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$107+ 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 6/15. Fares are subject to change and may not be available on all flights or dates of travel.
DCA — SJU
Jun 21 — Jun 281
Sun 6/21
Sun 6/28
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 22, 2026.

This American Airlines deal was found by Cheapflights users on 5/17. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/251:53 pm
DCA
-
SJU
1 stop8h 31m
American Airlines
Wed 8/266:00 am
SJU
-
DCA
1 stop6h 39m
American Airlines
Deal found 5/17$271
This American Airlines deal was found by Cheapflights users on 5/21. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/298:20 am
DCA
-
SJU
1 stop13h 35m
American Airlines
Wed 9/23:28 pm
SJU
-
DCA
1 stop8h 04m
American Airlines
Deal found 5/21$276
This American Airlines deal was found by Cheapflights users on 5/21. 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 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 stop9h 58m
American Airlines
Wed 8/267:05 am
SJU
-
DCA
1 stop8h 54m
American Airlines
Deal found 5/21$281
This American Airlines deal was found by Cheapflights users on 5/20. 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.
Sun 8/306:05 am
DCA
-
SJU
1 stop8h 33m
American Airlines
Sat 9/57:10 pm
SJU
-
DCA
1 stop13h 59m
American Airlines
Deal found 5/20$301
This American Airlines deal was found by Cheapflights users on 5/20. 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 8/126:52 am
DCA
-
SJU
1 stop7h 59m
American Airlines
Tue 8/181:38 pm
SJU
-
DCA
1 stop7h 21m
American Airlines
Deal found 5/20$306
This American Airlines deal was found by Cheapflights users on 5/19. 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.
Tue 9/18:20 am
DCA
-
SJU
1 stop10h 04m
American Airlines
Tue 9/154:10 pm
SJU
-
DCA
1 stop7h 49m
American Airlines
Deal found 5/19$308
This Southwest deal was found by Cheapflights users on 5/17. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/2511:55 am
DCA
-
SJU
2 stops10h 05m
Southwest
Wed 8/268:20 am
SJU
-
DCA
1 stop7h 45m
Southwest
Deal found 5/17$318
This Southwest deal was found by Cheapflights users on 5/18. 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.
Sun 8/94:35 pm
DCA
-
SJU
1 stop6h 10m
Southwest
Thu 8/136:00 am
SJU
-
DCA
1 stop12h 00m
Southwest
Deal found 5/18$323
This Southwest deal was found by Cheapflights users on 5/21. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/46:00 am
DCA
-
SJU
1 stop6h 20m
Southwest
Wed 8/125:15 am
SJU
-
DCA
1 stop7h 20m
Southwest
Deal found 5/21$326
This American Airlines deal was found by Cheapflights users on 5/18. 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 5/261:39 pm
DCA
-
SJU
1 stop9h 22m
American Airlines
Wed 5/276:20 am
SJU
-
DCA
1 stop10h 40m
American Airlines
Deal found 5/18$331
This Southwest deal was found by Cheapflights users on 5/19. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/56:00 am
DCA
-
SJU
1 stop8h 00m
Southwest
Wed 9/91:45 pm
SJU
-
DCA
2 stops9h 20m
Southwest
Deal found 5/19$333
This American Airlines deal was found by Cheapflights users on 5/19. 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.
Mon 10/511:59 am
DCA
-
SJU
1 stop11h 51m
American Airlines
Tue 10/68:35 am
SJU
-
DCA
1 stop11h 19m
American Airlines
Deal found 5/19$335

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 22, 2026.

Round-trip from

$271
(American Airlines)

One-way from

$105
(Super.com)

Popular in

March

Cheapest in

October

Average price

$360

Good round-trip deal

$394 or less

Good one-way deal

$207 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. 3% potential increase in price ($12 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 22, 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

Wed 8/19

6:59 am-1:34 pm

1 stop6h 35m

Saint Thomas Island Cyril E King

Fri 8/28

2:49 pm-11:48 pm

1 stop8h 59m

$369

Washington, D.C.San Juan

DCA - SJU

DCASJU

Washington, D.C. Reagan-National

Mon 7/6

11:57 am-8:34 pm

1 stop8h 37m

San Juan Luis Munoz Marin Intl

Wed 7/8

1:00 am-7:46 am

1 stop6h 46m

$370

Washington, D.C.San Juan

DCA - SJU

DCASJU

Washington, D.C. Reagan-National

Mon 9/7

5:00 pm-11:59 pm

1 stop6h 59m

San Juan Luis Munoz Marin Intl

Sun 9/13

1:32 pm-11:12 pm

1 stop9h 40m

$370

Washington, D.C.San Juan

DCA - SJU

DCASJU

Washington, D.C. Reagan-National

Fri 8/28

6:00 am-1:42 pm

1 stop7h 42m

San Juan Luis Munoz Marin Intl

Sun 8/30

1:19 pm-10:59 pm

1 stop9h 40m

$370

Washington, D.C.San Juan

DCA - SJU

DCASJU

Washington, D.C. Reagan-National

Wed 7/8

3:55 pm-11:59 pm

1 stop8h 04m

San Juan Luis Munoz Marin Intl

Tue 7/14

5:35 am-2:40 pm

1 stop9h 05m

$371

Washington, D.C.San Juan

DCA - SJU

DCASJU

Washington, D.C. Reagan-National

Mon 7/6

1:10 pm-11:35 pm

1 stop10h 25m

San Juan Luis Munoz Marin Intl

Fri 8/14

6:00 am-3:50 pm

2 stops9h 50m

$383

Washington, D.C.Oranjestad

DCA - AUA

DCAAUA

Washington, D.C. Reagan-National

Sun 9/6

6:00 am-1:34 pm

1 stop7h 34m

Oranjestad Reina Beatrix

Thu 9/10

2:29 pm-9:05 pm

1 stop6h 36m

$399

Washington, D.C.San Juan

DCA - SJU

DCASJU

Washington, D.C. Reagan-National

Sat 7/4

6:00 am-3:45 pm

2 stops9h 45m

San Juan Luis Munoz Marin Intl

Thu 7/9

7:00 am-6:20 pm

1 stop11h 20m

$411

Washington, D.C.San Juan

DCA - SJU

DCASJU

Washington, D.C. Reagan-National

Sat 7/4

6:30 am-2:44 pm

1 stop8h 14m

San Juan Luis Munoz Marin Intl

Mon 7/6

1:00 am-7:46 am

1 stop6h 46m

$413

Washington, D.C.Oranjestad

DCA - AUA

DCAAUA

Washington, D.C. Reagan-National

Tue 7/21

6:00 am-1:32 pm

1 stop7h 32m

Oranjestad Reina Beatrix

Mon 7/27

4:30 pm-7:49 am

1 stop15h 19m

$417

Flights are sorted by cheapest round-trip flights first.

Deals found on 5/20

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 August is currently the most expensive (average of $1,379). 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 22, 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 22, 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).

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 77 days in advance of your trip. Fares are likely to increase a fortnight or so before your departure date.

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 22, 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
4,277 reviews

Crew

8.6

Entertainment

7.5

Overall

7.9

Food

7.0

Boarding

8.1

Comfort

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
7.9
Good
4,277 reviews
Southwest
7.9
Good
4,277 reviews

Crew

8.6

Entertainment

7.5

Overall

7.9

Food

7.0

Boarding

8.1

Comfort

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
8,445 reviews
Southwest
7.9
Good
4,277 reviews

Crew

8.6

Entertainment

7.5

Overall

7.9

Food

7.0

Boarding

8.1

Comfort

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
9,752 reviews
Southwest
7.9
Good
4,277 reviews

Crew

8.6

Entertainment

7.5

Overall

7.9

Food

7.0

Boarding

8.1

Comfort

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
2,980 reviews
Southwest
7.9
Good
4,277 reviews

Crew

8.6

Entertainment

7.5

Overall

7.9

Food

7.0

Boarding

8.1

Comfort

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
11,643 reviews
Southwest
7.9
Good
4,277 reviews

Crew

8.6

Entertainment

7.5

Overall

7.9

Food

7.0

Boarding

8.1

Comfort

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 Delta, United Airlines, and JetBlue 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 2h 02m. 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 Frontier. According to our data, you can fly for as low as $62. 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 $128 while the most popular route, (Washington, D.C. Reagan-National - San Juan Luis Munoz Marin Intl) is currently priced at $301.

  • 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 August is currently the most expensive (average of $1,379). 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.
Dulles Intl to Dallas/Fort Worth flights
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Baltimore to Dallas/Fort Worth flights
Reagan-National to Seattle flights
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Baltimore to O'Hare Intl flights
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Baltimore to Miami flights
Dulles Intl to O'Hare Intl flights
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Baltimore to Seattle flights
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Dulles Intl to Denver flights
Dulles Intl to Heathrow flights
Dulles Intl to Atlanta flights
Dulles Intl to Boston flights
Dulles Intl to Hobby flights
Dulles Intl to Cancún flights
Reagan-National to Boston flights
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Reagan-National to Hobby flights
Baltimore to Orlando flights
Reagan-National to Orlando flights
Reagan-National to Miami flights
Baltimore to Heathrow flights
Dulles Intl to Fort Lauderdale flights
Dulles Intl to San Francisco flights
Baltimore to George Bush Intcntl flights
Dulles Intl to Midway flights
Reagan-National to Atlanta flights
Dulles Intl to Tampa flights
Baltimore to Tampa flights
Baltimore to Luis Munoz Marin Intl flights
Dulles Intl to George Bush Intcntl flights
Baltimore to Cancún flights
Reagan-National to San Francisco flights
Dulles Intl to Charles de Gaulle flights
Dulles Intl to San Diego flights
Dulles Intl to Luis Munoz Marin Intl flights
Reagan-National to George Bush Intcntl 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 May 22, 2026.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$103Average$386FlexibilityNo cancel feeOn-time62%
Spirit AirlinesCheapest$113Average$305FlexibilityNo cancel feeOn-time65%
DeltaCheapest$142Average$557FlexibilityNo cancel feeOn-timeN/A
JetBlueCheapest$180Average$494FlexibilityNo cancel feeOn-time62%
SouthwestCheapest$220Average$584FlexibilityNo cancel feeOn-time63%
American AirlinesCheapest$245Average$590FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$250Average$546FlexibilityNo cancel feeOn-time69%
Air CanadaCheapest$389Average$472FlexibilityNo cancel feeOn-time67%

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