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$101+ 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 10/22. Fares are subject to change and may not be available on all flights or dates of travel.
DCA — SJU
Oct 17 — Oct 241
Fri 10/17
Fri 10/24
1 adult, Economy
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Cheap 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 September 17, 2025.

Round-trip from

$219
(Trip.com)

One-way from

$101
(Trip.com)

Popular in

December

Cheapest in

July

Average price

$355

Good round-trip deal

$275 or less

Good one-way deal

$153 or less
From Washington, D.C. Reagan-National to Caribbean
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One-way flight from Washington, D.C. Reagan-National to Caribbean
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Highest demand for flights based on searches. 11% potential increase in price ($44 potential increase over avg. RT price).
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Cheapest flight prices on average. 3% potential price decrease ($11 potential savings vs. average RT price).
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Average for round-trip flights in September 2025
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Price to beat on a round-trip flight from Washington, D.C. Reagan-National to Caribbean.
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Price to beat on a one-way flight from Washington, D.C. Reagan-National to Caribbean.
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Find 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 September 17, 2025.

This Trip.com deal was found by Cheapflights users on 9/15. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/158:30 amDCA - SJU
Nonstop3h 45mJetBlue
Fri 10/176:05 pmSJU - DCA
Nonstop3h 52mJetBlue
Deal found 9/15$219
This Trip.com deal was found by Cheapflights users on 9/17. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/208:30 amDCA - SJU
Nonstop3h 45mJetBlue
Tue 10/286:02 pmSJU - DCA
Nonstop3h 57mJetBlue
Deal found 9/17$221
This Trip.com deal was found by Cheapflights users on 9/15. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/58:00 amDCA - SJU
Nonstop3h 50mJetBlue
Tue 11/1112:30 pmSJU - DCA
1 stop10h 45mJetBlue
Deal found 9/15$229
This JetBlue deal was found by Cheapflights users on 9/15. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/98:00 amDCA - SJU
Nonstop3h 51mJetBlue
Tue 12/96:51 pmSJU - DCA
Nonstop3h 57mJetBlue
Deal found 9/15$231
This JetBlue deal was found by Cheapflights users on 9/15. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/208:30 amDCA - SJU
Nonstop3h 45mJetBlue
Wed 11/56:57 pmSJU - DCA
Nonstop3h 57mJetBlue
Deal found 9/15$236
This CheapOair deal was found by Cheapflights users on 9/17. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/277:59 pmDCA - SJU
1 stop13h 59mJetBlue
Tue 10/286:02 pmSJU - DCA
Nonstop3h 57mJetBlue
Deal found 9/17$241
This Delta deal was found by Cheapflights users on 9/15. 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.
Mon 12/86:06 amDCA - SJU
1 stop7h 04mDelta
Wed 12/103:32 pmSJU - DCA
1 stop9h 07mDelta
Deal found 9/15$245
This JetBlue deal was found by Cheapflights users on 9/16. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/208:30 amDCA - SJU
Nonstop3h 45mJetBlue
Wed 10/228:50 amSJU - DCA
1 stop6h 12mJetBlue
Deal found 9/16$246
This Trip.com deal was found by Cheapflights users on 9/15. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/158:30 amDCA - SJU
Nonstop3h 45mJetBlue
Sat 10/186:05 pmSJU - DCA
Nonstop3h 52mJetBlue
Deal found 9/15$247
This Trip.com deal was found by Cheapflights users on 9/16. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/228:30 amDCA - SJU
Nonstop3h 45mJetBlue
Mon 11/36:51 pmSJU - DCA
Nonstop3h 57mJetBlue
Deal found 9/16$249
This Trip.com deal was found by Cheapflights users on 9/17. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/256:25 amDCA - SJU
1 stop7h 20mJetBlue
Tue 10/286:02 pmSJU - DCA
Nonstop3h 57mJetBlue
Deal found 9/17$251
This Mytrip deal was found by Cheapflights users on 9/17. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/16:00 amDCA - CUR
1 stop8h 10mAir Canada
Mon 11/104:10 pmCUR - DCA
1 stop19h 16mAir Canada
Deal found 9/17$281

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 September 17, 2025.
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

Reagan-National

Fly to

Caribbean

Route

Depart

Return

Price

Washington, D.C.San Juan

DCA - SJU

DCASJU

Washington, D.C. Reagan-National

Mon 10/20

8:30 am-12:15 pm

Nonstop3h 45m

San Juan Luis Munoz Marin Intl

Wed 11/5

6:57 pm-9:54 pm

Nonstop3h 57m

$236

Washington, D.C.San Juan

DCA - SJU

DCASJU

Washington, D.C. Reagan-National

Tue 10/21

7:37 am-1:52 pm

1 stop6h 15m

San Juan Luis Munoz Marin Intl

Fri 10/24

6:05 pm-9:57 pm

Nonstop3h 52m

$246

Washington, D.C.San Juan

DCA - SJU

DCASJU

Washington, D.C. Reagan-National

Wed 10/22

8:30 am-12:15 pm

Nonstop3h 45m

San Juan Luis Munoz Marin Intl

Mon 11/3

6:51 pm-9:48 pm

Nonstop3h 57m

$266

Washington, D.C.San Juan

DCA - SJU

DCASJU

Washington, D.C. Reagan-National

Tue 12/9

8:00 am-12:51 pm

Nonstop3h 51m

San Juan Luis Munoz Marin Intl

Mon 12/15

6:51 pm-9:48 pm

Nonstop3h 57m

$266

Washington, D.C.San Juan

DCA - SJU

DCASJU

Washington, D.C. Reagan-National

Tue 12/2

1:45 pm-11:54 pm

1 stop9h 09m

San Juan Luis Munoz Marin Intl

Thu 12/11

6:51 pm-9:48 pm

Nonstop3h 57m

$268

Washington, D.C.San Juan

DCA - SJU

DCASJU

Washington, D.C. Reagan-National

Fri 12/5

3:40 pm-11:54 pm

1 stop7h 14m

San Juan Luis Munoz Marin Intl

Thu 12/11

6:51 pm-9:48 pm

Nonstop3h 57m

$268

Washington, D.C.San Juan

DCA - SJU

DCASJU

Washington, D.C. Reagan-National

Sat 11/8

12:30 pm-10:04 pm

1 stop8h 34m

San Juan Luis Munoz Marin Intl

Wed 11/12

4:00 pm-10:15 pm

1 stop7h 15m

$273

Washington, D.C.San Juan

DCA - SJU

DCASJU

Washington, D.C. Reagan-National

Thu 10/30

8:59 am-4:33 pm

1 stop7h 34m

San Juan Luis Munoz Marin Intl

Tue 11/4

7:15 am-5:17 pm

1 stop11h 02m

$275

Washington, D.C.San Juan

DCA - SJU

DCASJU

Washington, D.C. Reagan-National

Sat 10/18

3:00 pm-11:41 pm

1 stop8h 41m

San Juan Luis Munoz Marin Intl

Tue 10/21

8:50 am-6:06 pm

1 stop9h 16m

$278

Washington, D.C.San Juan

DCA - SJU

DCASJU

Washington, D.C. Reagan-National

Wed 10/1

8:30 am-12:19 pm

Nonstop3h 49m

San Juan Luis Munoz Marin Intl

Sat 10/4

12:35 pm-8:54 pm

1 stop8h 19m

$300

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/17

Showing 1-10 of 60 results
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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 $254). Flying from Washington, D.C. Reagan-National Airport to Caribbean in June is currently the most expensive (average of $339). 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 September 17, 2025.

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 September 17, 2025.
See what other customers who have flown with Southwest, Delta, and United 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
4,242 reviews

Boarding

8.1

Crew

8.6

Overall

8.0

Food

7.0

Comfort

8.0

Entertainment

7.5

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
Southwest
8.0
Very good
4,242 reviews
Southwest
8.0
Very good
4,242 reviews

Boarding

8.1

Crew

8.6

Overall

8.0

Food

7.0

Comfort

8.0

Entertainment

7.5

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
Delta
8.0
Very good
7,961 reviews
Southwest
8.0
Very good
4,242 reviews

Boarding

8.1

Crew

8.6

Overall

8.0

Food

7.0

Comfort

8.0

Entertainment

7.5

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
United Airlines
7.4
Good
8,926 reviews
Southwest
8.0
Very good
4,242 reviews

Boarding

8.1

Crew

8.6

Overall

8.0

Food

7.0

Comfort

8.0

Entertainment

7.5

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
American Airlines
7.2
Good
10,000 reviews
Southwest
8.0
Very good
4,242 reviews

Boarding

8.1

Crew

8.6

Overall

8.0

Food

7.0

Comfort

8.0

Entertainment

7.5

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
JetBlue
7.2
Good
2,914 reviews
Southwest
8.0
Very good
4,242 reviews

Boarding

8.1

Crew

8.6

Overall

8.0

Food

7.0

Comfort

8.0

Entertainment

7.5

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines

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 JetBlue, Air Canada, and American Airlines fly from Washington, D.C. Reagan-National Airport to Caribbean in about 2h 53m. The time it takes to get you to your destination can typically vary by up to 26h 23m. Airlines will cover a distance of 954 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 $101. Users have also found prices from $119 and $152 on Air Canada and United 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 - Montego Bay Sangster 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 $303 for a flight from Washington, D.C. Reagan-National Airport to Caribbean. The cheapest flight overall is $99 while the most popular route, (Washington, D.C. Reagan-National - San Juan Luis Munoz Marin Intl) is currently priced at $219.

  • 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 $254). Flying from Washington, D.C. Reagan-National Airport to Caribbean in June is currently the most expensive (average of $339). 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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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 September 17, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$85Average$304FlexibilityNo cancel feeOn-time62%
Spirit AirlinesCheapest$115Average$272FlexibilityNo cancel feeOn-time65%
JetBlueCheapest$180Average$518FlexibilityNo cancel feeOn-time62%
SouthwestCheapest$220Average$736FlexibilityNo cancel feeOn-time63%
United AirlinesCheapest$220Average$628FlexibilityNo cancel feeOn-time69%
DeltaCheapest$237Average$552FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$248Average$612FlexibilityNo cancel feeOn-time71%
Air CanadaCheapest$430Average$504FlexibilityNo cancel feeOn-time67%

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