$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 1/21. 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

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

Punta Cana
Punta Cana1 stop$423
Montego Bay
Montego Bay1 stop$403
Santo Domingo
Santo Domingo1 stop$419
Oranjestad
Oranjestad1 stop$394
Nassau
Nassaunonstop$329
Simpson Bay
Simpson Bay1 stop$403
Kingston
Kingston1 stop$470
Providenciales
Providenciales1 stop$445
Bridgetown
Bridgetown1 stop$448
Port of Spain
Port of Spain1 stop$347
George Town
George Town1 stop$440
Willemstad
Willemstad2 stops$481
St. John's
St. John's1 stop$558
Puerto Plata
Puerto Plata1 stop$451
Aguadilla
Aguadilla1 stop$290

Good to know

Low season

September

High season

December

Cheapest flight

$114
Best time to beat the crowds with an average 13% drop in price.
Most popular time to fly with an average 36% 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 to Caribbean from Reagan Washington National Airport 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 to Caribbean with an airline and back to Reagan Washington National Airport 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 to Caribbean from Reagan Washington National Airport 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 $202 one-way - $365 round-trip
  • Morning departure is around 5% more expensive than an evening flight, on average*.
*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 5005 reviews
8.2Boarding
7.7Entertainment
8.1Comfort
7.2Food
8.7Crew
Airline reviews

This was a nicer flight - not fully booked and so we were able to spread out.

10.0 ExcellentJohn, Nov 2024LAS - IND
Read more Southwest reviews

This was a nicer flight - not fully booked and so we were able to spread out.

We had a nice flight. Boarding was easy, our seats were comfortable and the on board service was pleasant.

Planes are aged. The wifi is unreliable and on many fights, no-existent. The flight attendants were very good.

I had a wonderful flight, but the only thing that annoyed me was how crowded TSA was. I still believe airports and all planes work together to bunch everyone together to drive up cost.

Easy to book and to get check in and get on and off.

The last 30 min or so, they put the heat on full. We thought we were being basted.

Excellent experience. WiFi worked on this leg of My trip

Flight was great, but golf bag never made it until later in the day. Even though I had a nonstop flight it was placed on a different one. They made it right with flight credits and I was able to get it the same day.

It seems as though the provisions are even less. Although SWA used to be an economy Airline, that isn't really the case anymore. I paid over $700. for a round trip to Denver and I could have flown just about any airline for the price. The drinks are now in a 6-ounce cup and with ice I'm sure a can would fill more than 2 cups. However, I am very proud of SWA for using paper rather than continuing to contribute to the millions of plastic cups being used each day. I've thought of this fr many years and am so glad to see it come to fruition, if not by only SWA so far.

Exceptional crew! Friendly and professional. Pleasant attitude and treated everyone with respect.

I sat in comfort plus. It was fine. Seats were comfortable. I got drinks and snacks.

Crew was nice. Flight was timely. Seats could be better as well as the food considering it’s first class.

Left on time and arrived early this extending our 31 minute transfer. Bags made it also!

Good and consistent Printer in lounge did not work for me :(

Most of my discomfort was going through TSA. However, the Delta seats had inadequate leg room and I tried my very best to connect to the wi-fi and it was a cumbersome process that finally gave me the info that I needed to sign in AFTER I had completed the flight...Why make it so difficult to use? That said I really really appreciate the pilot taking a little extra time to avoid a bad storm area and both landings in Atlanta and Orlando were flawless to my delight!!!

Delayed in taking off because no flight crew. The in seat entertainment was working properly.

All fine save for the abominable catering. Really gone downhill. We found it all inedible.

I upgraded to first class only to find out that I still had no access to the sky lounge without a sky miles card or AmEx (something that should be emphasized outside of the fine print!) Also, no food or drink service provided during the flight, so I basically paid 4x more just for “free” checked baggage and a bigger seat. Not worth it.

I appreciated friendly service from check-in, to boarding, to in-flight amenities! Attendants were accommodating and helpful. Thank you! Elaine

Delta was really good about being transparent with why we were delayed it’s just that’s the plane was really old and outdated and a lot of the comfort and amenities we know Delta to have did not shine through

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

Communication with the customer and stay is important. Staff off with a minor inconvenience but it worked out of course. Also this was a very old Mint Class plane. They snuck this one in on us. The updated aircraft are much better.

The flight itself was fine, but the boarding process was extremely frustrating. There is no one scanning boarding passes - passengers just scan themselves and enter the jetway. By the time my husband and I got on the plane and were halfway to our seats they determined there were too many bags on the plane and everything at that point needed to be checked. This created a lot of unnecessary chaos. They should have alerted people before getting on the plane that they would need to start checking bags instead of waiting until people were already on the plane.

The best flight I’ve had in a while. The plane was like 25% capacity, if that. Smoothest boarding and deplaning process I’ve ever experienced. Wish all flights were this smooth.

Did not enjoy this flight at all. All of my coworkers flew delta and I chose JetBlue because I really value how simple the WiFi and entertainment is and this flight I didn’t get either. Crew staff was unsympathetic to my system not working, everyone I asked for help with was extremely bothered by my request for help.

In flight on demand didn't work at our seats. Only a single beverage/snack run.

Little snafu at boarding. Staff communicated with gate poorly. Flight attendant was rude making disembark early. This was an older mint class. Needs an overhaul for sure. Food was good. The male flight attendant was really nice.

My encounter with the entertainment services provided on board was moderate; the functionality of the Wi-Fi connection was either sluggish or nonoperational, while the display screens were antiquated and suffered from poor visibility. On the positive side, the cabin exuded a sense of expansiveness, and the crew exhibited amiable and accommodating behavior throughout the journey.

Everything was great except for some reason crew and ground crew could not figure out how to deal with an electric wheelchair and it delayed us 20-30mins. Was pretty frustrating for passengers and the captain.

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.

This was a 5 hour flight with no entertainment and with a snack being provided (pretzels and fruit bar), which are both high in carbs and sugar. Nuts would have been a better choice.

Never nice, United Express partners always do an amazing job.

Everything was perfect except the pad at the top of the seat back. It pushes my head forward in a very uncomfortable position and it is not removable.

Good plane, crew, and flight. Boarding was a bit chaotic. Bathrooms were unacceptable. United DESPERATELY needs a new terminal at IAD.

United Airlines changed my flight 5 hours before I arrived at the airport. This messed up my entire day that I arrived in Japan.

Being stick waiting for gate at ORD cause me to almost miss my connecting flight…being deaf United made no no effort to keep me updated as I couldn’t hear the PA

The Economy Plus rows weren’t as roomy as expected, and the meal service left a lot to be desired for.

United ground crew and pilots are friendly. The in-flight staff (flight attendants) are the worst in the world. Multiple trips, always unpleasant, combative, use implicit threats to not allow for a discussion on their decision. Authoritarian. This seems to stem from an internal corporate wide policy as I doubt that United is intentionally searching for people that are not fit for customer facing positions. I will not fly United again. Good luck fixing your business

The flight was mostly on time, smooth and deplaning was quick. Baggage was really quick at the claim. Comfort was so-so and I paid for economy plus. It was still too crowded and why was a family of 5 scattered all around the plane?

Plenty of overhead space but forced to check my carry-ons both legs

My flight attendant was attentive! The elderly person next to me was flatulent and the flight attendant could see that I was in distress and brought me some face masks

It was as expected for such a short flight. No complaints

The departing flight from Newark to Charlotte was fine. It was the returning flight from Charlotte to Newark that was awful. We had scheduled an 8:35pm return flight time. We got delayed TEN times all the way to 5am in the morning! We were told over 4 different excuses as to why the flight kept getting delayed. First it was the flight crew needed to rest, then it was something technical with the plane, then it was something with air traffic control, and finally it was because they couldn’t find a captain and had to wait until the morning so the captain could get some rest. It was terrible sleeping overnight in the airport. They offered a $12 meal voucher. That was it! And the only place open in the middle of the night was Dunkin’ Donuts who didn’t even accept the voucher. They should have cancelled the flight much earlier on in the evening instead of just stringing us along hour by hour with more delays. Not professional and unacceptable. There was no refund for inconvenience. I probably will not be flying American Airlines again.

This leg they tried and did well with what they had to work from.

It was nice being on a flight that had working wifi. The boarding was quick - why don’t all airlines have small boarding groups window to aisle? Makes so much sense!!! I was disappointed to be the first person stopped to have to gate check my carryon. Especially when there was plenty of overhead space at the back! But I get it…keeps it moving. Crew was nice.

The flight was as good as it gets when flying. On time departure and arrival plus no lost luggage.

My boarding pass wouldn't pull up in the app very easily and had to really dig through my email. That caused a delay in TSA..

Packed commercial flight was as comfortable as can be expected

No food, no entertainment. But the flight was really short so maybe they had to skip drinks. I was able to board early ONLY because I am old and decrepit and they let me pre-board. I RESENT your dumping us into category 9 if we do not pay up. And when I paid for a seat I was STILL given 9. The pre-boarding helps. THIS flight was exceptionally smooth, please congratulate the pilots.

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

Recent round-trip flight deals

12/11Wed
1 stopDelta
10h 15mDCA-SJU
12/13Fri
1 stopDelta
9h 04mSJU-DCA
$248
12/20Fri
nonstopJetBlue
3h 40mDCA-SJU
12/23Mon
1 stopJetBlue
8h 09mSJU-DCA
$267
12/8Sun
1 stopDelta
10h 15mDCA-SJU
12/10Tue
1 stopDelta
10h 51mSJU-DCA
$269
2/16Sun
1 stopAmerican Airlines
6h 45mDCA-SJU
2/19Wed
1 stopAmerican Airlines
7h 09mSJU-DCA
$273
12/20Fri
1 stopJetBlue
9h 53mDCA-SJU
12/23Mon
1 stopJetBlue
8h 09mSJU-DCA
$294
1/15Wed
1 stopAmerican Airlines
9h 45mDCA-SJU
1/15Wed
1 stopAmerican Airlines
6h 38mSJU-DCA
$295
1/9Thu
1 stopUnited Airlines
7h 53mDCA-NAS
1/12Sun
1 stopUnited Airlines
8h 02mNAS-DCA
$343
12/7Sat
1 stopUnited Airlines
8h 36mDCA-SJU
12/12Thu
1 stopUnited Airlines
7h 20mSJU-DCA
$344
1/17Fri
2 stopsSouthwest
12h 00mDCA-SJU
1/22Wed
2 stopsSouthwest
9h 20mSJU-DCA
$389
1/16Thu
2 stopsSouthwest
9h 00mDCA-SJU
1/21Tue
2 stopsSouthwest
11h 35mSJU-DCA
$399

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Recent one-way flight deals

1/21Tue
nonstopAmerican Airlines
2h 55mDCA-NAS
$114
12/16Mon
nonstopAmerican Airlines
2h 50mDCA-NAS
$115
1/20Mon
2 stopsDelta
8h 10mDCA-NAS
$118
1/6Mon
1 stopDelta
7h 13mDCA-SJU
$124
12/17Tue
1 stopJetBlue
8h 47mDCA-SXM
$161
1/21Tue
1 stopJetBlue
6h 11mDCA-STT
$162
12/17Tue
1 stopUnited Airlines
7h 33mDCA-NAS
$163
12/12Thu
1 stopUnited Airlines
8h 25mDCA-AUA
$171
2/10Mon
2 stopsSouthwest
9h 00mDCA-PLS
$178
1/22Wed
2 stopsSouthwest
10h 25mDCA-SJU
$222

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Last minute flights from Reagan-National to Caribbean

Last minute flight, train and bus deals

11/26Tue
multi-stopDelta
9h 14mDCA-SJU
12/5Thu
multi-stopDelta
8h 59mSJU-DCA
$336
11/24Sun
multi-stopDelta
6h 12mDCA-SJU
12/4Wed
multi-stopDelta
6h 51mSJU-DCA
$361
11/25Mon
nonstopAmerican Airlines
2h 50mDCA-NAS
11/28Thu
nonstopAmerican Airlines
2h 35mNAS-DCA
$379
11/25Mon
multi-stopAmerican Airlines
5h 09mDCA-NAS
11/28Thu
nonstopAmerican Airlines
2h 35mNAS-DCA
$383
11/23Sat
multi-stopUnited Airlines
5h 53mDCA-NAS
11/29Fri
multi-stopUnited Airlines
6h 38mNAS-DCA
$391
11/22Fri
nonstopJetBlue
3h 48mDCA-SJU
12/7Sat
multi-stopJetBlue
8h 35mSJU-DCA
$456
11/23Sat
multi-stopUnited Airlines
6h 36mDCA-SJU
11/27Wed
multi-stopUnited Airlines
12h 00mSJU-DCA
$475
11/22Fri
nonstopJetBlue
3h 48mDCA-SJU
12/4Wed
multi-stopJetBlue
10h 28mSJU-DCA
$482
11/22Fri
multi-stopSouthwest
8h 55mDCA-SJU
11/26Tue
multi-stopSouthwest
11h 25mSJU-DCA
$528
11/26Tue
multi-stopSouthwest
10h 20mDCA-SJU
12/3Tue
multi-stopSouthwest
8h 40mSJU-DCA
$533

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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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