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$127+ 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 7/28. Fares are subject to change and may not be available on all flights or dates of travel.
DCA — SJU
Jun 3 — Jun 101
Wed 6/3
Wed 6/10
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 May 4, 2026.

This Delta deal was found by Cheapflights users on 4/29. 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 8/76:02 am
DCA
-
SJU
1 stop10h 36m
Delta
Wed 8/191:06 pm
SJU
-
DCA
1 stop9h 15m
Delta
Deal found 4/29$266
This American Airlines deal was found by Cheapflights users on 4/29. 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 8/196:05 am
DCA
-
SJU
1 stop6h 43m
American Airlines
Wed 8/266:00 am
SJU
-
DCA
1 stop8h 46m
American Airlines
Deal found 4/29$271
This Cheapflightsfares deal was found by Cheapflights users on 4/30. 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 5/268:20 am
DCA
-
SJU
Nonstop3h 45m
JetBlue
Wed 6/105:10 pm
SJU
-
DCA
Nonstop3h 53m
JetBlue
Deal found 4/30$272
This Super.com deal was found by Cheapflights users on 5/2. 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.
Tue 6/28:20 am
DCA
-
SJU
Nonstop3h 45m
JetBlue
Wed 6/105:10 pm
SJU
-
DCA
Nonstop3h 53m
JetBlue
Deal found 5/2$274
This JetBlue deal was found by Cheapflights users on 5/2. 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.
Tue 8/48:20 am
DCA
-
SJU
Nonstop3h 59m
JetBlue
Tue 8/116:07 pm
SJU
-
DCA
Nonstop3h 52m
JetBlue
Deal found 5/2$277
This Delta deal was found by Cheapflights users on 5/1. 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 7/248:00 am
DCA
-
STT
1 stop6h 23m
Delta
Thu 7/303:33 pm
STT
-
DCA
1 stop7h 15m
Delta
Deal found 5/1$290
This American Airlines deal was found by Cheapflights users on 4/30. 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.
Sun 8/306:05 am
DCA
-
SJU
1 stop8h 33m
American Airlines
Sat 9/51:38 pm
SJU
-
DCA
1 stop8h 22m
American Airlines
Deal found 4/30$291
This SmartFares deal was found by Cheapflights users on 5/3. 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.
Wed 8/128:20 am
DCA
-
SJU
Nonstop3h 59m
JetBlue
Wed 8/198:55 am
SJU
-
DCA
1 stop7h 01m
JetBlue
Deal found 5/3$294
This Delta deal was found by Cheapflights users on 4/29. 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 8/76:02 am
DCA
-
SJU
1 stop10h 36m
Delta
Tue 8/117:30 am
SJU
-
DCA
1 stop10h 53m
Delta
Deal found 4/29$296
This Cheapflightsfares deal was found by Cheapflights users on 4/30. 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 9/18:20 am
DCA
-
SJU
Nonstop3h 59m
JetBlue
Wed 9/305:55 pm
SJU
-
DCA
Nonstop3h 51m
JetBlue
Deal found 4/30$310
This Delta deal was found by Cheapflights users on 4/29. 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 7/306:00 am
DCA
-
STT
1 stop8h 23m
Delta
Thu 8/63:33 pm
STT
-
DCA
1 stop8h 15m
Delta
Deal found 4/29$311
This American Airlines deal was found by Cheapflights users on 4/29. 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.
Sun 9/65:00 am
DCA
-
SJU
1 stop9h 38m
American Airlines
Fri 9/113:55 pm
SJU
-
DCA
1 stop8h 04m
American Airlines
Deal found 4/29$314

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 May 4, 2026.

Round-trip from

$266
(Delta)

One-way from

$127
(SmartFares)

Popular in

March

Cheapest in

October

Average price

$342

Good round-trip deal

$388 or less

Good one-way deal

$166 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 ($16 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 2% potential price decrease ($8 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in May 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 May 4, 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.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

Thu 6/4

1:16 pm-11:24 pm

1 stop10h 08m

$266

Washington, D.C.Saint Thomas Island

DCA - STT

DCASTT

Washington, D.C. Reagan-National

Tue 7/14

6:59 am-3:20 pm

1 stop8h 21m

Saint Thomas Island Cyril E King

Tue 7/21

3:33 pm-11:52 pm

1 stop8h 19m

$332

Washington, D.C.Saint Thomas Island

DCA - STT

DCASTT

Washington, D.C. Reagan-National

Thu 5/7

6:00 am-3:43 pm

1 stop9h 43m

Saint Thomas Island Cyril E King

Thu 5/14

1:22 pm-11:58 pm

1 stop10h 36m

$343

Washington, D.C.San Juan

DCA - SJU

DCASJU

Washington, D.C. Reagan-National

Sun 6/14

6:06 am-4:29 pm

1 stop10h 23m

San Juan Luis Munoz Marin Intl

Wed 6/17

7:05 am-4:59 pm

1 stop9h 54m

$351

Washington, D.C.Saint Thomas Island

DCA - STT

DCASTT

Washington, D.C. Reagan-National

Sun 6/7

6:00 am-3:21 pm

1 stop9h 21m

Saint Thomas Island Cyril E King

Thu 6/11

4:31 pm-11:21 pm

1 stop6h 50m

$379

Washington, D.C.San Juan

DCA - SJU

DCASJU

Washington, D.C. Reagan-National

Sun 5/31

6:05 am-1:20 pm

1 stop7h 15m

San Juan Luis Munoz Marin Intl

Tue 6/9

2:14 pm-10:59 pm

1 stop8h 45m

$381

Washington, D.C.San Juan

DCA - SJU

DCASJU

Washington, D.C. Reagan-National

Sun 6/7

4:30 pm-11:50 pm

1 stop7h 20m

San Juan Luis Munoz Marin Intl

Tue 6/9

1:00 am-1:04 pm

2 stops12h 04m

$382

Washington, D.C.San Juan

DCA - SJU

DCASJU

Washington, D.C. Reagan-National

Fri 7/31

12:35 pm-12:30 am

1 stop11h 55m

San Juan Luis Munoz Marin Intl

Tue 8/4

11:50 am-10:00 pm

1 stop10h 10m

$396

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-11:21 pm

1 stop6h 50m

$400

Washington, D.C.San Juan

DCA - SJU

DCASJU

Washington, D.C. Reagan-National

Tue 5/26

6:00 am-1:45 pm

1 stop7h 45m

San Juan Luis Munoz Marin Intl

Sat 5/30

1:00 am-7:46 am

1 stop6h 46m

$413

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/29

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 May 4, 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 May 4, 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 May 4, 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
7.9
Good
4,307 reviews

Food

7.0

Boarding

8.1

Crew

8.6

Comfort

8.0

Entertainment

7.5

Overall

7.9

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
7.9
Good
4,307 reviews
Southwest
7.9
Good
4,307 reviews

Food

7.0

Boarding

8.1

Crew

8.6

Comfort

8.0

Entertainment

7.5

Overall

7.9

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
8,460 reviews
Southwest
7.9
Good
4,307 reviews

Food

7.0

Boarding

8.1

Crew

8.6

Comfort

8.0

Entertainment

7.5

Overall

7.9

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
9,680 reviews
Southwest
7.9
Good
4,307 reviews

Food

7.0

Boarding

8.1

Crew

8.6

Comfort

8.0

Entertainment

7.5

Overall

7.9

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
11,670 reviews
Southwest
7.9
Good
4,307 reviews

Food

7.0

Boarding

8.1

Crew

8.6

Comfort

8.0

Entertainment

7.5

Overall

7.9

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
7.1
Good
2,970 reviews
Southwest
7.9
Good
4,307 reviews

Food

7.0

Boarding

8.1

Crew

8.6

Comfort

8.0

Entertainment

7.5

Overall

7.9

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 6h 35m. The time it takes to get you to your destination can typically vary by up to 5h 20m. 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 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 $339 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 $266.

  • 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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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 May 4, 2026.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$97Average$381FlexibilityNo cancel feeOn-time62%
Spirit AirlinesCheapest$113Average$305FlexibilityNo cancel feeOn-time65%
DeltaCheapest$142Average$550FlexibilityNo cancel feeOn-timeN/A
JetBlueCheapest$180Average$495FlexibilityNo cancel feeOn-time62%
SouthwestCheapest$220Average$588FlexibilityNo cancel feeOn-time63%
American AirlinesCheapest$245Average$589FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$250Average$534FlexibilityNo cancel feeOn-time69%
Air CanadaCheapest$389Average$472FlexibilityNo cancel feeOn-time67%

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