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$124+ 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 6/2. Fares are subject to change and may not be available on all flights or dates of travel.
DCA — SJU
May 19 — May 261
Tue 5/19
Tue 5/26
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 19, 2026.

This Cheapflightsfares deal was found by Cheapflights users on 4/13. 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.
Tue 6/28:20 am
DCA
-
SJU
Nonstop3h 45m
JetBlue
Tue 6/25:10 pm
SJU
-
DCA
Nonstop3h 53m
JetBlue
Deal found 4/13$247
This Cheapflightsfares deal was found by Cheapflights users on 4/14. 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.
Tue 6/28:20 am
DCA
-
SJU
Nonstop3h 45m
JetBlue
Thu 6/115:55 pm
SJU
-
DCA
Nonstop3h 52m
JetBlue
Deal found 4/14$252
This KAYAK deal was found by Cheapflights users on 4/14. 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.
Mon 5/258:20 am
DCA
-
SJU
Nonstop3h 45m
JetBlue
Sat 6/65:10 pm
SJU
-
DCA
Nonstop3h 53m
JetBlue
Deal found 4/14$257
This Delta deal was found by Cheapflights users on 4/17. 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 6/15:00 pm
DCA
-
SJU
1 stop6h 35m
Delta
Fri 6/52:48 pm
SJU
-
DCA
1 stop8h 56m
Delta
Deal found 4/17$266
This American Airlines deal was found by Cheapflights users on 4/14. 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 8/195:00 am
DCA
-
SJU
1 stop7h 48m
American Airlines
Wed 8/261:38 pm
SJU
-
DCA
1 stop7h 21m
American Airlines
Deal found 4/14$271
This Cheapflightsfares deal was found by Cheapflights users on 4/16. 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.
Tue 6/28:20 am
DCA
-
SJU
Nonstop3h 45m
JetBlue
Sat 6/65:10 pm
SJU
-
DCA
Nonstop3h 53m
JetBlue
Deal found 4/16$272
This Delta deal was found by Cheapflights users on 4/17. 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.
Sat 5/305:00 pm
DCA
-
SJU
1 stop6h 35m
Delta
Tue 6/27:05 am
SJU
-
DCA
1 stop10h 02m
Delta
Deal found 4/17$276
This Cheapflightsfares deal was found by Cheapflights users on 4/14. 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 4/14$277
This Super.com deal was found by Cheapflights users on 4/14. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/208:00 am
DCA
-
SJU
Nonstop3h 45m
JetBlue
Sat 5/235:10 pm
SJU
-
DCA
Nonstop3h 53m
JetBlue
Deal found 4/14$279
This KAYAK deal was found by Cheapflights users on 4/14. 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.
Sat 5/168:00 am
DCA
-
SJU
Nonstop3h 45m
JetBlue
Sat 5/235:10 pm
SJU
-
DCA
Nonstop3h 53m
JetBlue
Deal found 4/14$282
This United Airlines deal was found by Cheapflights users on 4/15. 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.
Thu 5/76:00 am
DCA
-
STT
1 stop9h 43m
United Airlines
Tue 5/122:10 pm
STT
-
DCA
1 stop7h 21m
United Airlines
Deal found 4/15$290
This Delta deal was found by Cheapflights users on 4/15. 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.
Tue 8/115:00 pm
DCA
-
SJU
1 stop6h 59m
Delta
Fri 8/142:40 pm
SJU
-
DCA
1 stop7h 41m
Delta
Deal found 4/15$291

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 19, 2026.

Round-trip from

$247
(Cheapflightsfares)

One-way from

$124
(Super.com)

Popular in

March

Cheapest in

July

Average price

$334

Good round-trip deal

$333 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 19, 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 5/5

6:00 am-1:08 pm

1 stop7h 08m

Saint Thomas Island Cyril E King

Fri 5/8

2:10 pm-9:31 pm

1 stop7h 21m

$290

Washington, D.C.Saint Thomas Island

DCA - STT

DCASTT

Washington, D.C. Reagan-National

Tue 5/12

6:00 am-3:43 pm

1 stop9h 43m

Saint Thomas Island Cyril E King

Fri 5/15

1:22 pm-11:58 pm

1 stop10h 36m

$290
Quickest round-trip

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

Thu 5/7

4:27 pm-11:24 pm

1 stop6h 57m

$311

Washington, D.C.San Juan

DCA - SJU

DCASJU

Washington, D.C. Reagan-National

Mon 6/1

5:00 pm-11:35 pm

1 stop6h 35m

San Juan Luis Munoz Marin Intl

Fri 6/5

7:30 am-6:28 pm

1 stop10h 58m

$316

Washington, D.C.Saint Thomas Island

DCA - STT

DCASTT

Washington, D.C. Reagan-National

Thu 5/7

7:59 am-3:17 pm

1 stop7h 18m

Saint Thomas Island Cyril E King

Fri 5/15

4:27 pm-11:35 pm

1 stop7h 08m

$319

Washington, D.C.Saint Thomas Island

DCA - STT

DCASTT

Washington, D.C. Reagan-National

Tue 6/16

6:00 am-3:21 pm

1 stop9h 21m

Saint Thomas Island Cyril E King

Wed 6/24

4:31 pm-11:15 pm

1 stop6h 44m

$322

Washington, D.C.San Juan

DCA - SJU

DCASJU

Washington, D.C. Reagan-National

Tue 6/2

12:00 pm-9:05 pm

2 stops9h 05m

San Juan Luis Munoz Marin Intl

Thu 6/11

7:00 am-6:20 pm

1 stop11h 20m

$331

Washington, D.C.Saint Thomas Island

DCA - STT

DCASTT

Washington, D.C. Reagan-National

Sun 4/26

6:30 am-3:31 pm

1 stop9h 01m

Saint Thomas Island Cyril E King

Fri 5/1

1:22 pm-11:58 pm

1 stop10h 36m

$343

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.San Juan

DCA - SJU

DCASJU

Washington, D.C. Reagan-National

Sat 6/20

5:00 pm-11:43 pm

1 stop6h 43m

San Juan Luis Munoz Marin Intl

Thu 6/25

7:30 am-6:33 pm

1 stop11h 03m

$366

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/13

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, 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 19, 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.

Weekly flight availability from Washington, D.C. Reagan-National Airport to Caribbean

Explore weekly flight availability from Reagan-National to Caribbean. Discover flights operating on different days of the week, giving you the flexibility to choose a travel day that best fits your plans. Compare info to find the most convenient option for your journey. Data last updated April 19, 2026.

The most flights from DCA to 0CB are scheduled on a Monday (1 on average). You will have fewer flight options on Monday, which is when the least amount of flights are scheduled (1 on average).

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 19, 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
4,329 reviews

Crew

8.6

Entertainment

7.5

Boarding

8.1

Comfort

8.0

Food

7.0

Overall

8.0

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
4,329 reviews
Southwest
8.0
Very good
4,329 reviews

Crew

8.6

Entertainment

7.5

Boarding

8.1

Comfort

8.0

Food

7.0

Overall

8.0

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
8,422 reviews
Southwest
8.0
Very good
4,329 reviews

Crew

8.6

Entertainment

7.5

Boarding

8.1

Comfort

8.0

Food

7.0

Overall

8.0

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
9,603 reviews
Southwest
8.0
Very good
4,329 reviews

Crew

8.6

Entertainment

7.5

Boarding

8.1

Comfort

8.0

Food

7.0

Overall

8.0

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
2,946 reviews
Southwest
8.0
Very good
4,329 reviews

Crew

8.6

Entertainment

7.5

Boarding

8.1

Comfort

8.0

Food

7.0

Overall

8.0

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
11,621 reviews
Southwest
8.0
Very good
4,329 reviews

Crew

8.6

Entertainment

7.5

Boarding

8.1

Comfort

8.0

Food

7.0

Overall

8.0

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 6h 12m. The time it takes to get you to your destination can typically vary by up to 2h 53m. 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 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 - 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 $352 for a flight from Washington, D.C. Reagan-National Airport to Caribbean. The cheapest flight overall is $162 while the most popular route, (Washington, D.C. Reagan-National - San Juan Luis Munoz Marin Intl) is currently priced at $252.

  • 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.

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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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Reagan-National to George Bush Intcntl flights
Baltimore to Boston flights
Dulles Intl to Midway flights
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Baltimore to Midway flights

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 19, 2026.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$88Average$279FlexibilityNo cancel feeOn-time65%
FrontierCheapest$103Average$381FlexibilityNo cancel feeOn-time62%
DeltaCheapest$142Average$552FlexibilityNo cancel feeOn-timeN/A
JetBlueCheapest$180Average$491FlexibilityNo cancel feeOn-time62%
SouthwestCheapest$220Average$591FlexibilityNo cancel feeOn-time63%
American AirlinesCheapest$245Average$586FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$250Average$563FlexibilityNo cancel feeOn-time69%
Air CanadaCheapest$389Average$472FlexibilityNo cancel feeOn-time67%

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