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Caribbean

$66+ 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 2/25. Fares are subject to change and may not be available on all flights or dates of travel.
BWI — SJU
Feb 26 — Mar 51
Thu 2/26
Thu 3/5
1 adult, Economy
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Cheap 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 January 27, 2026.

This Super.com deal was found by Cheapflights users on 1/26. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 3/268:35 pm
PHL
-
SJU
Nonstop3h 42m
Spirit Airlines
Sat 3/281:22 am
SJU
-
PHL
Nonstop4h 04m
Spirit Airlines
Deal found 1/26$141
This Kiwi.com deal was found by Cheapflights users on 1/26. 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.
Sat 2/2110:22 am
PHL
-
SJU
Nonstop3h 45m
Multiple Airlines
Thu 2/262:59 am
SJU
-
PHL
Nonstop4h 12m
Multiple Airlines
Deal found 1/26$142
This Kiwi.com deal was found by Cheapflights users on 1/27. 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 2/18:56 pm
PHL
-
SJU
Nonstop3h 45m
Multiple Airlines
Thu 2/58:31 pm
SJU
-
PHL
Nonstop4h 12m
Multiple Airlines
Deal found 1/27$143
This Kiwi.com deal was found by Cheapflights users on 1/25. 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 2/12:50 pm
PHL
-
SJU
Nonstop3h 45m
Multiple Airlines
Sat 2/72:59 am
SJU
-
PHL
Nonstop4h 12m
Multiple Airlines
Deal found 1/25$144
This Frontier deal was found by Cheapflights users on 1/27. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 2/112:12 pm
PHL
-
SJU
Nonstop3h 45m
Frontier
Thu 2/58:31 pm
SJU
-
PHL
Nonstop4h 12m
Frontier
Deal found 1/27$145
This CheapOair deal was found by Cheapflights users on 1/27. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 2/208:52 pm
PHL
-
SJU
Nonstop3h 45m
Multiple Airlines
Tue 2/242:59 am
SJU
-
PHL
Nonstop4h 16m
Multiple Airlines
Deal found 1/27$146
This Kiwi.com deal was found by Cheapflights users on 1/26. 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.
Fri 4/178:39 pm
PHL
-
SJU
Nonstop3h 50m
Multiple Airlines
Tue 4/289:52 am
SJU
-
PHL
Nonstop4h 11m
Multiple Airlines
Deal found 1/26$148
This Kiwi.com deal was found by Cheapflights users on 1/26. 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.
Fri 2/208:52 pm
PHL
-
SJU
Nonstop3h 45m
Spirit Airlines
Sun 3/12:59 am
SJU
-
PHL
Nonstop4h 12m
Spirit Airlines
Deal found 1/26$149
This Frontier deal was found by Cheapflights users on 1/26. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 4/118:39 pm
PHL
-
SJU
Nonstop3h 50m
Frontier
Wed 4/151:59 am
SJU
-
PHL
Nonstop4h 09m
Frontier
Deal found 1/26$150
This Kiwi.com deal was found by Cheapflights users on 1/26. 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 2/259:39 am
PHL
-
SJU
1 stop8h 19m
Multiple Airlines
Sat 2/286:00 am
SJU
-
PHL
Nonstop4h 12m
Multiple Airlines
Deal found 1/26$151
This Cheapflightsfares deal was found by Cheapflights users on 1/25. 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 2/812:12 pm
PHL
-
SJU
Nonstop3h 45m
Frontier
Wed 2/1111:07 am
SJU
-
PHL
1 stop8h 05m
Frontier
Deal found 1/25$152
This Expedia deal was found by Cheapflights users on 1/25. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 2/106:00 am
BWI
-
SJU
Nonstop3h 47m
Spirit Airlines
Sat 2/144:36 pm
SJU
-
BWI
1 stop7h 55m
Spirit Airlines
Deal found 1/25$170

Find flight deals from Maryland to Caribbean

Keep the following information in mind while searching for Maryland to Caribbean flight deals. Data was last updated January 27, 2026.

Round-trip from

$141
(Priceline)

One-way from

$66
(Cheapflightsfares)

Popular in

December

Cheapest in

July

Average price

$335

Good round-trip deal

$214 or less

Good one-way deal

$106 or less
From Maryland to Caribbean
Search Deals
One-way flight from Maryland to Caribbean
Search Deals
Highest demand for flights based on searches. 10% potential increase in price ($39 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 2% potential price decrease ($10 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in January 2026
Search Deals
Price to beat on a round-trip flight from Maryland to Caribbean.
Search Deals
Price to beat on a one-way flight from Maryland to Caribbean.
Search Deals

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 January 27, 2026.
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.Saint Thomas Island

IAD - STT

IADSTT

Washington, D.C. Dulles Intl

Sun 2/22

8:59 am-1:56 pm

Nonstop3h 57m

Saint Thomas Island Cyril E King

Thu 2/26

5:25 pm-11:21 pm

1 stop6h 56m

$196

Washington, D.C.Saint Thomas Island

IAD - STT

IADSTT

Washington, D.C. Dulles Intl

Mon 3/9

6:15 am-3:18 pm

1 stop9h 03m

Saint Thomas Island Cyril E King

Tue 3/17

12:02 pm-4:25 pm

Nonstop4h 23m

$196

Washington, D.C.Saint Thomas Island

IAD - STT

IADSTT

Washington, D.C. Dulles Intl

Wed 4/15

6:00 am-1:08 pm

1 stop7h 08m

Saint Thomas Island Cyril E King

Wed 4/22

2:10 pm-12:15 am

1 stop10h 05m

$200

Washington, D.C.Saint Thomas Island

IAD - STT

IADSTT

Washington, D.C. Dulles Intl

Sat 4/25

8:20 am-5:00 pm

1 stop8h 40m

Saint Thomas Island Cyril E King

Tue 4/28

2:10 pm-12:15 am

1 stop10h 05m

$200

Washington, D.C.Saint Thomas Island

IAD - STT

IADSTT

Washington, D.C. Dulles Intl

Tue 2/24

6:00 am-4:22 pm

1 stop9h 22m

Saint Thomas Island Cyril E King

Tue 3/3

1:50 pm-8:45 pm

1 stop7h 55m

$220

Washington, D.C.Saint Thomas Island

IAD - STT

IADSTT

Washington, D.C. Dulles Intl

Mon 2/23

7:15 am-3:04 pm

1 stop6h 49m

Saint Thomas Island Cyril E King

Tue 2/24

4:15 pm-12:21 am

1 stop9h 06m

$220

Washington, D.C.Saint Thomas Island

IAD - STT

IADSTT

Washington, D.C. Dulles Intl

Mon 3/2

7:15 am-3:04 pm

1 stop6h 49m

Saint Thomas Island Cyril E King

Tue 3/10

12:49 pm-8:46 pm

1 stop7h 57m

$220

PhiladelphiaSan Juan

PHL - SJU

PHLSJU

Philadelphia

Thu 3/5

8:52 pm-1:37 am

Nonstop3h 45m

San Juan Luis Munoz Marin Intl

Sun 3/8

1:59 am-6:11 am

Nonstop4h 12m

$236

BaltimoreSan Juan

BWI - SJU

BWISJU

Baltimore/Washington

Mon 2/9

10:05 am-12:36 am

2 stops13h 31m

San Juan Luis Munoz Marin Intl

Tue 2/10

7:45 am-4:06 pm

1 stop9h 21m

$247

Washington, D.C.San Juan

IAD - SJU

IADSJU

Washington, D.C. Dulles Intl

Sun 2/8

10:08 am-5:17 pm

1 stop6h 09m

San Juan Luis Munoz Marin Intl

Thu 2/12

7:30 am-2:45 pm

1 stop8h 15m

$252

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/24

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, May is the cheapest month in which you can book a flight from Maryland to Caribbean (average of $115). Flying from Maryland to Caribbean in December is currently the most expensive (average of $214). 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 January 27, 2026.

Unlike in the morning, when flights are generally more expensive, you can save up to 50% on flights from Maryland to Caribbean by exploring options for tickets in the afternoon.

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 January 24, 2026.

Travelers seeking maximum savings on their Maryland to Caribbean flight should consider departing on Monday afternoons 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. 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 1579 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?

    $58 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 Frontier and American Airlines, with prices starting from $67 and $88, 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, May is the cheapest month in which you can book a flight from Maryland to Caribbean (average of $115). Flying from Maryland to Caribbean in December is currently the most expensive (average of $214). 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 January 27, 2026.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$121Average$368FlexibilityNo cancel feeOn-time65%
FrontierCheapest$131Average$387FlexibilityNo cancel feeOn-time62%
DeltaCheapest$138Average$575FlexibilityNo cancel feeOn-timeN/A
JetBlueCheapest$156Average$376FlexibilityNo cancel feeOn-time62%
Copa AirlinesCheapest$183Average$438FlexibilityNo cancel feeOn-time70%
American AirlinesCheapest$225Average$579FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$235Average$544FlexibilityNo cancel feeOn-time69%
SouthwestCheapest$347Average$648FlexibilityNo cancel feeOn-time63%

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