$111 Find Cheap Flights from Caribbean to District of Columbia

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Low seasonSeptember
Cheapest flight$111
Best time to beat the crowds with an average 6% drop in price.
Most popular time to fly and prices are also 1% lower on average.
Flight from San Juan to Washington Dulles Airport

FAQs for booking flights from Caribbean to District of Columbia

  • How does KAYAK find such low prices on flights from Caribbean to District of Columbia?

    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 Caribbean to District of Columbia.

  • How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from Caribbean to District of Columbia?

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight from Caribbean to District of Columbia 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 Caribbean to District of Columbia?

    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 Caribbean to District of Columbia 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 Caribbean to District of Columbia?

    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 Caribbean to District of Columbia up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

  • Which airlines fly most frequently to District of Columbia?

    Caribbean and District of Columbia are connected by different airlines. The airlines that fly that route the most regularly are United Airlines (72 flights per week), Air Canada (14 flights per week), and American Airlines (13 flights per week).

  • How many airports are there in District of Columbia?

    There are 2 airports in District of Columbia. The busiest airport is Washington Dulles Airport (IAD), with 66% of all flights arriving there.

  • Which is the cheapest airport to fly into in District of Columbia?

    Prices will differ depending on the departure airport, but generally, the cheapest airport to fly to in District of Columbia is Baltimore/Washington Airport (BWI), with an average flight price of $286.

  • What is the cheapest day to fly to District of Columbia?

    Based on KAYAK data, the cheapest day to fly to District of Columbia is Thursday where round-trip tickets can be as cheap as $315. On the other hand, the most expensive day to fly is Monday, where round-trip prices are $600 on average.

  • What is the cheapest time of day to fly to District of Columbia?

    The cheapest time of day to fly to District of Columbia is generally in the evening, when round-trip flights cost $380 on average. Morning departures are around 23% more expensive than evening flights, on average. The most expensive time of day to fly to District of Columbia is generally in the afternoon, which is peak travel time and where the average cost of a ticket is $716.

  • What is the cheapest flight to District of Columbia?

    The cheapest ticket to District of Columbia from Caribbean found in the last 72 hours was to Baltimore, at $122 round-trip. The most popular route is Oranjestad (AUA) to Baltimore (BWI) and the cheapest round-trip airline ticket found on this route in the last 72 hours was $122.

  • What is the cheapest month to fly from Caribbean to District of Columbia?

    The cheapest month for flights from Caribbean to District of Columbia is October, when tickets cost $362 (return) on average. On the other hand, the most expensive months are April and November, when the average cost of round-trip tickets is $720 and $505 respectively.

  • How far in advance should I book a flight from Caribbean to District of Columbia?

    To get a below average price on the flight from Caribbean to District of Columbia, you should book around 2 weeks before departure, which saves you about 37% compared to booking last minute. For the absolute cheapest price, our data suggests you should book 5 weeks before departure.

  • How many cities have direct flights to District of Columbia?

    From Caribbean, there are direct flights to District of Columbia from 10 cities. The city with the most direct flights is San Juan, with 40 direct flights each week.

  • How many direct flights to District of Columbia are there each day?

    There are around 16 direct flights from within Caribbean to District of Columbia every day. Most flights (70%) depart in the afternoon.

  • How many direct flights to District of Columbia are there each week?

    Each week there are around 111 direct flights from within Caribbean to District of Columbia. The most common day for departures is Saturday, with 18% of flights taking off on this day.

  • How long is the flight to District of Columbia?

    An average nonstop flight from Caribbean to District of Columbia takes 9h 48m, covering a distance of 1542 miles. The shortest route is Nassau (NAS) to Washington, D.C. Dulles Intl Airport (IAD) with an average flight time of 2h 53m.

  • How many long-haul flights are there to District of Columbia each week?

    Each week, there are 51 medium-haul flights (3-6 hour flight duration) and 60 short-haul flights (up to 3 hour flight duration) to District of Columbia. There aren't any long-haul flights (6-12 hour flight duration).

  • What is the most popular destination in District of Columbia?

    Based on KAYAK flight searches, the most popular destination is Washington, D.C. (100% of total searches to District of Columbia).

Reviews of the top 5 airlines serving from Caribbean to District of Columbia

 
Need help choosing which airline to fly with from Caribbean to District of Columbia? 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
DeltaOverall score based on 8464 reviews
7.8Entertainment
8.1Boarding
7.2Food
8.5Crew
7.9Comfort
Airline reviews

Round trip flight to Canada and back to the US was smooth and efficient.

8.0 ExcellentBrent, Apr 2026
YWG - MSP
Read more Delta reviews

Round trip flight to Canada and back to the US was smooth and efficient.

The agent at check in and at the gate were less than thrilled to be at work. I'm not a fan of Kayak's placement on the plane. I got put in the middle seat and none of my preferences were used.

Spanish speaker flight attendants were incredibly rude. A male flight attendant named Allen, grabbed my bag out of the overhead bin and moved it without my permission. When I asked what he was doing, he informed me that the overhead bins were public space? It would be easy to ignore this comment, as you don’t know the whole story, but the flight attendants were militant and rude. Delta, you can do better!

In ATL they have two sets of departure screens. Follow what is on your airline's departure board - the ATL Airport Authority departure board had completely incorrect details about the gate assignment for my flight, which would have made me miss boarding.

Flight was delayed it was hot while sitting on the plane, one engine was working on the plane until they had to do some jimmy rigging down the runway in order for the other engine to charge up. It was ridiculous

The flight was very good and the staff was very friendly and helpful!

The only thing I would say is we tried to get on a standby earlier flight, but with our fair we couldn’t. That seems senseless to leave with open seats..

Very easy to use and convenient, you can perform any action within the same portal

In a world of delays, Delta was on time both ways! Boarding was fast and efficient. Staff was friendly. AND wifi worked.

My business class seat was inoperable and unable to recline for 10 hour flight.

Was great in general, try to respect time and excuses when slight changes have been made, appreciated!

Terrific in every way. On time, professional staff, multiple movie options to select, great food and drink.

My bags were misplaced!!! Im in a foreign country with no bags

I liked that it was on time, however, the food was not good.

Offered to check carry on to final destination. This is the most absurd thing in the world. I'm carrying on because I need what is in the carry-on. I'm okay with picking up at next stop but then I will be on much larger plane that can accommodate it. Also, if there is ever a change to your flight. Go to the airport and have the people there fix your ticket. Don't do it over the phone or online with United they screwed us up and ended up with flights for our last leg that took off before our first leg.

United is one airline which regardless of how many separate United tickets in existence, if one flight breaks down, the airline will take care of all the flights.

It was okay, the food was good, but after the landing there was not enough time for luggage and security to catch a connection. It was crowded on board.

When I went to check in at the United counter in Barcelona, Spain I had 2 different menat 2 different times in United uniforms (standing around with a couple other employees) ask me if I was traveling alone. The one man asked me 3 different ways if I was traveling alone. I am, 68 yeaers old and have all my faculties. I thought it was weird and it made me feel very uncomfortable. What difference does it make if I was traveling alone or with someone? What if I was a recent widow? That would have been horrible. They never gave me a reason why they needed to know who I was traveling with. I was hesitant to question them because I needed to be on that flight.

We were delayed for about an hour from taking off due to traffic control procedures at the destination airport. But once in the air, the flight went well. The crew members were great and provided cabin service despite moderate turbulence during much of the flight.

Crew was great. 2 1/2 hour delay was due to staff needing "rest" was avoidable and self inflicted as United not willing to hire enough crew to keep flight on time.. Ridiculous. The crew and the passengers both suffered due to this.

Right now I’m still in Jamaica waiting on a flight to New York which I should be in New York from the 30th and I’m here in Jamaica

Boarding was quick and efficient. The flight crew were friendly. There were limited food options available on the flight. The pocket guide said there would be salad and sandwich sections available on flights over 3.5 hours. The only food available were snack boxes. And those were limited as well. My flight was over 5 hours. The entertainment system worked well. I had both extra legroom seats and regular coach seats. The seats were not very comfortable. The entertainment controls in the armrest made it difficult to rest my arm without changing the channel on my neighbors TV. Overall, my experience was mediocre.

Purchased through 3rd party vendor which made everything difficult. Unable to check in online. Unable to get flight updates easily, tsa precheck information didn’t carry through, longer time to check in in person. Entertainment looked good but had to purchase conventional headphones to view.

Boarding was fast, easy, and we landed early. The entertainment system was very buggy and kept resetting throughout the flight.

Not having an assigned seat until boarding and then having to check my bag.

Boarding was done extremely poorly, with huge crowds gate loiterers blocking people from boarding, multiple lines of people trying to merge into one line. One of the male flight attendants who was doing drink service was not happy about having to let a passenger back to their seat and was unnecessarily sassy about it. I thought he was pretty entitled and not a great ambassador for JetBlue

Flight emergency landed in Chicago due to “Odor” in back of plane . Had to buy ANOTHER TICKET to get to Boston cash out of my own pocket . Then they would notchange my return flight time without a 400. Charge!!!! Insulting.

I purchased ticket so our daughter ( a minor) can sit next to her mother. No help at gate after kayak insisted that this could be done. She ended sitting by herself

Flight was as expected. But it was delayed an hour. Also, my luggage got damaged. So that sucked especially since the damage made navigating the airport difficult. Walking to get ground transportation is sooo far away now and my checked bag was difficult to carry.

we were an hour delayed after boarding and given no reason. Headsets cost money. Also there were openrows with no one setting in them but we were told we were not allowed to swtich.

The airplane was an old model, the overhead didn’t have enough room for people’s items and made boarding and boarding disappointing and stressful. Crew allowed passengers to bring more than the permitted baggage sizes.

It was great. Smooth flight, comfortable, left on time and landed on time.

Horrible experience upon landing. Probably more due to DCA utter incompetence than AA.

Easy boarding. Rows are smaller but that may be an older and bigger me now :)

Flight has been delayed every time I've ever taken it. Seats uncomfortable. Children behind me yelling the entire flight. Some of this is out of their control but overall just consistently not a great experience.

Poor communication ahead of time about flight delays and old planes/other equipment.

Never going to fly your airline again if it can be avoided.

Not to have gotten delayed by 2+ hours for the fourth straight American flight. They're the worst.

Other than nearly three hour delay for maintenance issues, everything went smooth

Snow delayed boarding several times, which I understand happens. Issue I had was that after we did board, pilot told us we were going to roll out to be de-iced, then on our way. We were de-iced once, taxied to the tarmac and then stopped. Sat for another 30 minutes or so, the another de-icing. Then we rolled out to a parking spot, only to sit for another hour due to a traffic stop in DCA, which I'm confident they knew would happen before we boarded. Pilot gave no updates other than we had to hold, attendants did speak to the crew, but when asked, said the pilot would be updating us. We on the ground in the plane waiting for over 2 hours. They did communicate that bathrooms would be open, but no other news until we left. Would have been better to be up front about status.

Flight was scheduled at 9:40pm. Got delayed to 10 am, the next day. crazy

The bag check, flight check-in, and onboard experience convinced my wife and me that we will actively go out of our way to avoid flying Frontier Airlines in the future. At bag check, we were informed that check-in could only be completed via the Frontier mobile app. Unfortunately, the app was extremely frustrating—sending us through repetitive, confusing loops that repeatedly forced us to decline add-on services with nearly every click. While most airline apps upsell, this one felt intentionally exhausting. As the process dragged on, we became genuinely concerned that my phone battery would die before check-in could be completed. We approached the bag check staff—who were standing together talking—and explained both our frustration and our predicament. They laughed. Later, my wife described the interaction as “gaslighting,” which felt accurate. We were then informed it would cost $25 per person simply to have our boarding passes printed. From that point forward, the tone of the experience was consistently hostile. The bag check employees were condescending and combative, behaving more like bullies than customer service staff. Unfortunately, that same attitude continued onboard. One flight attendant argued with me when I attempted to stow my backpack in the overhead bin. I explained that we had each paid $75 to check our bags specifically so we would not need to use carry-on space and could have adequate legroom. She demanded to see my ticket, pointed out that it said “no carry-on”—which I acknowledged—and I reiterated that this was precisely why we paid to check our bags. Her response was, “I don’t make the rules.” She then walked away, but not before asking if I “truly wanted to fly back to Chicago today?”—an unnecessary and unmistakable threat. It is also worth noting that despite booking our tickets together in the same transaction, we were not seated together. Upon our return to Chicago—where we could once again sit together—we compared onboard experiences. We both remarked on how unhappy the flight attendants appeared and how each of us was separately asked whether we would like to purchase a beverage. We declined. At no point was water mentioned as an option, leaving us with the clear impression that even water came at a cost—or that complimentary water, if available at all, was deliberately left unmentioned. Overall, the experience was shocking and deeply disappointing, but it was also a profound learning experience—one we will not forget and will not repeat. -Steve

Plane was hot and miserable and the crew was rude!

12 hour delay required getting on and off plane 3 times - would have at least liked to have been offered a snack or drink

They didn’t offer a water, even after I asked

Zero issues with this flight. Crew was outstanding and flight was super. Plane was clean and fine. The seats need more padding and water should be provided without cost. I recognize it's Frontier but there are some things that should still be part of the flight. But still very satisfied with the experience and quality.

They switched our terminal 3 times and we were delayed for four plus hours!!!

It was an early flight and most people napped/slept and the crew let us which was nice.

The crew acted like they had never done this and kept barking passive aggressive orders at people. + the security line + the delay + sitting on the tarmac for 2 hours + none of the apps or signage updating with correct times

More inflight connection. And leg space is horrible. And the paying for baggage I'd ridiculous!!!

Everything you need to know for your flight to District of Columbia

Cabin class types available on flights to Caribbean

Cabin classes available on flights to Caribbean. Prices are the lowest found on KAYAK over the last 7 days. Price and availability is not guaranteed.