$81 Find Cheap Flights from Caribbean to Maryland

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Good to know

Low seasonSeptember
Cheapest flight$81
Best time to beat the crowds with an average 10% drop in price.
Most popular time to fly and prices are also 2% lower on average.
Flight from San Juan Airport to Philadelphia

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.

  • Which airlines fly most frequently to Maryland?

    Caribbean and Maryland are connected by different airlines. The airlines that fly that route the most regularly are Southwest (52 flights per week), Spirit Airlines (7 flights per week), and BermudAir (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 $336.

  • 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 $308. On the other hand, the most expensive day to fly is Monday, where round-trip prices are $584 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 $376 on average. Morning departures are around 23% 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 72 hours was to Baltimore, at $103 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 72 hours was $103.

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

    The cheapest month for flights from Caribbean to Maryland is September, when tickets cost $361 (return) on average. On the other hand, the most expensive months are January and April, when the average cost of round-trip tickets is $500 and $497 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 2 weeks before departure, which saves you about 36% 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 9 cities. The city with the most direct flights is San Juan, with 25 direct flights each week.

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

    There are around 9 direct flights from within Caribbean to Maryland every day. Most flights (67%) 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 to Maryland. The most common day for departures is Saturday, with 21% of flights taking off on this day.

  • How long is the flight to Maryland?

    An average nonstop flight from Caribbean to Maryland takes 6h 42m, covering a distance of 1580 miles. The shortest route is Nassau (NAS) to Baltimore (BWI) with an average flight time of 2h 35m.

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

    Each week, there are 45 medium-haul flights (3-6 hour flight duration) and 18 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. (68% of total searches to Maryland). The next most popular destination is Philadelphia (32%).

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.
8.0
SouthwestOverall score based on 4325 reviews
8.6Crew
8.0Comfort
7.0Food
8.1Boarding
7.5Entertainment
Airline reviews

Southwest was greaat! The most expensive but the least upsetting for those we were flying to see.

10.0 ExcellentMartie, Mar 2026
LGB - BNA
Read more Southwest reviews

Southwest was greaat! The most expensive but the least upsetting for those we were flying to see.

I flew twice this week on Southwest, was delayed over 2 hours both ways. From Pittsburgh to Chicago it was due to weather but the gate agents, pilot etc were great at updating everyone. Today from Midway to Pittsburgh the plane had come from an international location, kept getting delayed, no information was given until we were delayed for the third time. It was ridiculous, whoever scheduled that plane to fly to Pittsburgh after didn’t consider a lot of things.

Boarding was easy. The seats are small and fairly uncomfortable

I was supposed to be on a later flight. When I showed up at the gate, the woman working there was extremely helpful getting moved up to this earlier flight.

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

I elected to pay for the upgrades and found very little difference

The new seating arrangement is so over priced for what you get.

The problem with the seat assignments is that there were a lot of rows in the front that were empty but my row at the back was full. Just not so pleasant.

No food or entertainment, just a quick 40 minute flight. A little bumpy due to Santa Ana winds but pilot has no control over that. Good flight and landing!

the crew cancel the morning service due to the weather. Then the flight got deverted to Nashville . we were on the ground for over two hours the only gave us water once... no food or any snacks.... the crew should have handled better and offered something to passengers.

My recent experience was excellent on Delta! I flew with Delta Comfort and I was really comfortable in my seat. I enjoyed the in-flight service. The flight attendants were so friendly and hospitable. I love the snack on the flight as well. This was my first time flying on Delta and I will definitely consider flying with them again.

My flight was cencaled due with the bad weather on Sunday the crew was poorly mistaken my luggage supposed depart with my flight instead I didn’t have my luggage for almost 3 days the website is poorly respond to my complain until I have someone to do it my connection smooth their not even respon or email me even the have my luggage

Delta needs to step its game up get a more reliable internet service. Internet service was non-existent for this flight.

Mechanical Delay of over an hour with multiple gate changes. Entertainment system down for rejuvenation.

I had a flight cancel and had it rerouted. When the rerouted they put me at a window seat instead of an isle. It was hard sitting by the window because the couple with masks on were making out. I get motion sickness which is why I need to have the isle seat.

NEVER MADE THE FLIGHT BECAUSE DELTA SAID THEY CAN NOT

THEY FAILED ME AND I NEVER GOT ON THE FLIGHT BECAUSE IT WAS SO DELAYED! I ENDED UP HAVING TO PAY OUT OF POCKET FOR A HOTEL AND STAY IN NASHVILLE TO CATCH A FLIGHT FOR THE FOLLOWING DAY. DELTA IS POOR CUSTOMER SERVICE>

8 hours late and the plane smelled like urine, that smell in the morning when your child wet the bed in the night.

My flight was canceled on Sunday. Rebooking took three hours. Had to pay for accommodations another night. New flight was delayed for 5 hours, all that was sent was a 12 dollar food voucher, which doesn’t tell you how to use it. Then when we landed we had to sit on the plane for an hour before we could get off.

Half of the TSA checkpoints at PHL are closed. Also, there is no standby for first class passengers. You can only standby for coach. Very dated policy and inconsistent with peers.

Flight was scheduled at 11:26am but they keep Delaying until midnight. They waited at airport restless.

Rough flight No beverage service due to turbulence Bottom Seat cushion was non existent

Great experience. Good dinner and service. FA's were very nice and attentive.

It was great. Smooth flight, comfortable, left on time and landed on time.

We hoarded. Then we deplaned. Then we waited for 10 hours in the MSP airport due to a wheel misfunction. We understand safety but communication between crew and airport staff was horrible. When we did finally board, we were rushed on and because we were waiting for a “fresh” pilot and crew, we sat in a roasting plane with no A/C for an hour. My question is why was this flight not cancelled right away when they knew this would be a huge issue OR, why did AA not get a substitute plane, considering this was already a full flight? To me, this appears to be a complete breakdown in leadership and utter systems failure. The compensation for completely disrupting travel plans for hundreds, which we paid dearly for, was measly. While we appreciated the lodging for the night, $12 in meal vouchers isn’t going to sustain anyone for over 12 hours. “We apologize; our hands are tied” is no longer an acceptable explanation. We are so completely turned off by this experience and will definitely seek alternative avenues when we need to fly.

Mostly good. The WiFi wasn’t working so that was not great.

I rated the experience "mediocre" because of the 2 hour delay in take off. This is the 4th flight from DFW on AA where there was a delay and in one of the instances (after 13 delays), the flight was cancelled. I understand weather but for the March 18th flight, there was no weather issue in Dallas or Detroit. I called Concierge Key and they were wonderful, booking me on a later flight in case my flight was cancelled. I have flown with American for many years and never has there been this consistent pattern of delays. Very disappointing.

They put me on an earlier and I got home sooner

Crew was rude, almost 6 hour flight after horrific customs re entry line and near flight miss (unable to bug airport food) without food offerings.

The airplane rattled near the left wing as if several screws were loose. Then after we landed in Fort Lauderdale, we had to sit and wait on the runway for quite some time. It was very scary and TOTALLY unacceptable!

Smooth flight staff very friendly and we arrived 15 mins earlier

I was in the airport when I'll check the status of my flight and it was canceled and without any reason. The worst of the worst ...

I never had an opportunity to experience them! They cancelled my flight TWICE!!!

Return flight was canceled. Needed to reschedule with another airline the next day. Cost an an additional $84. At another airport 45 miles further away

Spent seven hours in the airport with spirit pushing he flight time back two hours every two hours only to then have it canceled without explanation. The employees said, “They’ve been doing this for the last five days.” Would have been great if they told us to expect that when we arrived.

Seat do not reclined and tight space. Flight changed so many times hard to keep up.

Bad airline to travel with my flight was delayed for more than 3 hours they act like it’s normal

No WiFi, no outlets to charge phones, no complimentary beverages on a 6 hour flight

Length of flight was fine Delay of over 3 hours was very bad!! Flight down was delayed 1.5 hours

More inflight connection. And leg space is horrible. And the paying for baggage I'd ridiculous!!!

My flight was originally from SAT to MCO connecting from MCO to ORD. We got diverted to ATL and than Frontier staff there was sooo un helpful first they said they couldn’t give us any accommodation since our flight first got delayed that cancelled and now it’s 221am and I am still in ATL since they said they need to create a new flight my final destination is ORD and I have been delayed twice and cancelled. With no real help the frontier app didn’t work no email updates over all such a horrible experience

There's no seats that lean back with little leg space i wad uncomfortable the entire flight. Your charges for extra baggage is despicable and costly!!

Remind customers of the need to have passport or new ID for boarding.

Flight was canceled. Most upsetting was message from Kayak, stating that the flight was canceled and click with Kayak for details regarding rebook, refund details. THERE'S NO INFORMATION PROVIDED BY KAYAK EXCEPT THAT FLIGHT IS CANCELED. AND NOW THIS SURVEY TO FIND OUT HOW WAS THE FLIGHT !!!!!!!

The flight never took off and we spent 7 hours at the airport

Gate not determined until I got to the airport - hard to plan the trip to the airport.

Our flight was canceled. I will never use Kayak nor Frontier for travel again. The entire experience was a headache.

Frontier.. nickel and dime add-ons. Flight late, on time, late again, last minute gate change, arrival gate required a shuttle to the terminal. They sure keep you guessing.. if you like a little chaos and airport anxiety, this is the airline for you!

This is my second time flying with Frontier. My current experience was very favorable. The staff from the gate to the plane was friendly, warm and professional. The food options lacked in my opinion. This area needs some attention in my opinion.

Everything you need to know for your flight to Maryland

Cabin class types available on flights to Caribbean

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