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$85+ Cheap flights from Caribbean to Maryland

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 11/22. Fares are subject to change and may not be available on all flights or dates of travel.
SJU — BWI
Dec 3 — Dec 101
Wed 12/3
Wed 12/10
1 adult, Economy
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Cheap flight deals from Caribbean to Maryland

Keep the following information in mind while searching for Caribbean to Maryland flight deals. Data was last updated November 3, 2025.

Round-trip from

$138
(CheapOair)

One-way from

$85
(Kiwi.com)

Popular in

October

Cheapest in

July

Average price

$273

Good round-trip deal

$149 or less

Good one-way deal

$142 or less
From Caribbean to Maryland
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One-way flight from Caribbean to Maryland
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Highest demand for flights based on searches. 6% potential increase in price ($17 potential increase over avg. RT price).
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Cheapest flight prices on average. 1% potential price decrease ($6 potential savings vs. average RT price).
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Average for round-trip flights in November 2025
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Price to beat on a round-trip flight from Caribbean to Maryland.
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Price to beat on a one-way flight from Caribbean to Maryland.
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Find flight deals from Caribbean to Maryland

Cheapest flights from Caribbean to Maryland
Explore the most affordable flight options available from Caribbean to Maryland. Find the lowest fares from popular airlines and budget airlines, with prices last updated on November 3, 2025.

This CheapOair deal was found by Cheapflights users on 11/2. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/204:18 pmSJU - IAD
Nonstop4h 13mFrontier
Sun 1/48:26 pmIAD - SJU
Nonstop3h 54mFrontier
Deal found 11/2$138
This CheapOair deal was found by Cheapflights users on 11/1. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 12/214:18 pmSJU - IAD
Nonstop4h 13mFrontier
Sun 1/48:26 pmIAD - SJU
Nonstop3h 54mFrontier
Deal found 11/1$148
This Cheapflightsfares deal was found by Cheapflights users on 11/1. 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.
Fri 12/191:59 amSJU - PHL
Nonstop4h 05mFrontier
Sat 1/37:42 pmPHL - SJU
Nonstop3h 47mFrontier
Deal found 11/1$153
This eDestinos deal was found by Cheapflights users on 11/2. 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 eDestinos is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/242:25 amSJU - PHL
Nonstop4h 07mFrontier
Mon 12/86:00 amPHL - SJU
Nonstop3h 47mFrontier
Deal found 11/2$159
This Kiwi.com deal was found by Cheapflights users on 11/1. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/214:08 pmSJU - IAD
Nonstop4h 03mFrontier
Sun 11/238:06 pmIAD - SJU
Nonstop3h 47mFrontier
Deal found 11/1$161
This Cheapflightsfares deal was found by Cheapflights users on 11/3. 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.
Tue 12/231:59 amSJU - PHL
Nonstop4h 05mFrontier
Fri 1/27:42 pmPHL - SJU
Nonstop3h 47mFrontier
Deal found 11/3$164
This CheapOair deal was found by Cheapflights users on 11/2. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/219:54 pmSJU - PHL
Nonstop4h 07mFrontier
Sat 12/68:02 pmPHL - SJU
Nonstop3h 47mFrontier
Deal found 11/2$166
This Kiwi.com deal was found by Cheapflights users on 11/3. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/2112:37 pmSJU - PHL
Nonstop4h 07mFrontier
Sun 12/76:00 amPHL - SJU
Nonstop3h 47mFrontier
Deal found 11/3$167
This Frontier deal was found by Cheapflights users on 11/2. 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.
Mon 12/224:18 pmSJU - IAD
Nonstop4h 13mFrontier
Sat 1/38:26 pmIAD - SJU
Nonstop3h 54mFrontier
Deal found 11/2$168
This Kiwi.com deal was found by Cheapflights users on 11/2. 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.
Sat 12/2010:09 pmSJU - PHL
Nonstop4h 05mFrontier
Tue 1/63:08 pmPHL - SJU
Nonstop3h 47mFrontier
Deal found 11/2$168
This eDestinos deal was found by Cheapflights users on 11/2. 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 eDestinos is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/242:25 amSJU - PHL
Nonstop4h 07mFrontier
Mon 12/16:40 amPHL - SJU
Nonstop3h 47mFrontier
Deal found 11/2$174
This Frontier deal was found by Cheapflights users on 11/2. 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.
Tue 11/257:10 amSJU - BWI
Nonstop4h 04mFrontier
Mon 12/11:02 pmBWI - SJU
Nonstop3h 51mFrontier
Deal found 11/2$176

Cheapflights Fare Finder

 
Customize your flight search to find flights from Caribbean to Maryland 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 November 3, 2025.
Use the filters below to find and compare flights from Caribbean to Maryland that are best for you.

Fly from

Caribbean

Fly to

Maryland

Route

Depart

Return

Price

San JuanWashington, D.C.

SJU - DCA

SJUDCA

San Juan Luis Munoz Marin Intl

Fri 12/5

7:19 am-5:59 pm

1 stop11h 40m

Washington, D.C. Reagan-National

Mon 12/8

6:07 am-5:20 pm

1 stop10h 13m

$205

San JuanWashington, D.C.

SJU - IAD

SJUIAD

San Juan Luis Munoz Marin Intl

Fri 1/23

6:27 pm-12:24 am

1 stop6h 57m

Washington, D.C. Dulles Intl

Tue 1/27

6:00 am-2:10 pm

1 stop7h 10m

$205

San JuanWashington, D.C.

SJU - DCA

SJUDCA

San Juan Luis Munoz Marin Intl

Wed 1/21

6:45 pm-9:46 pm

Nonstop4h 01m

Washington, D.C. Reagan-National

Sun 1/25

8:00 am-12:42 pm

Nonstop3h 42m

$216

San JuanWashington, D.C.

SJU - IAD

SJUIAD

San Juan Luis Munoz Marin Intl

Thu 11/13

1:57 pm-9:32 pm

1 stop8h 35m

Washington, D.C. Dulles Intl

Mon 11/17

12:37 pm-11:13 pm

1 stop9h 36m

$245

San JuanPhiladelphia

SJU - PHL

SJUPHL

San Juan Luis Munoz Marin Intl

Fri 12/5

6:38 pm-12:51 am

1 stop7h 13m

Philadelphia

Mon 12/8

2:24 pm-11:20 pm

1 stop7h 56m

$247

San JuanBaltimore

SJU - BWI

SJUBWI

San Juan Luis Munoz Marin Intl

Thu 11/20

5:38 pm-8:42 pm

Nonstop4h 04m

Baltimore/Washington

Tue 12/2

4:01 pm-8:40 pm

Nonstop3h 39m

$249

San JuanWashington, D.C.

SJU - DCA

SJUDCA

San Juan Luis Munoz Marin Intl

Thu 11/6

2:06 pm-11:02 pm

1 stop9h 56m

Washington, D.C. Reagan-National

Mon 11/10

6:59 am-2:17 pm

1 stop6h 18m

$275

San JuanWashington, D.C.

SJU - IAD

SJUIAD

San Juan Luis Munoz Marin Intl

Thu 1/15

3:55 pm-11:37 pm

1 stop8h 42m

Washington, D.C. Dulles Intl

Sun 1/18

12:37 pm-11:44 pm

1 stop10h 07m

$279

San JuanPhiladelphia

SJU - PHL

SJUPHL

San Juan Luis Munoz Marin Intl

Mon 1/12

2:05 am-2:31 pm

2 stops13h 26m

Philadelphia

Tue 1/20

8:05 am-9:26 pm

1 stop12h 21m

$283

Punta CanaBaltimore

PUJ - BWI

PUJBWI

Punta Cana

Sat 1/10

1:21 pm-11:54 pm

1 stop11h 33m

Baltimore/Washington

Sat 1/31

5:10 am-12:16 pm

1 stop6h 06m

$289

Flights are sorted by cheapest round-trip flights first.

Deals found on 11/2

Showing 1-10 of 60 results
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Best time to book a flight from Caribbean to Maryland

Have a flexible travel schedule? Discover the best time to fly to Maryland from Caribbean 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 Caribbean to Maryland

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

Currently, December is the cheapest month in which you can book a flight from Caribbean to Maryland (average of $54). Flying from Caribbean to Maryland in August is currently the most expensive (average of $128). 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 CB to MD?

Find hourly flight availability from Caribbean to Maryland. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated November 3, 2025.

One of the essential ways to save on airfare from Caribbean to Maryland is to remain as flexible as possible. Flights that are at noon tend to be the most expensive. A flight in the evening could potentially save you up to 37% on airfare.

What is the cheapest day to fly from Caribbean to Maryland?

Use this chart to determine the cheapest time to fly round-trip from Caribbean to Maryland. Price data was last updated on December 16, 2024.

Travelers seeking maximum savings on their Caribbean to Maryland flight should consider departing on Saturday evenings when fares are most often at their lowest. Monday at noon flights should be avoided if possible as fares are typically the most expensive at this time.

Reviews of airlines servicing Maryland

Get insights into the airlines that provide service to Maryland. 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 Maryland. Reviews last updated November 3, 2025.
Get a feel of what it's like to fly with Southwest, United Airlines, and American Airlines from Caribbean to Maryland by reading reviews from past customers. You can also see how each airline compares in terms of entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.0
Very good
4,238 reviews

Overall

8.0

Entertainment

7.5

Boarding

8.1

Crew

8.6

Comfort

8.0

Food

7.0

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
Southwest
8.0
Very good
4,238 reviews
Southwest
8.0
Very good
4,238 reviews

Overall

8.0

Entertainment

7.5

Boarding

8.1

Crew

8.6

Comfort

8.0

Food

7.0

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
United Airlines
7.4
Good
8,997 reviews
Southwest
8.0
Very good
4,238 reviews

Overall

8.0

Entertainment

7.5

Boarding

8.1

Crew

8.6

Comfort

8.0

Food

7.0

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
American Airlines
7.2
Good
11,038 reviews
Southwest
8.0
Very good
4,238 reviews

Overall

8.0

Entertainment

7.5

Boarding

8.1

Crew

8.6

Comfort

8.0

Food

7.0

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
Spirit Airlines
6.3
Okay
8,115 reviews
Southwest
8.0
Very good
4,238 reviews

Overall

8.0

Entertainment

7.5

Boarding

8.1

Crew

8.6

Comfort

8.0

Food

7.0

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
Frontier
5.8
Fair
3,117 reviews
Southwest
8.0
Very good
4,238 reviews

Overall

8.0

Entertainment

7.5

Boarding

8.1

Crew

8.6

Comfort

8.0

Food

7.0

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines

Related info for your journey

Find useful and relevant information for your journey from Caribbean to Maryland. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • How long is the flight from Caribbean to Maryland?

    Airlines like Delta, JetBlue, and Spirit Airlines fly from Caribbean to Maryland in about 4h 01m. The time it takes to get you to your destination can typically vary by up to 7h 39m. Caribbean and Maryland are separated by a distance of 1557 mi. Both multi-stop and nonstop flights can be found to your destination and back.

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

    One-way options have recently been found by users for as low as $92 on Frontier. Other airlines that offer cheap prices include United Airlines from $98 and JetBlue from $108 one-way.

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

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

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

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

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

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

    Currently, December is the cheapest month in which you can book a flight from Caribbean to Maryland (average of $54). Flying from Caribbean to Maryland in August is currently the most expensive (average of $128). 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 Caribbean to Maryland

See prices for flight routes from nearby airports that may be better suited for you.
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Top 5 airlines flying from Caribbean to Maryland

Discover the top 5 airlines that operate flights from Caribbean to Maryland. 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 November 3, 2025.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$111Average$331FlexibilityNo cancel feeOn-time65%
FrontierCheapest$112Average$291FlexibilityNo cancel feeOn-time62%
American AirlinesCheapest$165Average$487FlexibilityNo cancel feeOn-time71%
DeltaCheapest$321Average$513FlexibilityNo cancel feeOn-timeN/A
SouthwestCheapest$328Average$589FlexibilityNo cancel feeOn-time63%

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