$67+ 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 1/16. Fares are subject to change and may not be available on all flights or dates of travel.
Find cheap flights from Caribbean to Maryland 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
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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 Caribbean to Maryland
Cheapest flights from Caribbean to MarylandExplore 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 December 27, 2025.
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 December 27, 2025.
This Super.com deal was found by Cheapflights users on 12/26. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
This Frontier deal was found by Cheapflights users on 12/26. 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.
This Cheapflightsfares deal was found by Cheapflights users on 12/25. 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.
This eDestinos deal was found by Cheapflights users on 12/25. 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.
This Kiwi.com deal was found by Cheapflights users on 12/25. 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.
This Expedia deal was found by Cheapflights users on 12/26. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
This Cheapflightsfares deal was found by Cheapflights users on 12/26. 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.
This CheapOair deal was found by Cheapflights users on 12/26. 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.
This Orbitz deal was found by Cheapflights users on 12/24. 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 Orbitz is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
This Cheapflightsfares deal was found by Cheapflights users on 12/26. 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.
This Frontier deal was found by Cheapflights users on 12/24. 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.
This Cheapflightsfares deal was found by Cheapflights users on 12/25. 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.
Find flight deals from Caribbean to Maryland
Keep the following information in mind while searching for Caribbean to Maryland flight deals. Data was last updated December 27, 2025.
Round-trip from | $120 (Cheapflightsfares) |
|---|---|
One-way from | $67 (eDestinos) |
Popular in | March |
Cheapest in | July |
Average price | $288 |
Good round-trip deal | $218 or less |
Good one-way deal | $151 or less |
Cheapflights Fare Finder
Use the filters below to find and compare flights from Caribbean to Maryland that are best for you.
Fly from
Fly to
Route
Depart
Return
Price
San JuanWashington, D.C.
SJU - IAD
SJUIAD
San Juan Luis Munoz Marin Intl
Fri 2/20
4:17 pm-7:25 pm
Nonstop4h 08m
Washington, D.C. Dulles Intl
Mon 2/23
8:20 pm-1:05 am
Nonstop3h 45m
San JuanWashington, D.C.
SJU - IAD
SJUIAD
San Juan Luis Munoz Marin Intl
Fri 1/16
3:11 pm-6:19 pm
Nonstop4h 08m
Washington, D.C. Dulles Intl
Mon 1/19
8:53 pm-3:26 pm
1 stop17h 33m
San JuanWashington, D.C.
SJU - IAD
SJUIAD
San Juan Luis Munoz Marin Intl
Thu 1/8
6:30 am-2:26 pm
1 stop8h 56m
Washington, D.C. Dulles Intl
Mon 1/12
7:19 pm-12:13 am
Nonstop3h 54m
San JuanPhiladelphia
SJU - PHL
SJUPHL
San Juan Luis Munoz Marin Intl
Wed 2/18
2:54 am-6:06 am
Nonstop4h 12m
Philadelphia
Thu 2/26
8:39 pm-1:24 am
Nonstop3h 45m
San JuanPhiladelphia
SJU - PHL
SJUPHL
San Juan Luis Munoz Marin Intl
Fri 1/16
6:48 pm-8:47 am
1 stop14h 59m
Philadelphia
Thu 1/22
8:56 pm-1:41 am
Nonstop3h 45m
San JuanWashington, D.C.
SJU - IAD
SJUIAD
San Juan Luis Munoz Marin Intl
Fri 1/9
10:47 pm-1:16 pm
1 stop15h 29m
Washington, D.C. Dulles Intl
Sun 1/11
7:19 pm-12:13 am
Nonstop3h 54m
San JuanBaltimore
SJU - BWI
SJUBWI
San Juan Luis Munoz Marin Intl
Thu 1/15
9:29 pm-12:38 am
Nonstop4h 09m
Baltimore/Washington
Sun 1/18
10:12 am-2:54 pm
Nonstop3h 42m
San JuanBaltimore
SJU - BWI
SJUBWI
San Juan Luis Munoz Marin Intl
Thu 1/22
9:29 pm-12:38 am
Nonstop4h 09m
Baltimore/Washington
Sat 1/31
6:15 pm-9:54 am
1 stop14h 39m
San JuanWashington, D.C.
SJU - IAD
SJUIAD
San Juan Luis Munoz Marin Intl
Fri 2/27
4:17 pm-7:25 pm
Nonstop4h 08m
Washington, D.C. Dulles Intl
Sun 3/1
2:04 pm-2:25 am
1 stop11h 21m
San JuanWashington, D.C.
SJU - IAD
SJUIAD
San Juan Luis Munoz Marin Intl
Sat 1/10
2:57 pm-6:10 pm
Nonstop4h 13m
Washington, D.C. Dulles Intl
Sat 1/17
4:17 pm-9:02 pm
Nonstop3h 45m
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.
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, April is the cheapest month in which you can book a flight from Caribbean to Maryland (average of $71). Flying from Caribbean to Maryland in November is currently the most expensive (average of $156). 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 December 27, 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 42% 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 Tuesday at noon 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.
Weekly flight availability from Caribbean to Maryland
Explore weekly flight availability from Caribbean to Maryland. 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 December 27, 2025.
The most flights from 0CB to USMD are scheduled on a Monday (5 on average). You will have fewer flight options on Tuesday, which is when the least amount of flights are scheduled (3 on average).
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 December 27, 2025.
Get a feel of what it's like to fly with Southwest, Delta, 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.
Comfort
Overall
Boarding
Food
Entertainment
Crew
Reviews
Thomas,Dec 2025
SEA - DEN
Comfort
Overall
Boarding
Food
Entertainment
Crew
Reviews
Thomas,Dec 2025
SEA - DEN
Comfort
Overall
Boarding
Food
Entertainment
Crew
Reviews
Thomas,Dec 2025
SEA - DEN
Comfort
Overall
Boarding
Food
Entertainment
Crew
Reviews
Thomas,Dec 2025
SEA - DEN
Comfort
Overall
Boarding
Food
Entertainment
Crew
Reviews
Thomas,Dec 2025
SEA - DEN
Comfort
Overall
Boarding
Food
Entertainment
Crew
Reviews
Thomas,Dec 2025
SEA - DEN
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.
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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.
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 December 27, 2025.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$111 | Average$233 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$121 | Average$310 | FlexibilityNo cancel fee | On-time65% | |
| Cheapest$165 | Average$490 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$321 | Average$520 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$328 | Average$532 | FlexibilityNo cancel fee | On-time63% |