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Useful Info

Good to know

Low season

September
Best time to beat the crowds with an average 18% drop in price.
Most popular time to fly with an average 2% increase in price.

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-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-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.

  • Which airlines fly most frequently to Maryland?

    Caribbean Islands and Maryland are connected by different airlines. The airlines that fly that route the most regularly are Southwest (51 flights per week), JetBlue (10 flights per week), and Frontier (2 flights per week).

  • 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 $295.

  • 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 $379. On the other hand, the most expensive day to fly is Sunday, where round-trip prices are $684 on average.

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

    The cheapest time of day to fly to Maryland is generally at night, when round-trip flights cost $377 on average. Morning departures are around 34% 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 $197 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 $197.

  • 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 $269 (return) on average. On the other hand, the most expensive months are August and January, when the average cost of round-trip tickets is $477 and $405 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 56% 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 6 cities. The city with the most direct flights is San Juan, with 27 direct flights each week.

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

    There are around 9 direct flights from within Caribbean Islands to Maryland every day. Most flights (87%) depart in the afternoon.

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

    Each week there are around 63 direct flights from within Caribbean Islands to Maryland. The most common day for departures is Monday, with 16% 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 24m, covering a distance of 1579 miles. The shortest route is Nassau (NAS) to Washington, D.C. Reagan-National Airport (DCA) with an average flight time of 2h 39m.

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

    Each week, there are 34 medium-haul flights (3-6 hour flight duration) and 29 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. (63% of total searches to Maryland). The next most popular destination is Philadelphia (37%).

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 4215 reviews
8.1Boarding
8.6Crew
7.5Entertainment
8.0Comfort
7.0Food
Airline reviews

Flight was delayed out of BWI unexpectedly / without a reason given but otherwise ok.

6.0 GoodDanielle, Oct 2026
Read more Southwest reviews

Flight was delayed out of BWI unexpectedly / without a reason given but otherwise ok.

the flight itself was totally fine. The crew were great and very helpful. The flight was delayed, however, over an hour without a lot of information as to why.

You made me miss my connecting flight. I can not go to Cleveland on teh revised flight you are sending as I will the entire meeting. I have no option that to fly back. I hope you compensate me for the loss.

It was the strangest thing. The flight attendant (who was not very friendly) took our drink orders and then never brought them. I’ve never had that happen before.

Trash experience on all my flights this week. Delay after delay. The flight I’m waiting for has been delayed 6 times and nearly 3 hours.

Flights delays were communicated timely and helpfully, but there was a significant delay without any real effort to make up for that. Also, the in-flight WiFi was very spotty. That said, this was my first time with Southwest and I was quite happy with the service and staff otherwise.

Very poor service with connecting flight. I missed the connection because of a delayed flight and significant delay in getting my bags in order to make the connection. The ground staff where unhelpful and rude!

Fairly good - the seats seemed more comfortable on this flight. The staff out of Detroit were quite friendly. But they directed us to the wrong carousel for luggage. :(

I liked the new boarding process. I thought the buyup options (legroom, early boarding) to be easy to request and reasonably priced. All the Southwest team from gate to in-flight were so nice.

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

Chairs don’t recline and the ones that do recline, barely do recline. It was most uncomfortable flight i ever been on.

Good service but not on par when compared to foreign flag carriers.

Travelling with 2 others for work. Delta asked to check their carry ons due to the fullness of the plane. This was all good until the next leg of the flight. One of the 3 had their carry on checked through to the final destination but their passport on in their checked bag. Which they could not get to and he was not allowed on to the plane. Even though Delta had to retrieve his bag, because he was not allowed on. So they got his bag and he was in the terminal, but even when the flight was delayed, due to mechanical issues, he was not allowed to come onto the plane. Since the delay was nearly 2 hours, he was finally allowed back on the plane.

good in general food is just snack and beverages (same snacks all the time) could you try to change them?

We experienced delays in small increments that added up to more than an hour. At the gate, staff showed little concern and compared our delay with the inbound flight’s two-hour tarmac wait, which didn’t address our situation. Once onboard, the flight attendants seemed tired and unfriendly. I understand delays are frustrating for everyone, but passengers shouldn’t feel blamed for them. During the flight, a bright light above the emergency exit stayed on. It was concerning, and no one explained it or offered passengers the option to move. After landing, we waited about 30 minutes on the tarmac for a gate, then waited again for an agent to connect the plane to the terminal. From the Reagan gate staff to the cabin crew and RDU personnel, the service felt dismissive throughout. Overall, this was a stressful trip and a very disappointing customer-service experience

I love how the flight crews are now saying what the weather will be like, when we can expect to be able to get up and use the restrooms etc. I have to say also that our flight crews this trip were incredible - fast and courteous - and somehow managed to do the service even on these short flights with a few bumps. The only reason for an ok rating on entertainment was because these short flights are on planes without seatback displays but that's ok because I just download shows on my iPhone beforehand.

Flight was delayed and we were on the runway after landing for 30 mins

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.

Comparing premium economy trips to other airlines United performs poorly in regard to food, service, bathroom cleanliness etc

They took us all the way to Monterrey to tell us they United were not allowed to land and we were sent back to Houston. Terrible experience.

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.

I want much more comfortable seats on these aircraft thank you.

The boarding agent and checked bag agent were both rude. It only takes a second to be kind. However, the flight crew was amazing. I got a turkey sandwich and it wasn't bad---not great but not bad. The internet was my biggest problem. This was a work trip and I REALLY needed the internet to meet a deadline but it didn't work for 80% of the trip. Very disappointing.

I tried to check in beforehand from Ireland. The Jet Blue website sent me to the Aer Lingus website and vice versa. I tried to get a boarding pass at Dublin Airport as well, but they said they couldn't help me either. I had to wait until I arrived at the gate in Boston to secure a boarding pass...it was a bit nerve wracking.

Great flight. Best in years. Very clean craft. Easy boarding. Communicative pilot. Friendly flight attendants. Absolutely smooth take off, in flight and landing. Very comfortable seats. Smoothest flight I've experienced in years. THANK YOU JET BLUE!

I was asked to pony up an additional $239 (over the $735 paid originally) for a one way middle seat, which was very uncomfortable. Where did you expect me to sit?

Jet Blue sevice was good. Just don't understand why they charge for earphones to listen to flight entertainment. Other than that, everything was excellent.

The whole experience at the airport in Istanbul should be made known beforehand. Four passport checks and a huge check-in line as I could not check in online made it a very lengthy and frustrating experience. The flights on Turkish Airlines however were just fine.

Mostly good, flight take off in time and land earlier I can’t ask for more..

The crew was not nice this time. I asked for a drink one time and the girl didn’t say anything to me and just got me the hot drink while walking super fast to the back. We were sitting in the back and she wasn’t doing anything except socializing. She was upset I asked for something and she had to do her job. I also didn’t fully have it in my hands when she handed it to me so it was dangerous. She was abrupt and rude. She wouldn’t allow for people to spread out like previous flights we had been on if they were empty, and there were empty rows. It was strange and she enjoyed being angry at us.

The plane was FREEZING COLD. Like I was wishing I'd brought gloves. Is this how JetBlue sells more blankets? Other than that, all fine. Crew just as nice as usual. A flight attendant asked (who? The pilot?) to have the air turned down for a great number of passengers who were as cold as I was. They (again -- who is "they") did not.

Flight was fine. Just delays leaving due to mechanical issues. But flight crew were kind and professional. Seats were spacious. American doesn't need to have 9 groups for boarding.

Both flights were late leaving due to repairs/switching gates. The crew and pilots, however, were professional and courteous. Most importantly, we arrived at our destination safely. The seats were comforable. That size should be standard for all economy class. American could improve its boarding process. I am not sure why you need 9 groups for a small regional plane.

There was no ground crew at HSV gate when we arrived. The were busy with another arrival. We had to wait 20 mins for them to arrive and direct the plane to the gate. It took almost 45 mins to get my luggage. The luggage belt had 3 flights bags on it and the other 2 luggage belts were not being used. It looked like there was only 1 crew serving .3 arriving flights.

It took 1.5 hours for maintenance to sign off on a repair that was completed the night before. When we landed in DC we had to wait 20 mins for a gate. As a result I missed my connection. American seems to be reducing the number of ground ground crew and causing delays. This us not the first time.

Liked: staff, no delays, Could use some improvement: Food, comfort, cleanliness, lack of chargers on the DCA -> DSM flight

The flight from DFW to SAT started out with a 2 hour delay. It was a five hour delay with no real explanation as to why. In addition, the time of arrival kept changing from 10:00 pm to 11:00pm to sometime after midnight. Driver picking me up in SAT was as confused as I was. Flight attendants were patient thank goodness since folks were a bit upset about a 2 hour delay that stretched into 5 hours.

The flight crew was amazing. Zac was very attentive and polite. Loved talking to him and the other flight attendant. My problem was that I was not able to get the meal that I ordered…Short rib with Mac and cheese. Very disappointing.

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.

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