$127 Find Cheap Flights from Reagan Washington National Airport 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 Reagan-National to Caribbean Islands departing on 7/28. 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, 0 bags

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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Cheap Flights from Reagan-National to Caribbean Islands

Cheapest round-trip prices found by our users on KAYAK in the last 72 hours
Punta Cana
Punta Cana1 stop$435
Santo Domingo
Santo Domingo1 stop$472
Montego Bay
Montego Bay1 stop$436
Oranjestad
Oranjestad1 stop$396
Nassau
Nassau1 stop$430
Kingston
Kingston1 stop$416
Simpson Bay
Simpson Bay1 stop$399
Providenciales
Providenciales1 stop$451
Port of Spain
Port of Spain1 stop$546
Bridgetown
Bridgetown2 stops$387
George Town
George Town1 stop$317
Willemstad
Willemstad1 stop$412
Aguadilla
Aguadilla1 stop$316
Puerto Plata
Puerto Plata1 stop$600
St. John's
St. John's2 stops$526
Punta Cana
Punta Cana1 stop$435
Santo Domingo
Santo Domingo1 stop$472
Montego Bay
Montego Bay1 stop$436
Oranjestad
Oranjestad1 stop$396
Nassau
Nassau1 stop$430
Kingston
Kingston1 stop$416
Simpson Bay
Simpson Bay1 stop$399
Providenciales
Providenciales1 stop$451
Port of Spain
Port of Spain1 stop$546
Bridgetown
Bridgetown2 stops$387
George Town
George Town1 stop$317
Willemstad
Willemstad1 stop$412
Aguadilla
Aguadilla1 stop$316
Puerto Plata
Puerto Plata1 stop$600
St. John's
St. John's2 stops$526

Book Cheap Reagan-National 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 Reagan-National 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 Reagan-National to Caribbean Islands

Fri, Aug 7 - Wed, Aug 19
Delta Logo
6:02 am - 4:38 pm
DCA
-
SJU
10h 36m
1 stop
Delta Logo
1:06 pm - 10:21 pm
SJU
-
DCA
9h 15m
1 stop
$266Delta
Sun, Aug 23 - Thu, Aug 27
American Airlines Logo
5:00 am - 2:53 pm
DCA
-
SJU
9h 53m
1 stop
American Airlines Logo
1:38 pm - 12:37 am
SJU
-
DCA
10h 59m
1 stop
$267American Airlines
Wed, Aug 19 - Wed, Aug 26
American Airlines Logo
3:11 pm - 11:59 pm
DCA
-
SJU
8h 48m
1 stop
American Airlines Logo
1:38 pm - 8:59 pm
SJU
-
DCA
7h 21m
1 stop
$271American Airlines
Tue, May 26 - Wed, Jun 10
JetBlue Logo
8:20 am - 12:05 pm
DCA
-
SJU
3h 45mnonstop
JetBlue Logo
5:10 pm - 9:03 pm
SJU
-
DCA
3h 53mnonstop
$272JetBlue
Tue, Jun 2 - Wed, Jun 10
JetBlue Logo
8:20 am - 12:05 pm
DCA
-
SJU
3h 45mnonstop
JetBlue Logo
5:10 pm - 9:03 pm
SJU
-
DCA
3h 53mnonstop
$274JetBlue
Fri, Jul 24 - Thu, Jul 30
Delta Logo
8:00 am - 2:23 pm
DCA
-
STT
6h 23m
1 stop
Delta Logo
3:33 pm - 10:48 pm
STT
-
DCA
7h 15m
1 stop
$290Delta
Fri, Jul 24 - Thu, Jul 30
United Airlines Logo
6:00 am - 3:43 pm
DCA
-
STT
9h 43m
1 stop
United Airlines Logo
1:22 pm - 10:15 pm
STT
-
DCA
8h 53m
1 stop
$349United Airlines
Fri, Jul 24 - Thu, Jul 30
United Airlines Logo
6:00 am - 3:43 pm
DCA
-
STT
9h 43m
1 stop
United Airlines Logo
1:22 pm - 10:15 pm
STT
-
DCA
8h 53m
1 stop
$366United Airlines
Sun, Aug 30 - Fri, Sep 11
Air Canada Logo
12:40 pm - 3:25 pm
DCA
-
BGI
26h 45m
2 stops
Air Canada Logo
4:20 pm - 6:15 pm
BGI
-
DCA
25h 55m
1 stop
$387Air Canada
Sun, Oct 4 - Fri, Oct 9
Air Canada Logo
8:40 pm - 3:25 pm
DCA
-
BGI
18h 45m
1 stop
Air Canada Logo
4:20 pm - 12:00 pm
BGI
-
DCA
19h 40m
2 stops
$388Air Canada
Booking Insights

KAYAK's insights & trends for Reagan-National to Caribbean Islands flights

Get data-powered insights and trends into flights from Reagan-National 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. Reagan-National Airport 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. Reagan-National Airport found in the last 72 hours was to San Juan, at $257 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 $257.

What is the cheapest time of day to fly to Caribbean Islands?

The average price for all round-trip flights from Washington, D.C. Reagan-National Airport to Caribbean Islands depending on the time of departure, clicked by users on KAYAK in the last 2 weeks.

The cheapest time of day to fly to Caribbean Islands is generally in the morning, when round-trip flights cost $408 on average. The most expensive time of day to fly to Caribbean Islands is generally in the morning, which is peak travel time and where the average cost of a ticket is $408.

Can I save money by flying with a layover from Washington, D.C. Reagan-National Airport 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 $436, prices are generally cheapest when you fly direct.

What is the cheapest month to fly from Washington, D.C. Reagan-National Airport 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. Reagan-National Airport 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. Reagan-National Airport to Caribbean Islands is March, when tickets cost $98 (return) on average. On the other hand, the most expensive months are December and June, when the average cost of round-trip tickets is $1,173 and $228 respectively.

What’s the cheapest day of the week to fly from Reagan Washington National Airport to Caribbean Islands?

The average price of all round-trip flights from Washington, D.C. Reagan-National Airport to Caribbean Islands clicked on KAYAK for each day over the last 12 months.

If you are looking for a flight deal from Reagan Washington National Airport to Caribbean Islands, look for departures on Tuesdays and avoid leaving on a Thursday, as it's usually the priciest day. When flying back from Caribbean Islands, Friday is the cheapest day to fly and Sunday is the most expensive.

How far in advance should I book a flight from Washington, D.C. Reagan-National Airport 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. Reagan-National Airport 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. Reagan-National Airport to Caribbean Islands, you should book around 3 weeks before departure, which saves you about 11% compared to booking last minute. For the absolute cheapest price, our data suggests you should book 22 weeks before departure.

Good to know

Low seasonSeptember
Cheapest flight$127
Best time to beat the crowds with an average 6% drop in price.
Most popular time to fly with an average 11% increase in price.
Flight from Reagan Washington National Airport to San Juan

FAQs - booking Caribbean Islands flights

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

  • 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 Islands?

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

Top tips for finding cheap flights to Caribbean Islands

  • 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 $166 one-way - $388 round-trip

Reviews of the top 5 airlines serving from Reagan-National 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 Reagan-National 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.
7.9
DeltaOverall score based on 8456 reviews
8.1Boarding
8.5Crew
7.9Comfort
7.8Entertainment
7.2Food
Airline reviews

Seats in Delta Main are unbelievably close to the seat in front of. Hard to get a backpack under the seat.

8.0 ExcellentMatthew, May 2026
OKC - ATL
Read more Delta reviews

Seats in Delta Main are unbelievably close to the seat in front of. Hard to get a backpack under the seat.

The flight was operated by Latam. The aircraft had a technical issue and the flight was delayed for the next day. They grounded other passengers to get their airplane assigned to my flight. Most of he ground staff don't speak English (Orlando Airport), but were very polite.The crew on the other hand could speak English and Portuguese. On board service was good.

The agent at check in and at the gate were less than thrilled to be at work. I'm not a fan of Kayak's placement on the plane. I got put in the middle seat and none of my preferences were used.

In ATL they have two sets of departure screens. Follow what is on your airline's departure board - the ATL Airport Authority departure board had completely incorrect details about the gate assignment for my flight, which would have made me miss boarding.

Flight was delayed it was hot while sitting on the plane, one engine was working on the plane until they had to do some jimmy rigging down the runway in order for the other engine to charge up. It was ridiculous

The flight was very good and the staff was very friendly and helpful!

The only thing I would say is we tried to get on a standby earlier flight, but with our fair we couldn’t. That seems senseless to leave with open seats..

Very easy to use and convenient, you can perform any action within the same portal

In a world of delays, Delta was on time both ways! Boarding was fast and efficient. Staff was friendly. AND wifi worked.

WiFi didn’t work. Flight delayed 3 hours Crew members were illiterate Seat lean back did not work.

Vegetarian selection could be better. Bread was too hard to chew.

Crew was friendly and competent. Food, wine, and entertainment were excellent except the raw tuna on the flight to Split. Recommend against serving that - at least as the only option. Many medical conditions do not allow people to eat raw fish.

After arriving in Chicago, we were taxiing for 1.5 hours with infrequent and untruthful updates about the amount of time it would take to arrive at the gate. Minimally, the team could have provided timing expectations that were more truthful, especially one their original expectations were not met.

United didn’t even try to hold the flight for me. They knew I had a tight connection and when I arrived at the gate less than 10 mins after final boarding the flight had already gone. The gate agent wasn’t even notified that I was on my way. She was told I wasn’t at the airport

Good quick flight on a small but comfortable plane. I'm 6'3 and had plenty of space.

The flight was delayed so we were dead tired, and after that the turbulence was horrible. I was very scared.

Wonderful. Quick boarding. Early departure and we arrived 30 minutes early at our destination. Unfortunately, when you arrive early, there is still a departing aircraft at our gate. We had to park for 30 minutes until the gate was clear. So our early arrival was not really early at the gate. Otherwise it was a quick and smooth flight. Appreciated the efficiency.

Wifi took a while to kick in and we had a maintenance issue that took over 40 mins at the gate in Washington before pulling back

Very good. Because of the delays with my previous flight, I missed my connection, but I was able to book another flight through the United app easily.

Was happy we finally got upgraded in 1st class. The seat getting old. The cushiness need some improvement.

Overall a good experience, however Wifi was not working on the flight.

THe flight was an hour late. You got us on the plan and we sat on the ground for 45 minutes with no information from the pilot whatsoever. Worst flight this year.

Going non stop to lax like I paid for. Not stopping in MCI for gas. Too long of delays

Incoming flight was delayed, delaying boarding. It then took 30 mins to take off. Took 20 mins to get to a gate because they changed the gate last minute, crew weren’t ready so there was no one staffed to work the jet bridge. Boarding was so disorganized as is usual with American because everyone just stands around the gate regardless of boarding group.

Delays with no explanation. It could have been handled better.

Flight delay for mechanical. Inbound arrived on time. No one said why mechanical delay.

Flight boarded, departed and landed on time. Excellent service from flight attendant in FIRST

This was one of the most frustrating travel experiences I've had to date. I had changed my flight day of to this one as it was slated to depart on time. It ended up being so delayed that my original flight took off before this one did. The boarding process began but eventually stopped and everyone had to get off the plane as a problem was identified. The person at the front desk just tried to laugh it off as if this wasn't already a huge inconvenience. From there, we eventually got to board only to sit at the gate for an additional hour because of some additional issue. This was extremely frustrating and caused a lot of stress.

It was a little concerning to hear the ground crew arguing with the flight crew over baggage space. Instead of taking them and checking them, they started checking for space in the first class cabin moving items around like the flight crew didn't know what they were doing. I was embarrassed for them.

delayed due to weather. Could not communicate with family since the wifi was broken

I did not like anything because the flight was cancelled yesterday and I did not get to arrive on time in Toronto as I was rebooked with another airline. This caused me to be really stressed out as I am an individual with back injury and to be forced to stay longer in an airport to accommodate a change of airline and the transfers associated with it Due to this I am probably not going to book through your website to eliminate this potentially chaos in the future

shittiest airline in the hemisphere. To improve - start thinking you're flying people, not cattle

Easy boarding, inflight refreshments came on time and comfortable seat

It was good that our flight left early. It was a nice smooth flight and landing.

All good……but luggage didn’t make it on the airplane. Had to wait 3 days. Was a bummer.

Small suitcase used for carryon the last time was refused by boarding crew this time. Appears to be at the discretion and mood of the person on the day. Flight was only half booked, there would have been no problem with space.

It was a problem because there was a delay where we sat before taking off from newark,then when landed in Toronto we sat on tarmac and they wouldn't let us out for a long period of time. When we finally were released to the airport in Toronto the attendant scanned our boarding pass that we were here for our connection to Brazil. We ran all the way to the gate and they said at the gate the door is shut so we can not let you on the plane. We explained that we were checked in by the attendant when we arrived at Toronto airport to go to Brazil and they should not have shut the door. We were ignored at the gate

Flight home was delayed multiple times, did not get home until 2am

the check-in lady at ORD was extremely rude and unprofessional. very disappointed as it was supposed to be a celebration for my wife's birthday and it really put a damper on things. if i wanted to be treated like trash, i would have flown Economy! (as opposed to business class)

My original flight was cancelled and then rebooked four hours later on a recovery flight, but I was checked in as stanby and had no seats so as a family of four we were concerned about not being seated altogether. Our flight then got delayed by another 1.5 hours and when seats were assigned at the gate, three of the four of us were together and we could get my wife closer, they offered no assistance.

Given us a free miles or free flight for waiting for 9 hours I didn’t get home till 5am in the morning and I was supposed to be home at 9:30 touch down.

Excellent price. Everything on time. two bad parts. Kayak said I couldn't sign in for the flight online, but I got an email at the same time from Jet Blue and they let me sign in online. Second bad part was that, although I had provided my known traveler number, neither of my boarding passes, for this flight and the previous one, had TSA pre-check showing.

Jet blue was great But the Jayak system Wasa pure nightmare and wasted so much of my time and energy by not giving me a way to access jet blue to check in the flight back I didn’t even get the number confirmation code 24 hours before. Because I didn’t receive the email with the confirmation code I could NoT CHECk IN. I spoke to a kayak third party and they informed me I could not carry a carry on, on the flight which caused me so much extra stress it was just too much. You can be sure I will not be using it recommending your site. Again.

There was a screen but no earphones that could use the older input so I could listen to anything.

My experience with JetBlue was fine BUT I am very upset with Kayak! JetBlue had delayed our scheduled departure by an hour and you NEVER notified me of the change. I did not hear directly from JetBlue because the trip was booked through Kayak, a mistake I will not repeat. Your reminder of the our trip last week still had the WRONG departure time. Our return trip has also changed, and again no notice from you.

Jet blue just had great service overall! Only a little turbulence heading out of Austin, otherwise the jet stream helped the speed of the trip!

Boarding was quick and efficient. The flight crew were friendly. There were limited food options available on the flight. The pocket guide said there would be salad and sandwich sections available on flights over 3.5 hours. The only food available were snack boxes. And those were limited as well. My flight was over 5 hours. The entertainment system worked well. I had both extra legroom seats and regular coach seats. The seats were not very comfortable. The entertainment controls in the armrest made it difficult to rest my arm without changing the channel on my neighbors TV. Overall, my experience was mediocre.

Purchased through 3rd party vendor which made everything difficult. Unable to check in online. Unable to get flight updates easily, tsa precheck information didn’t carry through, longer time to check in in person. Entertainment looked good but had to purchase conventional headphones to view.

Boarding was fast, easy, and we landed early. The entertainment system was very buggy and kept resetting throughout the flight.

Not having an assigned seat until boarding and then having to check my bag.

Everything you need to know for your flight to Caribbean Islands

Information on your arrival and departure airports