$102 Find Cheap Flights from Washington, D.C. to Caribbean Islands

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight from Washington, D.C. to Caribbean Islands departing on 5/7. Fares are subject to change and may not be available on all flights or dates of travel. Click the price to replicate the search for this deal.
1 adult
1 adult, Economy, 0 bags

KAYAK searches hundreds of travel sites at once for deals on flights to Caribbean Islands

 
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Washington, D.C. to Caribbean Islands.
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Washington, D.C. to Caribbean Islands.
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Flight Deals

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

Cheapest round-trip prices found by our users on KAYAK in the last 72 hours
Punta Cana
Punta Cana1 stop$410
Santo Domingo
Santo Domingo1 stop$333
Montego Bay
Montego Bay1 stop$264
Oranjestad
Oranjestad1 stop$250
Nassau
Nassau1 stop$383
Kingston
Kingston1 stop$445
Simpson Bay
Simpson Bay1 stop$262
Providenciales
Providenciales1 stop$441
Port of Spain
Port of Spain1 stop$424
Bridgetown
Bridgetown2 stops$397
George Town
George Townnonstop$307
Willemstad
Willemstad1 stop$359
Castries
Castries2 stops$861
Aguadilla
Aguadilla1 stop$194
Puerto Plata
Puerto Plata1 stop$535
St. John's
St. John's1 stop$446
Punta Cana
Punta Cana1 stop$410
Santo Domingo
Santo Domingo1 stop$333
Montego Bay
Montego Bay1 stop$264
Oranjestad
Oranjestad1 stop$250
Nassau
Nassau1 stop$383
Kingston
Kingston1 stop$445
Simpson Bay
Simpson Bay1 stop$262
Providenciales
Providenciales1 stop$441
Port of Spain
Port of Spain1 stop$424
Bridgetown
Bridgetown2 stops$397
George Town
George Townnonstop$307
Willemstad
Willemstad1 stop$359
Castries
Castries2 stops$861
Aguadilla
Aguadilla1 stop$194
Puerto Plata
Puerto Plata1 stop$535
St. John's
St. John's1 stop$446

Book Cheap Washington, D.C. to Caribbean Islands Plane Tickets

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Washington, D.C. to Caribbean Islands that are departing in the next months. While these flights were available on KAYAK in the last 72 hours, prices and availability are subject to change and deals may expire.
Discover the best prices for you by selecting your travel dates on KAYAK.

Recent round-trip flight deals from Washington, D.C. to Caribbean Islands

Wed, Jun 3 - Thu, Jun 4
Frontier Logo
6:28 pm - 4:49 am
BWI
-
SJU
10h 21m
1 stop
Frontier Logo
3:35 pm - 7:49 pm
SJU
-
BWI
4h 14mnonstop
$178Frontier
Sun, May 3 - Fri, May 8
Multiple Airlines Logo
9:10 pm - 9:54 am
BWI
-
SJU
12h 44m
1 stop
Multiple Airlines Logo
8:04 pm - 8:35 am
SJU
-
BWI
12h 31m
1 stop
$179Multiple Airlines
Fri, May 8 - Mon, May 11
Spirit Airlines Logo
8:01 pm - 11:54 pm
BWI
-
SJU
3h 53mnonstop
Spirit Airlines Logo
2:09 am - 6:05 am
SJU
-
BWI
3h 56mnonstop
$180Spirit Airlines
Mon, Aug 3 - Thu, Aug 6
JetBlue Logo
8:20 am - 12:19 pm
DCA
-
SJU
3h 59mnonstop
JetBlue Logo
6:07 pm - 9:59 pm
SJU
-
DCA
3h 52mnonstop
$252JetBlue
Wed, Aug 19 - Wed, Aug 26
American Airlines Logo
1:44 pm - 9:14 pm
DCA
-
SJU
7h 30m
1 stop
American Airlines Logo
10:33 am - 8:59 pm
SJU
-
DCA
10h 26m
1 stop
$271American Airlines
Tue, Jun 2 - Sat, Jun 6
JetBlue Logo
8:20 am - 12:05 pm
DCA
-
SJU
3h 45mnonstop
JetBlue Logo
5:10 pm - 9:03 pm
SJU
-
DCA
3h 53mnonstop
$272JetBlue
Mon, Aug 24 - Sat, Aug 29
American Airlines Logo
1:53 pm - 10:24 pm
DCA
-
SJU
8h 31m
1 stop
American Airlines Logo
7:10 pm - 9:09 am
SJU
-
DCA
13h 59m
1 stop
$291American Airlines
Thu, Aug 13 - Sun, Aug 16
Southwest Logo
12:55 pm - 8:05 pm
DCA
-
SJU
7h 10m
1 stop
Southwest Logo
6:00 am - 6:50 pm
SJU
-
DCA
12h 50m
1 stop
$296Southwest
Sat, Jun 6 - Tue, Jun 9
United Airlines Logo
7:00 pm - 3:30 pm
DCA
-
AUA
20h 30m
1 stop
United Airlines Logo
1:50 pm - 10:49 pm
AUA
-
DCA
8h 59m
1 stop
$384United Airlines
Tue, Jul 14 - Thu, Jul 23
United Airlines Logo
6:30 am - 3:20 pm
IAD
-
AUA
8h 50m
1 stop
United Airlines Logo
4:30 pm - 9:03 pm
AUA
-
IAD
4h 33mnonstop
$389United Airlines
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?

Data is based on round-trip flight searches on KAYAK over the past month.

The cheapest ticket to Caribbean Islands from Washington, D.C. found in the last 72 hours was to San Juan, at $164 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 72 hours was $164.

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

The average price for all round-trip flights from Washington, D.C. to Caribbean Islands depending on the time of departure, clicked by users on KAYAK in the last 2 weeks.

The cheapest time of day to fly to Caribbean Islands is generally at night, when round-trip flights cost $344 on average. Morning departures are around 10% cheaper than evening flights, on average. The most expensive time of day to fly to Caribbean Islands is generally in the evening, which is peak travel time and where the average cost of a ticket is $451.

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

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.

No, with an average price for the route of $463, prices are generally cheapest when you fly direct.

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

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for round-trip flights from Washington, D.C. to Caribbean Islands, 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. to Caribbean Islands is July, when tickets cost $298 (return) on average. On the other hand, the most expensive months are March and December, when the average cost of round-trip tickets is $436 and $435 respectively.

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

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

For Washington, D.C. to Caribbean Islands, Sunday is the cheapest day to fly on average and Wednesday 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 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. to Caribbean Islands, 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. to Caribbean Islands, you should book around 1 week before departure. For the absolute cheapest price, our data suggests you should book 20 weeks before departure.

Good to know

Low seasonSeptember
Cheapest flight$102
Best time to beat the crowds with an average 10% drop in price.
Most popular time to fly with an average 19% increase in price.
Flight from Baltimore to San Juan

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

 
See real verified KAYAK customer reviews for airlines flying from Washington, D.C. to Caribbean Islands. Airline scores are aggregated from all reviews left by passengers on KAYAK after flying with an airline. KAYAK doesn’t show reviews that are older than 5 years. Learn how KAYAK collects reviews.
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 4331 reviews
7.5Entertainment
7.0Food
8.0Comfort
8.1Boarding
8.6Crew
Airline reviews

Southwest is kind of a slum airline. It’s gotten more expensive over the years for less and less service. I am a Southwest Chase Visa card holder and was forced to choose a seat in the 26th row in the middle seat. However my wife who is a rewards member but doesn’t hold a card or anything else, gets randomly assigned a normally paid seat in row 6! How does that work?

4.0 OkayDavid, Apr 2026
COS - DAL
Read more Southwest reviews

Southwest is kind of a slum airline. It’s gotten more expensive over the years for less and less service. I am a Southwest Chase Visa card holder and was forced to choose a seat in the 26th row in the middle seat. However my wife who is a rewards member but doesn’t hold a card or anything else, gets randomly assigned a normally paid seat in row 6! How does that work?

For the first time in a long time, the Wi-Fi actually worked the entire flight! The flight crew was amazing as usual.

The seat was not comfortable. 1D. My back was sore all night and the next day.

Great flight. I didn't get a drink because I was asleep whole on the flight.

Great flight from Seattle to Phoenix and to Chicago-Midway from Phoenix

The new boarding process was easy and straightforward. Very pleasant.

The flight was okay. The pilots did an amazing job and kept us updated on the flight. The flight attendants were okay. They found time to be chatty with each other rather than focus on the guests. One of the attendants was a little less warm when asking about my bag I had on my lap that I was using during latter part of the mid- flight. Mind you, it was not the departure descent. I’m respectful to each and every attendant, it was the tone in her voice reminding me to place my carryon bag on the floor. I hope to have a better experience next time.

The entire travel day was a disaster from beginning to end. Woke up at two in the morning to make it to San Juan airport in time for a 5:30 am flight to Milwaukee which connected in Baltimore. Massive delays lead to me missing original connection out of Baltimore. Sixteen hours of delays/rebooking/layover time later, arrived in Milwaukee to find that only one of two checked bags made it there (despite the fact that Southwest brought another 737 jet to San Juan to fly us out to our original Baltimore connection—-not squeezed into another booked flight). The flight from Baltimore to Milwaukee was barely half full, so there was no logical reason to ship my bags out of Baltimore on a different flight to Chicago to then ship to Milwaukee. Southwest decided that my bags should not have been on the same connecting flight I WAS ON to Milwaukee, and then proceeded to accidentally leave my larger bag with the important items in Chicago. Terrible logic and support all around. Extremely angered and disappointed with SW. What a clownish operation your company has become!

It was as expected and I was grateful for the wheel chair help and ease of use.

One of the best airlines for fast boarding, on time arrivals, and top notch service!

Vegetarian selection could be better. Bread was too hard to chew.

Crew was friendly and competent. Food, wine, and entertainment were excellent except the raw tuna on the flight to Split. Recommend against serving that - at least as the only option. Many medical conditions do not allow people to eat raw fish.

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.

United didn’t even try to hold the flight for me. They knew I had a tight connection and when I arrived at the gate less than 10 mins after final boarding the flight had already gone. The gate agent wasn’t even notified that I was on my way. She was told I wasn’t at the airport

Good quick flight on a small but comfortable plane. I'm 6'3 and had plenty of space.

The flight was delayed so we were dead tired, and after that the turbulence was horrible. I was very scared.

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.

Wifi took a while to kick in and we had a maintenance issue that took over 40 mins at the gate in Washington before pulling back

Very good. Because of the delays with my previous flight, I missed my connection, but I was able to book another flight through the United app easily.

Was happy we finally got upgraded in 1st class. The seat getting old. The cushiness need some improvement.

The flight was delayed 4 hours and the JetBlue people at the counter kept lying to us and telling us it was due to weather however all other flights were going in and out of NY and FL. Then they lied that the plane had to stop to refuel. Then they lied and said the plane needed a tire change. JetBlue is the worst. Then they gave a lot of people meal vouchers however I didn’t know they did that and they didn’t offer anything to me.

My experience with Jet Blue was wonderful. My experience with Kayak sucked and will never use again.

Jet Blue has excellent everything, Friendly customer service and staff, clean aircraft’s and is always on time.

Entertainment and wifi were very sub-par - audio issues and no wifi

We were delayed and had to circle due to weather and had to divert for fuel. While I understand that you can’t control the weather I would have appreciated knowing that the crew wasn’t going to run out of hours and then having to spend the night in the Raleigh airport.

Messy plane that was falling apart Small screens that didn't work

I was traveling with two small kids and our TV s were the only ones not working. Informed the flight attendant who did nothing about them.

They forced me to check my hand luggage at the gate.

I specifically choose not to check bags to ensure I can proceed directly to ground transportation upon arrival. However, due to a recurring lack of cabin space, I was again forced to gate-check my rolling luggage after going through my luggage to take out electronics and batteries. This practice unilaterally changes the service agreement made at the time of purchase. JetBlue needs to find a better way to manage overhead space that honors the carry-on baggage allowance.

Still hasn’t left. Why are you asking how it was?

THe flight was an hour late. You got us on the plan and we sat on the ground for 45 minutes with no information from the pilot whatsoever. Worst flight this year.

Going non stop to lax like I paid for. Not stopping in MCI for gas. Too long of delays

Human interaction. Thought there would be more service-even a smile would have been nice.

Incoming flight was delayed, delaying boarding. It then took 30 mins to take off. Took 20 mins to get to a gate because they changed the gate last minute, crew weren’t ready so there was no one staffed to work the jet bridge. Boarding was so disorganized as is usual with American because everyone just stands around the gate regardless of boarding group.

Delays with no explanation. It could have been handled better.

Flight delay for mechanical. Inbound arrived on time. No one said why mechanical delay.

Flight boarded, departed and landed on time. Excellent service from flight attendant in FIRST

This was one of the most frustrating travel experiences I've had to date. I had changed my flight day of to this one as it was slated to depart on time. It ended up being so delayed that my original flight took off before this one did. The boarding process began but eventually stopped and everyone had to get off the plane as a problem was identified. The person at the front desk just tried to laugh it off as if this wasn't already a huge inconvenience. From there, we eventually got to board only to sit at the gate for an additional hour because of some additional issue. This was extremely frustrating and caused a lot of stress.

It was a little concerning to hear the ground crew arguing with the flight crew over baggage space. Instead of taking them and checking them, they started checking for space in the first class cabin moving items around like the flight crew didn't know what they were doing. I was embarrassed for them.

delayed due to weather. Could not communicate with family since the wifi was broken

baggage drop off was a bit much. I felt like I worked for spirit airlines since I did all the work.

Gate changed multiple times. The staff seemed annoyed that we asked for water. We had to pay for the water as well.

It was a full Spirit experience. Got to witness police officers having to deboard a passenger and cost us about an hour of delay. Front seat was spacious and better than expected.

Broke my bag and offered no support or solution afterwards

We didn't get on the flight, they canceled our flight and said there was no flights leaving this weekend and sent me our money back.

Horrible company: canceled flights and delayed flights. Spirit canceled my flight from Miami to Philadelphia the day before we were supposed to leave from Philadelphia to Miami, with no explanation. I had to rebook another flight, spending more money and instead of flying from Miami, I had to choose a flight from Fort Lauderdale because there were no direct flights available from Miami. That created additional cost. The flight with Spirit from Fort Lauderdale was scheduled to depart at 6am, so I had to wake up my 3 and 6 years old at 3am to get to the airport in time and then, at 5am while we were at the gate the delayed the flight until 7:45am with again no explanation.

Spirit is awful, and cost me an extra $400. On the flight to the destination they staff was rude and did not even offer water during the flight. On the return flight, while on the way to the terminal, Spirit cancelled the flight. This is the second time this has happened, and I believe they should compensate for the additional cost for incurred for the return flight. Spirit simply offered reimbursement for their cancelled flight, and did not take into consideration the cost for a last-minute flight home. The TSA agents expressed how Spirit often cancels evening/night flights, and shows no concern for the passengers.

The flight was delayed four times and finally cancelled. The hotel night we paid for and the connecting flight did not happen. There were also additional costs due to the extra night in Miami. I do not recommend this airline.

The repeated flight delays—this time nearly three hours without any weather-related cause—are unacceptable. Yet, passengers are penalized heavily even for being a minute late. It is unreasonable that there is no compensation for such significant delays, nor even basic provisions like water during the wait or in flight. This imbalance in accountability is deeply frustrating and needs to be addressed.

My flight with spirit airlines was canceled leaving me stranded until tomorrow.

Everything you need to know for your flight to Caribbean Islands

Cabin class types available on flights to Washington, D.C.

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