$105 Find Cheap Flights from Caribbean to District of Columbia

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Low seasonSeptember
Cheapest flight$105
Best time to beat the crowds with an average 10% drop in price.
Most popular time to fly and prices are also 2% 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 (66 flights per week), American Airlines (14 flights per week), and Air Canada (14 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 58% 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 Washington, D.C. Dulles Intl Airport (IAD), with an average flight price of $302.

  • 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 $308. On the other hand, the most expensive day to fly is Monday, where round-trip prices are $584 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 $376 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 $91 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 $91.

  • 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 September, when tickets cost $361 (return) on average. On the other hand, the most expensive months are January and April, when the average cost of round-trip tickets is $500 and $497 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 36% 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 (66%) depart in the afternoon.

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

    Each week there are around 106 direct flights from within Caribbean to District of Columbia. The most common day for departures is Saturday, with 17% 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 45m, 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 43m.

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

    Each week, there are 62 medium-haul flights (3-6 hour flight duration) and 44 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 8292 reviews
8.1Boarding
7.9Comfort
8.5Crew
7.2Food
7.8Entertainment
Airline reviews

First class is comfortable. Enjoyed a movie and was able to relax compared to coach.

10.0 ExcellentAnonymous, Mar 2026
ATL - DTW
Read more Delta reviews

First class is comfortable. Enjoyed a movie and was able to relax compared to coach.

Loved flying First Class. Very comfortable. The seat was amazing. Enjoyed a movie and was able to relax so much better than in coach.

No pilots so we were two hours late taking off and then no gate agents when we arrived in Salt Lake.

We landed and sat on the tarmac for 45 minutes because they only have one gate at the airport and there was another plane running late so we had to wait

The WiFi was not working. That made for a long flight.

Absolutely no communication on why there's a delay and multiple flight time reschedules. I would have canceled the flight and drove back home if I known it was going to be rescheduled 3 or 4 times.

Another late night flight and MORE men belligerently drinking and yelling. I had to move from first to economy because they were so obnoxious and disruptive. Crazy to go from a cozy chair to cardboard when you were supposed to be in first. Delta allows was too much drinking which leads to belligerent behavior.

I was in first class and literally the men behind me were so aggressively loud I moved myself to economy. This has become so common on Delta - people using audio without headphones, and men on 12am / late night flights drinking and yelling to talk to each other which prevents anyone around them from resting. Pretty crazy to have to move from first to economy (poorer service, less comfort...). Wild wild. Looking into other airlines.

Love delta smaller commuter plane so no entertainment and paid wifi on MKE-LGA leg was extremely unreliable and slow

Stop changing gates. Stop cancelling flights Stop moving my seat.

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.

Fine not above and beyond as I had a connection that was delayed due to maintenance

Bad food, bad service, cold cabin with no additional blankets when asked for (they told me they don’t provide additional blankets). I’m a frequent traveler and this is one of the worst companies I traveled with (by the way I thought that I booked my ticket with Lufthansa but I didn’t see that the flights were handled by United).

Great other than a couple very drunk guys that for a while kept bumping my seat from behind. The staff did their best to control them. Even refused serving them alcohol and allowed the gal sitting next to them to move.

Good crew. Boarding delays. Almost two hours wait for the bags in DC.

Unfortunately weather delayed our flight waiting for our plane to arrive and due to a little snow time was needed to deice the plane so departure was very delayed and I missed the connecting flight

It was great. There were some issues prior to takeoff. The weather was poor so we had to go through deicing, and we were delayed a bit by the pilots' concern about one of the engines, but that's aviation. The pilots handled everything with aplomb, and kept us apprised

Arrived as recommended at 8:15 a.m. for an 1115 flight, that kept getting delayed delayed and delayed and then finally canceled. Instructed for the split flight to go to Fort Lauderdale, and then find our way from there back to New York. I don't think I will ever trust flying with JetBlue again. This was my second horrific experience and I am really angry.

Delayed by 1.5 hours. Terrible apologies, half hearted at best. It will be a LONG time until i book w Jet Blue again. Very disappointed.

Qatar does not answer phone calls and communicate with travelers about trip cancellations

The seats have so much room. They give great free snacks. Staff was so nice.

My check in was stressful. I somehow lost my seat from my original booking, the plane showed no availability/no seat when it was time to check-in. I called and was instructed to try to get a seat at the airport. I asked if it was a full flight and the travel agent said the site showed some seating but was not able to secure one for me. Why not? On my way to the airport the app finally revealed one available seat towards the back of the aircraft that I was able to book. It ended up being an overbooked flight, so glad I wasn't stuck.

Flights with JetBlue from San Diego to Boston are a miserable experience. The flight was delayed about 1.5 hours due to “weather” supposedly but the flights for other airlines left on time so it just have been some kind of weather that only affects JetBlue. I had a small carry on - purse. The crew stored it in a bin 2 rows down from me because they were using the bin next to my seat for other people’s stuff. The TV screen in the emergency row seats does not work. It just was awful from start to finish. When we landed, we had to sit inside the plane for a very long time because the plane had to be moved to a different gate.

They made me check my bag and I didn't need to as there was overhead space available. I paid for a seat towards the front of the plane and it didn't recline. I requested a refund and they declined to give me one.

I have to congratulate Kayak (and Dylan the Chatdeal agent) because because when we decided extended our trip in Florida by two days, there were many direct flights oprions back to Boston available on the Friday we wanted to fly on the JetBlue website, but once I canceled the original JetBlue flight on their website, those direct return options disappeared immediatley! I think it's a game JetBlue plays. . Luckily, I checked Kayak and they had a direct flight that wasn't appearing on JetBlue's website and so I booked it, and we were able to fly home direct through the Kayak booking when JetBlue was offering nothing (even though I have been a True Blue member for 20 years, and also am a Mosaic member). So much for loyalty- their algorithm for booking is like a shell game. JetBlue used to be a good company but now they're worse than anyone. Also I was originally booked this trip to Florida, two months before the departure date, I booked the trip on JetBlue's website and then after the payment part, they said there was a problem and that I needed to do the booking again, so when I immediately went to rebook , the price had gone up 30%! I called them and it sounded like they had heard this so many times before and the guy told me to check back in 10 minutes and the price would be back to where it was when I was booking- it but it never was. How could the price go up 30% in one minute two months before the flight???? They're playing a game with their customers. Anyways, I booked a cheaper flight then at a less convenient time. So fast forward two months the night before the 7 AM flight, they sent me an email at midnight when I was sleeping to let me know that my flight at 7 AM had been canceled. The only thing they offered was a flight that night from from a different airport (Providence) to a different airport in Florida (West Palm Beach) or a flight two days later. No compensation, nothing. They couldn't of tried to get another plane to the Boston airport? They had all night to do it. I passed on their ridiculous options and flew with Delta and it was a great experience. Of course, I had to pay a lot more booking on the same day, but JetBlue doesn't care. I put in a lengthy complaint with the agent who assured me someone would get back to me by email within three days and I haven't heard a thing. JetBlue used to be a good company but now they're among the worst. The only thing they still have is decent legroom, but the corporate bean counters will probably start taking that away too.

We were made to wait in the airport for six hours for a flight that was ultimately canceled.

It was a pretty smooth flight, I tend to get mini anxiety attacks during flights, however, this time was pretty smooth and I was able to relax. The only thing, I was having issues to connect to the Flyfi internet. I was not able to connect at all, I turned off my phone a couple times and didnt work.

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 delayed. Not much information on when the flight would take off. Eventually we were told it was maintenance. App was not giving updates.

Flight was on time and there was an empty seat next to me. That makes for a good flight!

Maintenance took a very long time and then we were in a holding pattern. While a one-off maintenance issue is standard, there were delays on both of my flights for this trip based on maintenance issues with the planes, which delayed both flights over 45 minutes. Thankfully, I didn't have any connections but it wasn't an experience that would make me pick AA if I have other options.

My flight was originally from SAT to MCO connecting from MCO to ORD. We got diverted to ATL and than Frontier staff there was sooo un helpful first they said they couldn’t give us any accommodation since our flight first got delayed that cancelled and now it’s 221am and I am still in ATL since they said they need to create a new flight my final destination is ORD and I have been delayed twice and cancelled. With no real help the frontier app didn’t work no email updates over all such a horrible experience

There's no seats that lean back with little leg space i wad uncomfortable the entire flight. Your charges for extra baggage is despicable and costly!!

Remind customers of the need to have passport or new ID for boarding.

Flight was canceled. Most upsetting was message from Kayak, stating that the flight was canceled and click with Kayak for details regarding rebook, refund details. THERE'S NO INFORMATION PROVIDED BY KAYAK EXCEPT THAT FLIGHT IS CANCELED. AND NOW THIS SURVEY TO FIND OUT HOW WAS THE FLIGHT !!!!!!!

The flight never took off and we spent 7 hours at the airport

Gate not determined until I got to the airport - hard to plan the trip to the airport.

Our flight was canceled. I will never use Kayak nor Frontier for travel again. The entire experience was a headache.

Frontier.. nickel and dime add-ons. Flight late, on time, late again, last minute gate change, arrival gate required a shuttle to the terminal. They sure keep you guessing.. if you like a little chaos and airport anxiety, this is the airline for you!

This is my second time flying with Frontier. My current experience was very favorable. The staff from the gate to the plane was friendly, warm and professional. The food options lacked in my opinion. This area needs some attention in my opinion.

Frontier line changes my flight schedule with out my authorization. They never ask me and with out my concern they cut off 4 hours of my vacation they force my to leave 4 hours early from Puerto Rico.

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.