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$53+ Cheap flights from Dulles Intl (IAD) 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 1/3. Fares are subject to change and may not be available on all flights or dates of travel.
IAD — SJU
Dec 19 — Dec 261
Fri 12/19
Fri 12/26
1 adult, Economy
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Cheap flight deals from Dulles Intl to Caribbean

Keep the following information in mind while searching for Dulles Intl to Caribbean flight deals. Data was last updated November 19, 2025.

Round-trip from

$184
(Super.com)

One-way from

$53
(Expedia)

Popular in

December

Cheapest in

July

Average price

$352

Good round-trip deal

$308 or less

Good one-way deal

$77 or less
From Washington, D.C. Dulles Intl to Caribbean
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One-way flight from Washington, D.C. Dulles Intl to Caribbean
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Highest demand for flights based on searches. 11% potential increase in price ($42 potential increase over avg. RT price).
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Cheapest flight prices on average. 2% potential price decrease ($10 potential savings vs. average RT price).
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Average for round-trip flights in November 2025
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Price to beat on a round-trip flight from Washington, D.C. Dulles Intl to Caribbean.
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Price to beat on a one-way flight from Washington, D.C. Dulles Intl to Caribbean.
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Find flight deals from Dulles Intl to Caribbean

Cheapest flights from Dulles Intl to Caribbean
Explore the most affordable flight options available from Dulles Intl to Caribbean. Find the lowest fares from popular airlines and budget airlines, with prices last updated on November 19, 2025.

This Super.com deal was found by Cheapflights users on 11/18. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/18:06 pmIAD - SJU
Nonstop3h 47mFrontier
Sun 12/76:30 amSJU - IAD
Nonstop4h 13mFrontier
Deal found 11/18$184
This Kiwi.com deal was found by Cheapflights users on 11/18. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/297:56 pmIAD - SJU
Nonstop3h 47mFrontier
Fri 12/123:55 amSJU - IAD
1 stop17h 29mFrontier
Deal found 11/18$185
This Kiwi.com deal was found by Cheapflights users on 11/18. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/154:00 pmIAD - SJU
2 stops30h 25mMultiple Airlines
Fri 12/194:18 pmSJU - IAD
Nonstop4h 13mMultiple Airlines
Deal found 11/18$186
This CheapOair deal was found by Cheapflights users on 11/19. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/227:56 pmIAD - SJU
Nonstop3h 47mFrontier
Tue 11/254:08 pmSJU - IAD
Nonstop4h 03mFrontier
Deal found 11/19$188
This CheapOair deal was found by Cheapflights users on 11/18. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/410:38 amIAD - SJU
Nonstop3h 54mFrontier
Fri 12/123:55 amSJU - IAD
1 stop17h 29mFrontier
Deal found 11/18$190
This Frontier deal was found by Cheapflights users on 11/18. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 12/712:04 pmIAD - SJU
1 stop10h 46mFrontier
Sun 12/146:30 amSJU - IAD
Nonstop4h 13mFrontier
Deal found 11/18$191
This Kiwi.com deal was found by Cheapflights users on 11/18. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/18:06 pmIAD - SJU
Nonstop3h 47mMultiple Airlines
Sun 12/1411:05 amSJU - IAD
2 stops29h 05mMultiple Airlines
Deal found 11/18$193
This Super.com deal was found by Cheapflights users on 11/19. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/69:20 pmIAD - SJU
1 stop11h 35mFrontier
Thu 12/116:30 amSJU - IAD
Nonstop4h 13mFrontier
Deal found 11/19$194
This Super.com deal was found by Cheapflights users on 11/17. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/308:06 pmIAD - SJU
Nonstop3h 47mFrontier
Sun 12/76:30 amSJU - IAD
Nonstop4h 13mFrontier
Deal found 11/17$195
This Frontier deal was found by Cheapflights users on 11/19. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 12/1410:38 amIAD - SJU
Nonstop3h 54mFrontier
Fri 12/194:18 pmSJU - IAD
Nonstop4h 13mFrontier
Deal found 11/19$197
This Super.com deal was found by Cheapflights users on 11/16. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/238:06 pmIAD - SJU
Nonstop3h 47mFrontier
Fri 11/284:08 pmSJU - IAD
Nonstop4h 03mFrontier
Deal found 11/16$198
This United Airlines deal was found by Cheapflights users on 11/17. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/46:00 amIAD - NAS
1 stop7h 33mUnited Airlines
Sat 12/61:05 pmNAS - IAD
Nonstop2h 53mUnited Airlines
Deal found 11/17$343

Cheapflights Fare Finder

 
Customize your flight search to find flights from Dulles Intl 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 November 19, 2025.
Use the filters below to find and compare flights from Washington, D.C. Dulles Intl Airport to Caribbean that are best for you.

Fly from

Dulles Intl

Fly to

Caribbean

Route

Depart

Return

Price

Washington, D.C.San Juan

IAD - SJU

IADSJU

Washington, D.C. Dulles Intl

Tue 3/3

12:35 pm-11:49 pm

1 stop10h 14m

San Juan Luis Munoz Marin Intl

Wed 3/11

6:15 am-2:51 pm

1 stop8h 36m

$244

Washington, D.C.San Juan

IAD - SJU

IADSJU

Washington, D.C. Dulles Intl

Sun 1/25

5:32 pm-10:22 pm

Nonstop3h 50m

San Juan Luis Munoz Marin Intl

Thu 1/29

8:10 am-11:15 am

Nonstop4h 05m

$290

Washington, D.C.San Juan

IAD - SJU

IADSJU

Washington, D.C. Dulles Intl

Wed 1/28

6:03 am-4:36 pm

1 stop9h 33m

San Juan Luis Munoz Marin Intl

Wed 2/4

5:50 pm-8:55 pm

Nonstop4h 05m

$295

Washington, D.C.San Juan

IAD - SJU

IADSJU

Washington, D.C. Dulles Intl

Sun 5/3

5:24 pm-9:24 pm

Nonstop4h 00m

San Juan Luis Munoz Marin Intl

Tue 5/5

1:05 am-7:19 am

1 stop6h 14m

$295

Washington, D.C.San Juan

IAD - SJU

IADSJU

Washington, D.C. Dulles Intl

Sun 1/18

12:23 pm-11:57 pm

1 stop10h 34m

San Juan Luis Munoz Marin Intl

Sat 1/24

6:15 am-11:43 am

1 stop6h 28m

$299

Washington, D.C.San Juan

IAD - SJU

IADSJU

Washington, D.C. Dulles Intl

Mon 1/19

5:32 pm-10:22 pm

Nonstop3h 50m

San Juan Luis Munoz Marin Intl

Fri 1/23

5:50 pm-8:55 pm

Nonstop4h 05m

$326

Washington, D.C.Nassau

IAD - NAS

IADNAS

Washington, D.C. Dulles Intl

Wed 1/28

3:25 pm-10:28 am

1 stop19h 03m

Nassau Intl

Sat 1/31

11:35 am-11:30 pm

1 stop11h 55m

$341

Washington, D.C.Nassau

IAD - NAS

IADNAS

Washington, D.C. Dulles Intl

Wed 1/21

1:12 am-10:28 am

1 stop9h 16m

Nassau Intl

Wed 1/28

11:35 am-3:13 am

1 stop15h 38m

$341

Washington, D.C.San Juan

IAD - SJU

IADSJU

Washington, D.C. Dulles Intl

Fri 1/23

12:40 pm-11:45 pm

1 stop10h 05m

San Juan Luis Munoz Marin Intl

Mon 1/26

6:27 pm-12:24 am

1 stop6h 57m

$341

Washington, D.C.San Juan

IAD - SJU

IADSJU

Washington, D.C. Dulles Intl

Mon 5/4

3:00 pm-10:54 pm

1 stop7h 54m

San Juan Luis Munoz Marin Intl

Sat 5/9

6:15 am-4:39 pm

1 stop10h 24m

$341

Flights are sorted by cheapest round-trip flights first.

Deals found on 11/18

Showing 1-10 of 60 results
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Best time to book a flight from Dulles Intl to Caribbean

Have a flexible travel schedule? Discover the best time to fly to Caribbean from Dulles Intl 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. Dulles Intl Airport to Caribbean

What is the cheapest month to book a flight from Washington, D.C. Dulles Intl Airport to Caribbean?

Currently, June is the cheapest month in which you can book a flight from Washington, D.C. Dulles Intl Airport to Caribbean (average of $86). Flying from Washington, D.C. Dulles Intl Airport to Caribbean in April is currently the most expensive (average of $238). 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 IAD to CB?

Find hourly flight availability from Dulles Intl 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 November 19, 2025.

A simple way to save on the total cost of your ticket is to fly from Washington, D.C. Dulles Intl Airport to Caribbean at noon. If you’re flexible enough to do this you can expect to save up to 30% on your trip compared to booking a flight in the morning.

What is the cheapest day to fly from Washington, D.C. Dulles Intl Airport to Caribbean?

Use this chart to determine the cheapest time to fly round-trip from Dulles Intl to Caribbean. Price data was last updated on November 2, 2025.

Travelers seeking maximum savings on their Washington, D.C. Dulles Intl Airport to Caribbean flight should consider departing on Wednesday at noon when fares are most often at their lowest. Friday mornings flights should be avoided if possible as fares are typically the most expensive at this time.

Weekly flight availability from Washington, D.C. Dulles Intl Airport to Caribbean

Explore weekly flight availability from Dulles Intl 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 November 19, 2025.

The most flights from IAD to 0CB are scheduled on a Monday (5 on average). You will have fewer flight options on Monday, which is when the least amount of flights are scheduled (5 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 November 19, 2025.
Read reviews from past customers who have flown Delta, Copa Airlines, and United Airlines from Washington, D.C. Dulles Intl Airport to Caribbean. Users can see the overall rating for each airline as well as how each is rated in terms of entertainment options, comfort, food, crew/service, and boarding process.
Delta
7.9
Good
8,003 reviews

Crew

8.5

Food

7.3

Boarding

8.1

Entertainment

7.9

Comfort

7.9

Overall

7.9

Reviews

1 / 20
6.0
Good

Jim,Nov 2025

AVL - ATL

The exit row seats without a seat in front are great for leg room but don’t have a fold out entertainment console so you’re forced to use the screen several feet in front of you (there is, at least, a remote). Best to bring a tablet loaded with entertainment or a book.
Delta
7.9
Good
8,003 reviews
Delta
7.9
Good
8,003 reviews

Crew

8.5

Food

7.3

Boarding

8.1

Entertainment

7.9

Comfort

7.9

Overall

7.9

Reviews

1 / 20
6.0
Good

Jim,Nov 2025

AVL - ATL

The exit row seats without a seat in front are great for leg room but don’t have a fold out entertainment console so you’re forced to use the screen several feet in front of you (there is, at least, a remote). Best to bring a tablet loaded with entertainment or a book.
Copa Airlines
7.6
Good
1,566 reviews
Delta
7.9
Good
8,003 reviews

Crew

8.5

Food

7.3

Boarding

8.1

Entertainment

7.9

Comfort

7.9

Overall

7.9

Reviews

1 / 20
6.0
Good

Jim,Nov 2025

AVL - ATL

The exit row seats without a seat in front are great for leg room but don’t have a fold out entertainment console so you’re forced to use the screen several feet in front of you (there is, at least, a remote). Best to bring a tablet loaded with entertainment or a book.
United Airlines
7.4
Good
9,023 reviews
Delta
7.9
Good
8,003 reviews

Crew

8.5

Food

7.3

Boarding

8.1

Entertainment

7.9

Comfort

7.9

Overall

7.9

Reviews

1 / 20
6.0
Good

Jim,Nov 2025

AVL - ATL

The exit row seats without a seat in front are great for leg room but don’t have a fold out entertainment console so you’re forced to use the screen several feet in front of you (there is, at least, a remote). Best to bring a tablet loaded with entertainment or a book.
American Airlines
7.2
Good
11,046 reviews
Delta
7.9
Good
8,003 reviews

Crew

8.5

Food

7.3

Boarding

8.1

Entertainment

7.9

Comfort

7.9

Overall

7.9

Reviews

1 / 20
6.0
Good

Jim,Nov 2025

AVL - ATL

The exit row seats without a seat in front are great for leg room but don’t have a fold out entertainment console so you’re forced to use the screen several feet in front of you (there is, at least, a remote). Best to bring a tablet loaded with entertainment or a book.
Frontier
5.8
Fair
3,106 reviews
Delta
7.9
Good
8,003 reviews

Crew

8.5

Food

7.3

Boarding

8.1

Entertainment

7.9

Comfort

7.9

Overall

7.9

Reviews

1 / 20
6.0
Good

Jim,Nov 2025

AVL - ATL

The exit row seats without a seat in front are great for leg room but don’t have a fold out entertainment console so you’re forced to use the screen several feet in front of you (there is, at least, a remote). Best to bring a tablet loaded with entertainment or a book.

Related info for your journey

Find useful and relevant information for your journey from Dulles Intl 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. Dulles Intl Airport to Caribbean?

    For as low as $290, Delta can have you in Caribbean from Washington, D.C. Dulles Intl Airport in 3h 50m. The distance between Washington, D.C. Dulles Intl Airport and Caribbean is about 1573 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. Dulles Intl Airport to Caribbean one-way?

    The cheapest airlines for a one-way flight from Washington, D.C. Dulles Intl Airport to Caribbean are United Airlines ($108), Delta ($113), and American Airlines ($140).

  • What are the most popular routes from Washington, D.C. Dulles Intl Airport to Caribbean?

    The most popular flight routes from Washington, D.C. Dulles Intl Airport to Caribbean are Washington, D.C. Dulles Intl - San Juan Luis Munoz Marin Intl, Washington, D.C. Dulles Intl - Punta Cana and Washington, D.C. Dulles Intl - Oranjestad Reina Beatrix.

  • What are the most reliable airlines from Washington, D.C. Dulles Intl Airport to Caribbean?

    No one likes to see their flight delayed. When booking a flight from Washington, D.C. Dulles Intl Airport to Caribbean consider choosing Air Canada (72%), United Airlines (72%) or Brussels Airlines (57%) as they are the most reliable in getting you off to your destination on time.

  • What are the cheapest flights from Washington, D.C. Dulles Intl Airport to Caribbean?

    While on average a flight from Washington, D.C. Dulles Intl Airport to Caribbean is generally $295, our data shows the cheapest flight currently is $69. When looking at the most popular route, (Washington, D.C. Dulles Intl - San Juan Luis Munoz Marin Intl), you can expect to pay $154 for that flight.

  • Can I find deals for flights from Dulles Intl to Caribbean that include hotel bookings?

    Yes. In addition to deals on Dulles Intl to Caribbean flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Dulles Intl to Caribbean?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Dulles Intl to Caribbean.

  • Can I find deals for business class flights from Dulles Intl to Caribbean?

    Yes. Cheapflights offers flight deals from Dulles Intl 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. Dulles Intl Airport to Caribbean?

    Currently, June is the cheapest month in which you can book a flight from Washington, D.C. Dulles Intl Airport to Caribbean (average of $86). Flying from Washington, D.C. Dulles Intl Airport to Caribbean in April is currently the most expensive (average of $238). 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 Dulles Intl to Caribbean

See prices for flight routes from nearby airports that may be better suited for you.
Dulles Intl to Dallas/Fort Worth flights
Dulles Intl to Miami flights
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Baltimore to O'Hare Intl flights
Reagan-National to San Francisco flights
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Reagan-National to Hobby flights
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Baltimore to Denver flights
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Dulles Intl to Seattle flights
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Reagan-National to Seattle flights
Dulles Intl to Haneda flights
Dulles Intl to George Bush Intcntl flights

Top 9 airlines flying from Dulles Intl to Caribbean

Discover the top 9 airlines that operate flights from Dulles Intl 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 November 19, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$114Average$394FlexibilityNo cancel feeOn-time62%
American AirlinesCheapest$145Average$658FlexibilityNo cancel feeOn-time71%
Spirit AirlinesCheapest$153Average$302FlexibilityNo cancel feeOn-time65%
DeltaCheapest$158Average$680FlexibilityNo cancel feeOn-timeN/A
JetBlueCheapest$161Average$386FlexibilityNo cancel feeOn-time62%
AviancaCheapest$167Average$438FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$273Average$623FlexibilityNo cancel feeOn-time69%
Copa AirlinesCheapest$360Average$500FlexibilityNo cancel feeOn-time70%
Air CanadaCheapest$450Average$508FlexibilityNo cancel feeOn-time67%

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