$83 Find Cheap Flights from Caribbean to Maryland - Compare and Save

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Low season

September

Cheapest flight

$83
Best time to beat the crowds with an average 17% drop in price.
Most popular time to fly and prices are also 11% lower on average.
Flight from San Juan to Baltimore

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

Insights shared by verified travelers who flew the route from Caribbean 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 to Maryland

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

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

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight from Caribbean 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 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 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 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 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 $307.

  • 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 $373. On the other hand, the most expensive day to fly is Sunday, where round-trip prices are $661 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 $392 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 found in the last 5 days was to Baltimore, at $140 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 $140.

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

    The cheapest month for flights from Caribbean to Maryland is December, when tickets cost $164 (return) on average. On the other hand, the most expensive months are August and January, when the average cost of round-trip tickets is $412 and $347 respectively.

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

    To get a below average price on the flight from Caribbean to Maryland, you should book around 3 weeks before departure, which saves you about 53% 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, there are direct flights to Maryland from 4 cities. The city with the most direct flights is San Juan, with 14 direct flights each week.

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

    There are around 5 direct flights from within Caribbean to Maryland every day. Most flights (57%) depart in the afternoon.

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

    Each week there are around 30 direct flights from within Caribbean to Maryland. The most common day for departures is Sunday, with 20% of flights taking off on this day.

  • How long is the flight to Maryland?

    An average nonstop flight from Caribbean to Maryland takes 6h 56m, covering a distance of 1537 miles. The shortest route is Nassau (NAS) to Washington, D.C. Reagan-National Airport (DCA) with an average flight time of 2h 45m.

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

    Each week, there are 23 medium-haul flights (3-6 hour flight duration) and 7 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. (65% of total searches to Maryland). The next most popular destination is Philadelphia (35%).

Reviews of the top 5 airlines serving from Caribbean to Maryland

 
Need help choosing which airline to fly with from Caribbean 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.
7.9
SouthwestOverall score based on 4213 reviews
8.0Comfort
8.1Boarding
8.6Crew
7.4Entertainment
7.0Food
Airline reviews

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.

2.0 MediocreAshwani, Oct 2026
Read more Southwest reviews

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 -

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).

Very good- all went as planned. Flight was on time. Seating was a little sub , as always. Snacks and entertainment were basic. We arrived on time- no problems.

Everything was great, from the flight and crew to the seating and snacks.

Rude staff from baggage check to gate crew. Poor instructions. Inconsistent application of baggage rules.

There was an incredibly surly flight attendant that ruined the experience

Good but since we got in early we had to wait on runway for our gate. That was kind of a bummer but we still got in earlier than planned For entertainment I was watching a movie and getting close to the end of it with 15 min left but it kept jumping automatically to the next movie before finishing.

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.

I am always very pleased with the service u receive from JetBlue employees

My flight was poor because I haven't taken it yet. And you should know this since I had to rebook for a later flight through YOU. In addition to getting absolutely NONE of my money back, you have the audacity to be ignorant of your own operations. I am thoroughly pissed.

Your Jet Blue representative at the check in desk in Boston on Sunday morning, October 13, was unkind and unhelpful. For that reason alone I will avoid JetBlue airlines in the future. No food or beverage on the flight due to turbulence (not your fault). However I paid extra to sit in the upgraded section in the front and did not benefit from most amenities.

we used to fly with a different airline but it shut down. We had to find an alternative airline that we like in order to make domestic trips and this fits the bill. Not only is it a similar price but the customer service and the experience overall is much much better. We will be using JetBlue again.

Uncomfortable seat. No help for my disability. Staff refused to help me put my carry-on in the overhead bin. So I had to check the bag.

Terrible. Quality has gone down significantly. Plane was delayed. No instructions from the staff. Will try to avoid in the future!

The flight left unexpectedly early. Although I checked in at the gate, the crew made no attempt to contact me to inform me that what had been a delayed flight was now departing before the scheduled departure time. No announcement on the PA, no phone call. When I checked back at the gate for the delay status just before the scheduled departure time, I was told the doors were already locked and the flight had left.

Late boarding, had to check the bag even though there was space on the flight and I was I row 7

Our seats were moved for no reason. The plane was old and wifi and tv were slow. The flight was delayed over an hour for a paperwork issue. Only bright spot was the flight attendants good service.

Unacceptable pre-boarding ticket issues. Paid for and reserved Mint seat approximately a month in advance. Checked in to flight in Mint seat 24 hours before flight. Shortly before flight, was bumped out of Mint entirely, even though other Mint seats were still available and for sale. Was told it was "operational", however seats were still available/being sold. Got to gate and they could not explain it, but the gate agent was able to put me back into Mint (however to a different seat). Nothing proactive done by Jetblue, I would have been bumped had I not arrived at gate early enough to have a helpful gate agent rectify. No explanations from Jetblue.

Too little snack and drink for almost 6:00 hr flight. Should have serve some food.

At 5:46 am EST, when I arrived at my departing gate, your gqte agent told me that I could not board the flight because the flight is closed 15 minuets before departure. However, the same gate agent escorted a woman (standing right next to me) at the gate onto the flight which, proves that I could have boarded the flight just like the woman I watched board the flight. The gate agent stated "she was here before you". 1-why was she not already on the flight & 2-how and why was she able to board a "closed" flight that I was not. Additionally, although 6am EST was the time of departure, the plane did not 'pullback' from the gate until 6:15am EST The same gate agent told me that the "boarding closes 15 before departure time" is printed on my boarding pass. This statement is not displayed on my digital boarding pass that I downloaded from AA.com. She also told me that this in stated on AA.com whent I booked my ticket however, since am travelling for work, I booked my flight thru my firm's (Deloitte Consulting) corporate travel app, not AA.com. Marc W Brown

What an amazing plane! We flew a 787 to Miami. Although the Internet was not functioning, it was a wonderful flight.

Although it was a smaller plane, the flight was quick and uneventful.

This trip on American was the WORST I have ever experienced. The plan was LATE taking off from Tucson due to mechanical issues. It caused me to arrive late in Dallas, so I tried to move flights so I would not miss my dinner meeting. First attempt, that flight was delayed, Second attempt, that flight was also delayed. Got back on original flight, the mechanical issue was NOT fixed, so we de-planed and had to find the new gate. Overall, was which was 4 hours delayed and missed the dinner meeting. Friday return, flight from Orlando was on time and landed early. Then the next flight was delayed due to crew coming in late, and them waiting on other passengers. After 90 minutes of delay, we boarded, and then were informed the Fist Officer could not fly due to time constraints. At 12:15 AM we were offered a hotel for a 4:20 boarding flight. Not happening. DFW was COLD and no place to sleep. Plane delayed again to 6:50, but was late taking off AGAIN. Finally landed in Tucson at around 8AM. Should be refunded 75% of the ticket costs due to negligence, nothing more.

Same the delay was not ideal and the credits to move flights was not sufficient

The delay was not handled well and the offers to move flights and get travel credit was also not ideal.

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.

It got me to my destination? However we were an hour delayed departing, and we never received any updates or notifications from staff. Poor communication and customer service.

Frontier didn’t give us enough notice that our flight had been delayed. I was just entering the airport when I received the notice, less than 2hrs before my scheduled flight. They delayed it 1hr 22min because another jet left late out of Vegas. Frontier needs better communication with customers because I could have eaten at home and had someone drive me instead of paying for an Uber.

Great flight, no problems. I wish they would increase the checked bag weight limit. Packing was very stressful.

My experience with Frontier was terrible. We were delayed for 2 hours. At one point during the wait at the gate I left to go get a sandwich - I was gone probably 15 minutes. In my absence, they decided to move our flight up, boarded and left. When I came back the two attendants were very rude and I unavoidably had to purchase another ticket on the next flight. During this whole time, the Frontier app did not update the departure time, so I was SOL.

Flight delayed 9 hours. On tarmac for over an hour after arrival. Will never book with Frontier under any circumstances ever again.

Inbound plane was on time and flight departed on time with no issues while boarding.

After boarding and un-boarding twice over 6+hours, the flight was canceled.

The Boarding process in Denver was chaotic, and since the line was so long, we were lined up very far from the gate. If there were any announcements from the gate staff, we didn't hear them. The flight attendants were spectacular. The only negative part of the flight was sitting by a 2 1/2 year old who was unruly and unfortunately had parents that matched his behaviors. Also, the restaurants in Denver on the E concourse, they didn't have food (passengers could only order 1 item on the entire menu) or the restaurants had 12-14 people waiting for orders to be prepared and another 6 people waiting to order. If you have a layover in Denver and need to grab food, be prepared to visit the shops with pre-packaged sandwiches, or you can visit another concourse but it may take a while to transit throughout the airport.

30 minute delay due to boarding and settling of a family.

Flight was fine, but the legroom between seats for taller passengers is very tight and bad on the knees. I t is very hard to find an angle, that works, especially on a long flight!!!

More options for your flight to Maryland

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