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$82+ 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 11/25. Fares are subject to change and may not be available on all flights or dates of travel.
BWI — SJU
Nov 28 — Dec 51
Fri 11/28
Fri 12/5
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 October 29, 2025.

Round-trip from

$170
(Kiwi.com)

One-way from

$82
(Kiwi.com)

Popular in

December

Cheapest in

July

Average price

$333

Good round-trip deal

$326 or less

Good one-way deal

$164 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. 10% potential increase in price ($39 potential increase over avg. RT price).
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Cheapest flight prices on average. 2% potential price decrease ($10 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 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 October 29, 2025.

This Priceline deal was found by Cheapflights users on 10/27. 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.
Sun 11/166:00 amPHL - SJU
1 stop10h 19mMultiple Airlines
Mon 11/2412:37 pmSJU - PHL
Nonstop4h 07mMultiple Airlines
Deal found 10/27$171
This Kiwi.com deal was found by Cheapflights users on 10/29. 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.
Wed 11/197:30 amPHL - SJU
Nonstop3h 46mFrontier
Mon 11/242:25 amSJU - PHL
Nonstop4h 07mFrontier
Deal found 10/29$174
This Kiwi.com deal was found by Cheapflights users on 10/29. 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 11/288:08 pmPHL - SJU
Nonstop3h 47mFrontier
Tue 12/91:59 amSJU - PHL
Nonstop4h 05mFrontier
Deal found 10/29$175
This Priceline deal was found by Cheapflights users on 10/29. 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.
Fri 11/284:02 pmPHL - SJU
Nonstop3h 47mFrontier
Sat 12/61:59 amSJU - PHL
Nonstop4h 05mFrontier
Deal found 10/29$176
This Kiwi.com deal was found by Cheapflights users on 10/28. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/166:24 pmPHL - SJU
1 stop20h 46mMultiple Airlines
Sun 11/239:30 pmSJU - PHL
1 stop12h 23mMultiple Airlines
Deal found 10/28$178
This Frontier deal was found by Cheapflights users on 10/28. 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.
Wed 12/38:02 pmPHL - SJU
Nonstop3h 47mFrontier
Mon 12/810:42 amSJU - PHL
1 stop6h 56mFrontier
Deal found 10/28$180
This Kiwi.com deal was found by Cheapflights users on 10/26. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/318:18 pmBWI - SJU
Nonstop3h 48mMultiple Airlines
Wed 1/147:10 amSJU - BWI
2 stops17h 01mMultiple Airlines
Deal found 10/26$181
This Kiwi.com deal was found by Cheapflights users on 10/27. 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.
Wed 11/57:43 pmPHL - SJU
Nonstop3h 46mMultiple Airlines
Thu 11/133:37 pmSJU - PHL
1 stop8h 49mMultiple Airlines
Deal found 10/27$181
This Cheapflightsfares deal was found by Cheapflights users on 10/28. 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.
Fri 11/218:08 pmPHL - SJU
Nonstop3h 47mFrontier
Fri 11/282:25 amSJU - PHL
Nonstop4h 07mFrontier
Deal found 10/28$182
This Frontier deal was found by Cheapflights users on 10/28. 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.
Tue 11/187:30 amPHL - SJU
Nonstop3h 46mFrontier
Mon 12/810:42 amSJU - PHL
1 stop6h 56mFrontier
Deal found 10/28$183
This Kiwi.com deal was found by Cheapflights users on 10/29. 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 11/235:50 pmPHL - SJU
1 stop14h 50mFrontier
Tue 11/259:54 pmSJU - PHL
Nonstop4h 07mFrontier
Deal found 10/29$184
This Mytrip deal was found by Cheapflights users on 10/27. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/136:00 amPHL - SJU
Nonstop3h 47mFrontier
Sat 12/2011:57 amSJU - PHL
Nonstop4h 05mFrontier
Deal found 10/27$185

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 October 29, 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

Washington, D.C.San Juan

DCA - SJU

DCASJU

Washington, D.C. Reagan-National

Mon 1/19

8:00 am-12:42 pm

Nonstop3h 42m

San Juan Luis Munoz Marin Intl

Wed 1/28

6:45 pm-9:46 pm

Nonstop4h 01m

$216

Washington, D.C.San Juan

IAD - SJU

IADSJU

Washington, D.C. Dulles Intl

Wed 3/18

6:10 am-1:16 pm

1 stop7h 06m

San Juan Luis Munoz Marin Intl

Wed 3/25

2:21 pm-11:02 pm

1 stop8h 41m

$225

Washington, D.C.San Juan

IAD - SJU

IADSJU

Washington, D.C. Dulles Intl

Tue 3/24

7:00 am-1:14 pm

1 stop6h 14m

San Juan Luis Munoz Marin Intl

Wed 3/25

2:21 pm-11:02 pm

1 stop8h 41m

$225

Washington, D.C.San Juan

DCA - SJU

DCASJU

Washington, D.C. Reagan-National

Mon 1/19

6:59 am-2:30 pm

1 stop6h 31m

San Juan Luis Munoz Marin Intl

Mon 1/26

7:00 am-4:29 pm

1 stop10h 29m

$237

Washington, D.C.San Juan

DCA - SJU

DCASJU

Washington, D.C. Reagan-National

Mon 1/19

6:59 am-2:30 pm

1 stop6h 31m

San Juan Luis Munoz Marin Intl

Fri 1/23

6:15 am-4:58 pm

1 stop11h 43m

$240

Washington, D.C.San Juan

DCA - SJU

DCASJU

Washington, D.C. Reagan-National

Tue 11/18

8:00 am-12:50 pm

Nonstop3h 50m

San Juan Luis Munoz Marin Intl

Wed 11/19

5:15 am-12:27 pm

1 stop8h 12m

$241

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 1/25

8:00 am-12:42 pm

Nonstop3h 42m

San Juan Luis Munoz Marin Intl

Fri 1/30

6:00 am-12:00 pm

1 stop7h 00m

$258

Washington, D.C.San Juan

IAD - SJU

IADSJU

Washington, D.C. Dulles Intl

Mon 1/12

5:32 pm-10:22 pm

Nonstop3h 50m

San Juan Luis Munoz Marin Intl

Fri 1/23

8:35 am-5:35 pm

1 stop10h 00m

$281

PhiladelphiaSan Juan

PHL - SJU

PHLSJU

Philadelphia

Mon 1/26

12:15 pm-12:35 am

2 stops11h 20m

San Juan Luis Munoz Marin Intl

Fri 1/30

5:40 am-5:05 pm

2 stops12h 25m

$283

Flights are sorted by cheapest round-trip flights first.

Deals found on 10/29

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, November is the cheapest month in which you can book a flight from Maryland to Caribbean (average of $103). Flying from Maryland to Caribbean 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 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 October 29, 2025.

Unlike in the afternoon, when flights are generally more expensive, you can save up to 21% on flights from Maryland to Caribbean by exploring options for tickets in the evening.

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

Use this chart to determine the cheapest time to fly round-trip from Maryland to Caribbean. Price data was last updated on October 26, 2025.

Travelers seeking maximum savings on their Maryland to Caribbean flight should consider departing on Sunday mornings when fares are most often at their lowest. Sunday afternoons 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. 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 42m. Airlines will cover a distance of 1557 mi. Both multi-stop and nonstop flights can be found to your destination and back.

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

    $88 is the cheapest one-way deal found within the past few days, from Delta. You may also be able to find cheap deals on Spirit Airlines and United Airlines, with prices starting from $103 and $108, 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, November is the cheapest month in which you can book a flight from Maryland to Caribbean (average of $103). Flying from Maryland to Caribbean 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

Browse thousands of different options on Cheapflights for your next trip

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

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 October 29, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$122Average$378FlexibilityNo cancel feeOn-time62%
Spirit AirlinesCheapest$124Average$384FlexibilityNo cancel feeOn-time65%
JetBlueCheapest$173Average$381FlexibilityNo cancel feeOn-time62%
DeltaCheapest$198Average$579FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$199Average$552FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$215Average$620FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$347Average$658FlexibilityNo cancel feeOn-time63%
Copa AirlinesCheapest$375Average$424FlexibilityNo cancel feeOn-time70%

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