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$125+ 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 5/6. Fares are subject to change and may not be available on all flights or dates of travel.
DCA — SJU
Apr 25 — May 21
Sat 4/25
Sat 5/2
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 March 26, 2026.

This United Airlines deal was found by Cheapflights users on 3/25. 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 5/46:00 am
DCA
-
STT
1 stop7h 08m
United Airlines
Wed 5/131:22 pm
STT
-
DCA
1 stop10h 36m
United Airlines
Deal found 3/25$270
This American Airlines deal was found by Cheapflights users on 3/24. 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 4/206:00 am
DCA
-
STT
1 stop7h 15m
American Airlines
Wed 4/295:05 pm
STT
-
DCA
1 stop7h 29m
American Airlines
Deal found 3/24$271
This American Airlines deal was found by Cheapflights users on 3/25. 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 5/66:00 am
DCA
-
STT
2 stops10h 15m
American Airlines
Wed 5/132:05 pm
STT
-
DCA
1 stop7h 09m
American Airlines
Deal found 3/25$275
This United Airlines deal was found by Cheapflights users on 3/26. 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.
Sun 4/126:30 am
DCA
-
STT
1 stop9h 01m
United Airlines
Thu 4/161:22 pm
STT
-
DCA
1 stop8h 09m
United Airlines
Deal found 3/26$291
This American Airlines deal was found by Cheapflights users on 3/26. 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 4/155:00 am
DCA
-
STT
1 stop8h 15m
American Airlines
Tue 4/212:05 pm
STT
-
DCA
1 stop7h 09m
American Airlines
Deal found 3/26$296
This Delta deal was found by Cheapflights users on 3/26. 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.
Thu 5/76:00 am
DCA
-
STT
1 stop9h 17m
Delta
Tue 5/124:27 pm
STT
-
DCA
1 stop6h 57m
Delta
Deal found 3/26$302
This Delta deal was found by Cheapflights users on 3/23. 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.
Fri 5/16:00 am
DCA
-
STT
1 stop6h 12m
Delta
Tue 5/124:27 pm
STT
-
DCA
1 stop6h 57m
Delta
Deal found 3/23$318
This SmartFares deal was found by Cheapflights users on 3/24. 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 4/128:00 am
DCA
-
SJU
Nonstop3h 43m
JetBlue
Wed 4/156:00 pm
SJU
-
DCA
Nonstop3h 56m
JetBlue
Deal found 3/24$320
This American Airlines deal was found by Cheapflights users on 3/26. 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.
Tue 4/78:21 am
DCA
-
STT
1 stop7h 54m
American Airlines
Tue 4/141:15 pm
STT
-
DCA
1 stop6h 41m
American Airlines
Deal found 3/26$323
This American Airlines deal was found by Cheapflights users on 3/25. 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 4/15:00 am
DCA
-
STT
1 stop9h 46m
American Airlines
Wed 4/811:27 am
STT
-
DCA
1 stop8h 52m
American Airlines
Deal found 3/25$328
This Cheapflightsfares deal was found by Cheapflights users on 3/25. 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 5/48:00 am
DCA
-
SJU
Nonstop3h 45m
JetBlue
Tue 5/126:00 pm
SJU
-
DCA
Nonstop3h 54m
JetBlue
Deal found 3/25$328
This KAYAK deal was found by Cheapflights users on 3/26. 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 5/58:00 am
DCA
-
SJU
Nonstop3h 45m
JetBlue
Fri 5/156:00 pm
SJU
-
DCA
Nonstop3h 54m
JetBlue
Deal found 3/26$333

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 March 26, 2026.

Round-trip from

$270
(Delta)

One-way from

$125
(Air Canada)

Popular in

December

Cheapest in

July

Average price

$373

Good round-trip deal

$321 or less

Good one-way deal

$176 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. 10% potential increase in price ($38 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 March 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 March 26, 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

Sun 5/3

6:00 am-2:48 pm

1 stop8h 48m

Saint Thomas Island Cyril E King

Tue 5/12

4:27 pm-11:24 pm

1 stop6h 57m

$270

Washington, D.C.Saint Thomas Island

DCA - STT

DCASTT

Washington, D.C. Reagan-National

Sat 4/18

6:00 am-3:43 pm

1 stop9h 43m

Saint Thomas Island Cyril E King

Thu 4/23

2:10 pm-10:48 pm

1 stop8h 38m

$270

Washington, D.C.Saint Thomas Island

DCA - STT

DCASTT

Washington, D.C. Reagan-National

Sun 5/3

6:00 am-12:12 pm

1 stop6h 12m

Saint Thomas Island Cyril E King

Sat 5/9

4:27 pm-11:24 pm

1 stop6h 57m

$270

Washington, D.C.Saint Thomas Island

DCA - STT

DCASTT

Washington, D.C. Reagan-National

Mon 5/4

6:00 am-1:08 pm

1 stop7h 08m

Saint Thomas Island Cyril E King

Wed 5/13

1:22 pm-11:58 pm

1 stop10h 36m

$270

Washington, D.C.San Juan

DCA - SJU

DCASJU

Washington, D.C. Reagan-National

Fri 6/5

5:25 pm-1:20 am

1 stop7h 55m

San Juan Luis Munoz Marin Intl

Sat 6/6

6:00 am-2:15 pm

1 stop8h 15m

$337

Washington, D.C.San Juan

DCA - SJU

DCASJU

Washington, D.C. Reagan-National

Mon 5/4

8:00 am-11:45 am

Nonstop3h 45m

San Juan Luis Munoz Marin Intl

Thu 5/7

5:01 am-2:38 pm

1 stop9h 37m

$342

Washington, D.C.San Juan

DCA - SJU

DCASJU

Washington, D.C. Reagan-National

Wed 5/6

11:55 am-8:34 pm

1 stop8h 39m

San Juan Luis Munoz Marin Intl

Tue 5/12

7:40 am-5:04 pm

1 stop9h 24m

$342

Washington, D.C.San Juan

DCA - SJU

DCASJU

Washington, D.C. Reagan-National

Sun 5/10

6:00 am-12:01 pm

1 stop6h 01m

San Juan Luis Munoz Marin Intl

Tue 5/12

7:05 am-5:07 pm

1 stop10h 02m

$342

Washington, D.C.San Juan

DCA - SJU

DCASJU

Washington, D.C. Reagan-National

Mon 4/13

5:00 pm-11:59 pm

1 stop6h 59m

San Juan Luis Munoz Marin Intl

Fri 4/24

12:55 pm-10:34 pm

1 stop9h 39m

$342

Washington, D.C.San Juan

DCA - SJU

DCASJU

Washington, D.C. Reagan-National

Sat 5/2

7:00 am-8:34 pm

2 stops13h 34m

San Juan Luis Munoz Marin Intl

Thu 5/7

1:00 am-8:20 am

1 stop7h 20m

$342

Flights are sorted by cheapest round-trip flights first.

Deals found on 3/22

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

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

Currently, November is the cheapest month in which you can book a flight from Washington, D.C. Reagan-National Airport to Caribbean (average of $178). Flying from Washington, D.C. Reagan-National Airport to Caribbean in April is currently the most expensive (average of $268). 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 March 26, 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 March 26, 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
4,333 reviews

Food

7.0

Entertainment

7.5

Comfort

8.0

Boarding

8.1

Overall

8.0

Crew

8.6

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
4,333 reviews
Southwest
8.0
Very good
4,333 reviews

Food

7.0

Entertainment

7.5

Comfort

8.0

Boarding

8.1

Overall

8.0

Crew

8.6

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
8,331 reviews
Southwest
8.0
Very good
4,333 reviews

Food

7.0

Entertainment

7.5

Comfort

8.0

Boarding

8.1

Overall

8.0

Crew

8.6

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
9,484 reviews
Southwest
8.0
Very good
4,333 reviews

Food

7.0

Entertainment

7.5

Comfort

8.0

Boarding

8.1

Overall

8.0

Crew

8.6

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
2,905 reviews
Southwest
8.0
Very good
4,333 reviews

Food

7.0

Entertainment

7.5

Comfort

8.0

Boarding

8.1

Overall

8.0

Crew

8.6

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
11,496 reviews
Southwest
8.0
Very good
4,333 reviews

Food

7.0

Entertainment

7.5

Comfort

8.0

Boarding

8.1

Overall

8.0

Crew

8.6

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 Delta, United Airlines, and Southwest fly from Washington, D.C. Reagan-National Airport to Caribbean in about 7h 55m. The time it takes to get you to your destination can typically vary by up to 1h 48m. Airlines will cover a distance of 1557 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 JetBlue. According to our data, you can fly for as low as $67. Users have also found prices from $68 and $82 on Delta and Southwest, 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 - Nassau Intl 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 $503 for a flight from Washington, D.C. Reagan-National Airport to Caribbean. The cheapest flight overall is $146 while the most popular route, (Washington, D.C. Reagan-National - San Juan Luis Munoz Marin Intl) is currently priced at $328.

  • 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, November is the cheapest month in which you can book a flight from Washington, D.C. Reagan-National Airport to Caribbean (average of $178). Flying from Washington, D.C. Reagan-National Airport to Caribbean in April is currently the most expensive (average of $268). 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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Dulles Intl to Haneda flights
Reagan-National to San Francisco flights
Dulles Intl to Charles de Gaulle flights
Dulles Intl to George Bush Intcntl flights
Reagan-National to Fort Lauderdale flights
Baltimore to San Francisco flights
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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 March 26, 2026.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$88Average$279FlexibilityNo cancel feeOn-time65%
FrontierCheapest$103Average$381FlexibilityNo cancel feeOn-time62%
DeltaCheapest$142Average$546FlexibilityNo cancel feeOn-timeN/A
JetBlueCheapest$180Average$496FlexibilityNo cancel feeOn-time62%
SouthwestCheapest$220Average$594FlexibilityNo cancel feeOn-time63%
American AirlinesCheapest$245Average$586FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$250Average$572FlexibilityNo cancel feeOn-time69%
Air CanadaCheapest$389Average$472FlexibilityNo cancel feeOn-time67%

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