$59 Find Cheap Flights from Caribbean to Maryland

1 adult

KAYAK searches hundreds of travel sites at once for deals on flights to Maryland

Travelers love KAYAK
41,299,237 searches in the past 7 days on KAYAK

Save 22% or moreCompare multiple travel sites with one search.

Track pricesNot ready to book? Create a price alert for when prices drop.

Bundle and saveSave money when you bundle your flight + hotel.

Filter your dealsChoose cabin class, free Wi-Fi and more.

Useful Info
Useful Info

Good to know

Low seasonFebruary
High seasonJuly
Cheapest flight$59
Best time to beat the crowds with an average 13% drop in price.
Most popular time to fly and prices are also 2% lower on average.
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 $239.

  • 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 $378. On the other hand, the most expensive day to fly is Sunday, where round-trip prices are $601 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 30% 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 $530.

  • What is the cheapest flight to Maryland?

    The cheapest ticket to Maryland from Caribbean found in the last 72 hours was to Baltimore, at $98 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 $98.

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

    The cheapest month for flights from Caribbean to Maryland is January, when tickets cost $382 (return) on average. On the other hand, the most expensive months are November and June, when the average cost of round-trip tickets is $571 and $569 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 00m, covering a distance of 1584 miles. The shortest route is Nassau (NAS) to Washington, D.C. Reagan-National Airport (DCA) 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. (73% of total searches to Maryland). The next most popular destination is Philadelphia (27%).

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 4294 reviews
7.1Food
8.0Comfort
8.6Crew
7.6Entertainment
8.2Boarding
Airline reviews

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

8.0 ExcellentJohn, Apr 2025PVD - FLL
Read more Southwest reviews

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.

Plz don't take away free bags and free seating

The seats were a bit cramped and worn, but otherwise okay.

I would have liked to arrive on time - not 5 hours late!

After a 3 hour layover in Denver my flight was delayed over 5 hours! No explanation; no assistance; no offer to provide compensation; no one at Southwest was willing to offer any assistance. 8 hours in the Denver airport - ridiculous!

It was a perfect flight in all aspects! Both legs!

Only one drink pass through the cabin for a 4 hour flight. Quite rough and bumpy landing.

Boarding process, crew were good. But the seats were so uncomfortable that was all I could focus on. I literally had to sit forward so that all 3 of us could fit in row. I will try to avoid Southwest in the future for any flights over 60 minutes.

Fine except the person next to me took up her seat had raised the arm divide so she spilled into my seat. because of her size. Fortunately no one was in the seat on my right so I could use part of it.

Delta is my preferred airline. I've traveled with them for years. On time in most cases, good communication, easy to use app. Most planes are pretty nice. I was on a CRJ 700/900 however, which was pretty badly aged inside and needed a refresh. No infotainment, unreliable wifi, best to download before boarding or bring a book. Food choices are really just snacks on this flight, nice variety but about what you'd expect. Great staff and prompt in departure and early arrival too. Overall quite satisfied.

Crew was friendly Love the entertainment in the seat head rest.

Delta flight was on time, seats were comfortable, and crew was nice.

This had nothing to do with Delta… The flights were on time and flawless. The service was excellent. We purchased seats in (aisle/middle) comfort plus since this was a cross country flight. Unfortunately, the woman seated at the window was 300+ pounds and, as might be expected, covered up about a third of the middle seat also. there was absolutely nothing that Delta could have done about that… I just don’t know what the answer should be. If you purchase a seat, you should should be able to use the entire seat and not just the portion that someone else is not sitting/oozing in. Disappointing…there should be something that could be done….I'm just not sure what solution could be.

Delayed take-off. Very small plane so very scary with lots of bumps during the flight. Would never fly Delta on short flights in small 80 seaters plane again! Felt relieved when landed.

Delta is a cut above the others in customer service.

The worst part was I was NOT allowed in the lounge even though I was holding a first class ticket and have a premium American Express card. I have flown Business or First Class with many airlines. Delta is the ONLY one who does not extend this courtesy to anyone except people who hold the very expensive American Express card. As a result, I won’t fly Delta if I have any other choice.

A little bumpy ride . No food was being provided due the the turbulence. That was ok it was a short flight to my standards.

Simply outstanding. Their new lounge for Delta One customers is a cut above the rest.

Paid $35 and not able to access the internet at all.

Several delays. Next flight was worse. Did not arrive home until 2am PT

Very helpful ground crew after an earlier flight delay and being rebooked on a different flight.

Everything about the flight was lovely…We left early, arrived early, cabin crew were efficient and helpful. Flight was easy and most pleasant.

First world problems, but still… We were seated in first class and asked for a cocktail on a very short, 50 minute flight. After our drink order was taken, a half hour went by, and we noticed that every other person in the small plane had been served except for us. We got up to ask about it, the drinks finally came, then were taken away three minutes later since the flight was so short. Really strange situation, on the other hand, we were in Utah.

We missed our flight. The boarding pass had the wrong gate and by the time we received the text from Kayak, our flight was already gone. I’ll never use Kayak again and will go direct to the airlines in the future.

Boarding took forever, the plane was cramped and cold, and the seatbelt song came on constantly throughout the red eye flight with a loud pre-recorded message playing each time

Cabin felt crammed Snacks are lame But crew was super efficient getting us out on time despite delay

Flight was delayed bc of mechanical issue. New plane had different configuration so some seats had to be switched. They called all passengers who needed new boarding cards. They did not call us so we thought our seats were the same and fine. When we boarded they informed us our receipts had changed and we are now all sitting separate and in the back row. Both my daughters had meltdowns and started to cry and once we got on the flight, we figured out how we could sit closer to each other, but this was very upsetting.

Took off on time and successfully avoided weather that looked to be a problem along the way

I mean, it’s Spirit. But it was frustrating to have our flight canceled, get bumped to a later flight, and then Spirit was unwilling to check our bag until 4 hours before our flight… tell us we could not sit in the waiting area’s chairs… and really negative experience getting checked in and dropping the bag.

Not having it be changed after we bought the flight tickets from a direct flight getting in at a reasonable time to a connecting flight red eye of 9 hours, so that we would lose our 35 dollars in nonrefundable insurance would've been great! Our country really does need low-cost carrier options, but this type of "service" ain't it. Fortunately, had a little better success with them flying to and from San Juan PR last month at least.

All was good expecting the seats need a bit of cushion. Besides that I can’t complain.

You get what you pay for, and the flights went smoothly. There’s no reclining chairs, no screens, And there isn’t always wifi, but the plane was clean and staff was friendly and the takeoff/landing were smooth.

The only positive is that the flight made it both ways. Getting charged for every little thing after the cost of the ticket itself is comical, considering how the plane and services are as bottom-tier as possible. The self check-in kiosks are useless. It’s nice to think that you can print your boarding pass, tag your checked bag, and then just drop it off. But no, they still make you go through the line once you finish- what’s the point of the self check-in then? Any questions for the staff seem like the biggest inconvenience and were met with condescending responses. This was my first and now last time ever flying with Spirit. After all the extra costs, subpar plane and staff, I see no value. I’d rather drive the 13 hours than give Spirit another dime.

The flight was fine however what started as a reasonable priced ticket could have become an overpriced ticket with additional charge for carry on as well as checked bag $79 per bag per person each way. Additional charge for choosing one’s seat, additional charge for beverage and snack, we were on what was described as a new plane yet there were no audio/visual on the jet. A bare bones service but not at a bare bones price. Will think twice before flying Spirit again. 😕

Flight was delayed a bit, but that was expected (and updated), so really not bad at all for the price. Could’ve used one less email asking me to upgrade my seat; otherwise no significant complaints

I love Spirit. New aircraft, great cabin service, the airfares are low cost which helps me visit my hospitalized daughter anytime I can without paying a fortune.

Flight was 2hours late they had no crew or the pilot.

I paid for streaming wifi and the connection was poor.

The reps working at the airport counter were dumber than a second coat of paint.

My costume jewelry was stolen out of my bag. Got to airport and my bag weighed 45 pounds- 5 pounds over cost me $100 Long lines in tier one. No entertainment No WiFi no free drinks or snacks

Not very good. Paid in excess of $400 for assigned seating for my family and that was not provided. I want that money back.

The seats were hard molded plastic covered in plastic vinyl. And the scam to charge people extra to sit together. Don’t they know we can just ask someone to trade seats. And watching the staff separate young children from parents… super classy. We had to guilt them into offering up our seats. This companies policies suck. Don’t give them your money.

The seats were awful, hard plastic covered in sheet vinyl. The airline tries to scam you into paying extra to get seat together when the flight wasn’t full. They were going to separate a family with young children but my wife who had a row to herself gave up her seat so the young mom could be with her young boys. I’m never giving this airline my money again.

It was a short flight so no food or entertainment….

Seats are uncomfortable but price is good. Guess I can put up with misery for four hours.

I’ve never traveled on Frontier before. If you want basic, no frills, friendly service at great prices then give them a fly!

I guess you get what you pay for. The seats are very uncomfortable and very little space. The snacks were pricey.

Cancelled and declined to find alternatives Earlier flight is 2 days later Sent the cancellation notification very late, wish I knew earlier would have stayed to watch the Miami open final game Very disappointing service

Book cheap flights from Caribbean to Maryland

Recent round-trip flight deals

5/24Sat
nonstopSpirit Airlines
4h 01mSJU-BWI
5/27Tue
nonstopSpirit Airlines
3h 47mBWI-SJU
$116
5/24Sat
nonstopSpirit Airlines
4h 01mSJU-BWI
5/27Tue
nonstopSpirit Airlines
3h 47mBWI-SJU
$128
5/22Thu
nonstopFrontier
3h 55mSJU-IAD
5/25Sun
nonstopFrontier
3h 52mIAD-SJU
$128
5/22Thu
nonstopFrontier
3h 55mSJU-IAD
6/1Sun
nonstopFrontier
3h 50mIAD-SJU
$148
5/29Thu
1 stopDelta
9h 20mSJU-DCA
5/31Sat
1 stopDelta
10h 39mDCA-SJU
$225
5/29Thu
1 stopDelta
11h 17mSJU-IAD
5/31Sat
1 stopDelta
11h 22mIAD-SJU
$225
5/22Thu
1 stopAmerican Airlines
6h 12mSJU-DCA
5/26Mon
1 stopAmerican Airlines
6h 12mDCA-SJU
$236
5/29Thu
1 stopAmerican Airlines
12h 39mSJU-DCA
6/2Mon
1 stopAmerican Airlines
6h 36mDCA-SJU
$255
7/24Thu
1 stopSouthwest
10h 15mSJU-DCA
7/28Mon
2 stopsSouthwest
9h 20mDCA-SJU
$435
5/16Fri
2 stopsSouthwest
11h 15mSJU-DCA
5/19Mon
1 stopSouthwest
7h 50mDCA-SJU
$440

Search by stops

Search by airline

Search by price

Recent one-way flight deals

6/4Wed
nonstopSpirit Airlines
4h 01mSJU-BWI
$59
5/22Thu
nonstopSpirit Airlines
4h 01mSJU-BWI
$64
5/22Thu
nonstopFrontier
3h 55mSJU-IAD
$64
6/5Thu
nonstopFrontier
3h 53mSJU-IAD
$78
6/5Thu
nonstopSouthwest
4h 15mSJU-BWI
$113
5/28Wed
1 stopDelta
11h 07mSJU-DCA
$113
7/15Tue
1 stopDelta
10h 10mSJU-IAD
$113
5/22Thu
1 stopAmerican Airlines
6h 12mSJU-DCA
$118
6/4Wed
1 stopAmerican Airlines
16h 47mSJU-IAD
$138
6/24Tue
2 stopsSouthwest
12h 35mSJU-BWI
$183

Search by stops

Search by airline

Search by price

Last minute flights from Caribbean to Maryland

Last minute flight, train and bus deals

5/1Thu
nonstopSpirit Airlines
4h 07mSJU-PHL
5/5Mon
nonstopSpirit Airlines
3h 47mPHL-SJU
$171
5/2Fri
nonstopSpirit Airlines
4h 07mSJU-PHL
5/5Mon
multi-stopSpirit Airlines
15h 29mPHL-SJU
$190
5/1Thu
nonstopFrontier
4h 01mSJU-PHL
5/31Sat
nonstopFrontier
3h 53mPHL-SJU
$209
5/3Sat
nonstopFrontier
4h 01mSJU-PHL
5/6Tue
nonstopFrontier
3h 53mPHL-SJU
$212
5/2Fri
multi-stopDelta
8h 29mSJU-PHL
5/4Sun
multi-stopDelta
7h 19mPHL-SJU
$279
5/4Sun
multi-stopAmerican Airlines
9h 13mNAS-IAD
5/10Sat
multi-stopAmerican Airlines
16h 04mIAD-NAS
$385
5/4Sun
multi-stopAmerican Airlines
9h 13mNAS-IAD
5/10Sat
multi-stopAmerican Airlines
15h 04mIAD-NAS
$389
5/2Fri
multi-stopDelta
6h 48mNAS-IAD
5/4Sun
multi-stopDelta
5h 47mIAD-NAS
$402
5/3Sat
nonstopSouthwest
4h 20mSJU-BWI
5/10Sat
nonstopSouthwest
4h 00mBWI-SJU
$481
5/2Fri
multi-stopSouthwest
10h 25mSJU-DCA
5/5Mon
multi-stopSouthwest
6h 30mDCA-SJU
$490

Search by stops

Search by airline

Search by price

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.

Not what you’re looking for? Find thousands of other hotels, flights, car rentals and package deals with KAYAK.