$68 Find Cheap Flights from Caribbean to Maryland

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Low seasonJune
High seasonDecember
Cheapest flight$68
Best time to beat the crowds but there is an average 8% increase in price.
Most popular time to fly with an average 1% increase in price.
Flight from San Juan to Washington Dulles Airport

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 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 $210.

  • 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 $343. On the other hand, the most expensive day to fly is Monday, where round-trip prices are $590 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 $211 on average. Morning departures are around 8% more expensive than evening flights, on average. The most expensive time of day to fly to Maryland is generally in the morning, which is peak travel time and where the average cost of a ticket is $441.

  • What is the cheapest flight to Maryland?

    The cheapest ticket to Maryland from Caribbean found in the last 72 hours was to Baltimore, at $86 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 $86.

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

    The cheapest month for flights from Caribbean to Maryland is June, when tickets cost $368 (return) on average. On the other hand, the most expensive months are November and April, when the average cost of round-trip tickets is $552 and $539 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. For the absolute cheapest price, our data suggests you should book 16 weeks before departure.

  • How long is the flight to Maryland?

    An average nonstop flight from Caribbean to Maryland takes 6h 57m, covering a distance of 1592 miles. The shortest route is Nassau (NAS) to Washington, D.C. Dulles Intl Airport (IAD) with an average flight time of 2h 43m.

  • What are the most popular destinations in Maryland?

    Based on KAYAK flight searches, the most popular destination is Washington, D.C. (67% of total searches to Maryland). The next most popular destination is Philadelphia (33%).

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 4244 reviews
7.6Entertainment
8.6Crew
8.1Boarding
8.0Comfort
7.0Food
Airline reviews

The Southwest employees (all two of them) were very nice and cheerful despite the fact the line to self-check a bag (simply drop it off) was hundreds of people long. Thank God I arrived early to the airport because I stood in this line for at least an hour. Once on the flight that had been delayed by an hour, we had no Wi-Fi and thus no entertainment. Finally, I hope the investor strong arm tactics against Southwest pay off in a short-term windfall to your C-Suite because the rest of you are screwed. I have been a faithful Southwest customer for 15 years due to everything you just got rid of. I'm flying to Idaho and Washington in October, both places I used to simply book with Southwest without a second thought now with Frontier (Washington) and United (Idaho) because they offer everything the "new" Southwest does but cheaper and at better times, destinations, etc. This really makes me sad...

4.0 OkayGreg, Jul 2025PDX - DEN
Read more Southwest reviews

The Southwest employees (all two of them) were very nice and cheerful despite the fact the line to self-check a bag (simply drop it off) was hundreds of people long. Thank God I arrived early to the airport because I stood in this line for at least an hour. Once on the flight that had been delayed by an hour, we had no Wi-Fi and thus no entertainment. Finally, I hope the investor strong arm tactics against Southwest pay off in a short-term windfall to your C-Suite because the rest of you are screwed. I have been a faithful Southwest customer for 15 years due to everything you just got rid of. I'm flying to Idaho and Washington in October, both places I used to simply book with Southwest without a second thought now with Frontier (Washington) and United (Idaho) because they offer everything the "new" Southwest does but cheaper and at better times, destinations, etc. This really makes me sad...

It was okay. The plane was delayed from earlier in the day, but they kept updating the departure time, sometimes later, sometimes earlier. That was stressful. Once we finally got on and took off, it was fine. I was supposed to have a connection in Chicago to Los Angeles, and the time for so late I was rebooked to arrive in LA 3 hours late. The departure time to Chicago later became early enough to have taken my original connection and arrive earlier but that wasn't an option.

It was one and half hour late... Not sure if any other experience matters.

Delayed flight. Nicest crew member was a SW pilot flying seated next to me who kindly move to seat the final passenger. Flight extra delayed. My cup of refreshment of ginger ale was so packed with ice it was literally 2 sips.

For my birthday trip this was my second time ever flying, this trip was the best.

after landing, we stay 2 hours on the taxi way before reaching the gate The airline and the crew were good though

No trays in our seats, we sat in first row, purchased a business class fare. Had to hold our drinks and snack in our hands. No plugs for our cell phones. Had to pay for it a drink cocktail each. Seats so uncomfortable.

Flight wasn’t even full, but too many carry-ons caused us to run out of bin space. New bag fee has folks who would usually check their bags carrying on. Watching Southwest morph into Spirit/Frontier is so sad to watch

Sat on tarmac for 2 hours and then missed my connecting flight

First time traveling on Southwest since bag fees were implemented. Usual good service. Just more expensive now.

Everything was good until we were boarding our connection flight in Atlanta, we were told to gate check our carry-on, but when we got inside the plane, there was plenty of room in the overhead.

Did not know my son and I had different seating arrangements. He was fine, but it was disappointing.

Flight was canceled, and no effort was made to help with rebooking, no hotel vouchers, no car transportation and minimal food voucher and most places for food were closed by the time the voucher was given. Waited for 3 hours for bags. Simply the worst travel experience I have ever had

Our flight was canceled after several delays. No hotel vouchers offered, minimal help for resolution leave me ultimately to cancel and book on an other airline. Then waited to get bags for more than 3 hours This whole experience has been awful!!!

Food was surprisingly good but the WiFi was not great

this crew didn't care much. bumping carts into seats more times than i care to remember

Very late arrival at PWM. Late jet getting to ATL. Equipment problem with aircraft - could not get enough water onto plane., Another delay getting FAA approval for flight with bottled H2O. Not the crew’s problem.

Everything was fine except the entertainment was not working for half of the flight.

Easy boarding with an extremely kind attendant. Seats were spacious and we had 3 seats for 2 people so we could stretch out. Comfortable air flow and very attentive and hospital attendants. Bathrooms and food were the only negative. Bathrooms were so small you could hardly get in and close the door. I don’t think an obese person would fit or a person with a movement disability. Food was the trending food for flights, nonexistent. We spent $40 getting sandwich and snack at airport for our 6 hour flught.

At first, we were on the runway for about an hour, literally. The Captain did explain that the Control Tower just had a change shift (sounds like an unrealistic excuse) and then that we had to change a runway. A regular economy seat is made for 12 yo twiggy. I understand Delta wants to push for an upgrade, but after sitting in a Comfort seat and in First class. I would say First class is not worthy of my money. The landing was delayed because of the weather in NYC, I don't hold that against Delta, of course. The Captain did alert us to that upon takeoff in Vegas and again as we reached NY.

Flight delays numerous times. Everytime we would get close to boarding it would be delayed again. Strung along the entire time.

After a two hour delay, my flight was CANCELLED! No pilot available. Such BS.

Overall very good, only complaint I have is the crew from CLT to SAT could have collected trash sooner.

The AA app really sucks ... Every flight & connecting flights were delayed over 30 mins. One connecting flight on American Eagle said it was delayed in its arrival ... when it was actually parked across from the gate for over 1 hr before they pulled it to the gate. Seats in the economy/ main cabin are packed together like sardines ... no leg room.

Initial flight was cancelled at the time of arrival to the airport, flight alternative requires switching from direct to flight with a layover, and the plane felt like it would split apart, it was so rattle-y.

Amazing food, great staff, with one noticable detail missing ...but no seat entertainment in any of aircraft ...I am not a fan

AA re-routed flight from HNL to LAX due to delay. My group of 3 with reserved seats in row 9 was broken up, with one assigned to a middle seat, another in the last row of the plane. Not happy. No explanation to the delay. No apologies. No compensation. Would have been nice to be offered an Admiral Club admission or a voucher for the extra 3 hours of layover in LAX. Could not hear the boarding gate announcements in LAX. Adjacent gate was boarding at the same time. Loud speakers were competing against each other. Barely made my boarding group.

Boarding gate in Honolulu was staffed with a great clerk with a soothing voice despite the flight delay of over an hour. Flight attendants in the plane were all grumpy, not pleasant looking bunch. Their sour attitude showed throughout the flight. Inly able to get a select few movies started. Most of the movie links in the “free entertainment” did not work.

Above and beyond effort from this crew in a tough situation. So helpful and understanding. Thank you!

I flew Business Class. Rory, one of the Cabin stewards, was attentive, explained the menu, provided appropriate drinks. was

Although our flight had delays due to three different reasons, it was good. Staff continued to update us which made every one comfortable. We felt the captain and crew had our safety in mind the entire time and no one seemed to lose their patience.

I've flown Spirit many times. However, they seem to be getting worse. I don't understand how the contracts with the gates at the airport works, but Spirit never seems to have a gate ready when we land. This happened again on this flight. And once again, baggage took forever to arrive at the baggage claim belt. This time it was about 45 minutes to an hour, late at night, when the airport was not crowded. On a previous trip, they lost the luggage cart and we were all waiting for about 3 hours for our luggage. Plus, I did get a deal through Kayak on a flight that was shown sold out on Spirit's site. However, by the time I added all the luggage, and didn't even pick seats, I could have taken any direct flight I wanted through Delta. I'm about done with Spirit.

I enjoyed my flight, it was pretty smooth and we landed earlier than eta.

Booked through kayak, everything seemed normal but when it came time to go, my flight ticket didn’t exist, so I had to purchase another set of tickets at the airport the day of the flight, for about double. When I reached kayaks customer service, they claimed no responsibility, and pushed me onto another 3rd party booking service, airfare assist, where I have had no luck getting any kind of help or refund. I’ve used kayak many times, but I’ll never again after I’ve been burned by this.

The flight was delayed four and half hours for paperwork on a maintenance issue. Very frustrating.

It was okay delay was long but I made it

Flight was cancelled. No reason given. No apologies. Next available flight is two days later. Ruined our 4th of July plans.

The air fares are good, Charging me for every single thing 😩

It was very bad it got delayed by 2 hours.Never going to travel with spirit airlines in future.

Flight delayed over 3 or 4 hours because no captain to fly plane. I couldn’t make a connection and had to wait 9 hours for another flight. Had to fly red eye flight. Sucks

Late, terrible communication, horrible planning of passenger seating until the literal last minute. One of the worst flying experiences of my life. Y'all suck

Both legs of the flight were changed. The day of the flight and length of the trip.

First of all, we never got on the connecting flight to Denver. They delayed our flight for two hours. If we would have gotten on that flight, we would have been stuck in Denver for 13 hours. So we re- routed our flight for a straight through flight to Oklahoma two days later. THEN, they delayed that flight for two hours. After that we were able to finally get on our flight and come home. Frontier Airlines - one of the worst airlines I have ever been on.

Terrible communication with weather delay, lost baggage, near impossible to reach customer service

My tickets got canceled on me by your site and I didn't have a flight. Then you kept sending me emails on the status of q flight I didn't have tickets for.

The delay was ridiculous because nary a word escaped from the gate attendant regarding our flight status. It was a complete joke.

I missed a flight because of a delay. I had to buy a new ticket through Southwest.

The crew was mostly okay. The flight attendant who answered our questions was curt and unhelpful unfortunately. He seemed upset and I understand having off days.

Flight was delayed one hour. Notification to the crowd waiting near the gate was terrible…announcements were unclear and very hard to hear and therefore understand. Frontier does NOT send texts to notify, only email. The reader board over the gate itself was NEVER updated to indicate the gate had been changed. It’s like a bunch of children are running things.

I’m not gonna fly Frontier Airlines because booking is not an option. No water or food is for high price, not equipped for health emergency incompetent crew for emergency services. Cheap airline shows it is cheaper in all service categories. Boarding is the best of all airlines!

Book cheap flights from Caribbean to Maryland

Recent round-trip flight deals

7/31Thu
nonstopFrontier
3h 56mSJU-IAD
8/5Tue
nonstopFrontier
3h 57mIAD-SJU
$130
7/31Thu
nonstopFrontier
3h 56mSJU-IAD
8/5Tue
nonstopFrontier
3h 57mIAD-SJU
$131
8/3Sun
nonstopSpirit Airlines
3h 59mSJU-BWI
8/11Mon
nonstopSpirit Airlines
3h 41mBWI-SJU
$143
9/5Fri
2 stopsSouthwest
7h 50mSJU-DCA
9/8Mon
1 stopSouthwest
11h 50mDCA-SJU
$145
8/29Fri
1 stopAmerican Airlines
6h 21mSJU-BWI
9/1Mon
1 stopAmerican Airlines
8h 25mBWI-SJU
$145
8/29Fri
1 stopAmerican Airlines
15h 52mSJU-IAD
9/1Mon
1 stopAmerican Airlines
8h 21mIAD-SJU
$145
9/25Thu
nonstopSpirit Airlines
4h 00mSJU-BWI
9/28Sun
nonstopSpirit Airlines
4h 01mBWI-SJU
$151
8/21Thu
1 stopDelta
11h 14mSJU-DCA
9/9Tue
1 stopDelta
9h 37mDCA-SJU
$215
9/19Fri
1 stopDelta
8h 51mSJU-IAD
9/23Tue
1 stopDelta
5h 56mIAD-SJU
$215
8/3Sun
1 stopSouthwest
11h 50mSJU-DCA
8/17Sun
2 stopsSouthwest
9h 45mDCA-SJU
$238

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Recent one-way flight deals

11/7Fri
nonstopUnited Airlines
4h 05mSJU-IAD
$68
9/13Sat
1 stopAmerican Airlines
6h 23mSJU-BWI
$73
9/11Thu
2 stopsSouthwest
7h 50mSJU-DCA
$73
7/25Fri
nonstopSpirit Airlines
3h 59mSJU-BWI
$74
9/25Thu
nonstopSpirit Airlines
4h 00mSJU-BWI
$78
7/20Sun
1 stopSouthwest
11h 50mSJU-DCA
$78
10/24Fri
nonstopFrontier
3h 59mSJU-BWI
$88
8/29Fri
nonstopFrontier
4h 01mSJU-BWI
$89
8/13Wed
1 stopDelta
11h 14mSJU-DCA
$108
9/25Thu
1 stopDelta
11h 15mSJU-IAD
$108

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Last minute flights from Caribbean to Maryland

Last minute flight, train and bus deals

7/18Fri
nonstopFrontier
4h 01mSJU-PHL
8/4Mon
nonstopFrontier
3h 54mPHL-SJU
$151
7/18Fri
nonstopFrontier
4h 01mSJU-PHL
8/9Sat
nonstopFrontier
3h 54mPHL-SJU
$152
7/16Wed
multi-stopSouthwest
9h 55mSJU-DCA
7/20Sun
multi-stopSouthwest
8h 20mDCA-SJU
$180
7/17Thu
multi-stopAmerican Airlines
17h 02mSJU-BWI
7/22Tue
multi-stopAmerican Airlines
16h 35mBWI-SJU
$180
7/16Wed
multi-stopAmerican Airlines
10h 00mSJU-IAD
7/21Mon
multi-stopAmerican Airlines
6h 16mIAD-SJU
$180
7/15Tue
multi-stopSpirit Airlines
10h 42mSJU-BWI
7/19Sat
nonstopSpirit Airlines
3h 41mBWI-SJU
$186
7/17Thu
multi-stopSpirit Airlines
12h 05mSJU-BWI
7/22Tue
nonstopSpirit Airlines
3h 41mBWI-SJU
$198
7/15Tue
multi-stopSouthwest
9h 15mSJU-DCA
7/30Wed
multi-stopSouthwest
6h 35mDCA-SJU
$220
7/16Wed
multi-stopDelta
10h 10mSJU-IAD
7/19Sat
multi-stopDelta
8h 13mIAD-SJU
$300
7/19Sat
multi-stopDelta
10h 01mSJU-DCA
7/28Mon
multi-stopDelta
7h 08mDCA-SJU
$340

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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.

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