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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 5 days
Punta Cana
Punta Cana1 stop$490
Santo Domingo
Santo Domingo1 stop$459
Montego Bay
Montego Bay1 stop$384
Oranjestad
Oranjestad1 stop$454
Nassau
Nassau1 stop$378
Kingston
Kingston1 stop$434
Simpson Bay
Simpson Bay1 stop$257
Providenciales
Providenciales1 stop$324
Port of Spain
Port of Spain2 stops$410
Bridgetown
Bridgetown1 stop$372
George Town
George Town1 stop$307
Aguadilla
Aguadilla1 stop$346
St. John's
St. John's1 stop$492
Puerto Plata
Puerto Plata1 stop$437
Punta Cana
Punta Cana1 stop$490
Santo Domingo
Santo Domingo1 stop$459
Montego Bay
Montego Bay1 stop$384
Oranjestad
Oranjestad1 stop$454
Nassau
Nassau1 stop$378
Kingston
Kingston1 stop$434
Simpson Bay
Simpson Bay1 stop$257
Providenciales
Providenciales1 stop$324
Port of Spain
Port of Spain2 stops$410
Bridgetown
Bridgetown1 stop$372
George Town
George Town1 stop$307
Aguadilla
Aguadilla1 stop$346
St. John's
St. John's1 stop$492
Puerto Plata
Puerto Plata1 stop$437
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?

The cheapest ticket to Caribbean Islands from Washington, D.C. Reagan-National Airport found in the last 5 days was to San Juan, at $288 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 $288.

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

The cheapest time of day to fly to Caribbean Islands is generally in the morning, when round-trip flights cost $439 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 $439.

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

No, with an average price for the route of $457, 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?

The cheapest month for flights from Washington, D.C. Reagan-National Airport to Caribbean Islands is January, when tickets cost $514 (return) on average. On the other hand, the most expensive months are December and March, when the average cost of round-trip tickets is $669 and $624 respectively.

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

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 get a below average price on the flight from Washington, D.C. Reagan-National Airport to Caribbean Islands, you should book around 2 weeks before departure, which saves you about 12% 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

$95
Best time to beat the crowds but there is an average 1% increase in price.
Most popular time to fly with an average 13% increase in price.
Flight from Reagan Washington National Airport to Nassau

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.

Reviews of the top 5 airlines serving from Reagan-National to Caribbean Islands

 
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.
7.8
DeltaOverall score based on 8597 reviews
8.1Boarding
7.8Entertainment
8.5Crew
7.2Food
7.8Comfort
Airline reviews

I don't know why the crew decided to board 15 minutes early without informing anyone not at the gate. Why would you have the app send a notification that we're boarding on time, instead board early, and then rush me to the gate. Then have me check my carry-on when I specifically packed my bag as to not do so.

4.0 OkayKevin, Sep 2026
Read more Delta reviews

I don't know why the crew decided to board 15 minutes early without informing anyone not at the gate. Why would you have the app send a notification that we're boarding on time, instead board early, and then rush me to the gate. Then have me check my carry-on when I specifically packed my bag as to not do so.

Long delays at both DCA and MSP; Crew did not keep us informed (or very little). Airplane was showing signs of heavy use (not up to Delta standards). Food options for Business Class have dropped in quality. After landing we sat on tarmac for maybe 25 minutes with no provided chance to use the bathroom and crew did not tell us what was going on or give an estimated time to expect to be at a gate.

Flight was delayed for about an hour but overall good experience

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.

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.

Boarding was 2 hours late and then we were delayed another 5 hours on the tarmac. I'm sure the crew were also tired, but some of them were rather snappy. The special dinner I ordered was not served, and they only served a tapas box on takeoff and breakfast before landing. That was disappointing in premium economy. However United was good at rebooking my connecting flight.

It was pretty good, they give a small blanket, neck pillow and earphones. The only bad thing was not big enough leg room for your bag and feet. They gave us a snack, dinner, and breakfast on flight and food was good considering it was on a plane

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 only problem that I have is if you have questions about your flight ✈️ there's no one to communicate with when you call 📱.

The gate and flight crew were very responsive and professional. They went out of their way to make sure this senior had a good flight.

The upgraded seats on the smaller flights I guess is a toss up if you get a full meal. We paid less for the ticket on the way there and got a full meal where we got a snack and drink on the way home. The lounge was also in the other terminal too. No entertainment on the seat and no wifi on the plane.

I checked a bag and there was only one agent to assist all customers with any issues.

Super experience. Earlier than schedule departure and arrival. Baggage handling was very good

Check in agent was very helpful and polite. He helped me board the earlier flight back home instead of waiting 2 hours at the airport for the next flight

Our flight was canceled at the last minute. Someone on the flight said the exact same thing happened to her the day before. I will say they helped us book a flight on another airline so that we could still make our vacation with little delay.

The flight was delayed at the last moment quoting an absurd weather reason. This delay led to an issue with my connecting flight. I was made to run (literary) from this flight to the next one ( as they preponed departure. I was still in my DCA to YYZ flight when the boarding started for the next connecting flight. After my sprint to get the connecting flight, found that no place for my carry on. Had to sit for 3 hours with my back-pack on my lap , it was the most uncomfortable and inconvenient journey with little to no empathy shown by cabin crew in both flights. Another poor show from Air Canada!! Cant help because of lack of options !!

Made me check my carry on despite there being dozens of empty bins when I boarded which significantly inconvenienced me.

The people are great! The trip to Japan is simply never ending!!! Not the problem of the airlines, though.

Good experience with this flight. Boarding was smooth with no issues. The short flight was good with quick drink & snack service. Nice easy way to get back from DC.

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.

Flight was delayed which isn’t the airline’s fault, but the communication around it was terrible. I left the lounge to show up at the gate to board at the time in my app, and the flight in front of mine was still boarding and the inbound plane hadn’t even taken off yet. Delays were slow to show up in my app. Improved communication could have let me have a more pleasant experience in the lounge vs waiting 1.5 hours at the gate.

Wifi was good on the flight from DCA to Dallas and terrible on the flight from Dallas to Tucson. The forward head in the flight from Dallas to Tucson was putrid smelling entirely urine soaked. The flight from DCA to Dallas was delayed by almost 30 min with a plane change.

Sat on tarmac at arrival at DFw for more than 30 min waiting for a gate.

Business Class layout was excellent. The seats were not nearly as comfortable as UA, Delta or Air New Zealand (the best). Nor were the controls as flexible. Food was okay but not great. Breakfast pancakes were like cardboard.

I am Plstinum Pro snd was standby on earlier flight. They gave seats to people that asked rather than follow standby order. When realized what was happening was too late to get on as no seats left. My scheduled flight was late. Then filled the seat beside me Ruth rude person that they had to move from her original seat

I have yet to come across an AA agent or flight attendant that is friendly. They really inhibit a good experience.

Flight was good, little delayed because of busy plane traffic

Flight was delayed multiple times and rerouted to different concourses in the airport because of all of American's delays. App/boarding pass would not update with changed gate information.

Did not know that they didn’t have screens for entertainment. I didn’t have headphones so I couldn’t watch anything on my phone.

Disorganized boarding. Mandatory to gate check bags. Curt flight staff. No space for cabin bag, even when I was in first class.

More options for your flight to Caribbean Islands

Complete your trip to Caribbean Islands with a hotel stay or car rental