$75 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 12/21. 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.
1 adult
1 adult, Economy, 0 bags

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Cheap Flights from Reagan-National to Caribbean

Cheapest round-trip prices found by our users on KAYAK in the last 72 hours
Punta Cana
Punta Cana2 stops$367
Santo Domingo
Santo Domingo1 stop$412
Montego Bay
Montego Bay1 stop$380
Oranjestad
Oranjestad1 stop$355
Nassau
Nassaunonstop$338
Kingston
Kingston1 stop$369
Simpson Bay
Simpson Bay1 stop$386
Providenciales
Providenciales1 stop$427
Port of Spain
Port of Spain2 stops$369
Bridgetown
Bridgetown2 stops$438
George Town
George Town1 stop$307
Willemstad
Willemstad1 stop$366
St. John's
St. John's1 stop$459
Puerto Plata
Puerto Plata1 stop$382
Aguadilla
Aguadilla1 stop$230
Punta Cana
Punta Cana2 stops$367
Santo Domingo
Santo Domingo1 stop$412
Montego Bay
Montego Bay1 stop$380
Oranjestad
Oranjestad1 stop$355
Nassau
Nassaunonstop$338
Kingston
Kingston1 stop$369
Simpson Bay
Simpson Bay1 stop$386
Providenciales
Providenciales1 stop$427
Port of Spain
Port of Spain2 stops$369
Bridgetown
Bridgetown2 stops$438
George Town
George Town1 stop$307
Willemstad
Willemstad1 stop$366
St. John's
St. John's1 stop$459
Puerto Plata
Puerto Plata1 stop$382
Aguadilla
Aguadilla1 stop$230

Book Cheap Reagan-National to Caribbean 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 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

Sat, Jan 31 - Thu, Feb 5
JetBlue Logo
3:30 pm - 10:55 pmDCA-SJU
6h 25m1 stop
JetBlue Logo
6:45 pm - 9:46 pmSJU-DCA
4h 01mnonstop
$199JetBlue
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Mon, May 18 - Sun, May 24
JetBlue Logo
8:00 am - 11:57 amDCA-SJU
3h 57mnonstop
JetBlue Logo
6:00 am - 12:53 pmSJU-DCA
6h 53m1 stop
$206JetBlue
Find Deal
Mon, Jan 26 - Fri, Jan 30
JetBlue Logo
7:00 am - 6:02 pmDCA-SJU
10h 02m1 stop
JetBlue Logo
6:10 am - 1:19 pmSJU-DCA
8h 09m1 stop
$209JetBlue
Find Deal
Sun, Feb 1 - Thu, Feb 5
American Airlines Logo
1:44 pm - 11:56 pmDCA-SJU
9h 12m1 stop
American Airlines Logo
4:49 pm - 11:25 pmSJU-DCA
7h 36m1 stop
$215American Airlines
Find Deal
Tue, Feb 3 - Fri, Feb 6
American Airlines Logo
5:00 am - 5:01 pmDCA-SJU
11h 01m1 stop
American Airlines Logo
4:49 pm - 12:34 amSJU-DCA
8h 45m1 stop
$220American Airlines
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Mon, Jan 19 - Fri, Jan 30
Delta Logo
6:05 am - 2:10 pmDCA-SJU
7h 05m1 stop
Delta Logo
7:00 am - 4:29 pmSJU-DCA
10h 29m1 stop
$225Delta
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Mon, Jan 5 - Fri, Jan 16
Delta Logo
10:05 pm - 12:20 pmDCA-AUA
13h 15m1 stop
Delta Logo
4:35 pm - 11:32 pmAUA-DCA
7h 57m1 stop
$355Delta
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Tue, Jan 27 - Sat, Jan 31
United Airlines Logo
7:00 am - 4:40 pmDCA-AUA
8h 40m1 stop
United Airlines Logo
3:25 pm - 11:59 pmAUA-DCA
9h 34m1 stop
$383United Airlines
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Sun, Dec 14 - Sat, Dec 20
United Airlines Logo
6:30 am - 4:18 pmDCA-STT
8h 48m1 stop
United Airlines Logo
3:05 pm - 11:59 pmSTT-DCA
9h 54m1 stop
$393United Airlines
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Mon, Feb 2 - Thu, Feb 5
Southwest Logo
4:05 pm - 1:45 pmDCA-PLS
21h 40m2 stops
Southwest Logo
2:40 pm - 10:55 pmPLS-DCA
8h 15m1 stop
$435Southwest
Find Deal
Booking Insights

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

Get data-powered insights and trends into flights from Reagan-National to Caribbean 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 flight route?

Data is based on round-trip flight searches on KAYAK over the past month.

The cheapest ticket to Caribbean from Washington, D.C. Reagan-National Airport found in the last 72 hours was to San Juan, at $187 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 $187.

Can I save money by flying with a layover from Washington, D.C. Reagan-National Airport to Caribbean?

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 $447, prices are generally cheapest when you fly direct.

What is the cheapest month to fly from Washington, D.C. Reagan-National Airport to Caribbean?

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, 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 is October, when tickets cost $301 (return) on average. On the other hand, the most expensive months are December and August, when the average cost of round-trip tickets is $544 and $485 respectively.

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

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

When flying from Reagan Washington National Airport to Caribbean, you should consider leaving on a Monday and avoid Saturdays if you are looking for the best rates. For your return to Reagan Washington National Airport, you’ll find the best rates on Thursdays and the most expensive ones on Sundays.

How far in advance should I book a flight from Washington, D.C. Reagan-National Airport to Caribbean?

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, 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, you should book around 3 weeks before departure, which saves you about 13% compared to booking last minute. For the absolute cheapest price, our data suggests you should book 12 weeks before departure.

Good to know

Low seasonSeptember
Cheapest flight$75
Best time to beat the crowds with an average 11% drop in price.
Most popular time to fly with an average 11% increase in price.
Flight from Reagan Washington National Airport to Providenciales

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.

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

    The cheapest time of day to fly to Caribbean is generally at night, when round-trip flights cost $292 on average. Morning departures are around 14% more expensive than evening flights, on average. The most expensive time of day to fly to Caribbean is generally in the morning, which is peak travel time and where the average cost of a ticket is $419.

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 $168 one-way - $319 round-trip

Reviews of the 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.
8.0
SouthwestOverall score based on 4252 reviews
8.0Comfort
7.0Food
8.6Crew
7.5Entertainment
8.1Boarding
Airline reviews

No delays and arrived to destination 30 min early. Staff was super friendly.

10.0 ExcellentIlevba, Nov 2025DCA - DAL
Read more Southwest reviews

No delays and arrived to destination 30 min early. Staff was super friendly.

San Diego airport is brand new, spacious, airy and very smooth checkin at SW baggage drop.

It was rough. The staff was unprofessional, the choice of on board drinks terrible, it was cramped in space at every airport, they always ran out of overhead bin space so they pressured people to check bags for free or we couldn’t leave on the plane— so I did check my bag to help, and they nearly lost my bag. My bag did not arrive on the luggage belt, another man on my flight and I had to waste our time going to the baggage office to search for our bags. I would only fly southwest again if it was my last choice. Also, my flights were consistently delayed over and over again— at one point they straight up told us we were waiting for the pilot to arrive.

Crew could have been friendlier, maybe I'm spoiled by SW crews. In flight wifi was good. Would be nice to have more food offerings on a 4 plus hour flight

Had to get off plane from prior flight even though I had to reboard same plane to continue to my final destination.

Everything a cheap airline should be at normal airline rates.

Plane crashed into a bus or some other vehicle on the ground while pulling out of the gate. No injuries, but wing tip was damaged and returned to gate for “maintenance issues” and we departed 5 hours later because the plane went out of service and new plane was flown in from a nearby airport, Midway.

Ever since Southwest starting charging for bags, passengers don't want to pay to check their bags, so the gate agents have to beg people to check their roller bags now because there's "not enough space". This was a terrible business move by Southwest.

Full cans of soda would be nice. A choice between two snacks would be appreciated.

Tried watching free movie and it kept freezing so I couldn’t finish.

Our flight from SFO to MSP was right on time on 11/15/2025. No delays. As we approached MSP at about 8 pm, we circled in the air until 8:40 pm so I don't call that efficient for MSP. I think the captain should announce the delay and why. (as if we all don't know that we are just circling around the area, slowing down, speeding up, slowing down.) Thank you. Marilyn Fischer

Service in business class was not impressive. I ordered coffee with dinner and then watched other people get 2 refills before I got my 1 cup of coffee, and only after I pressed the attendant button overhead. Furthermore, the seats in the forward cabin need maintenance on this 737-800: the upholstery is detaching from the seat frame, at least on the backs of seats 1C, 1D.

Plenty of leg room, temperature was great and staff was excellent. Would do it more often.

The ticket agents in West Palm Beach on Friday afternoon Nov. 7th were incredible in getting us on an earlier plane to Atlanta during the government shutdown. Had the taken our original flight we would have missed our connection. She did this on her own, We didn't even have to ask, and she did it all with a smile and showing genuine concern that we would be taken care of. We are very grateful and thankful. We fly often, and now we will be sure to fly Delta.

Flight delayed then cancelled. Misplaced luggage. Still do not have. Rented car 1100 mile drive. I had to buy some overnight Hotels clothes toiletries gas food at my expense. Still not home. Not sure where luggage is. Over 4 hours on hold to Felta

I truly love flying with Delta. They have always treated me with the upmost respect

Our flight attendant in FIRST CLASS was one of the worst I’ve ever had. She was not at all pleasant, nor particularly good at her service.

Everything went well and was good. Nothing exceptional, but no complaints either. Cheap seats are pretty comfortable.

Staff were friendly and happy. Delta could make sure passengers that don't have the app know of changes. Without Kayak I would not have known about the change of gate or the delay. Kayak was faster to notify me.

They ended up paying for the bag twice, but the counter wouldn't take my baggage receipt. Left it to me to resolve. Not sure how to resolve the issue.

Starlink wifi on the Embraer E175 is an excellent experience. I was able to connect and work from IAD all the way to approach into BTV.

7 hours delayed due to operational issues on United’s end. Basically laziness.

Short flight but an "eager to help" crew made the journey more enjoyable!

During booking, I kept trying submitting my payment from the Mexican website and it didn't work. After I had the idea to change it to the Canadian website, it worked but I had to be charged the equivalent of 50 CAD more. I received the clear instruction that I would only be able to check-in at the airport and that it was impossible to select a seat 24 hours before departure, that I had to pay 144 CAD to do so, although not only was I able to check-in 24 hours before departure, but I could have selected my seats for free then. All in all, I almost threw $200 out the window due to misleading information. Besides, the app kept crashing, the information to get to the gate on the app was inaccurate, my gate was switched and I was only informed once in the air (luckily I had noticed the departure pannel), I was not addressed in my language beforehand and even if I tried I was immediately answered in English (which meant the crew understood but didn't want to answer accordingly), there was only one snack & beverage service on my medium haul flight and no beverage service on my short haul flight. To be fair, the planes were comfortable, the crew apart from the language issue was helpful, dynamic and engaging, the plane was clean and the directions were clear and direct. United has a lot of potential to be one of my favourite airlines, but the devil is in the details and a lot of them missed the target.

Better WiFi. I cannot understand that in 2025, United is so behind on a technology that is now a necessity and still painfully unreliable, slow and keeps disconnecting.

Great service on board. Boarding a bit slow due to process. Food was pretty average.

Very small cramped plane for an international flight. Everything else was good, but it was maybe the smallest comfort-wise I've ever been on for longer than 3-4 hours and the trip was 7.5

Flight was delayed 3 hours. No food and drink vouchers was provided. They offered a mini pretzel bag and water .

Staff was rude. Didn’t give water for 2 hours. Worst service

Was on time until within 1 hour of flight-how does that happen? Staff very friendly.

We were told the flight was delayed 5 times, then it was moved to the next day.

More choices on snacks. Built-in video screen to enjoy entertainment choices.

we landed at cmh ten minutes early but had to sit on tarmac for twenty minutes because a plane was at our gate despite the fact that 3 other gates were open.

The experience with American Airlines was good, although the Philippines Airlines flight was much better (better seats, better food, better entertainment options, overall better). Again, the MIA to LAX flight was fine, but nothing in comparison to the comfort and accommodations of the Philippines Airlines flight from LAX to MNL.

I have a gluten allergy so did have any food

I have a gluten allergy so didn't have any food

Loved the crew . Absolutely no complaints. Except for luggage lost

Flight delay was communicated before leaving for airport which caused it to be a non-event. Great flight and crew!

The flight attendant, a black woman with curly hair who sat near Row 21, was wonderful and kind.

It took way too long to diagnose and solve the problem of a broken crew member cabin seat. Though compensation for the volunteer who left the flight was very kind.

Checking In on JetBlue site was impossible. It hung up on REAL ID. Even my Global Entry did not help. Luckily, on Kayak site it was a breeze. Entire flight the temperature was COLD! Otherwise the crew was great!

The flight was two hours late due to a computer fault and resulting maintenance. Nothing was offered as compensation beyond bottles of water during the time we were deplaned and waiting in the terminal.

Very pleasant flight attendants. Gate crew rather loud chatting with each other.

Four plus hour flight delay in New York caused us to take off after 11:30pm. We didn’t arrive at our hotel until five hours after check in. Started the trip off feeling exhausted.

Plane was in bad shape. TV’s and WiFi didn’t work. Plane need a refresh. Not enough room for bags.

There was a fowl odour coming from the lavatory the entire flight

Everything was great. I liked the text updates so that I never miss a gate change & I have all the latest info.

I don’t usually fly budget airlines or airlines in the United States. It was as good as any other airline. The seats are comfortable and the airline attendants are not rude & surly. Very nice flight (s).

No internet on a flight over three hours in this age is criminal. Staff inattentive and dismissive

They have the most inexperienced / rude flight staff I’ve encountered

Everything you need to know for your flight to Caribbean

Information on your arrival and departure airports