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Cheap Flights from Washington, D.C. to Caribbean Islands

Cheapest round-trip prices found by our users on KAYAK in the last 5 days
Punta Cana
Punta Cana1 stop$370
Santo Domingo
Santo Domingo1 stop$334
Montego Bay
Montego Bay1 stop$301
Oranjestad
Oranjestad1 stop$403
Nassau
Nassau1 stop$387
Kingston
Kingston1 stop$466
Providenciales
Providenciales1 stop$355
Port of Spain
Port of Spain2 stops$422
Bridgetown
Bridgetown1 stop$373
George Town
George Town1 stop$349
Willemstad
Willemstad1 stop$397
Castries
Castries2 stops$708
Aguadilla
Aguadilla1 stop$246
St. John's
St. John's1 stop$460
Puerto Plata
Puerto Plata2 stops$447
Punta Cana
Punta Cana1 stop$370
Santo Domingo
Santo Domingo1 stop$334
Montego Bay
Montego Bay1 stop$301
Oranjestad
Oranjestad1 stop$403
Nassau
Nassau1 stop$387
Kingston
Kingston1 stop$466
Providenciales
Providenciales1 stop$355
Port of Spain
Port of Spain2 stops$422
Bridgetown
Bridgetown1 stop$373
George Town
George Town1 stop$349
Willemstad
Willemstad1 stop$397
Castries
Castries2 stops$708
Aguadilla
Aguadilla1 stop$246
St. John's
St. John's1 stop$460
Puerto Plata
Puerto Plata2 stops$447
Booking Insights

KAYAK's insights & trends for Washington, D.C. to Caribbean Islands flights

Get data-powered insights and trends into flights from Washington, D.C. 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. to Caribbean Islands flight route?

The cheapest ticket to Caribbean Islands from Washington, D.C. found in the last 5 days was to San Juan, at $208 round-trip. The most popular route is from Baltimore (BWI) 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 $208.

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

The cheapest time of day to fly to Caribbean Islands is generally at night, when round-trip flights cost $337 on average. Morning departures are around 3% more expensive than evening flights, 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 $491.

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

No, with an average price for the route of $487, prices are generally cheapest when you fly direct.

What is the cheapest month to fly from Washington, D.C. to Caribbean Islands?

The cheapest month for flights from Washington, D.C. to Caribbean Islands is January, when tickets cost $523 (return) on average. On the other hand, the most expensive months are December and July, when the average cost of round-trip tickets is $688 and $651 respectively.

What’s the cheapest day of the week to fly from Washington, D.C. to Caribbean Islands?

For Washington, D.C. to Caribbean Islands, Monday is the cheapest day to fly on average and Friday is the most expensive. Flying from Caribbean Islands back to Washington, D.C., the best deals are generally found on Thursday, with Monday being the most expensive.

How far in advance should I book a flight from Washington, D.C. to Caribbean Islands?

To get a below average price on the flight from Washington, D.C. to Caribbean Islands, you should book around 1 week before departure. For the absolute cheapest price, our data suggests you should book 5 weeks before departure.

Good to know

Low season

September

Cheapest flight

$110
Most popular time to fly with an average 17% increase in price.
Flight from Washington Dulles Airport to Montego Bay

FAQs - booking Caribbean Islands flights

  • How does KAYAK find such low prices on flights from Washington, D.C. 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 Washington, D.C. to Caribbean Islands.

  • How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from Washington, D.C. to Caribbean Islands?

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight from Washington, D.C. 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 Washington, D.C. 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 Washington, D.C. 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 Washington, D.C. 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 Washington, D.C. 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 Washington, D.C. to Caribbean Islands

 
Need help choosing which airline to fly with from Washington, D.C. 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.
8.0
SouthwestOverall score based on 4200 reviews
8.1Boarding
7.0Food
8.0Comfort
8.6Crew
7.5Entertainment
Airline reviews

Delayed and once landed waited very long for the luggage

6.0 GoodIngeborg, Sep 2026
Read more Southwest reviews

Delayed and once landed waited very long for the luggage

Nice managed … it was a smaller plane, so the seating wasn’t as comfortable.

The Southwest airline was ok. A big thank you to Kayak team (David), who worked with me on Sunday afternoon to rebook my travel from Burbank, CA, to CVG. My original flight on Sunday was delayed, so I had to cancel Sunday flight and rebook my travel to Monday. Could not have done it without help from David from Kayak team. Ante Soda GE Aerospace

Seated at front bulkhead for a smidge extra leg room away from home and on flight back home. Away crew was very proactive about assuring our carryons had space close behind us (because no seat in front of us our personal items had to be in a small bin overhead). They actively required passengers place overhead luggage on its side so more items could fit in bins. Home crew made no such efforts. I had to struggle back rows to get overhead bags upon landing, no crew help then either, and some disgruntled passengers as I and others retrieved our bags. There was a system that worked pretty well. The home bound crew just didn't feel like working.

Southwest has inacted unfriendly customer policies like other airlines. Watch the fine print very carefully if you are having to alter flight arrangements. Rules are now complicated and very stilted to travelers sacrificing travel funds (unlike before where the simple, straight forward flight change policy was worth the extra premium for ticket price.) On the positive side, SW Flight crews are still wonderfully helpful.

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!

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.

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.

Crew was great. Seats are cramped and uncomfortable and I’m a small person.

A little more friendliness from that crew of the day.

Staff didn't seem confident about the ingredients in my lactose intolerance meal

the seat has a problem. the back had a hole.

My flight was delayed so bad i missed u it so i just said never mind

Delayed 2 hours while stuck on the aircraft. If the luggage was properly loaded the first time we probably wouldn’t have been delayed at all

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.

The flight did not have its customary snacks during the flight. Apparently they were never loaded on the plane.

Worst service- attendants dont want to help and sat us in front of bathroom

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.

the flight is delayed, which is not uncommon but the communication was still getting hopes on reaching on time which didn't happen. When I boarded the flight it was so like unimaginably filthy. My seat belt had some sticky stuff to it like food or something from before and the space below the arm rest is accumulated dust and waste like from few months i have the pictures. Cheery on top, the airhostess was an old lady who was so bossy and mad for no reason and bossing around everyone!! worst experience ever!!

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.

Patrons with larger bags were asked to check the bags when boarding. Seems like the most effective, and least costly way, way to successfully use the cramped space.

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…

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.

More options for your flight to Caribbean Islands

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