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$64+ 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 5/10. Fares are subject to change and may not be available on all flights or dates of travel.
BWI — SJU
Apr 29 — May 61
Tue 4/29
Tue 5/6
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 April 24, 2025.

Round-trip from

$140
(Booking.com)

One-way from

$64
(eDestinos)

Popular in

December

Cheapest in

March

Average price

$384

Good round-trip deal

$198 or less

Good one-way deal

$93 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. 11% potential increase in price ($45 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 April 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 April 24, 2025.

This Booking.com deal was found by Cheapflights users on 4/23. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/176:45 pmBWI - SJU
Nonstop3h 42mSpirit Airlines
Thu 6/191:44 pmSJU - BWI
Nonstop4h 04mSpirit Airlines
Deal found 4/23$140
This CheapOair deal was found by Cheapflights users on 4/23. 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.
Sun 5/2512:10 pmIAD - SJU
Nonstop3h 52mFrontier
Thu 5/297:20 amSJU - IAD
Nonstop3h 55mFrontier
Deal found 4/23$156
This Kiwi.com deal was found by Cheapflights users on 4/23. 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 6/141:04 pmBWI - SJU
Nonstop3h 51mMultiple Airlines
Wed 6/181:44 pmSJU - BWI
Nonstop4h 04mMultiple Airlines
Deal found 4/23$161
This Cheapflightsfares deal was found by Cheapflights users on 4/23. 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 4/276:00 amPHL - SJU
1 stop10h 15mSpirit Airlines
Tue 4/297:00 pmSJU - PHL
1 stop15h 58mSpirit Airlines
Deal found 4/23$170
This eDestinos deal was found by Cheapflights users on 4/23. 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 eDestinos is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 6/78:22 pmBWI - SJU
Nonstop3h 51mFrontier
Sat 6/148:15 amSJU - BWI
Nonstop3h 54mFrontier
Deal found 4/23$186
This Kiwi.com deal was found by Cheapflights users on 4/23. 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 4/267:03 pmPHL - SJU
1 stop14h 29mMultiple Airlines
Sun 5/186:00 amSJU - PHL
Nonstop4h 02mMultiple Airlines
Deal found 4/23$193
This eDestinos deal was found by Cheapflights users on 4/23. 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 eDestinos is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/277:30 amPHL - SJU
Nonstop3h 53mFrontier
Thu 6/1212:59 amSJU - PHL
Nonstop3h 58mFrontier
Deal found 4/23$212
This American Airlines deal was found by Cheapflights users on 4/23. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 5/255:00 amBWI - SJU
1 stop10h 00mAmerican Airlines
Wed 5/286:10 amSJU - BWI
1 stop16h 06mAmerican Airlines
Deal found 4/23$225
This Delta deal was found by Cheapflights users on 4/23. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/169:00 amDCA - SJU
1 stop10h 44mDelta
Wed 7/2312:43 pmSJU - DCA
1 stop10h 47mDelta
Deal found 4/23$225
This American Airlines deal was found by Cheapflights users on 4/23. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 5/265:00 amDCA - SJU
1 stop10h 00mAmerican Airlines
Wed 5/286:10 amSJU - DCA
1 stop6h 12mAmerican Airlines
Deal found 4/23$231
This United Airlines deal was found by Cheapflights users on 4/23. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 6/17:00 amDCA - SJU
1 stop6h 45mUnited Airlines
Wed 6/41:05 amSJU - DCA
1 stop9h 22mUnited Airlines
Deal found 4/23$235
This American Airlines deal was found by Cheapflights users on 4/23. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 5/255:02 amIAD - SJU
1 stop9h 58mAmerican Airlines
Thu 5/297:15 amSJU - IAD
1 stop16h 47mAmerican Airlines
Deal found 4/23$245

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 April 24, 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

Tue 6/17

6:45 pm-10:27 pm

Nonstop3h 42m

San Juan Luis Munoz Marin Intl

Thu 6/19

1:44 pm-5:48 pm

Nonstop4h 04m

$140

Washington, D.C.San Juan

IAD - SJU

IADSJU

Washington, D.C. Dulles Intl

Sun 5/25

12:10 pm-4:02 pm

Nonstop3h 52m

San Juan Luis Munoz Marin Intl

Thu 5/29

7:20 am-11:15 am

Nonstop3h 55m

$156

BaltimoreSan Juan

BWI - SJU

BWISJU

Baltimore/Washington

Sat 6/14

1:04 pm-4:55 pm

Nonstop3h 51m

San Juan Luis Munoz Marin Intl

Fri 6/20

1:44 pm-5:48 pm

Nonstop4h 04m

$161

PhiladelphiaSan Juan

PHL - SJU

PHLSJU

Philadelphia

Sun 4/27

6:00 am-4:15 pm

1 stop10h 15m

San Juan Luis Munoz Marin Intl

Tue 4/29

7:00 pm-10:58 am

1 stop15h 58m

$170

BaltimoreSan Juan

BWI - SJU

BWISJU

Baltimore/Washington

Sat 6/7

8:22 pm-12:13 am

Nonstop3h 51m

San Juan Luis Munoz Marin Intl

Sat 6/14

8:15 am-12:09 pm

Nonstop3h 54m

$186

PhiladelphiaSan Juan

PHL - SJU

PHLSJU

Philadelphia

Sun 4/27

6:00 am-4:15 pm

1 stop10h 15m

San Juan Luis Munoz Marin Intl

Sun 5/18

9:58 pm-1:59 am

Nonstop4h 01m

$206

PhiladelphiaSan Juan

PHL - SJU

PHLSJU

Philadelphia

Tue 5/27

7:30 am-11:23 am

Nonstop3h 53m

San Juan Luis Munoz Marin Intl

Thu 6/12

12:59 am-4:57 am

Nonstop3h 58m

$212

BaltimoreSan Juan

BWI - SJU

BWISJU

Baltimore/Washington

Sun 5/25

5:00 am-3:00 pm

1 stop10h 00m

San Juan Luis Munoz Marin Intl

Wed 5/28

6:10 am-10:16 pm

1 stop16h 06m

$225

Washington, D.C.San Juan

DCA - SJU

DCASJU

Washington, D.C. Reagan-National

Wed 7/16

9:00 am-7:44 pm

1 stop10h 44m

San Juan Luis Munoz Marin Intl

Wed 7/23

12:43 pm-11:30 pm

1 stop10h 47m

$225

Washington, D.C.San Juan

DCA - SJU

DCASJU

Washington, D.C. Reagan-National

Mon 5/26

5:00 am-3:00 pm

1 stop10h 00m

San Juan Luis Munoz Marin Intl

Wed 5/28

6:10 am-12:22 pm

1 stop6h 12m

$231

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/23

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 December is currently the most expensive (average of $336). 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 April 24, 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.

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 April 24, 2025.

The most flights from USMD to 0CB are scheduled on a Monday (4 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (1 on average).

Rainfall in Caribbean by month

Plan your trip to Caribbean by taking into account the average rainfall totals by month.

In terms of precipitation, rainfall in Caribbean ranges from 2.2 - 6.1 inches per month. November is typically the wettest month, when rainfall can reach 6.1 in. February is typically the driest time to visit Caribbean when rainfall is around 2.2 in.

Temperature in Caribbean by month

Plan your trip to Caribbean by taking into account the average temperature totals by month.

If weather is an important factor for your trip to Caribbean, use this chart to help with planning. For those seeking warmer temperatures, June is the ideal time of year to visit, when temperatures reach an average of 82.4 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 77.0 F).

Reviews of airlines servicing Caribbean

Get insights into the airlines that provide service to Caribbean. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Caribbean. Reviews last updated April 24, 2025.
Southwest
8.0
Very good
4,286 reviews

Boarding

8.2

Overall

8.0

Crew

8.6

Entertainment

7.6

Comfort

8.0

Food

7.1

Reviews

1 / 20
10.0
Excellent

Gina,Apr 2025

LAS - DEN

Good, the crew was friendly and helpful. The pilot had great skills in keeping the plane stable through rough turbulence. Smooth landing, too! Thank you!
Southwest
8.0
Very good
4,286 reviews
Southwest
8.0
Very good
4,286 reviews

Boarding

8.2

Overall

8.0

Crew

8.6

Entertainment

7.6

Comfort

8.0

Food

7.1

Reviews

1 / 20
10.0
Excellent

Gina,Apr 2025

LAS - DEN

Good, the crew was friendly and helpful. The pilot had great skills in keeping the plane stable through rough turbulence. Smooth landing, too! Thank you!
Delta
8.0
Very good
7,920 reviews
Southwest
8.0
Very good
4,286 reviews

Boarding

8.2

Overall

8.0

Crew

8.6

Entertainment

7.6

Comfort

8.0

Food

7.1

Reviews

1 / 20
10.0
Excellent

Gina,Apr 2025

LAS - DEN

Good, the crew was friendly and helpful. The pilot had great skills in keeping the plane stable through rough turbulence. Smooth landing, too! Thank you!
Copa Airlines
7.6
Good
1,411 reviews
Southwest
8.0
Very good
4,286 reviews

Boarding

8.2

Overall

8.0

Crew

8.6

Entertainment

7.6

Comfort

8.0

Food

7.1

Reviews

1 / 20
10.0
Excellent

Gina,Apr 2025

LAS - DEN

Good, the crew was friendly and helpful. The pilot had great skills in keeping the plane stable through rough turbulence. Smooth landing, too! Thank you!
United Airlines
7.4
Good
8,685 reviews
Southwest
8.0
Very good
4,286 reviews

Boarding

8.2

Overall

8.0

Crew

8.6

Entertainment

7.6

Comfort

8.0

Food

7.1

Reviews

1 / 20
10.0
Excellent

Gina,Apr 2025

LAS - DEN

Good, the crew was friendly and helpful. The pilot had great skills in keeping the plane stable through rough turbulence. Smooth landing, too! Thank you!
JetBlue
7.3
Good
2,924 reviews
Southwest
8.0
Very good
4,286 reviews

Boarding

8.2

Overall

8.0

Crew

8.6

Entertainment

7.6

Comfort

8.0

Food

7.1

Reviews

1 / 20
10.0
Excellent

Gina,Apr 2025

LAS - DEN

Good, the crew was friendly and helpful. The pilot had great skills in keeping the plane stable through rough turbulence. Smooth landing, too! Thank you!

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.

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

    $64 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 Delta, with prices starting from $79 and $113, 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 December is currently the most expensive (average of $336). 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 April 24, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$119Average$344FlexibilityNo cancel feeOn-time62%
Spirit AirlinesCheapest$124Average$424FlexibilityNo cancel feeOn-time65%
JetBlueCheapest$167Average$410FlexibilityNo cancel feeOn-time62%
United AirlinesCheapest$199Average$549FlexibilityNo cancel feeOn-time69%
DeltaCheapest$272Average$529FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$282Average$611FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$322Average$669FlexibilityNo cancel feeOn-time63%
Copa AirlinesCheapest$332Average$455FlexibilityNo cancel feeOn-time70%

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