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$83+ 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 11/2. Fares are subject to change and may not be available on all flights or dates of travel.
IAD — SJU
Nov 22 — Nov 291
Sat 11/22
Sat 11/29
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 October 23, 2025.

Round-trip from

$184
(Frontier)

One-way from

$83
(Kiwi.com)

Popular in

December

Cheapest in

July

Average price

$333

Good round-trip deal

$296 or less

Good one-way deal

$69 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. 9% potential increase in price ($36 potential increase over avg. RT price).
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Cheapest flight prices on average. 2% potential price decrease ($9 potential savings vs. average RT price).
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Average for round-trip flights in October 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 October 23, 2025.

This Frontier deal was found by Cheapflights users on 10/20. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/36:00 amIAD - SJU
1 stop8h 19mFrontier
Thu 11/133:45 pmSJU - IAD
Nonstop3h 56mFrontier
Deal found 10/20$184
This Frontier deal was found by Cheapflights users on 10/20. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/242:11 pmIAD - SJU
1 stop7h 58mFrontier
Thu 12/46:30 amSJU - IAD
Nonstop4h 13mFrontier
Deal found 10/20$187
This Kiwi.com deal was found by Cheapflights users on 10/21. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 12/710:38 amIAD - SJU
Nonstop3h 54mFrontier
Thu 12/1110:42 amSJU - IAD
1 stop29h 23mFrontier
Deal found 10/21$189
This Kiwi.com deal was found by Cheapflights users on 10/20. 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 Kiwi.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
Thu 12/46:30 amSJU - IAD
Nonstop4h 13mFrontier
Deal found 10/20$191
This Frontier deal was found by Cheapflights users on 10/22. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/24:04 pmIAD - SJU
1 stop8h 28mFrontier
Thu 11/63:45 pmSJU - IAD
Nonstop3h 56mFrontier
Deal found 10/22$192
This Frontier deal was found by Cheapflights users on 10/23. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/18:06 pmIAD - SJU
Nonstop3h 47mFrontier
Thu 12/46:30 amSJU - IAD
Nonstop4h 13mFrontier
Deal found 10/23$195
This Frontier deal was found by Cheapflights users on 10/21. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/67:26 pmIAD - SJU
Nonstop3h 52mFrontier
Thu 11/133:45 pmSJU - IAD
Nonstop3h 56mFrontier
Deal found 10/21$197
This Kiwi.com deal was found by Cheapflights users on 10/21. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/85:58 amIAD - SJU
2 stops25h 47mFrontier
Thu 11/133:45 pmSJU - IAD
Nonstop3h 56mFrontier
Deal found 10/21$198
This Kiwi.com deal was found by Cheapflights users on 10/21. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/118:40 amIAD - SJU
2 stops41h 53mFrontier
Thu 11/133:45 pmSJU - IAD
Nonstop3h 56mFrontier
Deal found 10/21$201
This Frontier deal was found by Cheapflights users on 10/23. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/176:00 amIAD - SJU
1 stop8h 19mFrontier
Mon 11/244:08 pmSJU - IAD
Nonstop4h 03mFrontier
Deal found 10/23$203
This Frontier deal was found by Cheapflights users on 10/21. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/134:00 pmIAD - SJU
1 stop8h 32mFrontier
Sun 11/234:08 pmSJU - IAD
Nonstop4h 03mFrontier
Deal found 10/21$204
This United Airlines deal was found by Cheapflights users on 10/21. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/288:15 amIAD - AUA
Nonstop4h 25mUnited Airlines
Tue 11/45:35 pmAUA - IAD
Nonstop4h 35mUnited Airlines
Deal found 10/21$349

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 October 23, 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 11/11

12:11 pm-11:56 pm

1 stop10h 45m

San Juan Luis Munoz Marin Intl

Sat 12/6

7:00 am-2:40 pm

1 stop8h 40m

$247

Washington, D.C.San Juan

IAD - SJU

IADSJU

Washington, D.C. Dulles Intl

Sun 11/2

7:05 am-5:33 pm

1 stop9h 28m

San Juan Luis Munoz Marin Intl

Tue 11/11

3:32 pm-9:32 pm

1 stop7h 00m

$295

Washington, D.C.San Juan

IAD - SJU

IADSJU

Washington, D.C. Dulles Intl

Sat 11/1

6:00 am-4:33 pm

1 stop10h 33m

San Juan Luis Munoz Marin Intl

Wed 11/12

6:36 pm-12:16 am

1 stop6h 40m

$304

Washington, D.C.San Juan

IAD - SJU

IADSJU

Washington, D.C. Dulles Intl

Tue 11/4

6:00 am-4:36 pm

1 stop9h 36m

San Juan Luis Munoz Marin Intl

Wed 11/12

5:50 pm-8:55 pm

Nonstop4h 05m

$305

Washington, D.C.San Juan

IAD - SJU

IADSJU

Washington, D.C. Dulles Intl

Tue 11/11

5:32 pm-10:22 pm

Nonstop3h 50m

San Juan Luis Munoz Marin Intl

Sat 12/6

8:10 am-4:00 pm

1 stop8h 50m

$305

Washington, D.C.San Juan

IAD - SJU

IADSJU

Washington, D.C. Dulles Intl

Sat 11/1

6:00 am-4:33 pm

1 stop10h 33m

San Juan Luis Munoz Marin Intl

Wed 11/5

7:15 am-4:57 pm

1 stop10h 42m

$305

Washington, D.C.San Juan

IAD - SJU

IADSJU

Washington, D.C. Dulles Intl

Mon 11/3

8:27 am-1:17 pm

Nonstop3h 50m

San Juan Luis Munoz Marin Intl

Thu 11/6

5:50 pm-8:55 pm

Nonstop4h 05m

$315

Washington, D.C.San Juan

IAD - SJU

IADSJU

Washington, D.C. Dulles Intl

Tue 10/28

6:30 am-2:40 pm

1 stop8h 10m

San Juan Luis Munoz Marin Intl

Thu 10/30

4:50 pm-8:55 pm

Nonstop4h 05m

$360

Washington, D.C.Oranjestad

IAD - AUA

IADAUA

Washington, D.C. Dulles Intl

Sat 11/8

6:00 am-4:50 pm

1 stop9h 50m

Oranjestad Reina Beatrix

Thu 11/13

4:10 pm-10:58 pm

1 stop7h 48m

$364

Washington, D.C.Oranjestad

IAD - AUA

IADAUA

Washington, D.C. Dulles Intl

Fri 2/6

7:59 pm-12:00 pm

1 stop15h 01m

Oranjestad Reina Beatrix

Fri 2/13

4:25 pm-12:07 am

1 stop8h 42m

$364

Flights are sorted by cheapest round-trip flights first.

Deals found on 10/22

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 September is currently the most expensive (average of $272). 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 October 23, 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 October 19, 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.

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 October 23, 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
7,981 reviews

Comfort

7.9

Entertainment

7.9

Crew

8.5

Boarding

8.2

Food

7.3

Overall

7.9

Reviews

1 / 20
8.0
Excellent

Matthew,Oct 2025

GSP - ATL

This is always a full flight since it is the connecting route to primary destinations through Atlanta. That said, the crew handles the full load well. Not much more to say, it is a short flight with no in-flight services due to the length.
Delta
7.9
Good
7,981 reviews
Delta
7.9
Good
7,981 reviews

Comfort

7.9

Entertainment

7.9

Crew

8.5

Boarding

8.2

Food

7.3

Overall

7.9

Reviews

1 / 20
8.0
Excellent

Matthew,Oct 2025

GSP - ATL

This is always a full flight since it is the connecting route to primary destinations through Atlanta. That said, the crew handles the full load well. Not much more to say, it is a short flight with no in-flight services due to the length.
Copa Airlines
7.6
Good
1,558 reviews
Delta
7.9
Good
7,981 reviews

Comfort

7.9

Entertainment

7.9

Crew

8.5

Boarding

8.2

Food

7.3

Overall

7.9

Reviews

1 / 20
8.0
Excellent

Matthew,Oct 2025

GSP - ATL

This is always a full flight since it is the connecting route to primary destinations through Atlanta. That said, the crew handles the full load well. Not much more to say, it is a short flight with no in-flight services due to the length.
United Airlines
7.4
Good
8,991 reviews
Delta
7.9
Good
7,981 reviews

Comfort

7.9

Entertainment

7.9

Crew

8.5

Boarding

8.2

Food

7.3

Overall

7.9

Reviews

1 / 20
8.0
Excellent

Matthew,Oct 2025

GSP - ATL

This is always a full flight since it is the connecting route to primary destinations through Atlanta. That said, the crew handles the full load well. Not much more to say, it is a short flight with no in-flight services due to the length.
American Airlines
7.2
Good
11,028 reviews
Delta
7.9
Good
7,981 reviews

Comfort

7.9

Entertainment

7.9

Crew

8.5

Boarding

8.2

Food

7.3

Overall

7.9

Reviews

1 / 20
8.0
Excellent

Matthew,Oct 2025

GSP - ATL

This is always a full flight since it is the connecting route to primary destinations through Atlanta. That said, the crew handles the full load well. Not much more to say, it is a short flight with no in-flight services due to the length.
Frontier
5.8
Fair
3,128 reviews
Delta
7.9
Good
7,981 reviews

Comfort

7.9

Entertainment

7.9

Crew

8.5

Boarding

8.2

Food

7.3

Overall

7.9

Reviews

1 / 20
8.0
Excellent

Matthew,Oct 2025

GSP - ATL

This is always a full flight since it is the connecting route to primary destinations through Atlanta. That said, the crew handles the full load well. Not much more to say, it is a short flight with no in-flight services due to the length.

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 $383, Delta can have you in Caribbean from Washington, D.C. Dulles Intl Airport in 9h 16m. The distance between Washington, D.C. Dulles Intl Airport and Caribbean is about 960 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 Delta ($93), United Airlines ($108), and American Airlines ($142).

  • 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 Brussels Airlines (100%), Air Canada (92%) or United Airlines (92%) 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 $1,030, 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 $165 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 September is currently the most expensive (average of $272). 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.
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Reagan-National to Dallas/Fort Worth flights
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Baltimore to Miami flights
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Baltimore to Atlanta flights
Dulles Intl to Sky Harbor Intl flights
Reagan-National to Orlando flights
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Reagan-National to Seattle flights
Reagan-National to Boston flights
Reagan-National to Luis Munoz Marin Intl flights
Baltimore to Heathrow flights
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Baltimore to Tampa flights
Baltimore to San Francisco flights
Dulles Intl to George Bush Intcntl flights
Dulles Intl to Haneda flights
Dulles Intl to New Orleans flights
Baltimore to Denver 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 October 23, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$115Average$386FlexibilityNo cancel feeOn-time62%
Spirit AirlinesCheapest$135Average$302FlexibilityNo cancel feeOn-time65%
American AirlinesCheapest$145Average$633FlexibilityNo cancel feeOn-time71%
DeltaCheapest$158Average$671FlexibilityNo cancel feeOn-timeN/A
JetBlueCheapest$161Average$386FlexibilityNo cancel feeOn-time62%
AviancaCheapest$167Average$430FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$275Average$623FlexibilityNo cancel feeOn-time69%
Copa AirlinesCheapest$365Average$473FlexibilityNo cancel feeOn-time70%
Air CanadaCheapest$450Average$508FlexibilityNo cancel feeOn-time67%

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