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$133+ Cheap flights from Reagan-National (DCA) to Caribbean

This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 6/16. Fares are subject to change and may not be available on all flights or dates of travel.
DCA — SJU
May 23 — May 301
Sat 5/23
Sat 5/30
1 adult, Economy
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Cheap flight deals from Reagan-National to Caribbean

Cheapest flights from Reagan-National to Caribbean
Explore the most affordable flight options available from Reagan-National to Caribbean. Find the lowest fares from popular airlines and budget airlines, with prices last updated on April 23, 2026.

This SmartFares deal was found by Cheapflights users on 4/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure SmartFares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/108:20 am
DCA
-
SJU
Nonstop3h 59m
JetBlue
Wed 8/196:07 pm
SJU
-
DCA
Nonstop3h 52m
JetBlue
Deal found 4/22$249
This SmartFares deal was found by Cheapflights users on 4/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure SmartFares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 5/318:20 am
DCA
-
SJU
Nonstop3h 45m
JetBlue
Thu 6/45:10 pm
SJU
-
DCA
Nonstop3h 53m
JetBlue
Deal found 4/21$264
This Delta deal was found by Cheapflights users on 4/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/312:27 pm
DCA
-
SJU
1 stop10h 02m
Delta
Wed 8/52:05 pm
SJU
-
DCA
1 stop8h 50m
Delta
Deal found 4/23$266
This American Airlines deal was found by Cheapflights users on 4/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/193:11 pm
DCA
-
SJU
1 stop8h 48m
American Airlines
Wed 8/261:38 pm
SJU
-
DCA
1 stop8h 22m
American Airlines
Deal found 4/19$271
This Cheapflightsfares deal was found by Cheapflights users on 4/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 5/248:20 am
DCA
-
SJU
Nonstop3h 45m
JetBlue
Fri 5/295:10 pm
SJU
-
DCA
Nonstop3h 53m
JetBlue
Deal found 4/21$272
This KAYAK deal was found by Cheapflights users on 4/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/268:20 am
DCA
-
SJU
Nonstop3h 45m
JetBlue
Thu 6/45:10 pm
SJU
-
DCA
Nonstop3h 53m
JetBlue
Deal found 4/20$277
This JetBlue deal was found by Cheapflights users on 4/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 5/318:20 am
DCA
-
SJU
Nonstop3h 45m
JetBlue
Sat 6/65:10 pm
SJU
-
DCA
Nonstop3h 53m
JetBlue
Deal found 4/20$278
This United Airlines deal was found by Cheapflights users on 4/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 5/116:00 am
DCA
-
STT
1 stop9h 43m
United Airlines
Thu 5/141:22 pm
STT
-
DCA
1 stop10h 36m
United Airlines
Deal found 4/20$290
This American Airlines deal was found by Cheapflights users on 4/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/241:53 pm
DCA
-
SJU
1 stop8h 31m
American Airlines
Sat 8/297:10 pm
SJU
-
DCA
1 stop13h 59m
American Airlines
Deal found 4/20$291
This American Airlines deal was found by Cheapflights users on 4/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/228:10 pm
DCA
-
STT
1 stop16h 40m
American Airlines
Wed 7/2911:43 am
STT
-
DCA
1 stop6h 39m
American Airlines
Deal found 4/20$295
This Southwest deal was found by Cheapflights users on 4/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/116:55 am
DCA
-
SJU
1 stop12h 05m
Southwest
Sun 8/166:00 am
SJU
-
DCA
1 stop12h 50m
Southwest
Deal found 4/20$296
This Cheapflightsfares deal was found by Cheapflights users on 4/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 5/188:00 am
DCA
-
SJU
Nonstop3h 45m
JetBlue
Fri 5/225:10 pm
SJU
-
DCA
Nonstop3h 53m
JetBlue
Deal found 4/20$297

Find flight deals from Reagan-National to Caribbean

Keep the following information in mind while searching for Reagan-National to Caribbean flight deals. Data was last updated April 23, 2026.

Round-trip from

$249
(SmartFares)

One-way from

$133
(Delta)

Popular in

March

Cheapest in

July

Average price

$334

Good round-trip deal

$367 or less

Good one-way deal

$196 or less
From Washington, D.C. Reagan-National to Caribbean
Search Deals
One-way flight from Washington, D.C. Reagan-National to Caribbean
Search Deals
Highest demand for flights based on searches. 4% potential increase in price ($18 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 2% potential price decrease ($9 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in April 2026
Search Deals
Price to beat on a round-trip flight from Washington, D.C. Reagan-National to Caribbean.
Search Deals
Price to beat on a one-way flight from Washington, D.C. Reagan-National to Caribbean.
Search Deals

Cheapflights Fare Finder

 
Customize your flight search to find flights from Reagan-National to Caribbean that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated April 23, 2026.
Use the filters below to find and compare flights from Washington, D.C. Reagan-National Airport to Caribbean that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

Washington, D.C.Saint Thomas Island

DCA - STT

DCASTT

Washington, D.C. Reagan-National

Tue 5/12

6:00 am-1:08 pm

1 stop7h 08m

Saint Thomas Island Cyril E King

Thu 5/14

1:22 pm-11:58 pm

1 stop10h 36m

$311

Washington, D.C.Saint Thomas Island

DCA - STT

DCASTT

Washington, D.C. Reagan-National

Sun 5/31

6:00 am-1:51 pm

1 stop7h 51m

Saint Thomas Island Cyril E King

Mon 6/8

4:31 pm-11:15 pm

1 stop6h 44m

$311

Washington, D.C.Saint Thomas Island

DCA - STT

DCASTT

Washington, D.C. Reagan-National

Mon 5/11

6:00 am-3:17 pm

1 stop9h 17m

Saint Thomas Island Cyril E King

Fri 5/15

4:27 pm-11:35 pm

1 stop7h 08m

$311

Washington, D.C.Saint Thomas Island

DCA - STT

DCASTT

Washington, D.C. Reagan-National

Tue 6/16

6:59 am-3:21 pm

1 stop8h 22m

Saint Thomas Island Cyril E King

Wed 6/24

4:31 pm-11:15 pm

1 stop6h 44m

$322
Quickest round-trip

Washington, D.C.Saint Thomas Island

DCA - STT

DCASTT

Washington, D.C. Reagan-National

Tue 5/5

6:59 am-1:51 pm

1 stop6h 52m

Saint Thomas Island Cyril E King

Sat 5/9

4:27 pm-11:24 pm

1 stop6h 57m

$359

Washington, D.C.Simpson Bay

DCA - SXM

DCASXM

Washington, D.C. Reagan-National

Sat 5/9

6:09 am-2:06 pm

1 stop7h 57m

Simpson Bay Princess Juliana

Sat 5/16

3:35 pm-11:24 pm

1 stop7h 49m

$367

Washington, D.C.Saint Thomas Island

DCA - STT

DCASTT

Washington, D.C. Reagan-National

Sun 4/26

7:30 am-3:31 pm

1 stop8h 01m

Saint Thomas Island Cyril E King

Tue 4/28

1:22 pm-9:31 pm

1 stop8h 09m

$386

Washington, D.C.San Juan

DCA - SJU

DCASJU

Washington, D.C. Reagan-National

Sun 7/19

6:05 am-6:10 pm

1 stop12h 05m

San Juan Luis Munoz Marin Intl

Mon 8/10

6:30 am-3:50 pm

2 stops9h 20m

$399

Washington, D.C.San Juan

DCA - SJU

DCASJU

Washington, D.C. Reagan-National

Fri 5/8

11:05 am-8:38 pm

1 stop9h 33m

San Juan Luis Munoz Marin Intl

Fri 5/15

1:25 pm-9:31 pm

1 stop8h 06m

$410

Washington, D.C.San Juan

DCA - SJU

DCASJU

Washington, D.C. Reagan-National

Mon 7/13

1:42 pm-8:45 pm

1 stop7h 03m

San Juan Luis Munoz Marin Intl

Tue 7/21

7:35 am-4:59 pm

1 stop9h 24m

$410

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/18

Showing 1-10 of 60 resultsSorted by cheapest first
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Best time to book a flight from Reagan-National to Caribbean

Have a flexible travel schedule? Discover the best time to fly to Caribbean from Reagan-National with our price prediction graph.
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.

Cheapflights Insights

Everything you need to know about your flight from Washington, D.C. Reagan-National Airport to Caribbean

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

The price you pay for your flight from Washington, D.C. Reagan-National Airport to Caribbean may vary depending on when you book. For the best chance of a lower fare, look to book 49 days in advance of your trip. Fares are likely to increase a fortnight or so before your departure date.

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

Currently, September is the cheapest month in which you can book a flight from Washington, D.C. Reagan-National Airport to Caribbean (average of $108). Flying from Washington, D.C. Reagan-National Airport to Caribbean in October is currently the most expensive (average of $1,124). 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 DCA to CB?

Find hourly flight availability from Reagan-National to Caribbean. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated April 23, 2026.

Regardless of the time of day you decide to fly, the ticket price will remain around the same. Book flights from Washington, D.C. Reagan-National Airport to Caribbean as you normally would.

Reviews of airlines servicing Caribbean

Get insights into the airlines that provide service to Caribbean. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Caribbean. Reviews last updated April 23, 2026.
See what other customers who have flown with Southwest,Delta, andUnited Airlines from Washington, D.C. Reagan-National Airport to Caribbean have to say. You can also see how each airline compares in terms of entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.0
Very good
4,327 reviews

Crew

8.6

Entertainment

7.5

Overall

8.0

Comfort

8.0

Food

7.0

Boarding

8.1

Reviews

1 / 20
2.0
Mediocre

Dominic,Mar 2026

MCO - SMF

I had to try and sleep on the floor of the Austin airport. I spent 12 hours there. The airline policies were so poor, that a near violent argument broke out between the people in front of me and the flight attendants - making for a super stressful situation at 30,000 feet. Garbage airline choice by Kayak Garbage idea to book a flight with a layover. Next time I will pay for a quality booking myself, and somehow force the company to reimburse it.
Southwest
8.0
Very good
4,327 reviews
Southwest
8.0
Very good
4,327 reviews

Crew

8.6

Entertainment

7.5

Overall

8.0

Comfort

8.0

Food

7.0

Boarding

8.1

Reviews

1 / 20
2.0
Mediocre

Dominic,Mar 2026

MCO - SMF

I had to try and sleep on the floor of the Austin airport. I spent 12 hours there. The airline policies were so poor, that a near violent argument broke out between the people in front of me and the flight attendants - making for a super stressful situation at 30,000 feet. Garbage airline choice by Kayak Garbage idea to book a flight with a layover. Next time I will pay for a quality booking myself, and somehow force the company to reimburse it.
Delta
7.9
Good
8,438 reviews
Southwest
8.0
Very good
4,327 reviews

Crew

8.6

Entertainment

7.5

Overall

8.0

Comfort

8.0

Food

7.0

Boarding

8.1

Reviews

1 / 20
2.0
Mediocre

Dominic,Mar 2026

MCO - SMF

I had to try and sleep on the floor of the Austin airport. I spent 12 hours there. The airline policies were so poor, that a near violent argument broke out between the people in front of me and the flight attendants - making for a super stressful situation at 30,000 feet. Garbage airline choice by Kayak Garbage idea to book a flight with a layover. Next time I will pay for a quality booking myself, and somehow force the company to reimburse it.
United Airlines
7.4
Good
9,635 reviews
Southwest
8.0
Very good
4,327 reviews

Crew

8.6

Entertainment

7.5

Overall

8.0

Comfort

8.0

Food

7.0

Boarding

8.1

Reviews

1 / 20
2.0
Mediocre

Dominic,Mar 2026

MCO - SMF

I had to try and sleep on the floor of the Austin airport. I spent 12 hours there. The airline policies were so poor, that a near violent argument broke out between the people in front of me and the flight attendants - making for a super stressful situation at 30,000 feet. Garbage airline choice by Kayak Garbage idea to book a flight with a layover. Next time I will pay for a quality booking myself, and somehow force the company to reimburse it.
JetBlue
7.2
Good
2,952 reviews
Southwest
8.0
Very good
4,327 reviews

Crew

8.6

Entertainment

7.5

Overall

8.0

Comfort

8.0

Food

7.0

Boarding

8.1

Reviews

1 / 20
2.0
Mediocre

Dominic,Mar 2026

MCO - SMF

I had to try and sleep on the floor of the Austin airport. I spent 12 hours there. The airline policies were so poor, that a near violent argument broke out between the people in front of me and the flight attendants - making for a super stressful situation at 30,000 feet. Garbage airline choice by Kayak Garbage idea to book a flight with a layover. Next time I will pay for a quality booking myself, and somehow force the company to reimburse it.
American Airlines
7.1
Good
11,659 reviews
Southwest
8.0
Very good
4,327 reviews

Crew

8.6

Entertainment

7.5

Overall

8.0

Comfort

8.0

Food

7.0

Boarding

8.1

Reviews

1 / 20
2.0
Mediocre

Dominic,Mar 2026

MCO - SMF

I had to try and sleep on the floor of the Austin airport. I spent 12 hours there. The airline policies were so poor, that a near violent argument broke out between the people in front of me and the flight attendants - making for a super stressful situation at 30,000 feet. Garbage airline choice by Kayak Garbage idea to book a flight with a layover. Next time I will pay for a quality booking myself, and somehow force the company to reimburse it.

Related info for your journey

Find useful and relevant information for your journey from Reagan-National to Caribbean. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • How long is the flight from Washington, D.C. Reagan-National Airport to Caribbean?

    Airlines like United Airlines, Delta, and Southwest fly from Washington, D.C. Reagan-National Airport to Caribbean in about 7h 08m. The time it takes to get you to your destination can typically vary by up to 4h 57m. Airlines will cover a distance of 1591 mi. When browsing for deals, the options you’ll see will be for both nonstop flights and flights with stops.

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

    For one-way options, check prices for Delta. According to our data, you can fly for as low as $68. Users have also found prices from $82 and $91 on Southwest and American Airlines, respectively.

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

    Most travelers choose Washington, D.C. Reagan-National - San Juan Luis Munoz Marin Intl, Washington, D.C. Reagan-National - Punta Cana or Washington, D.C. Reagan-National - Oranjestad Reina Beatrix when deciding on the best route from Washington, D.C. Reagan-National Airport to Caribbean.

  • What are the cheapest flights from Washington, D.C. Reagan-National Airport to Caribbean?

    On average you can expect to pay $360 for a flight from Washington, D.C. Reagan-National Airport to Caribbean. The cheapest flight overall is $128 while the most popular route, (Washington, D.C. Reagan-National - San Juan Luis Munoz Marin Intl) is currently priced at $249.

  • Can I find deals for flights from Reagan-National to Caribbean that include hotel bookings?

    Yes. In addition to deals on Reagan-National to Caribbean flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Reagan-National to Caribbean?

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

  • Can I find deals for business class flights from Reagan-National to Caribbean?

    Yes. Cheapflights offers flight deals from Reagan-National 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. Reagan-National Airport to Caribbean?

    Currently, September is the cheapest month in which you can book a flight from Washington, D.C. Reagan-National Airport to Caribbean (average of $108). Flying from Washington, D.C. Reagan-National Airport to Caribbean in October is currently the most expensive (average of $1,124). 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

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Alternative routes for Reagan-National to Caribbean

See prices for flight routes from nearby airports that may be better suited for you.
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Top 8 airlines flying from Reagan-National to Caribbean

Discover the top 8 airlines that operate flights from Reagan-National to Caribbean. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated April 23, 2026.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$103Average$386FlexibilityNo cancel feeOn-time62%
Spirit AirlinesCheapest$113Average$305FlexibilityNo cancel feeOn-time65%
DeltaCheapest$142Average$550FlexibilityNo cancel feeOn-timeN/A
JetBlueCheapest$180Average$493FlexibilityNo cancel feeOn-time62%
SouthwestCheapest$220Average$593FlexibilityNo cancel feeOn-time63%
American AirlinesCheapest$245Average$585FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$250Average$581FlexibilityNo cancel feeOn-time69%
Air CanadaCheapest$389Average$472FlexibilityNo cancel feeOn-time67%

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