HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
Caribbean

$59+ 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 4/7. Fares are subject to change and may not be available on all flights or dates of travel.
BWI — SJU
Apr 8 — Apr 151
Tue 4/8
Tue 4/15
1 adult, Economy
We work with more than 300 partners to bring you better travel deals

Find cheap flights from Maryland to Caribbean with Cheapflights

1. Tell us where you want to go

Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”

2. Select your favorite providers

We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.

3. Compare prices and book

Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.

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 3, 2025.

Round-trip from

$130
(FlightHub)

One-way from

$59
(FlightHub)

Popular in

December

Cheapest in

September

Average price

$365

Good round-trip deal

$173 or less

Good one-way deal

$79 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 ($43 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 April 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

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 3, 2025.

This Kiwi.com deal was found by Cheapflights users on 4/2. 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 4/65:05 pmPHL - SJU
Nonstop3h 51mMultiple Airlines
Mon 4/712:59 amSJU - PHL
Nonstop4h 10mMultiple Airlines
Deal found 4/2$130
This Frontier deal was found by Cheapflights users on 4/2. 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 4/58:08 pmPHL - SJU
Nonstop3h 46mFrontier
Wed 4/912:59 amSJU - PHL
Nonstop4h 10mFrontier
Deal found 4/2$132
This Cheapflightsfares deal was found by Cheapflights users on 4/1. 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.
Mon 4/2111:42 amBWI - SJU
Nonstop3h 42mSpirit Airlines
Thu 4/242:12 amSJU - BWI
Nonstop4h 03mSpirit Airlines
Deal found 4/1$137
This Kiwi.com deal was found by Cheapflights users on 3/31. 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 4/2511:37 amBWI - SJU
Nonstop3h 45mMultiple Airlines
Wed 4/305:10 pmSJU - BWI
1 stop15h 10mMultiple Airlines
Deal found 3/31$144
This Cheapflightsfares deal was found by Cheapflights users on 4/2. 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.
Sat 4/54:58 pmPHL - SJU
1 stop16h 28mSpirit Airlines
Wed 4/91:31 amSJU - PHL
Nonstop4h 07mSpirit Airlines
Deal found 4/2$162
This Cheapflightsfares deal was found by Cheapflights users on 4/2. 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 5/2512:10 pmIAD - SJU
Nonstop3h 52mFrontier
Thu 5/297:20 amSJU - IAD
Nonstop3h 55mFrontier
Deal found 4/2$167
This Cheapflightsfares deal was found by Cheapflights users on 4/1. 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.
Sat 4/53:16 pmBWI - SJU
Nonstop3h 45mFrontier
Mon 4/74:22 pmSJU - BWI
Nonstop4h 07mFrontier
Deal found 4/1$216
This United Airlines deal was found by Cheapflights users on 4/2. 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 6/225:28 pmIAD - SJU
Nonstop3h 56mUnited Airlines
Thu 6/261:25 pmSJU - IAD
1 stop9h 02mUnited Airlines
Deal found 4/2$232
This JetBlue deal was found by Cheapflights users on 4/2. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/298:00 amDCA - SJU
Nonstop3h 46mJetBlue
Wed 5/76:02 pmSJU - DCA
Nonstop3h 57mJetBlue
Deal found 4/2$246
This Delta deal was found by Cheapflights users on 4/1. 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.
Sat 4/2612:11 pmIAD - SJU
1 stop11h 37mDelta
Tue 5/66:35 amSJU - IAD
1 stop6h 27mDelta
Deal found 4/1$255
This Southwest deal was found by Cheapflights users on 4/2. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/73:30 pmBWI - SJU
1 stop6h 20mSouthwest
Sat 5/107:05 amSJU - BWI
2 stops9h 05mSouthwest
Deal found 4/2$255
This Delta deal was found by Cheapflights users on 4/2. 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 4/286:00 amDCA - SJU
1 stop7h 10mDelta
Fri 5/21:19 pmSJU - DCA
1 stop9h 26mDelta
Deal found 4/2$255

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 3, 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

PhiladelphiaSan Juan

PHL - SJU

PHLSJU

Philadelphia

Mon 4/28

5:35 pm-8:26 am

1 stop14h 51m

San Juan Luis Munoz Marin Intl

Thu 5/1

9:58 pm-1:59 am

Nonstop4h 01m

$132

BaltimoreSan Juan

BWI - SJU

BWISJU

Baltimore/Washington

Mon 4/21

11:42 am-3:24 pm

Nonstop3h 42m

San Juan Luis Munoz Marin Intl

Thu 4/24

2:12 am-6:15 am

Nonstop4h 03m

$137

PhiladelphiaSan Juan

PHL - SJU

PHLSJU

Philadelphia

Mon 4/28

11:15 am-3:01 pm

Nonstop3h 46m

San Juan Luis Munoz Marin Intl

Thu 5/1

9:58 pm-1:59 am

Nonstop4h 01m

$139

BaltimoreSan Juan

BWI - SJU

BWISJU

Baltimore/Washington

Fri 4/25

11:37 am-3:22 pm

Nonstop3h 45m

San Juan Luis Munoz Marin Intl

Wed 4/30

5:10 pm-8:20 am

1 stop15h 10m

$144

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

$167

PhiladelphiaSan Juan

PHL - SJU

PHLSJU

Philadelphia

Mon 4/28

5:35 pm-8:26 am

1 stop14h 51m

San Juan Luis Munoz Marin Intl

Thu 5/1

9:59 pm-8:10 am

1 stop10h 11m

$186

BaltimoreSan Juan

BWI - SJU

BWISJU

Baltimore/Washington

Sat 4/5

3:16 pm-7:01 pm

Nonstop3h 45m

San Juan Luis Munoz Marin Intl

Mon 4/7

4:22 pm-8:29 pm

Nonstop4h 07m

$216

Washington, D.C.San Juan

IAD - SJU

IADSJU

Washington, D.C. Dulles Intl

Sun 6/22

5:28 pm-9:24 pm

Nonstop3h 56m

San Juan Luis Munoz Marin Intl

Thu 6/26

1:25 pm-10:27 pm

1 stop9h 02m

$232

Washington, D.C.San Juan

DCA - SJU

DCASJU

Washington, D.C. Reagan-National

Tue 4/29

8:00 am-11:46 am

Nonstop3h 46m

San Juan Luis Munoz Marin Intl

Tue 5/6

6:02 pm-9:59 pm

Nonstop3h 57m

$246

Washington, D.C.San Juan

IAD - SJU

IADSJU

Washington, D.C. Dulles Intl

Sat 4/26

12:11 pm-11:48 pm

1 stop11h 37m

San Juan Luis Munoz Marin Intl

Tue 5/6

6:35 am-1:02 pm

1 stop6h 27m

$255

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/2

Showing 1-10 of 60 results
1
2
3
...
6

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 3, 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 3, 2025.

The most flights from USMD to 0CB are scheduled on a Monday (5 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 3, 2025.
Delta
8.0
Very good
7,897 reviews

Boarding

8.2

Entertainment

7.9

Food

7.3

Comfort

7.9

Crew

8.5

Overall

8.0

Reviews

1 / 20
10.0
Excellent

Aaron,Oct 2024

LAX - LHR

This was a flight operated by Virgin Atlantic in their Upper Class cabin. Overall, an outstanding experience.
Delta
8.0
Very good
7,897 reviews
Delta
8.0
Very good
7,897 reviews

Boarding

8.2

Entertainment

7.9

Food

7.3

Comfort

7.9

Crew

8.5

Overall

8.0

Reviews

1 / 20
10.0
Excellent

Aaron,Oct 2024

LAX - LHR

This was a flight operated by Virgin Atlantic in their Upper Class cabin. Overall, an outstanding experience.
Southwest
8.0
Very good
4,274 reviews
Delta
8.0
Very good
7,897 reviews

Boarding

8.2

Entertainment

7.9

Food

7.3

Comfort

7.9

Crew

8.5

Overall

8.0

Reviews

1 / 20
10.0
Excellent

Aaron,Oct 2024

LAX - LHR

This was a flight operated by Virgin Atlantic in their Upper Class cabin. Overall, an outstanding experience.
Copa Airlines
7.6
Good
1,400 reviews
Delta
8.0
Very good
7,897 reviews

Boarding

8.2

Entertainment

7.9

Food

7.3

Comfort

7.9

Crew

8.5

Overall

8.0

Reviews

1 / 20
10.0
Excellent

Aaron,Oct 2024

LAX - LHR

This was a flight operated by Virgin Atlantic in their Upper Class cabin. Overall, an outstanding experience.
LATAM Airlines
7.5
Good
1,754 reviews
Delta
8.0
Very good
7,897 reviews

Boarding

8.2

Entertainment

7.9

Food

7.3

Comfort

7.9

Crew

8.5

Overall

8.0

Reviews

1 / 20
10.0
Excellent

Aaron,Oct 2024

LAX - LHR

This was a flight operated by Virgin Atlantic in their Upper Class cabin. Overall, an outstanding experience.
Avelo Airlines
7.5
Good
Delta
8.0
Very good
7,897 reviews

Boarding

8.2

Entertainment

7.9

Food

7.3

Comfort

7.9

Crew

8.5

Overall

8.0

Reviews

1 / 20
10.0
Excellent

Aaron,Oct 2024

LAX - LHR

This was a flight operated by Virgin Atlantic in their Upper Class cabin. Overall, an outstanding experience.

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?

    $59 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 Southwest, with prices starting from $61 and $110, 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

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.
Newark to Fort Lauderdale flights
LaGuardia to Fort Lauderdale flights
LaGuardia to Miami flights
John F Kennedy Intl to Miami flights
John F Kennedy Intl to Cancún flights
Newark to Cancún flights
Newark to Miami flights
John F Kennedy Intl to Los Angeles flights
John F Kennedy Intl to Heathrow flights
Newark to Orlando flights
Los Angeles to Haneda flights
Los Angeles to John F Kennedy Intl flights
John F Kennedy Intl to Las Vegas flights
Dallas/Fort Worth to Seattle flights
LaGuardia to Orlando flights
John F Kennedy Intl to Fort Lauderdale flights
Newark to Heathrow flights
Newark to Las Vegas flights
John F Kennedy Intl to Charles de Gaulle flights
LaGuardia to Dallas/Fort Worth flights
O'Hare Intl to John F Kennedy Intl flights
Newark to Luis Munoz Marin Intl flights
John F Kennedy Intl to Orlando flights
Dallas/Fort Worth to Cancún flights
John F Kennedy Intl to O'Hare Intl flights
Newark to Dallas/Fort Worth flights
Los Angeles to Narita flights
John F Kennedy Intl to Gatwick flights
John F Kennedy Intl to Haneda flights
Dallas/Fort Worth to LaGuardia flights
Newark to Charles de Gaulle flights
O'Hare Intl to Cancún flights
John F Kennedy Intl to West Palm Beach flights
LaGuardia to O'Hare Intl flights
San Francisco to John F Kennedy Intl flights
LaGuardia to Atlanta flights
John F Kennedy Intl to Leonardo da Vinci/Fiumicino flights
Los Angeles to Newark flights
Dallas/Fort Worth to Las Vegas flights
John F Kennedy Intl to Seattle flights
Newark to Seattle flights
Dallas/Fort Worth to O'Hare Intl flights
Los Angeles to Honolulu flights
George Bush Intcntl to Cancún flights
Dallas/Fort Worth to Newark flights
Newark to Leonardo da Vinci/Fiumicino flights
John F Kennedy Intl to Luis Munoz Marin Intl flights
Newark to Los Angeles flights
LaGuardia to Los Angeles flights
O'Hare Intl to Las Vegas flights

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 3, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$118Average$339FlexibilityNo cancel feeOn-time62%
Spirit AirlinesCheapest$125Average$405FlexibilityNo cancel feeOn-time65%
JetBlueCheapest$167Average$368FlexibilityNo cancel feeOn-time62%
United AirlinesCheapest$197Average$551FlexibilityNo cancel feeOn-time69%
DeltaCheapest$275Average$552FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$280Average$616FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$325Average$668FlexibilityNo cancel feeOn-time63%
Copa AirlinesCheapest$332Average$467FlexibilityNo cancel feeOn-time70%

100% Free

Cheapflights is completely free to use, so you can start saving the moment you arrive.

Book with Flexibility

Our users can plan ahead with confidence and find flights with no change fees

Travel Smart

Millions of people come to us for their flight needs every year. We help make travel planning easy by providing useful insights and data-driven graphs that can inform your decisions.