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Caribbean Islands

$100+ Cheap flights from District of Columbia to Caribbean Islands

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 10/28. Fares are subject to change and may not be available on all flights or dates of travel.
IAD — SJU
Oct 29 — Nov 51
Wed 10/29
Wed 11/5
1 adult, Economy
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Cheap flight deals from District of Columbia to Caribbean Islands

Keep the following information in mind while searching for District of Columbia to Caribbean Islands flight deals. Data was last updated September 29, 2025.

Round-trip from

$174
(Frontier)

One-way from

$100
(Trip.com)

Popular in

December

Cheapest in

July

Average price

$356
From District of Columbia to Caribbean Islands
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One-way flight from District of Columbia to Caribbean Islands
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Highest demand for flights based on searches. 10% potential increase in price ($42 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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Find flight deals from District of Columbia to Caribbean Islands

Cheapest flights from District of Columbia to Caribbean Islands
Explore the most affordable flight options available from District of Columbia to Caribbean Islands. Find the lowest fares from popular airlines and budget airlines, with prices last updated on September 29, 2025.

This Frontier deal was found by Cheapflights users on 9/28. 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 9/28$174
This Priceline deal was found by Cheapflights users on 9/28. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 10/269:07 pmIAD - SJU
Nonstop3h 52mFrontier
Sun 11/23:45 pmSJU - IAD
Nonstop3h 56mFrontier
Deal found 9/28$182
This Kiwi.com deal was found by Cheapflights users on 9/27. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 12/710:08 amIAD - SJU
Nonstop3h 54mFrontier
Thu 12/116:00 amSJU - IAD
Nonstop4h 13mFrontier
Deal found 9/27$184
This Priceline deal was found by Cheapflights users on 9/28. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/308:26 pmIAD - SJU
Nonstop3h 52mFrontier
Sun 11/23:45 pmSJU - IAD
Nonstop3h 56mFrontier
Deal found 9/28$192
This Frontier deal was found by Cheapflights users on 9/28. 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 11/238:06 pmIAD - SJU
Nonstop3h 47mFrontier
Tue 11/254:08 pmSJU - IAD
Nonstop4h 03mFrontier
Deal found 9/28$198
This Cheapflightsfares deal was found by Cheapflights users on 9/28. 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.
Thu 10/169:07 pmIAD - SJU
Nonstop3h 52mFrontier
Thu 10/234:26 pmSJU - IAD
Nonstop3h 56mFrontier
Deal found 9/28$204
This Gotogate deal was found by Cheapflights users on 9/28. 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 Gotogate is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/99:07 pmIAD - SJU
Nonstop3h 52mFrontier
Thu 10/164:26 pmSJU - IAD
Nonstop3h 56mFrontier
Deal found 9/28$209
This Trip.com deal was found by Cheapflights users on 9/27. 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 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
Fri 10/246:05 pmSJU - DCA
Nonstop3h 52mJetBlue
Deal found 9/27$209
This Trip.com deal was found by Cheapflights users on 9/28. 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.
Sun 10/198:30 amDCA - SJU
Nonstop3h 45mJetBlue
Tue 10/286:02 pmSJU - DCA
Nonstop3h 57mJetBlue
Deal found 9/28$217
This SmartFares deal was found by Cheapflights users on 9/26. 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 SmartFares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/412:30 pmDCA - SJU
1 stop8h 34mJetBlue
Wed 11/126:51 pmSJU - DCA
Nonstop3h 57mJetBlue
Deal found 9/26$230
This Priceline deal was found by Cheapflights users on 9/27. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/288:00 amDCA - SJU
Nonstop3h 51mJetBlue
Tue 10/286:02 pmSJU - DCA
Nonstop3h 57mJetBlue
Deal found 9/27$231
This JetBlue deal was found by Cheapflights users on 9/27. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/218:30 amDCA - SJU
Nonstop3h 45mJetBlue
Fri 10/246:05 pmSJU - DCA
Nonstop3h 52mJetBlue
Deal found 9/27$236

Cheapflights Fare Finder

 
Customize your flight search to find flights from District of Columbia to Caribbean Islands 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 29, 2025.
Use the filters below to find and compare flights from District of Columbia to Caribbean Islands that are best for you.

Fly from

District of Columbia

Fly to

Caribbean Islands

Route

Depart

Return

Price

Washington, D.C.San Juan

DCA - SJU

DCASJU

Washington, D.C. Reagan-National

Tue 10/21

8:30 am-12:15 pm

Nonstop3h 45m

San Juan Luis Munoz Marin Intl

Tue 10/28

6:02 pm-9:59 pm

Nonstop3h 57m

$236

Washington, D.C.San Juan

DCA - SJU

DCASJU

Washington, D.C. Reagan-National

Sat 11/1

4:55 pm-2:48 am

1 stop9h 53m

San Juan Luis Munoz Marin Intl

Wed 11/5

6:57 pm-9:54 pm

Nonstop3h 57m

$245

Washington, D.C.San Juan

DCA - SJU

DCASJU

Washington, D.C. Reagan-National

Fri 10/24

5:20 pm-12:47 am

1 stop7h 27m

San Juan Luis Munoz Marin Intl

Thu 10/30

6:02 pm-9:59 pm

Nonstop3h 57m

$245

Washington, D.C.San Juan

IAD - SJU

IADSJU

Washington, D.C. Dulles Intl

Wed 10/29

5:32 pm-9:22 pm

Nonstop3h 50m

San Juan Luis Munoz Marin Intl

Sun 11/2

8:30 am-11:35 am

Nonstop4h 05m

$263

Washington, D.C.San Juan

DCA - SJU

DCASJU

Washington, D.C. Reagan-National

Mon 11/3

8:00 am-12:50 pm

Nonstop3h 50m

San Juan Luis Munoz Marin Intl

Sun 11/9

6:57 pm-9:54 pm

Nonstop3h 57m

$263

Washington, D.C.San Juan

DCA - SJU

DCASJU

Washington, D.C. Reagan-National

Wed 10/15

8:30 am-12:15 pm

Nonstop3h 45m

San Juan Luis Munoz Marin Intl

Thu 10/23

1:10 pm-7:20 pm

1 stop6h 10m

$265

Washington, D.C.San Juan

IAD - SJU

IADSJU

Washington, D.C. Dulles Intl

Mon 1/19

8:27 am-1:17 pm

Nonstop3h 50m

San Juan Luis Munoz Marin Intl

Mon 2/9

5:50 pm-8:55 pm

Nonstop4h 05m

$290

Washington, D.C.San Juan

DCA - SJU

DCASJU

Washington, D.C. Reagan-National

Tue 1/27

8:00 am-12:42 pm

Nonstop3h 42m

San Juan Luis Munoz Marin Intl

Tue 2/10

6:45 pm-9:46 pm

Nonstop4h 01m

$290

Washington, D.C.San Juan

DCA - SJU

DCASJU

Washington, D.C. Reagan-National

Wed 3/18

8:00 am-11:48 am

Nonstop3h 48m

San Juan Luis Munoz Marin Intl

Tue 3/24

5:55 pm-9:56 pm

Nonstop4h 01m

$290

Washington, D.C.San Juan

DCA - SJU

DCASJU

Washington, D.C. Reagan-National

Tue 3/17

8:00 am-11:48 am

Nonstop3h 48m

San Juan Luis Munoz Marin Intl

Thu 3/19

5:55 pm-9:56 pm

Nonstop4h 01m

$290

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/29

Showing 1-10 of 60 results
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Best time to book a flight from District of Columbia to Caribbean Islands

Have a flexible travel schedule? Discover the best time to fly to Caribbean Islands from District of Columbia 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 District of Columbia to Caribbean Islands

What is the cheapest month to book a flight from District of Columbia to Caribbean Islands?

Currently, September is the cheapest month in which you can book a flight from District of Columbia to Caribbean Islands (average of $254). Flying from District of Columbia to Caribbean Islands 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 DC to EPX?

Find hourly flight availability from District of Columbia to Caribbean Islands. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated September 29, 2025.

When flying from District of Columbia to Caribbean Islands, the time of day you decide to fly out makes little to no difference towards the overall price you’ll pay on tickets.

Weekly flight availability from District of Columbia to Caribbean Islands

Explore weekly flight availability from District of Columbia to Caribbean Islands. 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 September 29, 2025.

The most flights from USDC to zzEPX are scheduled on a Monday (2 on average). You will have fewer flight options on Monday, which is when the least amount of flights are scheduled (2 on average).

Related info for your journey

Find useful and relevant information for your journey from District of Columbia to Caribbean Islands. 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 District of Columbia to Caribbean Islands?

    There are many flights that can get you from District of Columbia to Caribbean Islands in 3h 45m. Fly via JetBlue, United Airlines, or Avianca to get the fastest option. The distance from District of Columbia to Caribbean Islands is about 1557 mi. Both multi-stop and nonstop flights can be found to your destination and back.

  • What are the cheapest airlines to fly from District of Columbia to Caribbean Islands one-way?

    $105 is the cheapest one-way deal found within the past few days, from JetBlue. You may also be able to find cheap deals on United Airlines and Delta, with prices starting from $116 and $123, respectively.

  • Can I find deals for flights from District of Columbia to Caribbean Islands that include hotel bookings?

    Yes. In addition to deals on District of Columbia to Caribbean Islands flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from District of Columbia to Caribbean Islands?

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

  • Can I find deals for business class flights from District of Columbia to Caribbean Islands?

    Yes. Cheapflights offers flight deals from District of Columbia to Caribbean Islands 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 District of Columbia to Caribbean Islands?

    Currently, September is the cheapest month in which you can book a flight from District of Columbia to Caribbean Islands (average of $254). Flying from District of Columbia to Caribbean Islands 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 District of Columbia to Caribbean Islands

See prices for flight routes from nearby airports that may be better suited for you.
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Top 10 airlines flying from District of Columbia to Caribbean Islands

Discover the top 10 airlines that operate flights from District of Columbia to Caribbean Islands. 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 29, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$85Average$377FlexibilityNo cancel feeOn-time62%
Spirit AirlinesCheapest$115Average$355FlexibilityNo cancel feeOn-time65%
American AirlinesCheapest$145Average$637FlexibilityNo cancel feeOn-time71%
JetBlueCheapest$161Average$488FlexibilityNo cancel feeOn-time62%
DeltaCheapest$164Average$605FlexibilityNo cancel feeOn-timeN/A
AviancaCheapest$167Average$450FlexibilityNo cancel feeOn-time71%
Copa AirlinesCheapest$183Average$498FlexibilityNo cancel feeOn-time70%
United AirlinesCheapest$199Average$604FlexibilityNo cancel feeOn-time69%
SouthwestCheapest$220Average$687FlexibilityNo cancel feeOn-time63%
Air CanadaCheapest$430Average$504FlexibilityNo cancel feeOn-time67%

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