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Caribbean Islands

$83+ Cheap flights from Maryland 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 10/7. Fares are subject to change and may not be available on all flights or dates of travel.
BWI — SJU
Oct 23 — Oct 301
Thu 10/23
Thu 10/30
1 adult, Economy
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Cheap flight deals from Maryland to Caribbean Islands

Keep the following information in mind while searching for Maryland to Caribbean Islands flight deals. Data was last updated September 23, 2025.

Round-trip from

$150
(Trip.com)

One-way from

$83
(Kiwi.com)

Popular in

December

Cheapest in

July

Average price

$356
From Maryland to Caribbean Islands
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One-way flight from Maryland to Caribbean Islands
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Highest demand for flights based on searches. 11% potential increase in price ($43 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 Maryland to Caribbean Islands

Cheapest flights from Maryland to Caribbean Islands
Explore the most affordable flight options available from Maryland to Caribbean Islands. Find the lowest fares from popular airlines and budget airlines, with prices last updated on September 23, 2025.

This Trip.com deal was found by Cheapflights users on 9/22. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/47:32 pmPHL - SJU
Nonstop3h 51mFrontier
Wed 10/81:26 pmSJU - PHL
Nonstop3h 58mFrontier
Deal found 9/22$150
This Frontier deal was found by Cheapflights users on 9/21. 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.
Wed 10/17:32 pmPHL - SJU
Nonstop3h 51mFrontier
Sat 10/111:59 amSJU - PHL
Nonstop3h 58mFrontier
Deal found 9/21$152
This Frontier deal was found by Cheapflights users on 9/22. 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.
Fri 10/37:32 pmPHL - SJU
Nonstop3h 51mFrontier
Sat 10/412:28 amSJU - PHL
Nonstop3h 59mFrontier
Deal found 9/22$156
This Frontier deal was found by Cheapflights users on 9/22. 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.
Mon 9/297:10 amPHL - SJU
Nonstop3h 51mFrontier
Tue 10/71:59 amSJU - PHL
Nonstop3h 58mFrontier
Deal found 9/22$157
This Kiwi.com deal was found by Cheapflights users on 9/21. 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 9/287:15 amPHL - SJU
Nonstop3h 50mMultiple Airlines
Sat 10/412:28 amSJU - PHL
Nonstop3h 59mMultiple Airlines
Deal found 9/21$158
This Frontier deal was found by Cheapflights users on 9/22. 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.
Mon 10/68:38 pmPHL - SJU
Nonstop3h 51mFrontier
Thu 10/91:59 amSJU - PHL
Nonstop3h 58mFrontier
Deal found 9/22$159
This Kiwi.com deal was found by Cheapflights users on 9/22. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/297:10 amPHL - SJU
Nonstop3h 51mMultiple Airlines
Thu 10/212:05 pmSJU - PHL
Nonstop4h 10mMultiple Airlines
Deal found 9/22$160
This Kiwi.com deal was found by Cheapflights users on 9/22. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/168:43 pmPHL - SJU
Nonstop3h 46mFrontier
Sat 10/181:59 amSJU - PHL
Nonstop3h 58mFrontier
Deal found 9/22$161
This Frontier deal was found by Cheapflights users on 9/20. 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 10/138:43 pmPHL - SJU
Nonstop3h 46mFrontier
Wed 10/151:59 amSJU - PHL
Nonstop3h 58mFrontier
Deal found 9/20$162
This SmartFares deal was found by Cheapflights users on 9/22. 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 SmartFares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/178:43 pmPHL - SJU
Nonstop3h 46mFrontier
Sat 10/181:59 amSJU - PHL
Nonstop3h 58mFrontier
Deal found 9/22$163
This Kiwi.com deal was found by Cheapflights users on 9/22. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 9/285:00 amPHL - SJU
1 stop6h 04mMultiple Airlines
Fri 10/312:06 pmSJU - PHL
Nonstop3h 59mMultiple Airlines
Deal found 9/22$164
This CheapOair deal was found by Cheapflights users on 9/21. 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 CheapOair 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 9/21$169

Cheapflights Fare Finder

 
Customize your flight search to find flights from Maryland 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 23, 2025.
Use the filters below to find and compare flights from Maryland to Caribbean Islands that are best for you.

Fly from

Maryland

Fly to

Caribbean Islands

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

Thu 10/23

6:07 pm-9:59 pm

Nonstop3h 52m

$236

Washington, D.C.San Juan

DCA - SJU

DCASJU

Washington, D.C. Reagan-National

Wed 10/29

8:00 am-11:51 am

Nonstop3h 51m

San Juan Luis Munoz Marin Intl

Sat 11/1

12:10 pm-10:15 pm

1 stop10h 05m

$263

Washington, D.C.San Juan

DCA - SJU

DCASJU

Washington, D.C. Reagan-National

Wed 10/29

8:00 am-11:51 am

Nonstop3h 51m

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

Sun 10/12

8:30 am-12:15 pm

Nonstop3h 45m

San Juan Luis Munoz Marin Intl

Thu 10/16

1:25 pm-10:56 pm

1 stop9h 31m

$267

Washington, D.C.San Juan

IAD - SJU

IADSJU

Washington, D.C. Dulles Intl

Sat 11/15

12:11 pm-11:56 pm

1 stop10h 45m

San Juan Luis Munoz Marin Intl

Thu 11/27

1:57 pm-9:22 pm

1 stop8h 25m

$275

PhiladelphiaSan Juan

PHL - SJU

PHLSJU

Philadelphia

Tue 10/28

10:05 am-9:22 pm

2 stops11h 17m

San Juan Luis Munoz Marin Intl

Mon 11/3

8:30 am-11:03 pm

2 stops15h 33m

$288

BaltimoreSan Juan

BWI - SJU

BWISJU

Baltimore/Washington

Sat 9/27

8:16 pm-11:04 am

1 stop14h 48m

San Juan Luis Munoz Marin Intl

Tue 9/30

6:44 am-3:32 pm

1 stop8h 48m

$289

PhiladelphiaSan Juan

PHL - SJU

PHLSJU

Philadelphia

Tue 10/21

6:30 am-2:44 pm

1 stop8h 14m

San Juan Luis Munoz Marin Intl

Fri 10/24

1:05 am-2:17 pm

2 stops13h 12m

$290

PhiladelphiaPunta Cana

PHL - PUJ

PHLPUJ

Philadelphia

Fri 10/31

7:00 am-1:47 pm

1 stop6h 47m

Punta Cana

Wed 11/5

3:38 pm-10:58 pm

1 stop8h 20m

$300

Washington, D.C.San Juan

DCA - SJU

DCASJU

Washington, D.C. Reagan-National

Wed 12/3

3:40 pm-11:54 pm

1 stop7h 14m

San Juan Luis Munoz Marin Intl

Sat 12/6

1:40 pm-6:55 pm

1 stop6h 15m

$300

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/21

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

Have a flexible travel schedule? Discover the best time to fly to Caribbean Islands from Maryland 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 Maryland to Caribbean Islands

What is the cheapest month to book a flight from Maryland to Caribbean Islands?

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

Find hourly flight availability from Maryland 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 23, 2025.

When flying from Maryland 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.

Related info for your journey

Find useful and relevant information for your journey from Maryland 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 Maryland to Caribbean Islands?

    For as low as $236, JetBlue can have you in Caribbean Islands from Maryland in 3h 45m. The distance from Maryland to Caribbean Islands is about 1557 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 Maryland to Caribbean Islands one-way?

    The cheapest airline one-way is Frontier, with whom users have recently found tickets for as low as $88. However, be on the lookout for offers from Spirit Airlines and JetBlue, as they are both options that can get you from Maryland to Caribbean Islands for a low price.

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

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

  • How can I find direct flights from Maryland to Caribbean Islands?

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

  • Can I find deals for business class flights from Maryland to Caribbean Islands?

    Yes. Cheapflights offers flight deals from Maryland 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 Maryland to Caribbean Islands?

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

Browse thousands of different options on Cheapflights for your next trip

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Alternative routes for Maryland to Caribbean Islands

See prices for flight routes from nearby airports that may be better suited for you.
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Top 8 airlines flying from Maryland to Caribbean Islands

Discover the top 8 airlines that operate flights from Maryland 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 23, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$120Average$381FlexibilityNo cancel feeOn-time62%
Spirit AirlinesCheapest$124Average$388FlexibilityNo cancel feeOn-time65%
JetBlueCheapest$173Average$401FlexibilityNo cancel feeOn-time62%
Copa AirlinesCheapest$183Average$486FlexibilityNo cancel feeOn-time70%
United AirlinesCheapest$199Average$552FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$215Average$620FlexibilityNo cancel feeOn-time71%
DeltaCheapest$259Average$573FlexibilityNo cancel feeOn-timeN/A
SouthwestCheapest$346Average$659FlexibilityNo cancel feeOn-time63%

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