$87 Find Cheap Flights from Washington Dulles Airport to Caribbean

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KAYAK's insights & trends for Dulles Intl to Caribbean flights

Get data-powered insights and trends into flights from Dulles Intl to Caribbean to help you find the cheapest flights, the best time to fly and much more.

What is the cheapest Washington, D.C. Dulles Intl 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. Dulles Intl Airport found in the last 72 hours was to San Juan, at $114 round-trip. The most popular route is from Washington, D.C. Dulles Intl Airport (IAD) to San Juan Luis Munoz Marin Intl Airport (SJU), and the cheapest round-trip airline ticket found on this route in the last 72 hours was $114.

Can I save money by flying with a layover from Washington, D.C. Dulles Intl 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.

Yes, flying with a layover may cost you more time, but you can also save money on the route, with a 2 stops layover the cheapest option at $988 on average.

What is the cheapest month to fly from Washington, D.C. Dulles Intl 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. Dulles Intl 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. Dulles Intl Airport to Caribbean is June, when tickets cost $304 (return) on average. On the other hand, the most expensive months are December and April, when the average cost of round-trip tickets is $574 and $557 respectively.

What’s the cheapest day of the week to fly from Washington Dulles Airport to Caribbean?

The average price of all round-trip flights from Washington, D.C. Dulles Intl Airport to Caribbean clicked on KAYAK for each day over the last 12 months.

If you are looking for a flight deal from Washington Dulles Airport to Caribbean, look for departures on Tuesdays and avoid leaving on a Friday, as it's usually the priciest day. When flying back from Caribbean, Thursday is the cheapest day to fly and Monday is the most expensive.

How far in advance should I book a flight from Washington, D.C. Dulles Intl 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. Dulles Intl 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. Dulles Intl Airport to Caribbean, you should book around 2 weeks before departure, which saves you about 5% compared to booking last minute. For the absolute cheapest price, our data suggests you should book 16 weeks before departure.

Good to know

Low seasonSeptember
Cheapest flight$87
Best time to beat the crowds with an average 10% drop in price.
Most popular time to fly with an average 25% increase in price.
Flight from Washington Dulles Airport to San Juan

FAQs - booking Caribbean flights

  • What are some of the layover airports for flights from Washington Dulles Airport to the Caribbean?

    Some of the popular layover airports include Miami International Airport (MIA) used by American Airlines, and Hartsfield-Jackson Atlanta International Airport (ATL) by Delta Air Lines. Other airlines may use additional layover airports like Fort Lauderdale-Hollywood International Airport (FLL) or Charlotte Douglas International Airport (CLT).

  • Which airline(s) should I book when flying with kids from Washington Dulles Airport to the Caribbean?

    When flying with kids from Washington Dulles Airport to the Caribbean, consider booking with JetBlue Airways. They offer kid-friendly amenities like complimentary snacks and drinks, in-flight entertainment with kids' channels, and extra legroom options for more comfort. Additionally, JetBlue's friendly crew and accommodating services cater well to young travelers.

  • How convenient is it for people with reduced mobility flying from Washington Dulles Airport to Caribbean?

    Persons with reduced mobility have nothing to worry about when flying from IAD to the Caribbean. However, two airlines with outstanding services for persons with reduced mobility on flights from Washington Dulles Airport to the Caribbean are Delta Air Lines and United Airlines. They offer priority boarding and assistance, dedicated personnel for disabled passengers, and well-equipped cabins with spacious aisles for easy maneuverability, making travel more accessible and comfortable.

  • Which airline is more suitable to book when traveling with pet(s) from Washington Dulles Airport to the Caribbean?

    Traveling with pets from Washington Dulles Airport to the Caribbean is convenient, since all airlines along this route have pet-friendly policies. However, United Airlines is a better option, with a lower pet charge and a weight limit of 20 lb (9 kg) for pets to fly in-cabin. It's essential to comply with specific regulations and book in advance, ensuring a smooth and safe journey for your pet.

  • How does KAYAK find such low prices on flights from Washington Dulles 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 Washington Dulles Airport to Caribbean.

  • How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from Washington Dulles Airport to Caribbean?

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight from Washington Dulles 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 Washington Dulles 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 Washington Dulles 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 Washington Dulles 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 Washington Dulles Airport to Caribbean up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

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

    The cheapest time of day to fly to Caribbean is generally in the afternoon, when round-trip flights cost $238 on average. Morning departures are around 6% cheaper than evening flights, on average. The most expensive time of day to fly to Caribbean is generally at night, which is peak travel time and where the average cost of a ticket is $690.

Top tips for finding cheap flights to Caribbean

  • Travelers seeking to fly to the Caribbean from Washington Dulles Airport (IAD) have several transport options from downtown to the airport. The common option is to take the Silver Line Express Bus (Bus 5A) from Rosslyn Metro Station. The bus provides direct service to the airport, offering a convenient and affordable transportation option for travelers.
  • Booking United Airlines for your Caribbean flight from Washington Dulles Airport (IAD) offers various benefits. As a hub for United Airlines, you can expect extensive flight options, convenient connections, and potential cost savings. Additionally, United's loyalty program and reputable service enhance the overall travel experience.
  • The majority of flights departing from Washington Dulles Airport and heading to the Caribbean have San Juan Luis Muñoz Marín International Airport (SJU) in Puerto Rico as their primary arrival point. This is particularly advantageous for those planning to explore the eastern Caribbean. Alternatively, travelers can opt for Nassau Lynden Pindling International Airport (NAS) in the Bahamas, providing an excellent gateway to the northern Caribbean, or Queen Beatrix International Airport (AUA) in Aruba, which serves as a convenient entry point to the southern Caribbean.
  • When flying from Washington Dulles Airport to the Caribbean, passengers often have the option to upgrade their tickets to higher classes like Business or First. American Airlines and United Airlines are particularly popular for offering such upgrading options, providing travelers with enhanced comfort and amenities during their journey.
  • Consider booking JetBlue Airways or Alaska Airlines if you want to enjoy one of the eco-friendly flights from Washington Dulles Airport to the Caribbean. The two airlines are recognized for their efforts in sustainability and eco-friendly practices. These include increased use of fuel-efficient engines in its aircraft and use of sustainable aviation fuels.

Reviews of the top 5 airlines serving from Dulles Intl to Caribbean

 
Need help choosing which airline to fly with from Dulles Intl 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.
7.9
DeltaOverall score based on 7979 reviews
8.2Boarding
7.9Comfort
7.3Food
8.5Crew
7.9Entertainment
Airline reviews

This route with Delta always has delays or is cancelled. Aircrafts seem smaller and older. I fly Delta quite a bit - haven’t had issues with the international flights. But this route has always been the troublesome one

4.0 Okaypuravi, Aug 2025LGA - STL
Read more Delta reviews

This route with Delta always has delays or is cancelled. Aircrafts seem smaller and older. I fly Delta quite a bit - haven’t had issues with the international flights. But this route has always been the troublesome one

Nothing special. The crew never went out of their way for anything.

Three seats in first class were broken and while they were able to still acommodate us it was looking very touch and go and they had others they could not acommodate

Mechanic delay in addition to a 2 hour change in takeoff time was frustrating.

Delayed due to thunderstorms and no in-flight service due to rough weather — both of which are out of Delta’s control. Flight was good overall.

The flight attendants in SLC were rude. I arrived 40 minutes early to gate. Ticket said I needed check in for seat assignments and tried check in and attendants said they weren’t doing it. And proceeded to never call me to give me a ticket so when time to board I received the very last seat. Please relay to employees to do their job better..,

On this flight I felt the food offering was not as complete as on previous flights. The tomato salad was a bit off and there was nothing additional such a bread or butter. The breakfast was only one option, so you either ate what they had or ate nothing. The crew was efficient, but most seemed frustrated throughout the flight. The flight arrived early and was obstacle-free, so I’m overall quite happy, but the shine in the rest of the experience just wasn’t there.

The seats got pretty uncomfortable pretty fast. The armrests are bigger than on other planes, so I had less room in the actual seat. My butt hurt by the end of the flight. :/ comfort was the primary issue. The crew were fantastic!

I believe that a four-hour trip should have a meal. Delta had none.

Great flight with Delta! Boarding was quick and easy, the amenities were solid, and the plane was in great shape. The flight attendants had a fun, lively energy while staying professional. All in all, a smooth trip — even managed to catch up on some rest. Thanks, Delta!

horrible service, food was an embarrassment, no charging for cellphones, stay away

Very happy with my flight. I would definitely recommend it.

Did upgrade, travel in business it was great (more room I could sleep)

Had to go through security at the gate again. Had to take off shoes and go through the whole thing again even though we have global entry. They asked us to check in items bought at duty free during our layover and since we checked our luggage at the original departure airport, they forced us to check in a small backpack. None of this ever happened with other airlines. In addition, no vegetarian food option and no snacks during a 7 hr flight. Luggage limits are unusually small. This is unacceptable. Will NEVER fly Copa again and will tell friends and family to avoid this airline.

It was ok. However, the food was quite poor since I don't eat pasta.

Tell people to remain in their seats during the meal/beverage distribution. Enforce boarding by group numbers. No one was checking. Tell people to turn their electronics speakers off. Bigger cups for drinks.

Enforce the boarding process by group numbers. Tell people to stay seated during the meal/drink distribution. It took forever to get food and drinks because people would not stay out the isle and let the crew do their jobs. Everyone wanted to go to the bathroom forcing the crew to enter and leave the isle constantly so people can pass. Tell people to keep their electronics off speaker mode. No one wants to hear phone conversations and music playing.

Placed us in the last rear row of the plane so could not recline seats because of the rear wall, and also made it more of a tight space when the passenger in front reclined their seat. While understand seat assignments, every passenger should be afforded a reclining seat. The odor control scent from the restrooms was overwhelming strong. My wife and I could not deal with it, and she suffered a terrible headache as a result. I kept getting hit by the crew since I was on the ilse seat. No apologies, nothing. They made me feel like I was supposed to take the beating for a 3 hr flight.

There was no individual at the front check in when I arrived. I waited for at least 15 minutes and walked around asking security/janitors if they could help and they did not have a solution. So I had to take my checked bag through security and they threw away some of my items. I ended up making it to the gate only a few minutes before it closed due to my waiting for an agent at check in.

The flight was delayed twice and I could not speak with anyone at the airport about checking in. The phone number to Copa - the customer service agents were polite. They are just limited at helping because they are not at the airport

I had no checked baggage but was required to hand over carry on baggage at the door of the plane. There was a lot of overboard space in the plane and I was one of the last ones. I ran to get my carry on but it was gone. I was given back at the plane door in Toronto, so the wait was not as long as it would have been at the carousel.

Armrest controller on my seat 35D and nextbooennseat 35E did not work right. Hard to press buttons to recognize and 35D had constantnpressure either upmost down somit was nearly impossible to make selections. .

I flew with my dog and had already purchased my dog’s ticket. Even that morning I had called costumer service to insure that my husband and I had seats together since the website was giving me an error when choosing our seats and the representative mentioned our dog. I showed up early to the airport and when I got to the gate and we started boarding I was help back and told that I was supposed to have a yellow tag and that I should have checked in at the counter for them to give me that tag. I was not aware of this, the representative on the phone did not say anything. Nor did I see it anywhere in the checking process online, so if you travel with a pet and are not checking in luggage, just know that you still have to go to the check in counter when arriving at the airport unless you want to be the last one to board and not have room for your carry on in the overhead bins. Other than that, I had a great experience.

Very small cramped plane for an international flight. Everything else was good, but it was maybe the smallest comfort-wise I've ever been on for longer than 3-4 hours and the trip was 7.5

Flight was delayed 3 hours. No food and drink vouchers was provided. They offered a mini pretzel bag and water .

Staff was rude. Didn’t give water for 2 hours. Worst service

Was on time until within 1 hour of flight-how does that happen? Staff very friendly.

I liked the choice of lemon ginger tea. I think stewardesses can be more considerate of older people needs.

We were given vouchers we couldn’t use with a 5.5 hour delay

I fly UAL 7-8 times per year. This flight was not up to snuff because it boarded very late "due to unexpected delays in restocking the plane" and yet Flight Aware showed the plane had landed some 10 hours earlier--so I think they could have planned accordingly. The FA's were nice but harried. The video system had to be rebooted 3-4 times. The food service was rather abrupt; they forgot my row and when I asked for my meal, they brought it with some impatience. Overall, the flight was fine, but the little details made it feel somewhat mundane and hurried.

Internet was a bit expensive and did not work ask that week otherwise a good flight

Ring in first class for an overnight flight, there was no blankets nor pillows for first class customers.

My Internet did not work for Outlook email or basically anything. I paid for one hour of in-flight usage and it was terrible. I spent a lot of time on different sites and browsers with no luck and a lot of frustration. Other than that, the flight was on time, crew was nice, service was fine. Seat was OK even though I paid for the extra 6 inches. I cannot imagine how tight the seats in the back must be.

Delayed flight that lead to a missed connection and a 5-hour trip became a 12-hour flight 🙄

Any flight to ORD after about 2pm this summer has been challenging. Flight was delayed getting in (coming from ORD) and that led to it not leaving before a ground stop due to lightening before they could fuel the plane, and so forth. They made up some time but we were still late in arriving at ORD, and that led to missed connections.

Food was ok, but not as good as I have had before on AA.

No issues. They did change our gate FOUR times in about 30 minutes which was mildly annoying but the flight was fine.

Great flight. No issues at all. I still think boarding could be more efficient but otherwise, a good experience.

Pretty good. The food was just mediocre, the boarding and crew were good.

The comfort of the seats was great, the crew eased my child’s anxieties and the fact that I had full cans of my beverage choice was great.

Great for the price. No wifi or entertainment, but gate agents and crew were fantastic and we boarded quickly and left on time.

sluggish boarding and arrival procedures, fake nice flight attendants, and lots of delays.

Disaster. They lied every step of the way. We ended up being delayed due to crew and then allegedly abandoned the flight because of a curfew at LGA. No rebooking to LGA at any reasonable time. No hotel. No meal vouchers. Had to sleep in the airport and fly to Newark instead. Will never fly Frontier again.

What I expected, nickeled and dined and a frontier flight attendant loudly complained about her job and lack of communication as she headed to the gate on her cell phone. Not professional.

As every law enforcement agency I could imagine surrounded the plane and we didn’t disembark for 2 hours and then had to stick around for another hour to go get our personal belongings after leaving them behind and being bused away from the plane, it was scary and inconvenient. We were given no information as to why this was happening. Lack of communication with passengers was disappointing.

After boarding and un-boarding twice over 6+hours, the flight was canceled.

Severe turbulence. Captain never came on to reassure passengers after things settled down.

My first flight was delayed 5 hours. The 2nd flight was canceled til the next day and the never even tried to compensate for it. Worse I was delayed again on the flight the rebooked me on.

Boarding in Orlando was not good. Giant mob at the gate, should have been lines.

The worst. They don’t follow procedure for boarding per group. Flight got delayed for no understandably reasons, they changed our destination from PR to Miami, left us inside a plane for more than 8 hours, then cancelled flight in Miami leaving us stranded. Poorly managed re-accommodation for a new flight and overnight stay so I have to spend in a new ticket and my own hotel room to been able to get to my office next day. Lost 2 days of work and as a doctor, patients loosing their appointments. to other flights and besides

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