$113 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 8/22. 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$475
Santo Domingo
Santo Domingo1 stop$467
Montego Bay
Montego Bay1 stop$453
Oranjestad
Oranjestad2 stops$485
Nassau
Nassau1 stop$380
Kingston
Kingston2 stops$461
Simpson Bay
Simpson Bay1 stop$372
Providenciales
Providenciales2 stops$486
Port of Spain
Port of Spain1 stop$485
Bridgetown
Bridgetown1 stop$398
George Town
George Town1 stop$355
Willemstad
Willemstad1 stop$500
Aguadilla
Aguadilla1 stop$353
St. John's
St. John's2 stops$522
Puerto Plata
Puerto Plata1 stop$471
Punta Cana
Punta Cana2 stops$475
Santo Domingo
Santo Domingo1 stop$467
Montego Bay
Montego Bay1 stop$453
Oranjestad
Oranjestad2 stops$485
Nassau
Nassau1 stop$380
Kingston
Kingston2 stops$461
Simpson Bay
Simpson Bay1 stop$372
Providenciales
Providenciales2 stops$486
Port of Spain
Port of Spain1 stop$485
Bridgetown
Bridgetown1 stop$398
George Town
George Town1 stop$355
Willemstad
Willemstad1 stop$500
Aguadilla
Aguadilla1 stop$353
St. John's
St. John's2 stops$522
Puerto Plata
Puerto Plata1 stop$471

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, Sep 5 - Sat, Sep 12
JetBlue Logo
8:00 am - 11:59 am
DCA
-
SJU
3h 59mnonstop
JetBlue Logo
6:07 pm - 9:58 pm
SJU
-
DCA
3h 51mnonstop
$304JetBlue
Mon, Aug 24 - Fri, Aug 28
Southwest Logo
5:05 pm - 11:50 pm
DCA
-
SJU
6h 45m
1 stop
Southwest Logo
6:30 am - 2:40 pm
SJU
-
DCA
8h 10m
2 stops
$306Southwest
Mon, Aug 24 - Fri, Aug 28
American Airlines Logo
6:00 am - 12:40 pm
DCA
-
SJU
6h 40m
1 stop
American Airlines Logo
5:10 pm - 11:41 pm
SJU
-
DCA
6h 31m
1 stop
$307American Airlines
Tue, Jan 5 - Tue, Jan 12
American Airlines Logo
6:00 am - 1:51 pm
DCA
-
STT
6h 51m
1 stop
American Airlines Logo
1:50 pm - 11:34 pm
STT
-
DCA
10h 44m
1 stop
$360American Airlines
Wed, Aug 26 - Thu, Sep 3
Air Canada Logo
11:00 am - 5:30 pm
DCA
-
NAS
6h 30m
1 stop
Air Canada Logo
2:35 pm - 9:48 pm
NAS
-
DCA
7h 13m
1 stop
$380Air Canada
Thu, Oct 22 - Sun, Oct 25
Air Canada Logo
6:00 am - 5:30 pm
DCA
-
NAS
11h 30m
2 stops
Air Canada Logo
2:05 pm - 8:58 am
NAS
-
DCA
18h 53m
2 stops
$382Air Canada
Wed, Sep 9 - Tue, Sep 15
Delta Logo
6:59 am - 11:51 am
DCA
-
NAS
4h 52m
1 stop
Delta Logo
1:16 pm - 7:32 pm
NAS
-
DCA
6h 16m
1 stop
$392Delta
Sat, Dec 5 - Sat, Dec 19
Delta Logo
6:05 am - 1:20 pm
DCA
-
STT
6h 15m
1 stop
Delta Logo
1:50 pm - 8:13 pm
STT
-
DCA
7h 23m
1 stop
$394Delta
Sat, Sep 12 - Sat, Sep 19
Multiple Airlines Logo
6:00 am - 2:00 pm
DCA
-
SXM
8h 00m
1 stop
Multiple Airlines Logo
6:00 pm - 10:34 pm
SXM
-
DCA
28h 34m
1 stop
$395Multiple Airlines
Tue, Sep 8 - Wed, Sep 9
Multiple Airlines Logo
6:00 am - 3:27 pm
DCA
-
PUJ
9h 27m
1 stop
Multiple Airlines Logo
5:05 pm - 10:20 am
PUJ
-
DCA
17h 15m
1 stop
$480Multiple 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 $327 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 $327.

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 $429 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 $429.

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 $523, 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 January, when tickets cost $461 (return) on average. On the other hand, the most expensive months are December and June, when the average cost of round-trip tickets is $620 and $593 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 14% compared to booking last minute. For the absolute cheapest price, our data suggests you should book 22 weeks before departure.

Good to know

Low season

September

Cheapest flight

$113
Best time to beat the crowds with an average 8% 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 $249 one-way - $428 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 4238 reviews
8.0Comfort
8.6Crew
7.5Entertainment
8.1Boarding
7.0Food
Airline reviews

Friendly crew kept coming by to make sure all was ok, provide additional refreshments, etc.

10.0 ExcellentTamara, Jul 2026
MCO - DEN
Read more Southwest reviews

Friendly crew kept coming by to make sure all was ok, provide additional refreshments, etc.

It was good. Last flight was delayed but I always say that is in God's plan

Red eye from San Diego. Temperature of the cabin was way too warm and the air duct flowed very little air.

Overall good, just screaming kids in the area the whole flight.

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.

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!

The Columbus-based WestJet crews that cover Delta commuter flights between LGA and CMH are excellent - this team included. Our flight today landed 40 minutes early, which is unheard of when flying out of LaGuardia. I've flown with the same crew in more challenging conditions, and they always rise to the occasion with helpful communication to the passengers so that we may manage expectations.

Easy on easy off and the staff onboard were wonderful. Left on time, arrived a bit early.

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.

1. Everything was satisfactory concerning the flight. 2. Can't think of what could be better right now.

Onboard staff was courteous, helpful, responsive and friendly. The boarding process was disorganized, poorly communicated, and disheveled. Gate agents were yelling instead of using the PA system, didn’t communicate the timing delay of our flight, and created an atmosphere of chaos rather than order and communication. As far as I know, there was no reason for their. I would hate to see how it operated under extreme conditions. I’ve never seen United Airlines operations in such a state.

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.

They cancelled our flight two times after rebooking us for a later flight. We never got on the plane. We found another solution by driving.

Mostly great. Only issue was with the WiFi. Halfway through the flight it was spotty and I was unable to work as I planned. This impacted my work products as I am traveling for business and it was an unexpected hindrance which was inconvenient. Flight here was amazing. For a 5 hour flight something more than a Biscoff would be nice but I’m just swinging at windmills I guess…

Delayed boarding because a flight attendant couldn't find the gate...sat on the plane for over an hour at the gate because AA couldn't get one of the planes behind us to move

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 is delayed by more than an hour without any reason, the jet blue gates kept changing every 20 mins and there is no proper communication. No ear phones provided in flight, there is a screen with entertainment but what is the use, I have earphones but the console has outdated audio connections, no usb C or bluetooth, they are living 15 years behind

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.

Everything you need to know for your flight to Caribbean

Information on your arrival and departure airports