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$83+ 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 9/7. Fares are subject to change and may not be available on all flights or dates of travel.
BWI — SJU
Aug 4 — Aug 111
Mon 8/4
Mon 8/11
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 July 30, 2025.

Round-trip from

$165
(American Airlines)

One-way from

$83
(FlightHub)

Popular in

December

Cheapest in

March

Average price

$306

Good round-trip deal

$227 or less

Good one-way deal

$123 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 ($50 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 July 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 July 30, 2025.

This American Airlines deal was found by Cheapflights users on 7/30. 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 8/115:55 amDCA - SJU
1 stop9h 05mAmerican Airlines
Fri 8/155:15 pmSJU - DCA
1 stop15h 19mAmerican Airlines
Deal found 7/30$165
This CheapOair deal was found by Cheapflights users on 7/28. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/106:45 amBWI - SJU
1 stop8h 38mSpirit Airlines
Mon 11/176:00 amSJU - BWI
1 stop11h 49mSpirit Airlines
Deal found 7/28$166
This Kiwi.com deal was found by Cheapflights users on 7/28. 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 8/3112:11 pmBWI - SJU
Nonstop3h 52mMultiple Airlines
Thu 9/187:05 amSJU - BWI
Nonstop4h 00mMultiple Airlines
Deal found 7/28$171
This Frontier deal was found by Cheapflights users on 7/30. 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 11/910:09 amIAD - SJU
Nonstop3h 52mFrontier
Thu 11/136:25 amSJU - IAD
Nonstop3h 56mFrontier
Deal found 7/30$176
This Booking.com deal was found by Cheapflights users on 7/30. 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.
Sat 8/3012:54 pmPHL - SJU
Nonstop3h 48mSpirit Airlines
Thu 9/412:05 pmSJU - PHL
Nonstop4h 10mSpirit Airlines
Deal found 7/30$176
This United Airlines deal was found by Cheapflights users on 7/29. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/208:39 amIAD - SJU
Nonstop3h 55mUnited Airlines
Tue 10/287:30 amSJU - IAD
Nonstop4h 05mUnited Airlines
Deal found 7/29$181
This CheapOair deal was found by Cheapflights users on 7/28. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/277:21 amPHL - SJU
Nonstop3h 46mFrontier
Fri 10/311:11 amSJU - PHL
Nonstop3h 58mFrontier
Deal found 7/28$181
This Cheapflightsfares deal was found by Cheapflights users on 7/28. 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.
Sun 8/2412:11 pmBWI - SJU
Nonstop3h 52mFrontier
Thu 8/287:25 amSJU - BWI
Nonstop4h 01mFrontier
Deal found 7/28$183
This Trip.com deal was found by Cheapflights users on 7/28. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/412:43 pmPHL - SJU
1 stop11h 16mMultiple Airlines
Sun 9/712:05 pmSJU - PHL
Nonstop4h 10mMultiple Airlines
Deal found 7/28$188
This American Airlines deal was found by Cheapflights users on 7/30. 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.
Tue 10/2110:25 amIAD - SJU
1 stop11h 45mAmerican Airlines
Wed 10/294:45 pmSJU - IAD
1 stop17h 10mAmerican Airlines
Deal found 7/30$195
This Trip.com deal was found by Cheapflights users on 7/29. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 8/248:00 amDCA - SJU
Nonstop3h 58mJetBlue
Wed 8/276:00 amSJU - DCA
1 stop9h 08mJetBlue
Deal found 7/29$212
This Delta deal was found by Cheapflights users on 7/27. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/86:00 amIAD - SJU
1 stop7h 10mDelta
Sat 9/207:30 amSJU - IAD
1 stop11h 09mDelta
Deal found 7/27$215

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 July 30, 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 8/11

5:55 am-3:00 pm

1 stop9h 05m

San Juan Luis Munoz Marin Intl

Fri 8/15

5:15 pm-8:34 am

1 stop15h 19m

$165

BaltimoreSan Juan

BWI - SJU

BWISJU

Baltimore/Washington

Sun 9/14

8:42 pm-12:43 am

Nonstop4h 01m

San Juan Luis Munoz Marin Intl

Sun 9/21

7:05 am-11:05 am

Nonstop4h 00m

$168

BaltimoreSan Juan

BWI - SJU

BWISJU

Baltimore/Washington

Sun 8/31

12:11 pm-4:03 pm

Nonstop3h 52m

San Juan Luis Munoz Marin Intl

Thu 9/18

7:05 am-11:05 am

Nonstop4h 00m

$171

PhiladelphiaSan Juan

PHL - SJU

PHLSJU

Philadelphia

Sat 8/30

12:54 pm-4:42 pm

Nonstop3h 48m

San Juan Luis Munoz Marin Intl

Thu 9/4

12:05 pm-4:15 pm

Nonstop4h 10m

$176

Washington, D.C.San Juan

IAD - SJU

IADSJU

Washington, D.C. Dulles Intl

Thu 10/9

11:44 am-3:36 pm

Nonstop3h 52m

San Juan Luis Munoz Marin Intl

Sun 10/12

7:00 am-10:56 am

Nonstop3h 56m

$178

Washington, D.C.San Juan

IAD - SJU

IADSJU

Washington, D.C. Dulles Intl

Mon 10/20

8:39 am-12:34 pm

Nonstop3h 55m

San Juan Luis Munoz Marin Intl

Tue 10/28

7:30 am-11:35 am

Nonstop4h 05m

$181

PhiladelphiaSan Juan

PHL - SJU

PHLSJU

Philadelphia

Mon 10/27

7:21 am-11:07 am

Nonstop3h 46m

San Juan Luis Munoz Marin Intl

Fri 10/31

1:11 am-5:09 am

Nonstop3h 58m

$181

BaltimoreSan Juan

BWI - SJU

BWISJU

Baltimore/Washington

Sun 8/24

12:11 pm-4:03 pm

Nonstop3h 52m

San Juan Luis Munoz Marin Intl

Thu 8/28

7:25 am-11:26 am

Nonstop4h 01m

$183

PhiladelphiaSan Juan

PHL - SJU

PHLSJU

Philadelphia

Thu 9/4

12:43 pm-11:59 pm

1 stop11h 16m

San Juan Luis Munoz Marin Intl

Sun 9/7

12:05 pm-4:15 pm

Nonstop4h 10m

$188

Washington, D.C.San Juan

IAD - SJU

IADSJU

Washington, D.C. Dulles Intl

Tue 10/21

10:25 am-10:10 pm

1 stop11h 45m

San Juan Luis Munoz Marin Intl

Wed 10/29

4:45 pm-9:55 am

1 stop17h 10m

$195

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/29

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, 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 July 30, 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 July 30, 2025.

The most flights from USMD to 0CB are scheduled on a Monday (5 on average). You will have fewer flight options on Sunday, which is when the least amount of flights are scheduled (1 on average).

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 July 30, 2025.
Read through reviews of airlines operating flights from Maryland to Caribbean, such as Southwest, Delta, and Avelo Airlines. You can also see how each airline stacks up in terms of entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.0
Very good
4,241 reviews

Crew

8.6

Entertainment

7.5

Boarding

8.1

Food

7.0

Comfort

8.0

Overall

8.0

Reviews

1 / 20
8.0
Excellent

Gina,Jul 2025

LAS - DEN

We experienced bad weather, which turned our 1.5 hour flight from Las Vegas to Denver, into 3.5. The pilot and crew kept us updated and explained that we had to circle and or possibly redirect to another airport. After circling for sometime, we were able to land smoothly in Denver. Thank you to all the flight crew, tower control, and all who got us to our destination safely.
Southwest
8.0
Very good
4,241 reviews
Southwest
8.0
Very good
4,241 reviews

Crew

8.6

Entertainment

7.5

Boarding

8.1

Food

7.0

Comfort

8.0

Overall

8.0

Reviews

1 / 20
8.0
Excellent

Gina,Jul 2025

LAS - DEN

We experienced bad weather, which turned our 1.5 hour flight from Las Vegas to Denver, into 3.5. The pilot and crew kept us updated and explained that we had to circle and or possibly redirect to another airport. After circling for sometime, we were able to land smoothly in Denver. Thank you to all the flight crew, tower control, and all who got us to our destination safely.
Delta
8.0
Very good
7,980 reviews
Southwest
8.0
Very good
4,241 reviews

Crew

8.6

Entertainment

7.5

Boarding

8.1

Food

7.0

Comfort

8.0

Overall

8.0

Reviews

1 / 20
8.0
Excellent

Gina,Jul 2025

LAS - DEN

We experienced bad weather, which turned our 1.5 hour flight from Las Vegas to Denver, into 3.5. The pilot and crew kept us updated and explained that we had to circle and or possibly redirect to another airport. After circling for sometime, we were able to land smoothly in Denver. Thank you to all the flight crew, tower control, and all who got us to our destination safely.
Avelo Airlines
7.5
Good
Southwest
8.0
Very good
4,241 reviews

Crew

8.6

Entertainment

7.5

Boarding

8.1

Food

7.0

Comfort

8.0

Overall

8.0

Reviews

1 / 20
8.0
Excellent

Gina,Jul 2025

LAS - DEN

We experienced bad weather, which turned our 1.5 hour flight from Las Vegas to Denver, into 3.5. The pilot and crew kept us updated and explained that we had to circle and or possibly redirect to another airport. After circling for sometime, we were able to land smoothly in Denver. Thank you to all the flight crew, tower control, and all who got us to our destination safely.
Copa Airlines
7.5
Good
1,493 reviews
Southwest
8.0
Very good
4,241 reviews

Crew

8.6

Entertainment

7.5

Boarding

8.1

Food

7.0

Comfort

8.0

Overall

8.0

Reviews

1 / 20
8.0
Excellent

Gina,Jul 2025

LAS - DEN

We experienced bad weather, which turned our 1.5 hour flight from Las Vegas to Denver, into 3.5. The pilot and crew kept us updated and explained that we had to circle and or possibly redirect to another airport. After circling for sometime, we were able to land smoothly in Denver. Thank you to all the flight crew, tower control, and all who got us to our destination safely.
United Airlines
7.4
Good
8,896 reviews
Southwest
8.0
Very good
4,241 reviews

Crew

8.6

Entertainment

7.5

Boarding

8.1

Food

7.0

Comfort

8.0

Overall

8.0

Reviews

1 / 20
8.0
Excellent

Gina,Jul 2025

LAS - DEN

We experienced bad weather, which turned our 1.5 hour flight from Las Vegas to Denver, into 3.5. The pilot and crew kept us updated and explained that we had to circle and or possibly redirect to another airport. After circling for sometime, we were able to land smoothly in Denver. Thank you to all the flight crew, tower control, and all who got us to our destination safely.

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?

    $83 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 American Airlines and United Airlines, with prices starting from $84 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, 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 July 30, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$120Average$371FlexibilityNo cancel feeOn-time62%
Spirit AirlinesCheapest$124Average$402FlexibilityNo cancel feeOn-time65%
JetBlueCheapest$173Average$413FlexibilityNo cancel feeOn-time62%
United AirlinesCheapest$199Average$549FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$215Average$608FlexibilityNo cancel feeOn-time71%
DeltaCheapest$259Average$542FlexibilityNo cancel feeOn-timeN/A
SouthwestCheapest$326Average$655FlexibilityNo cancel feeOn-time63%
Copa AirlinesCheapest$332Average$443FlexibilityNo cancel feeOn-time70%

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