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Caribbean Islands

$78+ 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 1/8. Fares are subject to change and may not be available on all flights or dates of travel.
BWI — SJU
Dec 13 — Dec 201
Sat 12/13
Sat 12/20
1 adult, Economy
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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 November 13, 2025.

This Kiwi.com deal was found by Cheapflights users on 11/12. 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 12/48:02 pmPHL - SJU
Nonstop3h 47mMultiple Airlines
Fri 12/54:10 amSJU - PHL
1 stop8h 07mMultiple Airlines
Deal found 11/12$178
This Kiwi.com deal was found by Cheapflights users on 11/11. 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 11/2510:00 amPHL - SJU
1 stop12h 44mMultiple Airlines
Mon 12/84:10 amSJU - PHL
1 stop11h 34mMultiple Airlines
Deal found 11/11$179
This Kiwi.com deal was found by Cheapflights users on 11/11. 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 12/141:24 pmPHL - SJU
Nonstop3h 40mMultiple Airlines
Fri 12/191:59 amSJU - PHL
Nonstop4h 05mMultiple Airlines
Deal found 11/11$180
This Cheapflightsfares deal was found by Cheapflights users on 11/11. 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.
Mon 12/86:00 amPHL - SJU
1 stop19h 50mFrontier
Mon 12/229:06 pmSJU - PHL
Nonstop4h 05mFrontier
Deal found 11/11$181
This Kiwi.com deal was found by Cheapflights users on 11/13. 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.
Fri 12/124:34 pmPHL - SJU
1 stop6h 42mMultiple Airlines
Fri 12/191:59 amSJU - PHL
Nonstop4h 05mMultiple Airlines
Deal found 11/13$182
This Kiwi.com deal was found by Cheapflights users on 11/12. 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 12/141:24 pmPHL - SJU
Nonstop3h 40mMultiple Airlines
Fri 12/1911:57 amSJU - PHL
Nonstop4h 05mMultiple Airlines
Deal found 11/12$183
This Kiwi.com deal was found by Cheapflights users on 11/12. 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.
Fri 12/127:11 pmPHL - SJU
2 stops40h 21mMultiple Airlines
Thu 12/181:59 amSJU - PHL
Nonstop4h 05mMultiple Airlines
Deal found 11/12$184
This Kiwi.com deal was found by Cheapflights users on 11/11. 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 12/135:15 amPHL - SJU
1 stop6h 17mMultiple Airlines
Sun 12/219:06 pmSJU - PHL
Nonstop4h 05mMultiple Airlines
Deal found 11/11$185
This Kiwi.com deal was found by Cheapflights users on 11/12. 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 12/156:00 amPHL - SJU
Nonstop3h 47mFrontier
Thu 12/181:59 amSJU - PHL
Nonstop4h 05mFrontier
Deal found 11/12$186
This Kiwi.com deal was found by Cheapflights users on 11/12. 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 11/2411:03 amPHL - SJU
Nonstop3h 50mMultiple Airlines
Fri 11/286:10 amSJU - PHL
1 stop9h 01mMultiple Airlines
Deal found 11/12$187
This Kiwi.com deal was found by Cheapflights users on 11/12. 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 11/248:06 pmIAD - SJU
Nonstop3h 47mFrontier
Thu 12/46:30 amSJU - IAD
Nonstop4h 13mFrontier
Deal found 11/12$188
This Kiwi.com deal was found by Cheapflights users on 11/10. 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.
Fri 11/286:00 amPHL - SJU
2 stops13h 27mMultiple Airlines
Sat 12/201:59 amSJU - PHL
Nonstop4h 05mMultiple Airlines
Deal found 11/10$188

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 November 13, 2025.

Round-trip from

$178
(Kiwi.com)

One-way from

$78
(Kiwi.com)

Popular in

December

Cheapest in

July

Average price

$360
From Maryland to Caribbean Islands
Search Deals
One-way flight from Maryland to Caribbean Islands
Search Deals
Highest demand for flights based on searches. 11% potential increase in price ($45 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 3% potential price decrease ($10 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in November 2025
Search Deals

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 November 13, 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

IAD - SJU

IADSJU

Washington, D.C. Dulles Intl

Sun 1/25

12:40 pm-8:57 pm

1 stop7h 17m

San Juan Luis Munoz Marin Intl

Thu 1/29

6:27 pm-12:24 am

1 stop6h 57m

$195

PhiladelphiaSan Juan

PHL - SJU

PHLSJU

Philadelphia

Sun 2/8

8:05 am-9:26 pm

1 stop12h 21m

San Juan Luis Munoz Marin Intl

Thu 2/12

8:35 am-5:14 pm

1 stop9h 39m

$223

PhiladelphiaSan Juan

PHL - SJU

PHLSJU

Philadelphia

Mon 12/8

10:15 am-10:22 pm

2 stops11h 07m

San Juan Luis Munoz Marin Intl

Tue 12/9

2:05 am-5:39 pm

2 stops16h 34m

$225

Washington, D.C.San Juan

DCA - SJU

DCASJU

Washington, D.C. Reagan-National

Wed 1/21

3:40 pm-11:44 pm

1 stop7h 04m

San Juan Luis Munoz Marin Intl

Fri 1/30

7:30 am-2:35 pm

1 stop8h 05m

$244

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

$253

Washington, D.C.San Juan

DCA - SJU

DCASJU

Washington, D.C. Reagan-National

Sun 1/18

8:00 am-12:42 pm

Nonstop3h 42m

San Juan Luis Munoz Marin Intl

Fri 1/23

6:45 pm-9:46 pm

Nonstop4h 01m

$253

Washington, D.C.San Juan

DCA - SJU

DCASJU

Washington, D.C. Reagan-National

Sat 1/17

7:10 am-3:30 pm

1 stop7h 20m

San Juan Luis Munoz Marin Intl

Sat 1/24

10:45 am-7:53 pm

1 stop10h 08m

$260

PhiladelphiaSan Juan

PHL - SJU

PHLSJU

Philadelphia

Thu 1/29

10:10 am-9:00 pm

1 stop9h 50m

San Juan Luis Munoz Marin Intl

Wed 2/4

2:05 am-2:31 pm

2 stops13h 26m

$261

PhiladelphiaSan Juan

PHL - SJU

PHLSJU

Philadelphia

Mon 1/26

1:50 pm-12:35 am

2 stops9h 45m

San Juan Luis Munoz Marin Intl

Fri 1/30

6:10 am-5:05 pm

2 stops11h 55m

$273

Washington, D.C.San Juan

IAD - SJU

IADSJU

Washington, D.C. Dulles Intl

Mon 11/24

6:00 am-5:26 pm

1 stop10h 26m

San Juan Luis Munoz Marin Intl

Tue 12/9

1:55 pm-9:29 pm

1 stop8h 34m

$282

Flights are sorted by cheapest round-trip flights first.

Deals found on 11/11

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, January is the cheapest month in which you can book a flight from Maryland to Caribbean Islands (average of $111). Flying from Maryland to Caribbean Islands in September is currently the most expensive (average of $160). 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 November 13, 2025.

Unlike in the afternoon, when flights are generally more expensive, you can save up to 23% on flights from Maryland to Caribbean Islands by exploring options for tickets in the evening.

What is the cheapest day to fly from Maryland to Caribbean Islands?

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

Travelers seeking maximum savings on their Maryland to Caribbean Islands flight should consider departing on Sunday mornings when fares are most often at their lowest. Sunday at noon flights should be avoided if possible as fares are typically the most expensive at this time.

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 $253, Delta can have you in Caribbean Islands from Maryland in 3h 42m. 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 Delta, with whom users have recently found tickets for as low as $93. However, be on the lookout for offers from Spirit Airlines and Frontier, 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, January is the cheapest month in which you can book a flight from Maryland to Caribbean Islands (average of $111). Flying from Maryland to Caribbean Islands in September is currently the most expensive (average of $160). 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 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 November 13, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$123Average$381FlexibilityNo cancel feeOn-time62%
Spirit AirlinesCheapest$124Average$393FlexibilityNo cancel feeOn-time65%
JetBlueCheapest$173Average$381FlexibilityNo cancel feeOn-time62%
DeltaCheapest$198Average$554FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$199Average$548FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$215Average$584FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$346Average$657FlexibilityNo cancel feeOn-time63%
Copa AirlinesCheapest$375Average$424FlexibilityNo cancel feeOn-time70%

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