HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
Caribbean Islands

$58+ Cheap flights from Maryland to Caribbean Islands

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 3/19. Fares are subject to change and may not be available on all flights or dates of travel.
BWI — SJU
Feb 25 — Mar 41
Tue 2/25
Tue 3/4
1 adult, Economy
We work with more than 300 partners to bring you better travel deals

Find cheap flights from Maryland to Caribbean Islands 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 Islands

Keep the following information in mind while searching for Maryland to Caribbean Islands flight deals. Data was last updated February 20, 2025.

Round-trip from

$133
(CheapOair)

One-way from

$58
(Cheapflightsfares)

Popular in

December

Cheapest in

September

Average price

$326
From Maryland to Caribbean Islands
Search Deals
One-way flight from Maryland to Caribbean Islands
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 February 2025
Search Deals

Find flight deals from Maryland to Caribbean Islands

Cheapest flights from Maryland to Caribbean Islands
Explore the most affordable flight options available from Maryland to Caribbean Islands. Find the lowest fares from popular airlines and budget airlines, with prices last updated on February 20, 2025.

This CheapOair deal was found by Cheapflights users on 2/19. 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.
Wed 3/2611:34 amBWI - SJU
1 stop14h 18mMultiple Airlines
Wed 4/29:35 pmSJU - BWI
1 stop17h 22mMultiple Airlines
Deal found 2/19$133
This Cheapflightsfares deal was found by Cheapflights users on 2/20. 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.
Fri 3/216:35 amBWI - SJU
Nonstop3h 42mSpirit Airlines
Tue 3/255:39 pmSJU - BWI
1 stop6h 45mSpirit Airlines
Deal found 2/20$135
This Frontier deal was found by Cheapflights users on 2/20. 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.
Thu 5/19:57 pmPHL - SJU
Nonstop3h 53mFrontier
Thu 5/811:20 amSJU - PHL
1 stop14h 01mFrontier
Deal found 2/20$138
This Mytrip deal was found by Cheapflights users on 2/20. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 2/253:50 pmPHL - SJU
Nonstop3h 43mSpirit Airlines
Tue 3/45:56 pmSJU - PHL
1 stop25h 56mSpirit Airlines
Deal found 2/20$139
This FlightHub deal was found by Cheapflights users on 2/20. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 3/178:21 amBWI - SJU
1 stop24h 14mFrontier
Thu 3/209:35 pmSJU - BWI
1 stop12h 07mFrontier
Deal found 2/20$142
This Kiwi.com deal was found by Cheapflights users on 2/20. 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 4/48:04 pmPHL - SJU
Nonstop3h 46mMultiple Airlines
Wed 4/165:00 amSJU - PHL
Nonstop4h 06mMultiple Airlines
Deal found 2/20$145
This Priceline deal was found by Cheapflights users on 2/19. 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.
Mon 4/285:25 pmIAD - SJU
1 stop9h 24mFrontier
Fri 5/29:30 pmSJU - IAD
1 stop14h 12mFrontier
Deal found 2/19$154
This United Airlines deal was found by Cheapflights users on 2/20. 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.
Tue 3/115:35 pmIAD - SJU
Nonstop3h 47mUnited Airlines
Tue 3/183:52 pmSJU - IAD
1 stop8h 07mUnited Airlines
Deal found 2/20$165
This United Airlines deal was found by Cheapflights users on 2/20. 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.
Tue 3/43:00 pmDCA - SJU
1 stop8h 36mUnited Airlines
Wed 3/52:05 amSJU - DCA
1 stop8h 37mUnited Airlines
Deal found 2/20$169
This American Airlines deal was found by Cheapflights users on 2/20. 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.
Wed 4/308:16 amDCA - SJU
1 stop8h 58mAmerican Airlines
Wed 5/711:50 amSJU - DCA
1 stop12h 09mAmerican Airlines
Deal found 2/20$170
This American Airlines deal was found by Cheapflights users on 2/20. 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.
Sat 3/15:13 pmIAD - SJU
1 stop10h 56mAmerican Airlines
Wed 3/54:45 pmSJU - IAD
1 stop17h 05mAmerican Airlines
Deal found 2/20$194
This JetBlue deal was found by Cheapflights users on 2/20. 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 3/41:43 pmDCA - SJU
1 stop6h 19mJetBlue
Wed 3/55:45 amSJU - DCA
1 stop8h 03mJetBlue
Deal found 2/20$213

Find flights from Maryland to Caribbean Islands within your budget

Customize your flight search to find flights from Maryland to Caribbean Islands 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 February 20, 2025.

Fly from

Maryland

Fly to

Caribbean Islands

Route

Depart

Return

Price

BaltimoreSan Juan

BWI - SJU

BWISJU

Baltimore/Washington

Wed 3/26

11:34 am-1:52 am

1 stop14h 18m

San Juan Luis Munoz Marin Intl

Mon 3/31

12:59 am-5:10 am

Nonstop4h 11m

$133

BaltimoreSan Juan

BWI - SJU

BWISJU

Baltimore/Washington

Fri 3/28

9:28 pm-1:10 am

Nonstop3h 42m

San Juan Luis Munoz Marin Intl

Tue 4/1

12:59 am-5:10 am

Nonstop4h 11m

$134

PhiladelphiaSan Juan

PHL - SJU

PHLSJU

Philadelphia

Thu 5/1

9:57 pm-1:50 am

Nonstop3h 53m

San Juan Luis Munoz Marin Intl

Thu 5/8

11:20 am-1:21 am

1 stop14h 01m

$138

PhiladelphiaSan Juan

PHL - SJU

PHLSJU

Philadelphia

Wed 3/5

6:38 pm-10:32 am

1 stop14h 54m

San Juan Luis Munoz Marin Intl

Wed 3/12

5:00 am-9:10 am

Nonstop4h 10m

$141

BaltimoreSan Juan

BWI - SJU

BWISJU

Baltimore/Washington

Mon 3/17

8:21 am-8:35 am

1 stop24h 14m

San Juan Luis Munoz Marin Intl

Thu 3/20

9:35 pm-9:42 am

1 stop12h 07m

$142

PhiladelphiaSan Juan

PHL - SJU

PHLSJU

Philadelphia

Fri 4/4

8:04 pm-11:50 pm

Nonstop3h 46m

San Juan Luis Munoz Marin Intl

Wed 4/16

5:00 am-9:06 am

Nonstop4h 06m

$145

Washington, D.C.San Juan

IAD - SJU

IADSJU

Washington, D.C. Dulles Intl

Mon 4/28

5:25 pm-2:49 am

1 stop9h 24m

San Juan Luis Munoz Marin Intl

Fri 5/2

9:30 pm-11:42 am

1 stop14h 12m

$154

Washington, D.C.San Juan

IAD - SJU

IADSJU

Washington, D.C. Dulles Intl

Tue 3/11

5:35 pm-9:22 pm

Nonstop3h 47m

San Juan Luis Munoz Marin Intl

Tue 3/18

3:52 pm-11:59 pm

1 stop8h 07m

$165

Washington, D.C.San Juan

DCA - SJU

DCASJU

Washington, D.C. Reagan-National

Tue 3/4

3:00 pm-12:36 am

1 stop8h 36m

San Juan Luis Munoz Marin Intl

Wed 3/5

2:05 am-9:42 am

1 stop8h 37m

$169

Washington, D.C.San Juan

DCA - SJU

DCASJU

Washington, D.C. Reagan-National

Wed 4/30

8:16 am-5:14 pm

1 stop8h 58m

San Juan Luis Munoz Marin Intl

Wed 5/7

11:50 am-11:59 pm

1 stop12h 09m

$170

Flights are sorted by cheapest round-trip flights first.

Deals found on 2/20

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

Best time to book a flight from Maryland to Caribbean Islands

Have a flexible travel schedule? Discover the best time to fly to Caribbean Islands 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.

Travel insights for flights from Maryland to Caribbean Islands

Get recent, data-driven insights about flights from Maryland to Caribbean Islands including ideal travel times, pricing trends, and more.

What is the cheapest month to book a flight from Maryland to Caribbean Islands?

Currently, September is the cheapest month in which you can book a flight from Maryland to Caribbean Islands (average of $254). Flying from Maryland to Caribbean Islands in March is currently the most expensive (average of $363). 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 EPX?

Find hourly flight availability from Maryland to Caribbean Islands. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated February 20, 2025.

When flying from Maryland to Caribbean Islands, 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 Islands

Explore weekly flight availability from Maryland to Caribbean Islands. 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 February 20, 2025.

The most flights from USMD to zzEPX 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).

Rainfall in Caribbean Islands by month

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

In terms of precipitation, rainfall in Caribbean Islands 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 Islands when rainfall is around 2.2 in.

Temperature in Caribbean Islands by month

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

If weather is an important factor for your trip to Caribbean Islands, 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 Islands

Get insights into the airlines that provide service to Caribbean Islands. 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 Islands. Reviews last updated February 20, 2025.
Read reviews from past customers who have flown Southwest, Delta and Alaska Airlines from Maryland to Caribbean Islands. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.1
Very good
4,411 reviews

Entertainment

7.6

Boarding

8.2

Overall

8.1

Comfort

8.1

Food

7.1

Crew

8.7

Reviews

1 / 20

2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.

Southwest
8.1
Very good
4,411 reviews
Southwest
8.1
Very good
4,411 reviews

Entertainment

7.6

Boarding

8.2

Overall

8.1

Comfort

8.1

Food

7.1

Crew

8.7

Reviews

1 / 20

2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.

Delta
8.0
Very good
8,219 reviews
Southwest
8.1
Very good
4,411 reviews

Entertainment

7.6

Boarding

8.2

Overall

8.1

Comfort

8.1

Food

7.1

Crew

8.7

Reviews

1 / 20

2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.

Alaska Airlines
8.0
Very good
9,697 reviews
Southwest
8.1
Very good
4,411 reviews

Entertainment

7.6

Boarding

8.2

Overall

8.1

Comfort

8.1

Food

7.1

Crew

8.7

Reviews

1 / 20

2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.

Copa Airlines
7.6
Good
1,510 reviews
Southwest
8.1
Very good
4,411 reviews

Entertainment

7.6

Boarding

8.2

Overall

8.1

Comfort

8.1

Food

7.1

Crew

8.7

Reviews

1 / 20

2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.

Related info for your journey

Find useful and relevant information for your journey from Maryland to Caribbean Islands. 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 Islands one-way?

    The cheapest airline one-way is Frontier, with whom users have recently found tickets for as low as $58. However, be on the lookout for offers from Spirit Airlines and United Airlines, as they are both options that can get you from Maryland to Caribbean Islands for a low price.

  • Can I find deals for flights from Maryland to Caribbean Islands that include hotel bookings?

    Yes. In addition to deals on Maryland to Caribbean Islands flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Maryland to Caribbean Islands?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Maryland to Caribbean Islands.

  • Can I find deals for business class flights from Maryland to Caribbean Islands?

    Yes. Cheapflights offers flight deals from Maryland to Caribbean Islands 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 Islands?

    Currently, September is the cheapest month in which you can book a flight from Maryland to Caribbean Islands (average of $254). Flying from Maryland to Caribbean Islands in March is currently the most expensive (average of $363). 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 Islands

See prices for flight routes from nearby airports that may be better suited for you.
John F Kennedy Intl to Miami flights
Newark to Fort Lauderdale flights
Newark to Miami flights
Newark to Cancún flights
LaGuardia to Fort Lauderdale flights
LaGuardia to Miami flights
John F Kennedy Intl to Fort Lauderdale flights
John F Kennedy Intl to Cancún flights
John F Kennedy Intl to Los Angeles flights
Newark to Orlando flights
Los Angeles to John F Kennedy Intl flights
John F Kennedy Intl to Las Vegas flights
Newark to Los Angeles flights
John F Kennedy Intl to Orlando flights
O'Hare Intl to Cancún flights
Los Angeles to Newark flights
John F Kennedy Intl to West Palm Beach flights
LaGuardia to Dallas/Fort Worth flights
John F Kennedy Intl to Dallas/Fort Worth flights
O'Hare Intl to Fort Lauderdale flights
Dallas/Fort Worth to Cancún flights
O'Hare Intl to Las Vegas flights
John F Kennedy Intl to O'Hare Intl flights
Dallas/Fort Worth to LaGuardia flights
LaGuardia to Orlando flights
Dallas/Fort Worth to Seattle flights
San Francisco to John F Kennedy Intl flights
Dallas/Fort Worth to Las Vegas flights
Newark to Las Vegas flights
Newark to Tampa flights
Boston to Fort Lauderdale flights
Seattle to Los Angeles flights
Newark to Dallas/Fort Worth flights
Dallas/Fort Worth to Orlando flights
O'Hare Intl to John F Kennedy Intl flights
O'Hare Intl to Miami flights
LaGuardia to Cancún flights
Seattle to Sky Harbor Intl flights
O'Hare Intl to Sky Harbor Intl flights
John F Kennedy Intl to Mexico City flights
Dallas/Fort Worth to John F Kennedy Intl flights
John F Kennedy Intl to San Francisco flights
LaGuardia to Tampa flights
John F Kennedy Intl to Sky Harbor Intl flights
John F Kennedy Intl to Tampa flights
Reagan-National to Miami flights
Minneapolis to Sky Harbor Intl flights
Dulles Intl to Orlando flights
Seattle to Las Vegas flights
Minneapolis to Las Vegas flights

Top 8 airlines flying from Maryland to Caribbean Islands

Discover the top 8 airlines that operate flights from Maryland to Caribbean Islands. 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 February 20, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$116Average$339FlexibilityNo cancel feeOn-time62%
Spirit AirlinesCheapest$132Average$392FlexibilityNo cancel feeOn-time65%
JetBlueCheapest$167Average$370FlexibilityNo cancel feeOn-time62%
United AirlinesCheapest$197Average$565FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$276Average$635FlexibilityNo cancel feeOn-time71%
DeltaCheapest$276Average$544FlexibilityNo cancel feeOn-timeN/A
SouthwestCheapest$325Average$677FlexibilityNo cancel feeOn-time63%
Copa AirlinesCheapest$352Average$517FlexibilityNo 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.