George Town1 stop$404
Willemstad
Willemstad1 stop$463
St. John's
St. John's1 stop$536
Puerto Plata
Puerto Plata1 stop$423
Aguadilla
Aguadilla1 stop$254

Good to know

Low season

September

High season

March

Cheapest flight

$114
Best time to beat the crowds with an average 16% drop in price.
Most popular time to fly and prices are also 1% lower on average.
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 $198 one-way - $338 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 February.
  • Morning departure is around 8% 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 4662 reviews
8.2Boarding
8.1Comfort
7.2Food
8.7Crew
7.7Entertainment
Airline reviews

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.

10.0 ExcellentRachel, Jan 2025TPA - MDW
Read more Southwest reviews

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.

Crew was great flight was great baggage claim was a failure. It took over 1 hour for bags to arrive. Poor communication poor effort when I spoke to the supervisor about the delay

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

Flight left early and arrived early. the whole trip was excellent.

Seats were really tight and the seat belts did not give enough slack.

I like in St George and prefer to fly out of CDC than SGU. Hopefully, they will continue the flights out of Cedar

Broken jer bridge. Poor communication about it. Lost 2 of 4 luggage pieces

Overall, it was okay. Seat was a little cramped. Would’ve liked more substantial snacks or opportunity to buy some.

Newer plane, relatively easy boarding, not a full flight and was told that we could not be moved up because of weight and balance issues. Otherwise, a very good experience.

Other then mechanical/ computer problem and 3.5 hours flight delay the flight was great. I guess that what happened when you fly an old airplane now a day.

I was with one of the last zones to board. It was kind of annoying to finally get called to board and my whole section was already on the plane. Clearly they boarded with previous zones. So by the time I got on board, there were no spaces for my luggage above my head. I had to put my luggage 4+ rows behind me, which meant that I had to wait even longer to get off the plane, since I had to wait for those rows to clear the aisle before I could retrieve my luggage and exit the plane. This also held up the plane cleaners, as they couldn't service my row until I cleared it, so they were all standing there waiting for me, while I'm standing there waiting for the other passengers to clear the aisle. Anyways, I wasn't in a rush this time, so I just waited, but I could see that being a problem in the future. Now, I could have checked my luggage, of course, but coincidentally, a friend of mine on the same flight got their luggage damaged (wheel completely knocked off) and was told by the Baggage Attendant in the airport that Delta doesn't "cover wheel damage" on luggage. This was disappointing to hear. I'm glad I didn't check mine through. If it were my luggage, I'd be highly frustrated to hear that. It makes me not want to check my luggage in the future.

The dear was very limited in space. I could put my water bottle in seat basket. Also, there was no inflight entertainment in the delta app?

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

Maybe add a seat trade app for flyers that didn’t get seats together

It’s been awhile since I have traveled on United. I, along with my family who were on the flight noted how smoothly everything went . Boarding, flight crew and service was excellent.

The seats on this flight were almost roomy enough to be the basic amount needed for human existence. I think my favorite part of this flight was it landed at an A gate, which was the most palatial part of Sea-Tac I've ever seen - a massive improvement from the S gates.

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.

Fast checkin with the self serve terminal, good communication at the boarding gate.

Very friendly staff. The flight was on time. Need a bit heavy covers/blankets. It can get colder with a thin blanket.

The plane was clean. The staff was excellent. The flight attendants were very good. Enjoyable flight. Overall. The seats in the back are too small but, will always be.

I paid for what I got which was cheap, I brought my own entertainment. I knew what to expect, so I could be prepared. If you’re flying economy, check in early like me. I have no problems with my flight, was on time, staff were friendly, and overall good experience.

Boarded over an hour late, no communication, the sign just changed, no attendant to answer questions - she disappeared forever (hiding). Small plane and couldn’t hear the overhead nor understand.

Service in first class no longer exists on American Airlines .

Customer service in first class does not exist on American Airlines

I never have a good experience with American and this was no different. The airplane was INCREDIBLY hot. Like unbearably so. Everyone was fanning themselves with pamphlets and sweating. When someone asked the flight attendant to turn down the temperature they were told there was nothing the crew could do. Once we pushed back from the gate we then had to wait an hour to take off and the communication from the crew was not good. People were getting up this whole time and a man was even in the bathroom when we took off. Once we landed at our destination we waited another 30 minutes at the gate to deplane with, again, no communication from the crew as to what was going on.

Flight was delayed due to a steering issue with plane. The delay caused me to miss the connecting flight. The delay caused me to spend an extra 21 hours in airports and flights to get to my destination. The plane issue obviously should have been found and fixed before we even boarded. Ridiculous.

First, to be fair, the flight was on time and the trip through the air was relatively smooth. But the flight was full, and they were checking carryons. As this process went on, the crew got increasingly rude and overbearing. During the drink service, a young girl (maybe 9) who had gotten up to use the lavatory got stuck behind the cart. At some point, she started feeling fearful and overwhelmed. Passengers noticed this and asked the crew to let her return to her seat. They refused. Then she started crying, and they still refused to move the cart forward to let her sit. The poor girl was trying to be brave and compose herself. The crew handled the situation terribly and with zero grace or decency. That episode, to me, encapsulates AA’s attitude toward its passengers. Disgraceful. The plane itself was cramped and miserable, as usual. There was zero inflight media or entertainment, other than the lane and borderline inappropriate jokes the steward made during the safety briefing. Then, of course, it took the better part of an hour for the checked bags to show up at the carousel. AA is no better than the el cheapo airlines these days and a far, far cry from its former self.

This particular flight wasn't very full at the back, so there were three seats available for spreading out and getting relatively comfortable

First class flight attendant was rude and lacked any customer service skills.

Customer service for American Airlines first class is at an all time low.

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

Recent round-trip flight deals

2/2Sun
1 stopAmerican Airlines
6h 59mDCA-SJU
2/7Fri
1 stopAmerican Airlines
8h 23mSJU-DCA
$169
3/3Mon
1 stopUnited Airlines
7h 40mDCA-SJU
3/5Wed
1 stopUnited Airlines
8h 37mSJU-DCA
$193
3/11Tue
nonstopJetBlue
3h 41mDCA-SJU
3/11Tue
nonstopJetBlue
4h 14mSJU-DCA
$265
4/1Tue
nonstopJetBlue
3h 46mDCA-SJU
4/2Wed
nonstopJetBlue
3h 59mSJU-DCA
$270
2/17Mon
1 stopDelta
8h 08mDCA-SJU
2/19Wed
1 stopDelta
7h 34mSJU-DCA
$297
3/8Sat
1 stopDelta
6h 34mDCA-SJU
3/13Thu
1 stopDelta
10h 15mSJU-DCA
$299
3/4Tue
1 stopSouthwest
7h 00mDCA-SJU
3/11Tue
2 stopsSouthwest
9h 20mSJU-DCA
$319
2/10Mon
1 stopSouthwest
10h 55mDCA-SJU
2/13Thu
2 stopsSouthwest
11h 15mSJU-DCA
$327
4/4Fri
2 stopsAir Canada
24h 35mDCA-CUR
4/8Tue
1 stopAir Canada
26h 08mCUR-DCA
$470
4/4Fri
1 stopAir Canada
18h 00mDCA-CUR
4/8Tue
1 stopAir Canada
26h 08mCUR-DCA
$476

Search by stops

Search by airline

Search by price

Recent one-way flight deals

3/19Wed
nonstopAmerican Airlines
3h 00mDCA-NAS
$114
2/21Fri
2 stopsDelta
8h 10mDCA-NAS
$119
3/18Tue
nonstopJetBlue
3h 41mDCA-SJU
$125
2/19Wed
1 stopDelta
6h 07mDCA-SJU
$130
1/26Sun
1 stopAmerican Airlines
6h 30mDCA-SJU
$134
1/26Sun
1 stopUnited Airlines
5h 40mDCA-NAS
$144
2/23Sun
nonstopJetBlue
3h 40mDCA-SJU
$145
3/8Sat
1 stopSouthwest
7h 25mDCA-SJU
$150
2/16Sun
1 stopUnited Airlines
9h 13mDCA-SJU
$151
5/12Mon
1 stopSouthwest
7h 05mDCA-SJU
$173

Search by stops

Search by airline

Search by price

Last minute flights from Reagan-National to Caribbean

Last minute flight, train and bus deals

1/26Sun
nonstopJetBlue
3h 40mDCA-SJU
1/30Thu
nonstopJetBlue
4h 06mSJU-DCA
$250
1/26Sun
multi-stopDelta
9h 46mDCA-SJU
1/30Thu
multi-stopDelta
9h 00mSJU-DCA
$259
1/24Fri
multi-stopAmerican Airlines
6h 59mDCA-SJU
1/25Sat
multi-stopAmerican Airlines
12h 14mSJU-DCA
$262
1/23Thu
multi-stopAmerican Airlines
9h 14mDCA-SJU
1/29Wed
multi-stopAmerican Airlines
6h 38mSJU-DCA
$263
1/26Sun
nonstopJetBlue
3h 40mDCA-SJU
1/28Tue
nonstopJetBlue
4h 06mSJU-DCA
$270
1/25Sat
multi-stopUnited Airlines
8h 36mDCA-SJU
1/27Mon
multi-stopUnited Airlines
7h 20mSJU-DCA
$294
1/24Fri
multi-stopUnited Airlines
8h 25mDCA-SJU
1/24Fri
multi-stopUnited Airlines
7h 20mSJU-DCA
$296
1/24Fri
multi-stopDelta
8h 47mDCA-SJU
1/31Fri
multi-stopDelta
9h 00mSJU-DCA
$297
1/23Thu
multi-stopSouthwest
10h 40mDCA-SJU
1/29Wed
multi-stopSouthwest
6h 50mSJU-DCA
$362
1/26Sun
multi-stopSouthwest
11h 40mDCA-SJU
1/29Wed
multi-stopSouthwest
6h 50mSJU-DCA
$392

Search by stops

Search by airline

Search by price

Everything you need to know for your flight to Caribbean

Information on your arrival and departure airports

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