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$85+ Cheap flights from Maryland 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 9/25. Fares are subject to change and may not be available on all flights or dates of travel.
BWI — SJU
Oct 11 — Oct 181
Sat 10/11
Sat 10/18
1 adult, Economy
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Cheap flight deals from Maryland to Caribbean

Keep the following information in mind while searching for Maryland to Caribbean flight deals. Data was last updated September 11, 2025.

Round-trip from

$155
(CheapOair)

One-way from

$85
(Cheapflightsfares)

Popular in

December

Cheapest in

July

Average price

$316

Good round-trip deal

$233 or less

Good one-way deal

$111 or less
From Maryland to Caribbean
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One-way flight from Maryland to Caribbean
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Highest demand for flights based on searches. 12% potential increase in price ($46 potential increase over avg. RT price).
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Cheapest flight prices on average. 3% potential price decrease ($12 potential savings vs. average RT price).
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Average for round-trip flights in September 2025
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Price to beat on a round-trip flight from Maryland to Caribbean.
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Price to beat on a one-way flight from Maryland to Caribbean.
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Find flight deals from Maryland to Caribbean

Cheapest flights from Maryland to Caribbean
Explore the most affordable flight options available from Maryland to Caribbean. Find the lowest fares from popular airlines and budget airlines, with prices last updated on September 11, 2025.

This CheapOair deal was found by Cheapflights users on 9/11. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/36:15 amPHL - SJU
Nonstop3h 46mFrontier
Thu 11/62:11 amSJU - PHL
Nonstop3h 58mFrontier
Deal found 9/11$155
This Kiwi.com deal was found by Cheapflights users on 9/9. 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 11/25:15 amPHL - SJU
Nonstop3h 46mFrontier
Thu 11/62:11 amSJU - PHL
Nonstop3h 58mFrontier
Deal found 9/9$156
This Cheapflightsfares deal was found by Cheapflights users on 9/11. 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.
Thu 10/168:43 pmPHL - SJU
Nonstop3h 46mFrontier
Mon 10/201:59 amSJU - PHL
Nonstop3h 58mFrontier
Deal found 9/11$158
This Cheapflightsfares deal was found by Cheapflights users on 9/9. 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 9/187:10 amPHL - SJU
Nonstop3h 51mFrontier
Sat 9/2012:28 amSJU - PHL
Nonstop3h 59mFrontier
Deal found 9/9$159
This Cheapflightsfares deal was found by Cheapflights users on 9/11. 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.
Sat 9/277:32 pmPHL - SJU
Nonstop3h 51mFrontier
Thu 10/212:06 pmSJU - PHL
Nonstop3h 59mFrontier
Deal found 9/11$160
This Cheapflightsfares deal was found by Cheapflights users on 9/11. 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.
Sat 9/207:32 pmPHL - SJU
Nonstop3h 51mFrontier
Fri 10/312:28 amSJU - PHL
Nonstop3h 59mFrontier
Deal found 9/11$161
This Cheapflightsfares deal was found by Cheapflights users on 9/9. 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.
Sun 9/215:00 amPHL - SJU
1 stop6h 04mSpirit Airlines
Thu 9/2512:05 pmSJU - PHL
Nonstop4h 10mSpirit Airlines
Deal found 9/9$162
This Cheapflightsfares deal was found by Cheapflights users on 9/9. 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 11/137:26 pmIAD - SJU
Nonstop3h 52mFrontier
Sat 11/224:05 pmSJU - IAD
Nonstop4h 03mFrontier
Deal found 9/9$166
This Cheapflightsfares deal was found by Cheapflights users on 9/8. 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.
Sun 9/217:10 amPHL - SJU
Nonstop3h 51mFrontier
Sat 9/2712:28 amSJU - PHL
Nonstop3h 59mFrontier
Deal found 9/8$166
This Cheapflightsfares deal was found by Cheapflights users on 9/11. 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 12/17:53 pmIAD - SJU
Nonstop3h 47mFrontier
Thu 12/46:00 amSJU - IAD
Nonstop4h 13mFrontier
Deal found 9/11$167
This Kiwi.com deal was found by Cheapflights users on 9/11. 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.
Thu 9/257:10 amPHL - SJU
Nonstop3h 51mFrontier
Fri 10/241:59 amSJU - PHL
Nonstop3h 58mFrontier
Deal found 9/11$167
This Cheapflightsfares deal was found by Cheapflights users on 9/11. 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.
Tue 10/148:43 pmPHL - SJU
Nonstop3h 46mFrontier
Fri 10/171:59 amSJU - PHL
Nonstop3h 58mFrontier
Deal found 9/11$168

Cheapflights Fare Finder

 
Customize your flight search to find flights from Maryland 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 September 11, 2025.
Use the filters below to find and compare flights from Maryland to Caribbean that are best for you.

Fly from

Maryland

Fly to

Caribbean

Route

Depart

Return

Price

PhiladelphiaSan Juan

PHL - SJU

PHLSJU

Philadelphia

Thu 9/25

7:10 am-11:01 am

Nonstop3h 51m

San Juan Luis Munoz Marin Intl

Sat 9/27

12:28 am-4:27 am

Nonstop3h 59m

$170

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

6:07 pm-9:59 pm

Nonstop3h 52m

$234

Washington, D.C.San Juan

DCA - SJU

DCASJU

Washington, D.C. Reagan-National

Thu 10/30

8:00 am-11:51 am

Nonstop3h 51m

San Juan Luis Munoz Marin Intl

Tue 11/4

6:51 pm-9:48 pm

Nonstop3h 57m

$234

Washington, D.C.San Juan

DCA - SJU

DCASJU

Washington, D.C. Reagan-National

Wed 10/8

8:30 am-12:15 pm

Nonstop3h 45m

San Juan Luis Munoz Marin Intl

Tue 10/21

6:05 pm-9:57 pm

Nonstop3h 52m

$234

Washington, D.C.San Juan

IAD - SJU

IADSJU

Washington, D.C. Dulles Intl

Wed 10/29

8:27 am-12:17 pm

Nonstop3h 50m

San Juan Luis Munoz Marin Intl

Fri 10/31

1:20 pm-10:58 pm

1 stop9h 38m

$239

PhiladelphiaSan Juan

PHL - SJU

PHLSJU

Philadelphia

Thu 9/18

7:10 am-11:01 am

Nonstop3h 51m

San Juan Luis Munoz Marin Intl

Tue 9/23

1:06 pm-5:05 pm

Nonstop3h 59m

$240

Washington, D.C.San Juan

IAD - SJU

IADSJU

Washington, D.C. Dulles Intl

Thu 10/30

5:32 pm-9:22 pm

Nonstop3h 50m

San Juan Luis Munoz Marin Intl

Tue 11/4

3:46 pm-11:44 pm

1 stop8h 58m

$243

Washington, D.C.San Juan

DCA - SJU

DCASJU

Washington, D.C. Reagan-National

Sat 10/25

6:00 am-3:42 pm

1 stop9h 42m

San Juan Luis Munoz Marin Intl

Tue 10/28

1:05 am-8:29 am

1 stop7h 24m

$243

PhiladelphiaSan Juan

PHL - SJU

PHLSJU

Philadelphia

Thu 9/25

4:03 pm-9:52 am

1 stop17h 49m

San Juan Luis Munoz Marin Intl

Sat 9/27

12:28 am-4:27 am

Nonstop3h 59m

$244

PhiladelphiaSan Juan

PHL - SJU

PHLSJU

Philadelphia

Tue 10/21

10:35 am-9:59 pm

1 stop11h 24m

San Juan Luis Munoz Marin Intl

Thu 10/23

7:15 am-6:20 pm

1 stop11h 05m

$259

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/10

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

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

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

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

Find hourly flight availability from Maryland 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 September 11, 2025.

When flying from Maryland to Caribbean, 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. 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?

    Departing from Maryland to Caribbean will take you 3h 45m. Airlines will cover a distance of 1557 mi. Generally, flights for this route are nonstop.

  • What are the cheapest airlines to fly from Maryland to Caribbean one-way?

    $103 is the cheapest one-way deal found within the past few days, from Spirit Airlines. You may also be able to find cheap deals on United Airlines and JetBlue, with prices starting from $117 and $117, respectively.

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

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

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

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

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

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

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

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

Discover the top 8 airlines that operate flights from Maryland 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 September 11, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$121Average$381FlexibilityNo cancel feeOn-time62%
Spirit AirlinesCheapest$124Average$389FlexibilityNo cancel feeOn-time65%
Copa AirlinesCheapest$174Average$461FlexibilityNo cancel feeOn-time70%
DeltaCheapest$198Average$577FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$199Average$555FlexibilityNo cancel feeOn-time69%
JetBlueCheapest$207Average$390FlexibilityNo cancel feeOn-time62%
American AirlinesCheapest$215Average$606FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$344Average$656FlexibilityNo cancel feeOn-time63%

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