$78 Find Cheap Flights from Caribbean to Maryland

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Low seasonFebruary
High seasonJuly
Cheapest flight$78
Best time to beat the crowds with an average 13% drop in price.
Most popular time to fly with an average 1% increase in price.
Flight from San Juan Airport to Baltimore

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 $247.

  • 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 $353. On the other hand, the most expensive day to fly is Monday, where round-trip prices are $588 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 17% 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 $471.

  • What is the cheapest flight to Maryland?

    The cheapest ticket to Maryland from Caribbean found in the last 72 hours was to Baltimore, at $85 round-trip. The most popular route is Montego Bay (MBJ) to Baltimore (BWI) and the cheapest round-trip airline ticket found on this route in the last 72 hours was $85.

  • 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 $369 (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 7h 16m, covering a distance of 1575 miles. The shortest route is Nassau (NAS) to Baltimore (BWI) with an average flight time of 2h 40m.

  • What are the most popular destinations in Maryland?

    Based on KAYAK flight searches, the most popular destination is Washington, D.C. (61% of total searches to Maryland). The next most popular destination is Philadelphia (39%).

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 4278 reviews
8.0Comfort
7.1Food
8.2Boarding
8.6Crew
7.6Entertainment
Airline reviews

Southwest is Southwest. No frills. If you're luck enough to get a happy crew (we did), then it makes for a nicer flight.

10.0 ExcellentMichael, Jun 2025SMF - SEA
Read more Southwest reviews

Southwest is Southwest. No frills. If you're luck enough to get a happy crew (we did), then it makes for a nicer flight.

Southwest is typically delayed, and it gets wearisome. It is no longer a discount airline and you get way less than you pay for when it comes to comfort and Ce.

We sat on the plane on the tarmac for 4 hours.

I'm not a fan of Southwest's model. I don't like the herding style of boarding.

Flight crew and cabin crew were great. I had to rearrange flights because my original flight was 3hrs delayed for weather, the rub is the flight I moved to boarded on time then we sat at the gate for 2 hours because scheduling stole our first officer for another flight, TWICE. Then our actual FO was an hour delayed. To make it worse my original flight went from a 3 hour delay to departing 15min EARLY. Just poor scheduling operations all around.

Bring back peanuts Take our drink orders when were all seated, especially after you switch to assigned seating.

Staff was far less than helpful at all times. Departure and arrival times mean nothing to Southwest. Extremely disappointed, will never fly with them again, and I’ll be sure to share my experience with all.

It is southwest seat was ok. Not the most comfortable seat

I’ve always loved Southwest. No issues at all. I was flying standby and the gate agent was extremely friendly and helpful. Boarding was smooth and I was able to get a window seat in the emergency exit row. Crew was fantastic! They were very professional and accommodating. We had to divert from our destination due to weather but the flight crew kept everyone at ease and informed us of all pertinent information. Excellent flight

The price of the tickets isn't matching the flight experience. No matter how long the flight is, you're only getting pretzels. The flight attendants looked unkept and over it.

I like for how they process during check in. It was very smoothly.

The flight was scheduled for 2:30 PM. Early in the morning we got a text message saying the flight was delayed and rescheduled for 3:00 PM. We got to the airport with that in mind. Then we got a message during check-in at the flight was rescheduled again for 2:30 PM. We almost missed our flight. In fact, our bags Were told that they would not make it. At the end, everything worked out. But it is very stressful.

Most aspects were good however if they assign boarding zones they ought to enforce them or why bother? My luggage from SAN-JFK-MAD was lost in NY so I without my main bag for two days upon arrival in Spain. They were helpful in tracking it and eventually delivered it to my hotel. The flub was because of a delay upon arrival in NYC. I had booked 2 1/2 hours between flights but we had to hold on the taxiway for an hour after landing while waiting for a clear gate which likely caused the baggage error.

Excellent check-in. Crew was good. Excellent communication from flight deck.

Great overall. There was a bit of turbulence so they could only serve water because too much turbulence for the carts. Was glad they prioritized safety though

Excellent flight, the planes were newer, they did a nice job with boarding, great service overall.

Great service. Flight was delayed while we sat on the runway for a couple of hours. Weather related. Staff made is very bearable. The steward servicing the first class cabin was exceptional. Thank you! 💗

5 hours of delay that could've been much shorter if Delta had taken the 1 hour delay they imposed on the flight before boarding to run any of the plane checks required for flight to find the hydraulic issue that required nearly 3 hours to fix. $24 of meal credit buys a sandwich and a soft drink. Poor communication within the terminal about what gate we'd be re-boarding from and when we'd be re-boarding.

Amazing flight! I have never noticed the uniforms of the attendants before in twenty years of flying except today when one female had the most amazing dress on. It was beautifully designed and showed she was in charge. I never dreamed I would google who designed Delta uniforms . The ultimate compliment is when another woman admires your outfit. . I hope your designer puts it on the market

It would be nice if was given wires ear buds. Overall was a good experience was able to sleep on the plane

They cancelled my flight and downgraded me to economy and only gave me $250 for the downgrade

Loved the staff, boarding and drink options! Wish the comfort of the seat could have been better nevertheless

The flight crew were friendly and attentive. Food was good and they passed out ice cream and drinks awhile after Lunch was done. The ice cream was a nice treat! I found several movies to watch during the flight. There was many movies and tv shows to choose from. We flew Premium economy and there was enough leg room to be comfortable. The seats were also comfortable. I would fly AA again if the airfare isn’t expensive.

The chair cushions may need an upgrade. I have been noticing they are so worn out, thin so you’d sit in a dip 😄. Other than that, all was an enjoyable trip. Thanks AA!

I’m impressed that we were on time in Sacramento after having a late departure in Newark and our made it. The staff was friendly and warm.

Cramped seats. FAA should make airlines have more legroom, for even short people complain

5.5 hour delay with no explanation on why, along with no proactive effort to reaccomodate me.

It was one of my worst flight ever. First they were changing the gate for at least 4 times, changing from gate D7 to D12 to D44. Considering the size of the Miami Airport, we are talking about long distance and the train at the airport was not working. Then the flight was delayed around one hour. Then finally we boarded into the plane and when everybody was seated, there was an announcement that there is an issue with one of the tire of the plane, so we all had to get out of the plane with our belongings, to replace the tire. So we had around 2.5-hour delay

Most miserable flight ever. We waited almost 2 hours on the runway because the flight was oversold. American offered $1200 credit. Then there was some nonsense about weight distribution. Ridiculous. No food for 8 plus hours on the flight. I will be writing a letter.

Honestly, I haven’t flown American in years, probably due to the pandemic and my being unable to travel for certain periods in the last two years, but it was a good experience to dig out or obtain a new American Airlines account after many years of traveling for business with American in the past.

It was absolutely awesome. The crew was welcoming to all, not just the first class. They were full of energy. The in-cabin music was an excellent choice, not boring like most airlines. We were ready for takeoff ahead of time. Pilots were great. Smooth takeoff and landing. The plane was beautiful and nicely cleaned. This was truly a fantastic flight. I fly Delta and American all the time. I was apprehensive about Spirit. I will definitely be looking for Spirit first. Thanks for a great experience.

Didn't like size of seats. Found charges for checked luggage and carry on too high

Great! We boarded on time! Everything went so smoothly! The flight was so smooth

Spirit gets you there; it's no worse than any other aircraft, all things considered. (It's not like everyone else is such a hero). But - holy moses - do they nickel and dime you to absolutely every nickel - I was really expecting to have to pay to use the bathroom. And when the captain comes on with a 5 minute sales pitch about getting "points", that was like something on Bizarro world. Other than that, everyone else was professional and worked hard to get us from point A to point B. I'm not loving all the "self-service" stuff but there it is - just when the machines don't work you don't have anyone to talk to.

Boarding was a breeze, however, two of the flights that I boarded with Spirit did not have Wi-Fi available.

Seats uncomfortable, hard to check luggage, etc. It was like the last flight out of Hanoi

Need screens for tv/movies. Seats are more cramped than any other airlines. Seats are hard. They don’t recline. And in flight time should not be used for sales pitches.

Good experience except for the drunk woman who was with a child. Sad

The ease of booking the flight was very good. Speaking with customer service was also good. However, the crew people are unfriendly and unwelcoming which I found this as unprofessional. As far as comfort it was mediocre. This was my first time flying Spirit and I chose them because of the flight times met my needs and my budget. However, I would be reluctant to fly on Spirit again. In addition, if the crew were more friendly and at least appeared somewhat happy and welcoming personally it would probably make the experience of flying with Spirit better.

Tell them to chose a better, less bumpy route :( my seat had no window all the way at the end 😔

They canceled flight. Hard to believe there was even a plane incoming for us to get on

The worst. We never made our connection and they did absolutely nothing to help us at the airport.

Our flight was cancelled. They could do nothing to help us get another flight that was timely. Because the first leg was cancelled we were unable to get to our connection. We had to book on an entirely different airline for today. So we spent more money, lost a day of vacation and will never fly Frontier again, so the 'we are sorry, here is $100 credit' is a joke since we won't be flying on Frontier.

No way to get boarding pass on my phone. In order to print the bag ticket a boarding pass is needed. Asked the agent to print me one, they said they typically do not due this as its so much work. I showed the email confirmation and I asked how i could do it my self the agent replied he did not know as there was no link. The flight was delayed due to an attendant forgetting to come to work. On the flight no drinks were offered only for purchase meals.

No way to get boarding pass on my phone. In order to print the bag ticket a boarding pass is needed. Asked the agent to print me one, they said they typically do not due this as its so much work. I showed the email confirmation and I asked how i could do it my self the agent replied he did not know as there was no link. On the flight no drinks were offered only for purchase meals.

Since you have to pay for overhead bags then they shouldn't be running out of space and asking individuals who paid to remove stuff from the overhead

Cancelled flight after I arrived at airport after 75 min drive and parking. Next flight was 4 days in the future. Had to scramble and buy a much more expensive flight on another carrier.

Book with frontier airlines with the mentality that they'll cancel your flight, kick you off and lose your luggage. Anything besides that is a win. Compare prices with other airlines (to include luggage) and if frontier is still worth it, book it but know all of their policies.

You get what you pay for nothing essentially but a hard uncomfortable seat that doesn’t recline and kids screaming all around you and chaotic boarding and limited check bag weight allowance when compared to other airlines

I never got to experience the flight because they delayed my first flight and I missed this one. Then Frontier didn't want to help me rebook a flight to get me to my final destination.

Book cheap flights from Caribbean to Maryland

Recent round-trip flight deals

7/4Fri
nonstopSpirit Airlines
4h 04mSJU-BWI
7/5Sat
nonstopSpirit Airlines
3h 42mBWI-SJU
$152
8/28Thu
nonstopFrontier
4h 01mSJU-BWI
8/31Sun
nonstopFrontier
3h 52mBWI-SJU
$156
7/16Wed
1 stopDelta
8h 23mSJU-DCA
8/18Mon
1 stopDelta
10h 22mDCA-SJU
$215
7/31Thu
1 stopDelta
9h 54mSJU-IAD
8/12Tue
1 stopDelta
9h 14mIAD-SJU
$215
7/15Tue
1 stopSouthwest
8h 00mSJU-DCA
7/19Sat
1 stopSouthwest
8h 15mDCA-SJU
$235
9/10Wed
1 stopSouthwest
6h 30mSJU-PHL
9/17Wed
2 stopsSouthwest
12h 00mPHL-SJU
$290
7/16Wed
1 stopAmerican Airlines
9h 15mSJU-IAD
8/18Mon
1 stopAmerican Airlines
13h 46mIAD-SJU
$305
7/30Wed
1 stopUnited Airlines
7h 12mSJU-DCA
8/3Sun
1 stopUnited Airlines
6h 45mDCA-SJU
$313
6/27Fri
1 stopAmerican Airlines
12h 44mSJU-DCA
6/30Mon
1 stopAmerican Airlines
8h 43mDCA-SJU
$315
7/30Wed
1 stopUnited Airlines
7h 12mSJU-DCA
8/9Sat
1 stopUnited Airlines
8h 54mDCA-SJU
$323

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Recent one-way flight deals

7/2Wed
nonstopFrontier
3h 54mSJU-BWI
$78
8/28Thu
nonstopFrontier
4h 01mSJU-BWI
$79
7/15Tue
nonstopSpirit Airlines
3h 59mSJU-BWI
$80
6/27Fri
1 stopAmerican Airlines
17h 01mSJU-BWI
$83
7/15Tue
1 stopSouthwest
8h 00mSJU-DCA
$83
6/27Fri
1 stopAmerican Airlines
17h 01mSJU-BWI
$85
7/29Tue
nonstopSpirit Airlines
3h 59mSJU-BWI
$86
7/16Wed
1 stopDelta
8h 23mSJU-DCA
$108
7/16Wed
1 stopDelta
8h 19mSJU-IAD
$108
7/20Sun
1 stopSouthwest
11h 50mSJU-DCA
$148

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Last minute flights from Caribbean to Maryland

Last minute flight, train and bus deals

6/21Sat
nonstopAmerican Airlines
4h 00mSJU-PHL
6/21Sat
nonstopAmerican Airlines
4h 00mPHL-SJU
$198
6/19Thu
nonstopFrontier
3h 53mSJU-IAD
6/22Sun
nonstopFrontier
3h 50mIAD-SJU
$215
6/19Thu
nonstopUnited Airlines
3h 59mSJU-IAD
6/22Sun
nonstopUnited Airlines
3h 56mIAD-SJU
$216
6/19Thu
nonstopSpirit Airlines
4h 04mSJU-BWI
7/9Wed
nonstopSpirit Airlines
3h 40mBWI-SJU
$219
6/19Thu
multi-stopUnited Airlines
9h 45mSJU-IAD
6/22Sun
nonstopUnited Airlines
3h 56mIAD-SJU
$221
6/18Wed
nonstopSpirit Airlines
4h 09mSJU-PHL
6/24Tue
nonstopSpirit Airlines
3h 43mPHL-SJU
$235
6/19Thu
multi-stopSouthwest
7h 10mSJU-PHL
6/22Sun
multi-stopSouthwest
10h 45mPHL-SJU
$323
6/19Thu
multi-stopSouthwest
10h 55mSJU-DCA
7/1Tue
multi-stopSouthwest
6h 35mDCA-SJU
$374
6/20Fri
multi-stopDelta
12h 39mSDQ-IAD
6/26Thu
multi-stopDelta
6h 11mIAD-SDQ
$1,724
6/19Thu
multi-stopDelta
9h 54mSJU-BWI
7/9Wed
multi-stopDelta
11h 17mBWI-SJU
$2,840

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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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