$99 Find Cheap Flights from Caribbean Islands to Maryland - Compare and Save

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight from Caribbean Islands to Maryland departing on 8/21. Fares are subject to change and may not be available on all flights or dates of travel. Click the price to replicate the search for this deal.
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1 adult, Economy, 0 bags

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Low season

September

Cheapest flight

$99
Best time to beat the crowds with an average 10% drop in price.
Most popular time to fly and prices are also 19% lower on average.
Flight from San Juan Airport to Philadelphia

Flights from Caribbean Islands to Maryland: the best tips from KAYAK users

Insights shared by verified travelers who flew the route from Caribbean Islands to Maryland 
JoseFlew with Frontier
SJU
-
BWI
Apr 2026
San Juan airport is just like any other airport, just remember to do the agricultural inspection thing, but only usually take like an extra 10 minutes.
AlexisFlew with Spirit Airlines
SJU
-
BWI
Apr 2025
Go early to the airport. Pay for your baggage early to get a discount.

FAQs for booking flights from Caribbean Islands to Maryland

  • How does KAYAK find such low prices on flights from Caribbean Islands to Maryland?

    KAYAK is a travel search engine. That means we look across the web to find the best prices we can find for our users. With over 2 billion flight queries processed yearly, we are able to display a variety of prices and options on flights from Caribbean Islands to Maryland.

  • How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from Caribbean Islands to Maryland?

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight from Caribbean Islands to Maryland is likely to change within 7 days, so travelers know whether to wait or book now.

  • What is the Hacker Fare option on flights from Caribbean Islands to Maryland?

    Hacker Fares allow you to combine one-way tickets in order to save you money over a traditional round-trip ticket. You could then fly from Caribbean Islands to Maryland with an airline and back with another airline.

  • What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from Caribbean Islands to Maryland?

    Sometimes travel dates aren't set in stone. If your preferred travel dates have some wiggle room, flexible dates will show you all the options when flying from Caribbean Islands to Maryland up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

  • How many airports are there in Maryland?

    There are 3 airports in Maryland. The busiest airport is Baltimore/Washington Airport (BWI), with 98% of all flights arriving there.

  • Which is the cheapest airport to fly into in Maryland?

    Prices will differ depending on the departure airport, but generally, the cheapest airport to fly to in Maryland is Baltimore/Washington Airport (BWI), with an average flight price of $341.

  • What is the cheapest day to fly to Maryland?

    Based on KAYAK data, the cheapest day to fly to Maryland is Thursday where round-trip tickets can be as cheap as $351. On the other hand, the most expensive day to fly is Monday, where round-trip prices are $668 on average.

  • What is the cheapest time of day to fly to Maryland?

    The cheapest time of day to fly to Maryland is generally in the evening, when round-trip flights cost $378 on average. Morning departures are around 37% more expensive than evening flights, on average. The most expensive time of day to fly to Maryland is generally in the afternoon, which is peak travel time and where the average cost of a ticket is $716.

  • What is the cheapest flight to Maryland?

    The cheapest ticket to Maryland from Caribbean Islands found in the last 5 days was to Baltimore, at $267 round-trip. The most popular route is Oranjestad (AUA) to Baltimore (BWI) and the cheapest round-trip airline ticket found on this route in the last 5 days was $267.

  • What is the cheapest month to fly from Caribbean Islands to Maryland?

    The cheapest month for flights from Caribbean Islands to Maryland is December, when tickets cost $278 (return) on average. On the other hand, the most expensive months are March and January, when the average cost of round-trip tickets is $390 and $383 respectively.

  • How far in advance should I book a flight from Caribbean Islands to Maryland?

    To get a below average price on the flight from Caribbean Islands to Maryland, you should book around 3 weeks before departure, which saves you about 60% compared to booking last minute. For the absolute cheapest price, our data suggests you should book 5 weeks before departure.

  • How many cities have direct flights to Maryland?

    From Caribbean Islands, there are direct flights to Maryland from 7 cities. The city with the most direct flights is San Juan, with 29 direct flights each week.

  • How many direct flights to Maryland are there each day?

    There are around 10 direct flights from within Caribbean Islands to Maryland every day. Most flights (62%) depart in the afternoon.

  • How many direct flights to Maryland are there each week?

    Each week there are around 65 direct flights from within Caribbean Islands to Maryland. The most common day for departures is Sunday, with 28% of flights taking off on this day.

  • How long is the flight to Maryland?

    An average nonstop flight from Caribbean Islands to Maryland takes 6h 12m, covering a distance of 1546 miles. The shortest route is Nassau (NAS) to Philadelphia (PHL) with an average flight time of 2h 54m.

  • How many long-haul flights are there to Maryland each week?

    Each week, there are 40 medium-haul flights (3-6 hour flight duration) and 25 short-haul flights (up to 3 hour flight duration) to Maryland. There aren't any long-haul flights (6-12 hour flight duration).

  • What are the most popular destinations in Maryland?

    Based on KAYAK flight searches, the most popular destination is Washington, D.C. (62% of total searches to Maryland). The next most popular destination is Philadelphia (38%).

Reviews of the top 5 airlines serving from Caribbean Islands to Maryland

 
Need help choosing which airline to fly with from Caribbean Islands to Maryland? KAYAK airline reviews give an overall score for each airline based on loads of factors, including comfort, boarding, in-flight entertainment and more, to make your decision easier. See airline scores according to verified KAYAK customer reviews.
8.0
SouthwestOverall score based on 4224 reviews
8.6Crew
8.0Comfort
8.1Boarding
7.5Entertainment
7.0Food
Airline reviews

The flight was fine. Seats were very comfortable. Attendants were very friendly -

10.0 ExcellentMaggie, Jul 2026
SJO - BWI
Read more Southwest reviews

The flight was fine. Seats were very comfortable. Attendants were very friendly -

Flight coming out of Buffalo was delayed, so we had to be rescheduled on another flight from Baltimore to Phoenix which means we had a long layover and got home 3.5 hours late. Shuttle to parking stopped at 10pm, so we had to pay for an Uber to the parking lot and got charged an extra day of parking since it was after midnight. Not the best experience. Long day!

Terrible all around. Left prior review detailing massive delay/cancellation to then rebook travel. Topping on the cake was lost luggage even after travel to ultimate destination was secured on a new plane(s).

I am very please with the service received from Southwest. Although there was a refuel stop in Fl before we got the Baltimore. The service and kindness of the staff was excellent.

Southwest continues to do less for more money. Flight attendants used to be fun and friendly. But now it’s like they don’t even see you. Such a shame.

I liked it better when you were truer to your roots Am paying more for less fun

We had a 5 hour delay on the tarmac in Baltimore

Long layover between flights to Long Island from BWI - need better coordination between flights

The last 3 flights between BWI and BDL canceled the beverage service mid- way. Just say up front that the fight is too short. Thanks!

I was assigned seat 7E, yet my boarding was Group 5, which caused me to have to put my luggage in the back of the plance above `19 or 20 aisle, as passengers who had boarded earlier took the overhead bins in the front. SW needs to monitor bin space and ensure that bin space above the seat are aligned to those sitting near their seats. Also the seating assignments needs to align with group number. Maybe board those last first and so on? Having said the ALL the passengers on the plane were gracious enough to allow me and other passengers in this dilema to retrieve our luggage and helped us along the way. I always love the flight staff, as always their fantastic and I can't rave about them enough!

Internet connectivity still seems to be touchy on these flights, making it difficult to rely on it for getting work done.

The ac must have died, it was way to hot on this flight. Boarding g was chaotic. The flight was delayed for boarding. Not a great experience.

Delta continues to decline. This was international flight with paid meals & minimal knacks. All drinks were served in paper coffee cups including wine & bee that was purchased, The bathrooms were not cleaned & maintained. Trash container was overfilled with no placed to dispose paper towels. The flight arrived safely. That counts.

Comfortable seats. Nice service online. Short flight, so not a lot of time to enjoy.

Awful. There was an unexpected delay of nearly three hours because there were not enough flight attendants. I understand this is likely due to FAA regulations; but in that case, Delta should coordinate with smaller airports such as RDU to have extra flight attendants on the ground and "on call". In addition, this was the second 2-hour+ delay to Boston on this route in one week.

It was strange that the flight attendant was so adamant about having phones turned to airplane mode that he was calling out names from networks shown and waiting until they were all gone. I've never experienced that before, and after already working through an hour+ delay, it felt tone deaf. I take dozens of flights per year and have never experienced anything similar.

The flight was done by SkyWest only WIFI no entertainment center are available on the CRJ

DTW line is too long. The flights from DTW to BWI are always delayed for unknown reasons.

Service was good for such a short flight. Small plane but smooth flight.

Could not hear any of the announcements. The speakers seemed out of service. I wish the entertainment system would allow me to watch on my own iPad than the airplane ‘s old display.

Flight staff and all was fine. Food always sucks on planes so nothing new.

The flight crew were very helpful. The seats were very close together. There was barely room to sit without touching the person next to you.

Baggage claim signs were not updated with my flight information, so I had to guess. The app wasn't updated either.

Not being stranded in Chicago for her airport to 11:30 tomorrow morning the 3rd

Everything was great. Only thing that could’ve made it better was buy on board options for hot food, but the snacks were decent. The flight attendants were great. I had no complaints. I was able to make it to my destination safely

David went above and beyond to make our flight the best that it could be

The crew and flight was amazing. I haven't flown United in years but plan to switch to you being my main airline

Wouldn’t let me check in said couldn’t find a ticket had to wait very long Time

Seat cushions were worn down and it hurts as I seated under 5 hours of the plane ride.

I wish I had another choice. Domestic flight in the USA is atrocious.

A more comfortable seat. Padding would be really helpful but I've read the airlines don't want customers to be satisfied with economy seats.

Everything was good except checking bags . I had paid for two bags but it didn’t show so we had to do it again while people waited and we were struggling to get to our flight

Flight was delayed. But my finances flight with JetBlue a week before same route was extra delayed and then cancelled at 2am when his flight was suppose to take off at 7pm was never provided a hotel or anything. Came back to airport and his rescheduled flight was cancelled again for 2 days later. Was told since it was a weather issue they don’t do refunds. But that’s a lie because I booked him on another airline at the same time and they were able to take off perfectly fine

Flight delayed 4 times on a non-stop from BOS to SFO. Then when landed in SFO had to wait for 30 mins for a gate AT 3:30AM.

Plane was delayed multiple times. I would like to request a refund. Was due to arrive Thursday evening ended up arriving Friday morning.

The seats were roomier than other airplanes I’ve been on.

The security line at JFK was one of the longest I’ve ever experienced - probably 45 minutes. I don’t know if JetBlue has control over it, but it detracted from the overall experience. Entertainment had good options, but the volume control was a bit small to tap on and the screen had a fair amount of interference blips. Clearer picture would have been better.

I liked the entertainment on JetBlue, the service from JFK to JAX was terrible at best

Checking-in in Barbados was excellent, connecting in JFK to JAX was a nightmare, had to wait over 1 hour and 20 minutes to receive my check bag. After receiving my checked bag and going to the gate to check in for my flight to Jax the crew there had no clue. They first told me that I had missed the flight and had to rebooked.. after trying to speak with JetBlue reservations (without luck) I was asked to leave my Phone number for a recall, I did so and my call was returned after 15 hours. I finally looked at the information board and saw the flight that I was originally scheduled for was still at the gate. I alerted an JetBlue employee of my findings and was told to rush to the gate and see if I could still board. The agent at the boarding gate apparently was having a very bad day, after lecturing me on how late I was (which was not a fault of mine) let me on the flight. A VERY BAD EXPERIENCE. I will NEVER fly JetBlue ever in my life again.

I usually dont fly JeTBlue and I dont think I will ever do it again. The flight was delayed fee time, nobody was giving us any info at at the airport, gate changing, the slowest and poorly organized boarding ever, rude staff.. huh

Great. Clean. Seats comfortable. Food was free. Had new release movies.

The airplane I love and I love I came back safe thank you American airlines

Although there were two delays, they were communicated clearly and the boarding process was expedited. The crew was pleasant and efficient.

The flight I booked was conveniently timed, had one brief stop and was going to be quick. The flight I ended up getting was delayed, took longer, had a far longer layover and arrived hours later than planned. Thanks for nothing.

Flight attendant made the flight very enjoyable. He was courteous and gave great care to the passengers

Food horrible, even because there was no food the personal was rude and show off and the landing and take off ,was an adventure.

Flight was delayed, boarded, sat at the gate for more than 30 minutes, left the gate then waited on the pad for another 30 to 60 minutes then returned to the gate, deboarded and was cancelled... alternative flight was not booked automatically. Waited in line for 30 minutes but fortunately an alternate flight to a different destination was found ... no thanks to the travel agent used by kayak

The flight changed gates multiple times and flight had to be delayed multiple times

I like that the crew kept us informed but we moved back and forth from gate to gate before the aircraft arrived.

Boarding went fine, the plane was clean, and the crew was very friendly. Seats were a bit cramped, but that seems to be typical on all airlines anymore. Cookies and pretzels were offered as were beverages - the usual. I’d fly American again.

Everything you need to know for your flight to Maryland

Cabin class types available on flights to Caribbean Islands

Cabin classes available on flights to Caribbean Islands. Prices are the lowest found on KAYAK over the last 7 days. Price and availability is not guaranteed.