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$74+ 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 1/4. Fares are subject to change and may not be available on all flights or dates of travel.
BWI — SJU
ene. 11 — ene. 181
dom. 1/11
dom. 1/18
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 diciembre 12, 2025.

This Kiwi.com deal was found by Cheapflights users on 12/10. 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.
mié. 12/318:04 pmPHL - SJU
Nonstop3h 46mMultiple Airlines
vie. 1/95:18 pmSJU - PHL
1 stop8h 13mMultiple Airlines
Deal found 12/10$161
This Kiwi.com deal was found by Cheapflights users on 12/10. 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.
mié. 12/315:25 amPHL - SJU
1 stop15h 41mMultiple Airlines
vie. 1/238:31 pmSJU - PHL
Nonstop4h 12mMultiple Airlines
Deal found 12/10$170
This Expedia deal was found by Cheapflights users on 12/11. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
dom. 12/144:34 pmPHL - SJU
1 stop6h 42mMultiple Airlines
jue. 1/156:00 amSJU - PHL
1 stop14h 24mMultiple Airlines
Deal found 12/11$172
This Kiwi.com deal was found by Cheapflights users on 12/10. 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.
mié. 12/317:42 pmPHL - SJU
Nonstop3h 47mMultiple Airlines
vie. 1/92:59 amSJU - PHL
Nonstop4h 12mMultiple Airlines
Deal found 12/10$176
This Frontier deal was found by Cheapflights users on 12/10. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mié. 12/317:42 pmPHL - SJU
Nonstop3h 47mFrontier
jue. 1/82:29 amSJU - PHL
Nonstop4h 03mFrontier
Deal found 12/10$179
This Kiwi.com deal was found by Cheapflights users on 12/11. 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.
lun. 12/158:00 amPHL - SJU
1 stop15h 45mMultiple Airlines
jue. 1/1511:15 amSJU - PHL
1 stop9h 09mMultiple Airlines
Deal found 12/11$181
This Priceline deal was found by Cheapflights users on 12/9. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
lun. 12/299:58 pmIAD - SJU
1 stop27h 52mFrontier
vie. 1/163:11 pmSJU - IAD
Nonstop4h 08mFrontier
Deal found 12/9$185
This Kiwi.com deal was found by Cheapflights users on 12/10. 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.
mar. 12/3010:00 pmPHL - SJU
1 stop16h 59mFrontier
vie. 1/95:18 pmSJU - PHL
1 stop8h 13mFrontier
Deal found 12/10$188
This Kiwi.com deal was found by Cheapflights users on 12/11. 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.
dom. 12/1410:38 amIAD - SJU
Nonstop3h 54mFrontier
dom. 12/214:18 pmSJU - IAD
Nonstop4h 13mFrontier
Deal found 12/11$193
This Super.com deal was found by Cheapflights users on 12/11. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
dom. 12/1410:38 amIAD - SJU
Nonstop3h 54mFrontier
mar. 12/234:07 pmSJU - IAD
Nonstop4h 13mFrontier
Deal found 12/11$194
This Frontier deal was found by Cheapflights users on 12/11. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
dom. 12/1410:38 amIAD - SJU
Nonstop3h 54mFrontier
sáb. 12/204:18 pmSJU - IAD
Nonstop4h 13mFrontier
Deal found 12/11$195
This Frontier deal was found by Cheapflights users on 12/10. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
sáb. 12/135:05 amPHL - SJU
1 stop9h 29mFrontier
lun. 1/123:58 amSJU - PHL
1 stop10h 59mFrontier
Deal found 12/10$199

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 diciembre 12, 2025.

Round-trip from

$161
(Kiwi.com)

One-way from

$74
(Super.com)

Popular in

December

Cheapest in

July

Average price

$449

Good round-trip deal

$255 or less

Good one-way deal

$128 or less
From Maryland to Caribbean
Search Deals
One-way flight from Maryland to Caribbean
Search Deals
Highest demand for flights based on searches. 11% potential increase in price ($42 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 3% potential price decrease ($11 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in December 2025
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 diciembre 12, 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

BaltimoreSan Juan

BWI - SJU

BWISJU

Baltimore/Washington

mar. 1/6

11:45 am-11:44 pm

2 stops10h 59m

San Juan Luis Munoz Marin Intl

vie. 1/9

8:05 pm-11:17 am

1 stop16h 12m

$229

PhiladelphiaSan Juan

PHL - SJU

PHLSJU

Philadelphia

jue. 1/29

9:02 pm-10:24 am

1 stop12h 22m

San Juan Luis Munoz Marin Intl

lun. 2/2

4:22 pm-12:52 am

1 stop9h 30m

$231

PhiladelphiaSan Juan

PHL - SJU

PHLSJU

Philadelphia

vie. 12/19

8:40 am-7:25 pm

1 stop9h 45m

San Juan Luis Munoz Marin Intl

sáb. 1/3

1:19 pm-10:49 pm

1 stop10h 30m

$234

Washington, D.C.San Juan

DCA - SJU

DCASJU

Washington, D.C. Reagan-National

mar. 2/3

12:00 pm-12:35 am

2 stops11h 35m

San Juan Luis Munoz Marin Intl

mar. 2/10

12:10 pm-10:55 pm

1 stop11h 45m

$238

PhiladelphiaSan Juan

PHL - SJU

PHLSJU

Philadelphia

mar. 1/27

7:00 am-3:30 pm

1 stop7h 30m

San Juan Luis Munoz Marin Intl

vie. 1/30

6:01 am-11:25 am

1 stop6h 24m

$245

PhiladelphiaSan Juan

PHL - SJU

PHLSJU

Philadelphia

mié. 1/28

7:00 am-3:30 pm

1 stop7h 30m

San Juan Luis Munoz Marin Intl

vie. 1/30

6:01 am-11:25 am

1 stop6h 24m

$245

Washington, D.C.San Juan

IAD - SJU

IADSJU

Washington, D.C. Dulles Intl

mar. 5/26

5:24 pm-9:24 pm

Nonstop4h 00m

San Juan Luis Munoz Marin Intl

lun. 6/1

1:05 am-7:19 am

1 stop6h 14m

$247

Washington, D.C.San Juan

IAD - SJU

IADSJU

Washington, D.C. Dulles Intl

lun. 5/4

6:00 am-1:45 pm

1 stop7h 45m

San Juan Luis Munoz Marin Intl

vie. 5/8

1:00 am-7:19 am

1 stop6h 19m

$251

BaltimoreSan Juan

BWI - SJU

BWISJU

Baltimore/Washington

mar. 1/20

10:05 am-12:36 am

2 stops13h 31m

San Juan Luis Munoz Marin Intl

sáb. 1/24

7:45 am-4:06 pm

1 stop9h 21m

$251

Washington, D.C.San Juan

DCA - SJU

DCASJU

Washington, D.C. Reagan-National

mié. 1/21

3:15 pm-12:36 am

1 stop8h 21m

San Juan Luis Munoz Marin Intl

mié. 1/28

2:15 pm-11:59 pm

2 stops10h 44m

$251

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/10

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, January is the cheapest month in which you can book a flight from Maryland to Caribbean (average of $113). Flying from Maryland to Caribbean in December is currently the most expensive (average of $180). 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 diciembre 12, 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 December 6, 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 at noon flights should be avoided if possible as fares are typically the most expensive at this time.

Weekly flight availability from Maryland to Caribbean

Explore weekly flight availability from Maryland to Caribbean. Discover flights operating on different days of the week, giving you the flexibility to choose a travel day that best fits your plans. Compare info to find the most convenient option for your journey. Data last updated diciembre 12, 2025.

The most flights from USMD to 0CB are scheduled on a Monday (3 on average). You will have fewer flight options on Friday, which is when the least amount of flights are scheduled (1 on average).

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 9h 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 $63 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, January is the cheapest month in which you can book a flight from Maryland to Caribbean (average of $113). Flying from Maryland to Caribbean in December is currently the most expensive (average of $180). 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 diciembre 12, 2025.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$124Average$372FlexibilityNo cancel feeOn-time65%
FrontierCheapest$129Average$381FlexibilityNo cancel feeOn-time62%
JetBlueCheapest$167Average$390FlexibilityNo cancel feeOn-time62%
DeltaCheapest$192Average$579FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$214Average$546FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$222Average$575FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$346Average$651FlexibilityNo cancel feeOn-time63%
Copa AirlinesCheapest$360Average$457FlexibilityNo cancel feeOn-time70%

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