HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
Caribbean

$121+ 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 9/17. Fares are subject to change and may not be available on all flights or dates of travel.
DCA — SJU
May 27 — Jun 31
Wed 5/27
Wed 6/3
1 adult, Economy
We work with more than 300 partners to bring you better travel deals

Find cheap flights from Reagan-National to Caribbean with Cheapflights

1. Tell us where you want to go

Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”

2. Select your favorite providers

We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.

3. Compare prices and book

Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.

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 27, 2026.

This Delta 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/265:00 pm
DCA
-
SJU
1 stop6h 35m
Delta
Wed 6/107:05 am
SJU
-
DCA
1 stop9h 54m
Delta
Deal found 4/22$266
This American Airlines deal was found by Cheapflights users on 4/26. 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 8/191:44 pm
DCA
-
SJU
1 stop7h 30m
American Airlines
Wed 8/261:38 pm
SJU
-
DCA
1 stop8h 22m
American Airlines
Deal found 4/26$271
This Cheapflightsfares 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 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 4/22$272
This KAYAK 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 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
Fri 5/295:10 pm
SJU
-
DCA
Nonstop3h 53m
JetBlue
Deal found 4/22$277
This American Airlines 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/156:00 am
DCA
-
STT
1 stop7h 35m
American Airlines
Mon 5/185:05 pm
STT
-
DCA
1 stop15h 55m
American Airlines
Deal found 4/22$290
This American Airlines deal was found by Cheapflights users on 4/27. 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 6/15:00 pm
DCA
-
SJU
1 stop6h 01m
American Airlines
Fri 6/57:16 pm
SJU
-
DCA
1 stop13h 44m
American Airlines
Deal found 4/27$291
This Southwest deal was found by Cheapflights users on 4/27. 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.
Fri 9/46:00 am
DCA
-
SJU
1 stop10h 55m
Southwest
Tue 9/85:15 am
SJU
-
DCA
1 stop7h 20m
Southwest
Deal found 4/27$296
This Cheapflightsfares 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 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 4/22$297
This American Airlines deal was found by Cheapflights users on 4/26. 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 5/261:39 pm
DCA
-
SJU
1 stop9h 22m
American Airlines
Tue 6/27:15 pm
SJU
-
DCA
1 stop13h 45m
American Airlines
Deal found 4/26$299
This Cheapflightsfares 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/98:00 am
DCA
-
SJU
Nonstop3h 45m
JetBlue
Fri 5/295:10 pm
SJU
-
DCA
Nonstop3h 53m
JetBlue
Deal found 4/22$302
This Cheapflightsfares 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/192:45 pm
DCA
-
SJU
1 stop6h 33m
JetBlue
Fri 5/225:10 pm
SJU
-
DCA
Nonstop3h 53m
JetBlue
Deal found 4/23$306
This KAYAK deal was found by Cheapflights users on 4/25. 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 KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/128:00 am
DCA
-
SJU
Nonstop3h 45m
JetBlue
Thu 5/215:10 pm
SJU
-
DCA
Nonstop3h 53m
JetBlue
Deal found 4/25$307

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 27, 2026.

Round-trip from

$266
(Delta)

One-way from

$127
(SmartFares)

Popular in

March

Cheapest in

October

Average price

$335

Good round-trip deal

$393 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 ($18 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 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 27, 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

Fri 9/4

6:00 am-4:55 pm

1 stop10h 55m

San Juan Luis Munoz Marin Intl

Tue 9/8

5:15 am-12:35 pm

1 stop7h 20m

$296

Washington, D.C.Saint Thomas Island

DCA - STT

DCASTT

Washington, D.C. Reagan-National

Mon 5/11

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

$311

Washington, D.C.Saint Thomas Island

DCA - STT

DCASTT

Washington, D.C. Reagan-National

Sun 5/10

6:00 am-3:43 pm

1 stop9h 43m

Saint Thomas Island Cyril E King

Wed 5/13

1:22 pm-11:58 pm

1 stop10h 36m

$311

Washington, D.C.Saint Thomas Island

DCA - STT

DCASTT

Washington, D.C. Reagan-National

Thu 5/7

6:00 am-1:51 pm

1 stop7h 51m

Saint Thomas Island Cyril E King

Tue 5/12

4:27 pm-11:24 pm

1 stop6h 57m

$343
Quickest round-trip

Washington, D.C.Saint Thomas Island

DCA - STT

DCASTT

Washington, D.C. Reagan-National

Thu 5/7

6:59 am-1:51 pm

1 stop6h 52m

Saint Thomas Island Cyril E King

Thu 5/14

4:27 pm-11:24 pm

1 stop6h 57m

$343

Washington, D.C.Saint Thomas Island

DCA - STT

DCASTT

Washington, D.C. Reagan-National

Sat 8/1

6:00 am-3:43 pm

1 stop9h 43m

Saint Thomas Island Cyril E King

Fri 8/7

1:22 pm-10:15 pm

1 stop8h 53m

$355

Washington, D.C.Saint Thomas Island

DCA - STT

DCASTT

Washington, D.C. Reagan-National

Tue 5/12

6:00 am-3:17 pm

1 stop9h 17m

Saint Thomas Island Cyril E King

Sat 5/16

4:27 pm-11:24 pm

1 stop6h 57m

$359

Washington, D.C.San Juan

DCA - SJU

DCASJU

Washington, D.C. Reagan-National

Wed 8/5

6:55 am-7:00 pm

1 stop12h 05m

San Juan Luis Munoz Marin Intl

Mon 8/10

5:45 pm-11:55 pm

1 stop6h 10m

$361

Washington, D.C.San Juan

DCA - SJU

DCASJU

Washington, D.C. Reagan-National

Mon 8/10

2:50 pm-11:05 pm

1 stop8h 15m

San Juan Luis Munoz Marin Intl

Fri 8/14

5:00 am-2:10 pm

2 stops9h 10m

$361

Washington, D.C.San Juan

DCA - SJU

DCASJU

Washington, D.C. Reagan-National

Tue 8/18

11:30 am-11:50 pm

2 stops12h 20m

San Juan Luis Munoz Marin Intl

Tue 8/25

7:00 am-3:55 pm

1 stop8h 55m

$362

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/24

Showing 1-10 of 60 resultsSorted by cheapest first
1
2
3
...
6

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 27, 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 27, 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
4,321 reviews

Overall

8.0

Food

7.0

Boarding

8.1

Entertainment

7.5

Comfort

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
4,321 reviews
Southwest
8.0
Very good
4,321 reviews

Overall

8.0

Food

7.0

Boarding

8.1

Entertainment

7.5

Comfort

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
8,466 reviews
Southwest
8.0
Very good
4,321 reviews

Overall

8.0

Food

7.0

Boarding

8.1

Entertainment

7.5

Comfort

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
9,669 reviews
Southwest
8.0
Very good
4,321 reviews

Overall

8.0

Food

7.0

Boarding

8.1

Entertainment

7.5

Comfort

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
2,964 reviews
Southwest
8.0
Very good
4,321 reviews

Overall

8.0

Food

7.0

Boarding

8.1

Entertainment

7.5

Comfort

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
11,671 reviews
Southwest
8.0
Very good
4,321 reviews

Overall

8.0

Food

7.0

Boarding

8.1

Entertainment

7.5

Comfort

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 Southwest, Delta, and United Airlines fly from Washington, D.C. Reagan-National Airport to Caribbean in about 7h 18m. The time it takes to get you to your destination can typically vary by up to 3h 37m. 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 $351 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.

See more FAQs

Browse thousands of different options on Cheapflights for your next trip

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

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 Seattle flights
Dulles Intl to Dallas/Fort Worth flights
Baltimore to Dallas/Fort Worth flights
Reagan-National to Seattle flights
Dulles Intl to Las Vegas flights
Dulles Intl to Orlando flights
Baltimore to Miami flights
Baltimore to Seattle flights
Dulles Intl to Miami flights
Reagan-National to Dallas/Fort Worth flights
Dulles Intl to O'Hare Intl flights
Baltimore to Los Angeles flights
Dulles Intl to Cancún flights
Baltimore to Las Vegas flights
Reagan-National to Miami flights
Baltimore to O'Hare Intl flights
Baltimore to Atlanta flights
Dulles Intl to Denver flights
Dulles Intl to Atlanta flights
Reagan-National to Los Angeles flights
Reagan-National to Las Vegas flights
Dulles Intl to Boston flights
Reagan-National to O'Hare Intl flights
Baltimore to Orlando flights
Baltimore to Denver flights
Dulles Intl to San Francisco flights
Baltimore to Fort Lauderdale flights
Dulles Intl to Los Angeles flights
Dulles Intl to Heathrow flights
Reagan-National to Atlanta flights
Reagan-National to Hobby flights
Reagan-National to Orlando flights
Baltimore to Hobby flights
Dulles Intl to Hobby flights
Reagan-National to San Francisco flights
Dulles Intl to Tampa flights
Dulles Intl to New Orleans flights
Baltimore to San Francisco flights
Reagan-National to Boston flights
Baltimore to Heathrow flights
Baltimore to Boston flights
Dulles Intl to Luis Munoz Marin Intl flights
Baltimore to Tampa flights
Reagan-National to Fort Lauderdale flights
Dulles Intl to Fort Lauderdale flights
Baltimore to Luis Munoz Marin Intl flights
Dulles Intl to George Bush Intcntl flights
Dulles Intl to Midway flights
Baltimore to Minneapolis flights
Dulles Intl to Charles de Gaulle 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 27, 2026.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$97Average$381FlexibilityNo cancel feeOn-time62%
Spirit AirlinesCheapest$113Average$305FlexibilityNo cancel feeOn-time65%
DeltaCheapest$142Average$542FlexibilityNo cancel feeOn-timeN/A
JetBlueCheapest$180Average$496FlexibilityNo cancel feeOn-time62%
SouthwestCheapest$220Average$589FlexibilityNo cancel feeOn-time63%
American AirlinesCheapest$245Average$587FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$250Average$585FlexibilityNo cancel feeOn-time69%
Air CanadaCheapest$389Average$472FlexibilityNo cancel feeOn-time67%

100% Free

Cheapflights is completely free to use, so you can start saving the moment you arrive.

Book with Flexibility

Our users can plan ahead with confidence and find flights with no change fees

Travel Smart

Millions of people come to us for their flight needs every year. We help make travel planning easy by providing useful insights and data-driven graphs that can inform your decisions.
Site
©2026 Cheapflights