$119 Find Cheap Flights from Caribbean to Maryland

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight from Caribbean to Maryland departing on 7/17. Fares are subject to change and may not be available on all flights or dates of travel. Click the price to replicate the search for this deal.
1 adult
1 adult, Economy, 0 bags

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Low seasonSeptember
Cheapest flight$119
Best time to beat the crowds with an average 9% drop in price.
Most popular time to fly and prices are also 17% lower on average.
Flight from San Juan Airport to Philadelphia

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
SJU
-
BWI
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
SJU
-
BWI
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 97% 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 $312.

  • 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 $329. On the other hand, the most expensive day to fly is Monday, where round-trip prices are $637 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 $381 on average. Morning departures are around 32% 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 $282 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 $282.

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

    The cheapest month for flights from Caribbean to Maryland is October, when tickets cost $69 (return) on average. On the other hand, the most expensive months are March and November, when the average cost of round-trip tickets is $470 and $414 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 58% 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 37 direct flights each week.

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

    There are around 12 direct flights from within Caribbean to Maryland every day. Most flights (62%) depart in the afternoon.

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

    Each week there are around 82 direct flights from within Caribbean to Maryland. The most common day for departures is Saturday, with 22% of flights taking off on this day.

  • How long is the flight to Maryland?

    An average nonstop flight from Caribbean to Maryland takes 8h 09m, covering a distance of 1569 miles. The shortest route is Nassau (NAS) to Washington, D.C. Reagan-National Airport (DCA) with an average flight time of 2h 48m.

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

    Each week, there are 61 medium-haul flights (3-6 hour flight duration) and 21 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. (66% of total searches to Maryland). The next most popular destination is Philadelphia (34%).

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 4246 reviews
8.6Crew
8.0Comfort
8.1Boarding
7.5Entertainment
7.0Food
Airline reviews

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!

2.0 MediocreDawn, Jun 2026
BUF - BWI
Read more Southwest reviews

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).

I am very please with the service received from Southwest. Although there was a refuel stop in Fl before we got the Baltimore. The service and kindness of the staff was excellent.

Southwest continues to do less for more money. Flight attendants used to be fun and friendly. But now it’s like they don’t even see you. Such a shame.

I liked it better when you were truer to your roots Am paying more for less fun

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

The last 3 flights between BWI and BDL canceled the beverage service mid- way. Just say up front that the fight is too short. Thanks!

I was assigned seat 7E, yet my boarding was Group 5, which caused me to have to put my luggage in the back of the plance above `19 or 20 aisle, as passengers who had boarded earlier took the overhead bins in the front. SW needs to monitor bin space and ensure that bin space above the seat are aligned to those sitting near their seats. Also the seating assignments needs to align with group number. Maybe board those last first and so on? Having said the ALL the passengers on the plane were gracious enough to allow me and other passengers in this dilema to retrieve our luggage and helped us along the way. I always love the flight staff, as always their fantastic and I can't rave about them enough!

WIFI was great. My selection for seating is an aisle, but during my trip, I never had an aisle seat. If we can get that corrected, I will be thrilled.

Everything about this flight was good except for the very end when I reached my destination. Everyone from the tune to the wheelchair escorts were great with the case were great but I miss you with people at the check in this at the very end. I need help from the chicken desk because I forgot my pillow on the plane The female worker at the chicken desk said that they found my pillow and she was going to retrieve it for me. She left a 30 minutes without any update and her so she saw me walking back and forth waiting for her and they didn't even bother calling her or radioing her for any updates. They were busy because they were behind schedule and they were overwhelmed but thanks because at least glanced me and try to give me an update just a quick radio check or phone call. I don't care about the pillow but if you tell me to wait, I waited for at least half an hour before I said something and I just left because they wouldn't bother talking to me so I could, so everything's going in the review. I took pictures of the two men that were left working at the check-in counter. The totally ignored me despite the signals I've been giving them. I don't see any offers in the kayak review to add pictures or screenshots so I'm going to post another review I don't know their name but I'm pretty sure Delta will find other names when they see the review. Google with pictures. There was another guy at the chicken counter bring an orange workers vest who finally left after telling me that the girl that was retrieving my pillow is working the gates now. That would have been if they just told me that's what happened. But I had no update. Make me wait for nothing. Thank you Delta airlines!

We had a great experience with Delta. They helped us from the start at the kiosk all the way to our final destination, including help reassigning and upgrading our seats free of charge at the gates, escorts with the wheelchair for my brother and even getting our luggage at baggage claim for us. I also had special help because I forgot my pillow on the plane. The wheelchair escort contacted for associates at the check-in desk all the way back to the plane and retrieved my pillow for me.

I am a Diamond Medallion Delta traveller and this was a disappointing flight. They allowed half the flight to preboard before Delta One and Diamond Medallion. Once on the plane in my Delta Premium Select seat we were not given any welcome or greeting. Throughout the flight the flight attendant also did not make us feel any sort of special service or attention and even rushed us when she did bring us a snack to pick in the dark not even offering a light to look at what it was -- she was overall not helpful and not accommodating. for the extra cost of the seat it was honestly not a special experience this flight. heads up that even the warm cookies are now packaged. I ate nothing. There really was nothing that was special, stood out or exceptional. Luckily I mostly slept. But I was disappointed and question if I may try a different flight next time I go to Tokyo. The last few Delta flights have been less than great. which makes me very sad.

Crew was real good, flight was smooth and came in early.

The CRJ-900 was clean but the overhead air vents were broken in our First Class row, making the cabin very hot until about 30 mins into the flight. The flight attendants were both extremely apologetic and accommodating though so that is why I rated the flight as very good. They checked on us many times and truly showed they cared. The snacks for an hour and a half flight could be better. Would be nice if there was a small plated meal over convenient store snacks. WiFi also was not working. And it would be nice if Delta had adjustable headrests on these planes.

New high end luggage ruined/zippers broken, items missing. All happened on return flight from msp to mso. Do better! Not store bought luggage but high end personalized ogio custom embroidered luggage. Total slap in the face ontop of an extra luggage fee that took me 3 hrs on chat to resolve.

The internet that was free was terrible, the turbulence was pretty bad - uncontrollable I know.

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.

Flight attendants on United are the worst in the business. Can’t be bothered to provide even basic levels of service and are as rude as anyone can get. This flight was not an exception to that rule.

The staff was incredible, very attentive, polite, made you feel like the center of the universe. They even all wrote me a happy birthday card. Truly just an amazing crew, cannot stress it enough.

Compared to our Lufthansa flight out, it was pretty poor. Check-in was a nightmare trying to figure out if it was Lufthansa or United, the Kayak link kept sending us to a dead link with United. Then figuring out which code was United was a mess - it took way too long. On the flight, the seats were uncomfortable, they were out of all wines but red when the flight started, then out of red after the first beverage. The flight attendant said they never get restocked before they turn around to the US, so it happens all the time. The food was so bad we threw it away. For a long flight, it was pretty terrible.

Not being stranded in Chicago for her airport to 11:30 tomorrow morning the 3rd

Everything was great. Only thing that could’ve made it better was buy on board options for hot food, but the snacks were decent. The flight attendants were great. I had no complaints. I was able to make it to my destination safely

David went above and beyond to make our flight the best that it could be

The crew and flight was amazing. I haven't flown United in years but plan to switch to you being my main airline

Wouldn’t let me check in said couldn’t find a ticket had to wait very long Time

Seat cushions were worn down and it hurts as I seated under 5 hours of the plane ride.

I wish I had another choice. Domestic flight in the USA is atrocious.

The planes can use an actual cleaning. The armrest and seats do not appear to be cleaned on this one and most other planes.

The flight attendant was very polite and attentive. The food was good.

we had flown from Okinawa and had breakfast in Okinawa. There were issues with the plane so service was postponed. I asked a crew member if we could get something to eat as I was very hungry. Shevwas so nice that shev brought nuts for all of us. The sad part is that thevnuts were stale but I was hungry so I ate them. My side of the rew was really very nice. Both my wife and I travel quite a bit even though we cannot lift our bags as we get help. My wife asked her dso=ide crew if she could help put up the computer bag. She told he that its not her job. Oh well

For some unknown reason, my checked bag didn't arrive at the same time. I got to my destination about 30 minutes late (5pm) and my bag was delivered to my hotel at 2:06am.... in the past 4 flights with AA, they been delayed and I've missed connections and my bags. Poor service.

I had a comfortable and enjoyable experience. The entertainment options were plentiful, the food was appetizing, the snacks were tasty, and the staff was friendly, professional, and helpful.

Flight was delayed…once landed at ORD, no gates were available so made us wait for 56 minutes after we landed to let us out of the aircraft!

I cancelled this flight 2 days before departure but I followed your texts and emails and IF you were correct this flight turned into a nightmare.

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.

Boarding went fine, the plane was clean, and the crew was very friendly. Seats were a bit cramped, but that seems to be typical on all airlines anymore. Cookies and pretzels were offered as were beverages - the usual. I’d fly American again.

Crew was kind of grumpy and there was no beverage service at all. Sodas were $4. Disappointing.

There weren't enough employees at check in took awhile to get bags checked. There wasn't a wheel chair for me, I was sent to someone who turns out to work for a different airline, if My flight hadn't been delayed I probably would have missed my flight as it was, by the time I arrived at my gate, they started boarding in about 15 minutes. I don't know who took me to my gate, definitely was not the normal people who take passengers to the gate. I'm guessing she may have been in a management position. I wish I knew her name, she went beyond to help me. With that said everyone was kind, and were doing the best they could. So, I choose to say it was an Adventure, stressful start, but good. In the end went well. The situation was not only difficult for passengers but the employee's.

The staff at the check in counter was so rude. Made you feel Incompetent

Frontier scheduled a 40 minute connection in DEN. What they failed to mention was that they “close the doors” 20 mins prior to departure, which means you only have 20 mins. Not enough time. Possibly against DOT regulations. Filing complaint.

Flight was scheduled at 9:40pm. Got delayed to 10 am, the next day. crazy

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!!!

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.