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Caribbean Islands

$83+ 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 8/18. Fares are subject to change and may not be available on all flights or dates of travel.
BWI — SJU
Aug 9 — Aug 161
Sat 8/9
Sat 8/16
1 adult, Economy
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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 August 4, 2025.

Round-trip from

$166
(Frontier)

One-way from

$83
(FlightHub)

Popular in

December

Cheapest in

March

Average price

$326
From Maryland to Caribbean Islands
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One-way flight from Maryland to Caribbean Islands
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Highest demand for flights based on searches. 12% potential increase in price ($49 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 August 2025
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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 August 4, 2025.

This Frontier deal was found by Cheapflights users on 8/2. 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.
Sun 8/1712:31 pmIAD - SJU
Nonstop3h 57mFrontier
Sat 8/236:30 amSJU - IAD
Nonstop3h 56mFrontier
Deal found 8/2$166
This Cheapflightsfares deal was found by Cheapflights users on 8/2. 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.
Thu 9/188:42 pmBWI - SJU
Nonstop4h 01mSpirit Airlines
Thu 9/257:05 amSJU - BWI
Nonstop4h 00mSpirit Airlines
Deal found 8/2$168
This FlightHub deal was found by Cheapflights users on 7/31. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 8/173:51 pmPHL - SJU
1 stop17h 14mMultiple Airlines
Wed 8/2012:59 amSJU - PHL
Nonstop4h 01mMultiple Airlines
Deal found 7/31$180
This United Airlines deal was found by Cheapflights users on 8/1. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/165:32 pmIAD - SJU
Nonstop3h 50mUnited Airlines
Thu 11/208:30 amSJU - IAD
Nonstop4h 05mUnited Airlines
Deal found 8/1$186
This Cheapflightsfares deal was found by Cheapflights users on 8/3. 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 8/173:51 pmPHL - SJU
1 stop17h 14mSpirit Airlines
Thu 8/212:11 amSJU - PHL
1 stop10h 50mSpirit Airlines
Deal found 8/3$188
This Cheapflightsfares deal was found by Cheapflights users on 8/1. 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.
Wed 11/127:10 amPHL - SJU
Nonstop3h 46mFrontier
Sat 11/151:11 amSJU - PHL
Nonstop3h 58mFrontier
Deal found 8/1$189
This American Airlines deal was found by Cheapflights users on 8/1. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/235:55 pmDCA - SJU
1 stop17h 16mAmerican Airlines
Wed 9/244:43 pmSJU - DCA
1 stop6h 18mAmerican Airlines
Deal found 8/1$190
This American Airlines deal was found by Cheapflights users on 8/1. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/257:44 amIAD - SJU
1 stop13h 46mAmerican Airlines
Fri 8/293:50 pmSJU - IAD
1 stop8h 02mAmerican Airlines
Deal found 8/1$195
This Kiwi.com deal was found by Cheapflights users on 8/2. 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 8/3112:11 pmBWI - SJU
Nonstop3h 52mMultiple Airlines
Sun 9/76:44 amSJU - BWI
1 stop8h 48mMultiple Airlines
Deal found 8/2$198
This Delta deal was found by Cheapflights users on 8/1. 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 10/183:33 pmIAD - SJU
1 stop6h 26mDelta
Sat 10/257:15 amSJU - IAD
1 stop7h 23mDelta
Deal found 8/1$215
This JetBlue deal was found by Cheapflights users on 7/31. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/18:30 amDCA - SJU
Nonstop3h 49mJetBlue
Wed 10/16:05 pmSJU - DCA
Nonstop3h 50mJetBlue
Deal found 7/31$221
This American Airlines deal was found by Cheapflights users on 8/3. 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.
Fri 10/108:10 pmPHL - SJU
Nonstop3h 49mAmerican Airlines
Fri 10/175:30 amSJU - PHL
Nonstop4h 20mAmerican Airlines
Deal found 8/3$230

Cheapflights Fare Finder

 
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 August 4, 2025.
Use the filters below to find and compare flights from Maryland to Caribbean Islands that are best for you.

Fly from

Maryland

Fly to

Caribbean Islands

Route

Depart

Return

Price

Washington, D.C.San Juan

IAD - SJU

IADSJU

Washington, D.C. Dulles Intl

Sun 8/17

12:31 pm-4:28 pm

Nonstop3h 57m

San Juan Luis Munoz Marin Intl

Sat 8/23

6:30 am-10:26 am

Nonstop3h 56m

$166

BaltimoreSan Juan

BWI - SJU

BWISJU

Baltimore/Washington

Thu 9/18

8:42 pm-12:43 am

Nonstop4h 01m

San Juan Luis Munoz Marin Intl

Thu 9/25

7:05 am-11:05 am

Nonstop4h 00m

$168

PhiladelphiaSan Juan

PHL - SJU

PHLSJU

Philadelphia

Sun 8/17

3:51 pm-9:05 am

1 stop17h 14m

San Juan Luis Munoz Marin Intl

Wed 8/20

12:59 am-5:00 am

Nonstop4h 01m

$180

Washington, D.C.San Juan

IAD - SJU

IADSJU

Washington, D.C. Dulles Intl

Sun 11/16

5:32 pm-10:22 pm

Nonstop3h 50m

San Juan Luis Munoz Marin Intl

Thu 11/20

8:30 am-11:35 am

Nonstop4h 05m

$186

PhiladelphiaSan Juan

PHL - SJU

PHLSJU

Philadelphia

Sun 8/17

3:51 pm-9:05 am

1 stop17h 14m

San Juan Luis Munoz Marin Intl

Thu 8/21

2:11 am-1:01 pm

1 stop10h 50m

$188

PhiladelphiaSan Juan

PHL - SJU

PHLSJU

Philadelphia

Wed 11/12

7:10 am-11:56 am

Nonstop3h 46m

San Juan Luis Munoz Marin Intl

Sat 11/15

1:11 am-4:09 am

Nonstop3h 58m

$189

Washington, D.C.San Juan

DCA - SJU

DCASJU

Washington, D.C. Reagan-National

Tue 9/23

5:55 pm-11:11 am

1 stop17h 16m

San Juan Luis Munoz Marin Intl

Wed 9/24

4:43 pm-11:01 pm

1 stop6h 18m

$190

Washington, D.C.San Juan

IAD - SJU

IADSJU

Washington, D.C. Dulles Intl

Mon 8/25

7:44 am-9:30 pm

1 stop13h 46m

San Juan Luis Munoz Marin Intl

Fri 8/29

3:50 pm-11:52 pm

1 stop8h 02m

$195

BaltimoreSan Juan

BWI - SJU

BWISJU

Baltimore/Washington

Sun 8/31

12:11 pm-4:03 pm

Nonstop3h 52m

San Juan Luis Munoz Marin Intl

Sun 9/7

6:44 am-3:32 pm

1 stop8h 48m

$198

Washington, D.C.San Juan

IAD - SJU

IADSJU

Washington, D.C. Dulles Intl

Sat 10/18

3:33 pm-9:59 pm

1 stop6h 26m

San Juan Luis Munoz Marin Intl

Sat 10/25

7:15 am-2:38 pm

1 stop7h 23m

$215

Flights are sorted by cheapest round-trip flights first.

Deals found on 8/1

Showing 1-10 of 60 results
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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.

Cheapflights Insights

Everything you need to know about your flight from Maryland to Caribbean Islands

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 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 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 August 4, 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 August 4, 2025.

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

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 August 4, 2025.
Read reviews from past customers who have flown Southwest, Delta, and Copa Airlines from Maryland to Caribbean Islands. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.0
Very good
4,246 reviews

Comfort

8.0

Overall

8.0

Crew

8.6

Entertainment

7.5

Food

7.0

Boarding

8.1

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
4,246 reviews
Southwest
8.0
Very good
4,246 reviews

Comfort

8.0

Overall

8.0

Crew

8.6

Entertainment

7.5

Food

7.0

Boarding

8.1

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
7,986 reviews
Southwest
8.0
Very good
4,246 reviews

Comfort

8.0

Overall

8.0

Crew

8.6

Entertainment

7.5

Food

7.0

Boarding

8.1

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
1,496 reviews
Southwest
8.0
Very good
4,246 reviews

Comfort

8.0

Overall

8.0

Crew

8.6

Entertainment

7.5

Food

7.0

Boarding

8.1

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
8,909 reviews
Southwest
8.0
Very good
4,246 reviews

Comfort

8.0

Overall

8.0

Crew

8.6

Entertainment

7.5

Food

7.0

Boarding

8.1

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.
American Airlines
7.2
Good
10,000 reviews
Southwest
8.0
Very good
4,246 reviews

Comfort

8.0

Overall

8.0

Crew

8.6

Entertainment

7.5

Food

7.0

Boarding

8.1

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 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 Spirit Airlines, with whom users have recently found tickets for as low as $83. However, be on the lookout for offers from American Airlines and Frontier, 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 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

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Alternative routes for Maryland to Caribbean Islands

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 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 August 4, 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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