Caribbean

$133+ Cheap flights from Washington, D.C. (WAS) to Caribbean

WAS — SJU
Dec 4 — Dec 111
We work with more than 300 partners to bring you better travel deals

Find cheap flights from Washington, D.C. to Caribbean with Cheapflights

1. Tell us where you want to go

Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”

2. Select your favorite providers

We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.

3. Compare prices and book

Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.

Cheap flight deals from Washington, D.C. to Caribbean

Cheapest flights from Washington, D.C. to Caribbean

Sat 11/211:05 pm -
Nonstop3h 47m
Wed 11/258:53 am -
Nonstop4h 17m
Deal found 11/2$250
Mon 12/711:20 am -
1 stop7h 07m
Sat 12/126:10 pm -
1 stop6h 14m
Deal found 10/30$250
Fri 12/48:33 pm -
1 stop16h 49m
Sat 12/198:40 am -
Nonstop4h 03m
Deal found 11/1$251
Tue 12/811:20 am -
1 stop7h 07m
Tue 12/155:01 am -
1 stop7h 05m
Deal found 11/3$251
Wed 12/23:34 pm -
1 stop28h 03m
Sun 12/611:19 am -
1 stop28h 03m
Deal found 11/2$252
Sat 12/53:10 pm -
1 stop6h 34m
Wed 12/95:01 am -
1 stop7h 05m
Deal found 11/3$252
Sat 11/76:07 pm -
1 stop18h 18m
Tue 11/103:55 am -
1 stop7h 26m
Deal found 10/30$253
Sun 12/69:59 am -
1 stop8h 28m
Wed 12/95:01 am -
1 stop7h 05m
Deal found 11/2$253
Sat 11/146:07 pm -
1 stop18h 18m
Sun 11/225:19 am -
1 stop7h 55m
Deal found 11/1$254
Mon 12/78:00 am -
Nonstop3h 52m
Wed 12/162:04 pm -
1 stop7h 52m
Deal found 10/30$254
Fri 11/136:07 pm -
1 stop27h 47m
Fri 11/207:31 am -
1 stop15h 31m
Deal found 11/2$255
Tue 11/1711:16 am -
1 stop21h 59m
Tue 11/248:53 am -
Nonstop4h 17m
Deal found 11/1$256

Find flight deals from Washington, D.C. to Caribbean

Round-trip from

$250
(Cheapflightsfares)

One-way from

$133
(Priceline)

Popular in

December

Cheapest in

February

Average price

$372

Good round-trip deal

$255 or less

Good one-way deal

$132 or less
From Washington, D.C. (WAS) to Caribbean
One-way flight from Washington, D.C. (WAS) to Caribbean
Highest demand for flights based on searches. 0% potential increase in price ($2 potential increase over avg. RT price).
Cheapest flight prices on average. 1% potential price decrease ($6 potential savings vs. average RT price).
Average for round-trip flights in November 2026
Price to beat on a round-trip flight from Washington, D.C. (WAS) to Caribbean.
Price to beat on a one-way flight from Washington, D.C. (WAS) to Caribbean.

Cheapflights Fare Finder

 
Use the filters below to find and compare flights from Washington, D.C. to Caribbean that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

Washington, D.C.San Juan

DCA Washington, D.C. Reagan-National - SJU San Juan Luis Munoz Marin Intl

DCASJU

Washington, D.C. Reagan-National

Sat 11/14

3:54 pm-1:13 am

1 stop8h 19m

San Juan Luis Munoz Marin Intl

Wed 12/31

12:00 am-11:00 pm

Nonstop0h 00m

$143

Washington, D.C.Saint Thomas Island

IAD Washington, D.C. Dulles Intl - STT Saint Thomas Island Cyril E King

IADSTT

Washington, D.C. Dulles Intl

Wed 1/13

8:56 am-1:56 pm

Nonstop4h 00m

Saint Thomas Island Cyril E King

Wed 12/31

12:00 am-11:00 pm

Nonstop0h 00m

$149

Washington, D.C.Saint Thomas Island

IAD Washington, D.C. Dulles Intl - STT Saint Thomas Island Cyril E King

IADSTT

Washington, D.C. Dulles Intl

Tue 3/23

8:56 am-12:56 pm

Nonstop4h 00m

Saint Thomas Island Cyril E King

Wed 12/31

12:00 am-11:00 pm

Nonstop0h 00m

$149
Quickest round-trip

Washington, D.C.San Juan

DCA Washington, D.C. Reagan-National - SJU San Juan Luis Munoz Marin Intl

DCASJU

Washington, D.C. Reagan-National

Mon 1/11

8:00 am-12:46 pm

Nonstop3h 46m

San Juan Luis Munoz Marin Intl

Wed 12/31

12:00 am-11:00 pm

Nonstop0h 00m

$149

Washington, D.C.Saint Thomas Island

IAD Washington, D.C. Dulles Intl - STT Saint Thomas Island Cyril E King

IADSTT

Washington, D.C. Dulles Intl

Mon 1/18

8:56 am-1:56 pm

Nonstop4h 00m

Saint Thomas Island Cyril E King

Wed 12/31

12:00 am-11:00 pm

Nonstop0h 00m

$149

Washington, D.C.Nassau

DCA Washington, D.C. Reagan-National - NAS Nassau Intl

DCANAS

Washington, D.C. Reagan-National

Wed 11/25

6:55 pm-8:25 pm

1 stop25h 30m

Nassau Intl

Wed 12/31

12:00 am-12:00 am

Nonstop0h 00m

$154

Washington, D.C.San Juan

DCA Washington, D.C. Reagan-National - SJU San Juan Luis Munoz Marin Intl

DCASJU

Washington, D.C. Reagan-National

Wed 11/18

7:00 am-2:33 pm

1 stop6h 33m

San Juan Luis Munoz Marin Intl

Wed 12/31

12:00 am-11:00 pm

Nonstop0h 00m

$158

Washington, D.C.Saint Thomas Island

IAD Washington, D.C. Dulles Intl - STT Saint Thomas Island Cyril E King

IADSTT

Washington, D.C. Dulles Intl

Mon 1/11

8:56 am-1:56 pm

Nonstop4h 00m

Saint Thomas Island Cyril E King

Wed 12/31

12:00 am-11:00 pm

Nonstop0h 00m

$159

Washington, D.C.Nassau

DCA Washington, D.C. Reagan-National - NAS Nassau Intl

DCANAS

Washington, D.C. Reagan-National

Mon 11/16

6:00 am-1:15 pm

1 stop7h 15m

Nassau Intl

Wed 12/31

12:00 am-12:00 am

Nonstop0h 00m

$160

Washington, D.C.San Juan

DCA Washington, D.C. Reagan-National - SJU San Juan Luis Munoz Marin Intl

DCASJU

Washington, D.C. Reagan-National

Mon 12/21

3:05 pm-2:21 am

1 stop10h 16m

San Juan Luis Munoz Marin Intl

Wed 12/31

12:00 am-11:00 pm

Nonstop0h 00m

$161

Flights are sorted by cheapest round-trip flights first.

Deals found on 10/31

Showing 1-10 of 60 resultsSorted by cheapest first
1
2
3
...
6

Best time to book a flight from Washington, D.C. to Caribbean

Have a flexible travel schedule? Discover the best time to fly to Caribbean from Washington, D.C. with our price prediction graph.
Estimated round-trip price

Cheapflights Insights

Everything you need to know about your flight from Washington, D.C. to Caribbean

What is the cheapest month to book a flight from Washington, D.C. to Caribbean?

Currently, January is the cheapest month in which you can book a flight from Washington, D.C. to Caribbean (average of $476). Flying from Washington, D.C. to Caribbean in December is currently the most expensive (average of $611). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

What is the cheapest time of day to fly from WAS to CB?

One of the essential ways to save on airfare from Washington, D.C. to Caribbean is to remain as flexible as possible. Flights that are in the morning tend to be the most expensive. A flight in the afternoon could potentially save you up to 30% on airfare.

Weekly flight availability from Washington, D.C. to Caribbean

The most flights from WAS to 0CB are scheduled on a Monday (6 on average). You will have fewer flight options on Monday, which is when the least amount of flights are scheduled (6 on average).

How often are flights from Washington, D.C. to Caribbean delayed?

About 19% of weekly flights between Washington, D.C. and Caribbean have experienced delays in the past year, with the average delay time being 132 minutes.

What is the most punctual flight time for Washington, D.C. to Caribbean flights?

Historically, flights departing in the morning are less likely to be delayed, whereas flights leaving in the evening tend to experience delays more often.

What day of the week experiences the fewest flight delays on this route?

Wednesday tends to have the lowest number of delays on this route, whereas Friday has historically faced a higher average of delays compared to other days of the week.

Which airline has the best punctuality record on Washington, D.C. to Caribbean flights?

Over the last year, United Airlines have had the lowest number of delays on this route, with just 16% of flights being delayed.

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

The price you pay for your flight from Washington, D.C. to Caribbean may vary depending on when you book. For the best chance of a lower fare, look to book 60 days in advance of your trip. Fares are likely to increase a fortnight or so before your departure date.

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

Travelers seeking maximum savings on their Washington, D.C. to Caribbean flight should consider departing on Sunday afternoons when fares are most often at their lowest. Wednesday afternoons flights should be avoided if possible as fares are typically the most expensive at this time.

Reviews of airlines servicing Caribbean

Read through reviews of airlines operating flights from Washington, D.C. to Caribbean, such as Southwest,United Airlines, andJetBlue. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.

Crew

8.6

Comfort

8.0

Entertainment

7.5

Overall

8.0

Boarding

8.1

Food

7.0

Reviews

1 / 20
8.0
Excellent

Patricia,Oct 2026

DAL - TPA

I love flying southwest, Both flights were packed full full - so not room for all carry one and bags had to be checked but still good flights.

Crew

8.6

Comfort

8.0

Entertainment

7.5

Overall

8.0

Boarding

8.1

Food

7.0

Reviews

1 / 20
8.0
Excellent

Patricia,Oct 2026

DAL - TPA

I love flying southwest, Both flights were packed full full - so not room for all carry one and bags had to be checked but still good flights.

Crew

8.6

Comfort

8.0

Entertainment

7.5

Overall

8.0

Boarding

8.1

Food

7.0

Reviews

1 / 20
8.0
Excellent

Patricia,Oct 2026

DAL - TPA

I love flying southwest, Both flights were packed full full - so not room for all carry one and bags had to be checked but still good flights.

Crew

8.6

Comfort

8.0

Entertainment

7.5

Overall

8.0

Boarding

8.1

Food

7.0

Reviews

1 / 20
8.0
Excellent

Patricia,Oct 2026

DAL - TPA

I love flying southwest, Both flights were packed full full - so not room for all carry one and bags had to be checked but still good flights.

Crew

8.6

Comfort

8.0

Entertainment

7.5

Overall

8.0

Boarding

8.1

Food

7.0

Reviews

1 / 20
8.0
Excellent

Patricia,Oct 2026

DAL - TPA

I love flying southwest, Both flights were packed full full - so not room for all carry one and bags had to be checked but still good flights.

Crew

8.6

Comfort

8.0

Entertainment

7.5

Overall

8.0

Boarding

8.1

Food

7.0

Reviews

1 / 20
8.0
Excellent

Patricia,Oct 2026

DAL - TPA

I love flying southwest, Both flights were packed full full - so not room for all carry one and bags had to be checked but still good flights.

Related info for your journey

  • How long is the flight from Washington, D.C. to Caribbean?

    Departing from Washington, D.C. to Caribbean will take you 3h 52m. The distance between Washington, D.C. and Caribbean is about 1557 mi. Both multi-stop and nonstop flights can be found to your destination and back.

  • What are the cheapest airlines to fly from Washington, D.C. to Caribbean one-way?

    One-way options have recently been found by users for as low as $54 on Frontier. Other airlines that offer cheap prices include JetBlue from $91 and American Airlines from $91 one-way.

  • What are the most popular routes from Washington, D.C. to Caribbean?

  • What are the most reliable airlines from Washington, D.C. to Caribbean?

    Before booking your flight to Caribbean from Washington, D.C., check out the most reliable airlines to get you to your destination on time: Air Canada (83%), United Airlines (83%), Brussels Airlines( 71%).

  • What are the cheapest flights from Washington, D.C. to Caribbean?

    The cheapest flight price from Washington, D.C. to Caribbean is $158. On average you can expect to pay $737. The most popular route, (Baltimore/Washington - San Juan Luis Munoz Marin Intl), can usually be booked for $195.

  • Can I find deals for flights from Washington, D.C. to Caribbean that include hotel bookings?

    Yes. In addition to deals on Washington, D.C. to Caribbean flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Washington, D.C. to Caribbean?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Washington, D.C. to Caribbean.

  • Can I find deals for business class flights from Washington, D.C. to Caribbean?

    Yes. Cheapflights offers flight deals from Washington, D.C. to Caribbean by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

  • What is the cheapest month to book a flight from Washington, D.C. to Caribbean?

    Currently, January is the cheapest month in which you can book a flight from Washington, D.C. to Caribbean (average of $476). Flying from Washington, D.C. to Caribbean in December is currently the most expensive (average of $611). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

See more FAQs

Browse thousands of different options on Cheapflights for your next trip

Alternative routes for Washington, D.C. to Caribbean

Top 9 airlines flying from Washington, D.C. to Caribbean

AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$84Average$515FlexibilityNo cancel feeOn-time62%
DeltaCheapest$135Average$631FlexibilityNo cancel feeOn-timeN/A
AviancaCheapest$167Average$537FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$172Average$624FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$208Average$600FlexibilityNo cancel feeOn-time71%
JetBlueCheapest$240Average$524FlexibilityNo cancel feeOn-time62%
Air CanadaCheapest$256Average$432FlexibilityNo cancel feeOn-time67%
SouthwestCheapest$301Average$650FlexibilityNo cancel feeOn-time63%
Copa AirlinesCheapest$310Average$644FlexibilityNo cancel feeOn-time70%

100% Free

Cheapflights is completely free to use, so you can start saving the moment you arrive.

Book with Flexibility

Our users can plan ahead with confidence and find flights with no change fees

Travel Smart

Millions of people come to us for their flight needs every year. We help make travel planning easy by providing useful insights and data-driven graphs that can inform your decisions.