$98 Find Cheap Flights from Reagan Washington National Airport to Caribbean - Compare and Save

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 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.
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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$483
Santo Domingo
Santo Domingo1 stop$471
Montego Bay
Montego Bay2 stops$452
Oranjestad
Oranjestad1 stop$473
Nassau
Nassau2 stops$381
Kingston
Kingston1 stop$430
Simpson Bay
Simpson Bay1 stop$369
Providenciales
Providenciales2 stops$504
Port of Spain
Port of Spain2 stops$535
Bridgetown
Bridgetown1 stop$484
George Town
George Town1 stop$337
Willemstad
Willemstad1 stop$519
Aguadilla
Aguadilla1 stop$333
Puerto Plata
Puerto Plata1 stop$610
St. John's
St. John's1 stop$620
Punta Cana
Punta Cana2 stops$483
Santo Domingo
Santo Domingo1 stop$471
Montego Bay
Montego Bay2 stops$452
Oranjestad
Oranjestad1 stop$473
Nassau
Nassau2 stops$381
Kingston
Kingston1 stop$430
Simpson Bay
Simpson Bay1 stop$369
Providenciales
Providenciales2 stops$504
Port of Spain
Port of Spain2 stops$535
Bridgetown
Bridgetown1 stop$484
George Town
George Town1 stop$337
Willemstad
Willemstad1 stop$519
Aguadilla
Aguadilla1 stop$333
Puerto Plata
Puerto Plata1 stop$610
St. John's
St. John's1 stop$620

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

Tue, Aug 18 - Tue, Aug 25
Southwest Logo
8:00 am - 6:10 pm
DCA
-
SJU
10h 10m
2 stops
Southwest Logo
5:15 am - 4:05 pm
SJU
-
DCA
10h 50m
1 stop
$316Southwest
Wed, Aug 12 - Wed, Aug 19
JetBlue Logo
8:00 am - 11:59 am
DCA
-
SJU
3h 59mnonstop
JetBlue Logo
5:39 pm - 9:31 pm
SJU
-
DCA
3h 52mnonstop
$319JetBlue
Sun, Aug 23 - Tue, Sep 1
Southwest Logo
4:35 pm - 10:45 pm
DCA
-
SJU
6h 10m
1 stop
Southwest Logo
8:20 am - 6:25 pm
SJU
-
DCA
10h 05m
2 stops
$321Southwest
Fri, Sep 4 - Sun, Sep 6
American Airlines Logo
5:35 pm - 11:59 pm
DCA
-
SJU
6h 24m
1 stop
American Airlines Logo
5:47 pm - 12:57 am
SJU
-
DCA
7h 10m
1 stop
$322American Airlines
Fri, Sep 11 - Mon, Sep 14
American Airlines Logo
9:00 pm - 12:51 pm
DCA
-
STT
15h 51m
1 stop
American Airlines Logo
1:41 pm - 10:00 pm
STT
-
DCA
8h 19m
1 stop
$360American Airlines
Thu, Sep 17 - Mon, Sep 21
Delta Logo
6:10 am - 11:41 am
DCA
-
NAS
5h 31m
1 stop
Delta Logo
3:18 pm - 11:43 pm
NAS
-
DCA
8h 25m
1 stop
$382Delta
Sun, Aug 9 - Sat, Aug 22
Delta Logo
7:45 pm - 1:53 pm
DCA
-
SXM
18h 08m
1 stop
Delta Logo
3:18 pm - 9:10 am
SXM
-
DCA
17h 52m
1 stop
$397Delta
Wed, Oct 14 - Sun, Oct 18
Air Canada Logo
4:20 pm - 1:25 pm
DCA
-
NAS
21h 05m
1 stop
Air Canada Logo
6:30 pm - 12:00 pm
NAS
-
DCA
17h 30m
2 stops
$398Air Canada
Wed, Oct 14 - Sun, Oct 18
Air Canada Logo
12:40 pm - 1:25 pm
DCA
-
NAS
24h 45m
2 stops
Air Canada Logo
6:30 pm - 12:00 pm
NAS
-
DCA
17h 30m
2 stops
$399Air Canada
Thu, Jul 23 - Mon, Jul 27
United Airlines Logo
7:15 am - 3:35 pm
DCA
-
AUA
8h 20m
1 stop
United Airlines Logo
1:50 pm - 8:54 am
AUA
-
DCA
19h 04m
1 stop
$478United Airlines
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 5 days was to San Juan, at $361 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 5 days was $361.

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

The average price for all round-trip flights from Washington, D.C. Reagan-National Airport to Caribbean 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 is generally in the morning, when round-trip flights cost $424 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 $424.

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 $547, 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 September, when tickets cost $108 (return) on average. On the other hand, the most expensive months are May and August, when the average cost of round-trip tickets is $933 and $931 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 Tuesday and avoid Thursdays if you are looking for the best rates. For your return to Reagan Washington National Airport, you’ll find the best rates on Fridays 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 2 weeks before departure, which saves you about 9% compared to booking last minute. For the absolute cheapest price, our data suggests you should book 5 weeks before departure.

Good to know

Low seasonSeptember
Cheapest flight$98
Best time to beat the crowds with an average 7% drop in price.
Most popular time to fly with an average 6% increase in price.
Flight from Reagan Washington National Airport to Saint Thomas Island

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.

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 $208 one-way - $433 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.
7.9
SouthwestOverall score based on 4250 reviews
7.5Entertainment
7.0Food
8.0Comfort
8.6Crew
8.1Boarding
Airline reviews

My experience will Southwest was good. I wish there was more entertainment and the boarding process was slow at time but other than that my experience was great definitely will be flying with SouthWest again.

8.0 ExcellentAnonymous, Jul 2026
PHL - BNA
Read more Southwest reviews

My experience will Southwest was good. I wish there was more entertainment and the boarding process was slow at time but other than that my experience was great definitely will be flying with SouthWest again.

Flight was delayed by 2 hours, meaning that a flight to Dwnver which should have arrived at 11pm came into the airport at 1 am. Made for a very long day.

I think Southwest is the number one airline that anyone can fly I have flown for the first time Frontier and what a joke and their customer service United was a very strange experience I'm only sticking to Southwest from here on out for sure

Great job! My family doesnt fly often but we felt safe 100%

Great job Southwest! My family doesn't fly often but we felt safe the whole time.

Haven’t flown on SW in years. Flight was on time departing and arriving. Served vegan butter onion flavored pretzels which were bad. Coke served was in a tiny paper cup. Crew was not engaging. Felt like they were going through the motions. Old plane, tight seats and no leg room.

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

Pretty standard flight. We left late, but arrived early. The wifi entertainment is always nice. The free snacks and beverages are simple, but appreciated. I'm tall and the seats are an issue. I can deal with a short flight, but any longer, I have to find another airline where I know beforehand I have extra legroom.

Awesome experience. No in-flight video or meal. Still do not like the boarding process.

On time, good crew, easy flight. Just like the old days!

Everything about this flight was good except for the very end when I reached my destination. Everyone from the tune to the wheelchair escorts were great with the case were great but I miss you with people at the check in this at the very end. I need help from the chicken desk because I forgot my pillow on the plane The female worker at the chicken desk said that they found my pillow and she was going to retrieve it for me. She left a 30 minutes without any update and her so she saw me walking back and forth waiting for her and they didn't even bother calling her or radioing her for any updates. They were busy because they were behind schedule and they were overwhelmed but thanks because at least glanced me and try to give me an update just a quick radio check or phone call. I don't care about the pillow but if you tell me to wait, I waited for at least half an hour before I said something and I just left because they wouldn't bother talking to me so I could, so everything's going in the review. I took pictures of the two men that were left working at the check-in counter. The totally ignored me despite the signals I've been giving them. I don't see any offers in the kayak review to add pictures or screenshots so I'm going to post another review I don't know their name but I'm pretty sure Delta will find other names when they see the review. Google with pictures. There was another guy at the chicken counter bring an orange workers vest who finally left after telling me that the girl that was retrieving my pillow is working the gates now. That would have been if they just told me that's what happened. But I had no update. Make me wait for nothing. Thank you Delta airlines!

We had a great experience with Delta. They helped us from the start at the kiosk all the way to our final destination, including help reassigning and upgrading our seats free of charge at the gates, escorts with the wheelchair for my brother and even getting our luggage at baggage claim for us. I also had special help because I forgot my pillow on the plane. The wheelchair escort contacted for associates at the check-in desk all the way back to the plane and retrieved my pillow for me.

The gentleman at the gate I think his name is RIE was exceptional

This flight was no comparison to our prior flight. I'm thinking it all has to do with the age of the aircraft.

2 of the seats in row 31 the entertainment system was not working, and one seat the tray table did not go all the way down. Flight arrived early and departed on time which was great.

Waited at the usual crowded gate at DCA where one ends up standing up because there aren't enough seats.

Delayed take-off. Very small plane so very scary with lots of bumps during the flight. Would never fly Delta on short flights in small 80 seaters plane again! Felt relieved when landed.

Inexpensive, got an exit row aisle aeat with no middle passenger, bought a great breakfast sandwich, flight comfortable & arrived ahead of schedule.

I wouldn't say I liked being forced to check my small roller bag at the gate; too many people had bags and were in a higher boarding group.

715PM departure was 2.5 hours late. Received hotel & food voucher but after we already booked a room. Entire team just seemed like they were 2-3 steps behind in execution, and notifcations.

Staff could’ve been a little more cordial. The men were much more friendlier than the women. My daughter and I also missed the 2nd to last meal as we were sleeping but that is on us.

Like: departed and arrived on time. Unlike: Food options for purchase allways bad, 1 of 2 of the crew members not very friendly at all. Seats and leg room aweful. At this point I am thinking on switching to AA.

Over 5 hour delay with minimal updates or ability to standby for alternative flights. During boarding and 1 hr+ wait for takeoff, seats were drenched w water from air conditioning condensation and always leftover crumbs on carpet and seats

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.

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.

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

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 flight was on time and the crew were great.

I was forced to gate check my carry on luggage. Somehow it did not arrive at my destination. I still have yet to receive my bag r days after arrival.

Boarding area is a mess. Lines not bounded and gate area too small. Food options (on this specific flight) were poor and you couldn’t pick part of it since it was like a mash of chicken and other unrecognisable stuff. Comfort of seats along with child noise made it difficult to get a good sleep. Last, the flight attendant that served my aisle was rude (others seemed fine) towards me and others.

The seats were extremely cramped, with very little legroom or personal space. There was no room left in the overhead bins for a backpack, and the space under the seat in front was so limited that I could barely fit my bag underneath. Overall, the seating arrangement felt very uncomfortable and overcrowded.

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.

A nightmare. Scheduled flight delayed 2 hours then cancelled because pilot timed out . Unable to find another pilot. Really?! Weather certainly a factor, but JetBlue seemed totally unprepared for the chaos that ensued when flight routes were cancelled. More cancelled flights, finally many of us who had been bumped from other flights were allowed to board a Boston bound plane around 3:00am, delay after delay, sat on tarmac for another half hour while pilot dealt with weight distribution issues (?), arrived in Boston 4:30. Crew were wonderful- same attendants all day and night and they were exhausted. Fortunately for me and my son that Boston was our final destination, not so lucky for many who missed connecting flights.

The flight was delayed 14 hours and communication was very poor. No one seemed to know what was happening and the gate agent was trying to help people for several flights. She was by herself trying to help 100s of people.

JetBlue worker, Blythe, was so amazing at the DCA counter. If it wasn’t for her, I’m not sure we would’ve made it through. Please thank her!

On time, friendly attendants, quick wheelchair assistance and help checking in bags. Also appreciated change in seats, more forward to make it easier for my 97 year old mother to board and exit the plane. Thank you, JetBlue!

Flight was on time and smooth. Customer service was decent

They forced me to check my hand luggage at the gate.

Still hasn’t left. Why are you asking how it was?

My flight got delayed and eventually canceled, then rescheduled. I and several others had a connection from Boston to Paris and asked several times if we would make it. They assured us we would and then rebooked us mid flight without our consent and closed doors early even though they said they communicated we were a bit delayed. We got stranded in Boston and I opted with being rebooked for a different connection to France since they refused to pay for a Hotel. I've now been in Europe for 5 days and still haven't recieved my bags. There was absolutely no urgency for the fact that I'm in a foreign country with absolutely no change of clothes or any of my medication. Such an overwhelming and frustrating experience.

One hour delayed departure resulted in problems with planned ground transportation at my destination.

Plane is old and seats are worn. Add to it the plane was dirty. No plugs for laptop.

Everything you need to know for your flight to Caribbean

Information on your arrival and departure airports