$97 Find Cheap Flights from Caribbean to Maryland - Compare and Save

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 9/10. 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.
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Low season

September

Cheapest flight

$97
Best time to beat the crowds with an average 7% drop in price.
Most popular time to fly and prices are also 19% lower on average.
Flight from San Juan 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-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-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 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 $345.

  • 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 $667 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 $377 on average. Morning departures are around 40% 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 $262 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 $262.

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

    The cheapest month for flights from Caribbean to Maryland is December, when tickets cost $171 (return) on average. On the other hand, the most expensive months are January and February, when the average cost of round-trip tickets is $338 and $304 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 60% 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 4 cities. The city with the most direct flights is San Juan, with 26 direct flights each week.

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

    There are around 7 direct flights from within Caribbean to Maryland every day. Most flights (51%) depart in the afternoon.

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

    Each week there are around 45 direct flights from within Caribbean to Maryland. The most common day for departures is Sunday, 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 6h 59m, covering a distance of 1592 miles. The shortest route is Nassau (NAS) to Washington, D.C. Reagan-National Airport (DCA) with an average flight time of 2h 45m.

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

    Each week, there are 29 medium-haul flights (3-6 hour flight duration) and 16 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. (65% of total searches to Maryland). The next most popular destination is Philadelphia (35%).

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 4218 reviews
7.0Food
7.5Entertainment
8.6Crew
8.1Boarding
8.0Comfort
Airline reviews

Fairly good - the seats seemed more comfortable on this flight. The staff out of Detroit were quite friendly. But they directed us to the wrong carousel for luggage. :(

8.0 ExcellentDavid, Aug 2026
Read more Southwest reviews

Fairly good - the seats seemed more comfortable on this flight. The staff out of Detroit were quite friendly. But they directed us to the wrong carousel for luggage. :(

I liked the new boarding process. I thought the buyup options (legroom, early boarding) to be easy to request and reasonably priced. All the Southwest team from gate to in-flight were so nice.

The flight was fine. Seats were very comfortable. Attendants were very friendly -

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

One of the restrooms didn’t work. The ones that did never got replenished. Flight attendant just sitting there on their phone. No notification that the bathroom was broken so long lines. Apathetic crew.

Pushing back flight and ultimately cancelling it after multiple changes and hours of delays. Comm were terrible as to what was going on and what options were available.

Even though we arrived early and checked in, for some unexplained reason, our bags were removed from the plane and put on the next flight. It took over 12 hours after arriving to get our bags.

WiFi was not working. Flight was delayed in Paris as luggage needed to be removed from the plane that didn’t match a passenger on board. Upon arrival in Detroit the plane couldn’t get to the gate as the pilot turned onto a runway with construction in progress . We waited to be towed back onto the runway. We were almost an hour late causing many passengers to miss their connecting flights.

Stewardess was not accommodating when I requested a second drink.

Some of the passengers are coming on board with luggage so overstuffed and/or too large that have no business going into the overhead bins.

I am in a wheelchair The gate agent knew exactly how to boarding A wheelchair first also the flight attendant knew exactly what she was doing

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.

I had 1 hour to connect flights. Boarded the first plane with a broken restroom and captain decided that the 1.25 hour flight couldn’t leave until fixed. Needless to say, I missed my connecting flight and will arrive at my final destination 6 hours late.

I understand that the plane is a regional jet, but American Airlines can do better! They have been operating these planes for 25 years by now. The seats are uncomfortable, and both boarding and deplaning are painful and waste a lot of time due to carry-on baggage.

The flight had a 6 hours delay. This should not happen to anyone. Airlines should provide an alternative with no additional costs.

Flying on this airline is nothing short of a full blown circus clown show. On a recent return from my mother’s funeral, my only available choice from IND to PWM was American, which I hesitantly booked as I rarely fly them for many of the following reasons and never will again. I was booked IND-PHL-PWM totaling about six hours. The flight was cancelled due to NE weather. They rebooked me on a two stop flight IND-DFW (Yes DALLAS)-PHL-PWM, still all on the same day. After arriving in DFW, they continually delayed the DFW-PHL flight due to maintenance issues on the arriving flight. Finally it was delayed to the point that my PHL-PWM connection was no longer possible. They then rebooked me thru LGA with the short flight the NEXT DAY to PWM and offered to put me up for the night in NYC (or so I assumed). The flight DFW-LGA was then delayed so much that I asked to be put in an earlier flight with a lessor delay. Throughout this day chats with their AI assistant were useless as were subsequent chats supposedly with a real person(?). Only one customer service agent in DFW was actually helpful and appeared to care. Upon arrival at LGA post midnight, they issued me car and hotel vouchers in Trenton NEW JERSEY at a very old Howard Johnsons ONE HALF HOUR from LGA. The hotel was an $85, 1.5 rated hotel in a very sketchy area of NJ that I would have never voluntarily booked. As I prepared to catch the car back to LGA the next morning I received a text that my flight was cancelled. TWICE IN TWO DAYS. I went to LGA hoping to have AA book me on an earlier Delta flight. The full service line was at least 200 people deep, so I tried to reach a real person agent by phone. After 1/2 hours on hold I gave up and waited for my later LGA-PWM flight. It actually started boarding on-time, but only shortly after announced a maintenance hold. We were told it was nothing serious, just an adjustment to the Captains seat. Only one update was given while we waited 1.5+ hours for a “SEAT ADJUSTMENT”. Can’t forget to mention that on all of these planes the WiFi only worked on two. During that time at least three others flights in my area announced that they were overbooked and were taking volunteers before bumping people. Another flight to ORD announced a gate change and less than five minutes after announced that they were really not changing and announced for everyone to return to that gate. Can’t forget to mention that on all of these planes the WiFi only worked on two.🤡🤡

Paid for wifi but it didn't work once. Seats were incredibly cramped and passengers sitting in front was reclined the entire time and staff did nothing

Delays and cancellations. Mechanics weren’t on site. Replacement plane took hours to arrive although it should have arrived within 90 minutes. Flight back was cancelled. Ended up driving over 12 hours and wasting 3 days between everything.

Flight was delayed multiple times and rerouted to different concourses in the airport because of all of American's delays. App/boarding pass would not update with changed gate information.

Flight was delayed, boarded, sat at the gate for more than 30 minutes, left the gate then waited on the pad for another 30 to 60 minutes then returned to the gate, deboarded and was cancelled... alternative flight was not booked automatically. Waited in line for 30 minutes but fortunately an alternate flight to a different destination was found ... no thanks to the travel agent used by kayak

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.

It was my first time in Jetblue flight in 10+ years(?) and the experience was horrible. You were better before. There were ATC delays sitting/waiting in the tarmac for 2 hours, I understand that this isn't Jetblue's problem but how the matter was handled poorly is. Cabin was so warm and hot couldn't get it to cool down for the entire waiting period worse, even during cruise flight. Start, the passengers were spoken to and treated like a little children with no respect. Constant/multiple annoying tone/voice PA announcements of mentioning "... only big/large suitcases are for the bin and small ones need to be placed under the seat, etc,..." I see that flight was delayed and crew were trying to get the plane ready to board as soon as they can but the way they presented was lack of better word, condesending and scolding tone to cattle. It was definite unpleasant, unwelcoming flight experience I have ever had with Jetblue. Whatever happen to smiles and fun employees , pleasant/helpful gate agents, flight attendants, crews, where have they gone? It was dissapointing flight experience overall from everyone. Sorry for the direct transparency.

Flight was cancelled as JetBlue could not find a pilot. Communication was poor and they did nothing for stranded passengers. Flight they rebooked us on was 4 days out.

JetBlue cancelled the flight. We had to rebook on another airline.

JetBlue cancelled the flight along with hundreds of others, for no apparent reason. no recourse, no rebooking options. never booking with them again

Jet Blue cancelled my flight after I had boarded. They attempted to rebook me for a new flight two days later. I was able to rebook with a different airline, but not until the next morning. As such, I was forced to get an expensive hotel and missed important work meetings Monday morning. I am very disappointed with the customer service and will be pursuing full reimbursement for my hotel cost.

You did a great job rescheduling my cancelled flight. However, you made me pay for two seats for $118 even though the seats on the original flight were free. I think that was a very unfair thing to do.

They cancelled the flight after 5 hours at the airport and the only flight they offered was for the next day with a 7.5 layover in fll. This was not going to work for me as this was only a weekend trip and getting into providence at 10 pm a day later caused me to lose Mo ey on hotels money on airport parking a dog sitter etc. they wouldn’t offer any type of a voucher or anything else. All they did was refund the flight which didn’t help me with all the money in time I lost. I was going to see my very sick father

The plane took off very late upon arrival and departure

The flight was on time the crew was courteous that makes for a good flight.

A more comfortable seat. Padding would be really helpful but I've read the airlines don't want customers to be satisfied with economy seats.

Frontier is good until they cancel your flight. Way too many cancellations.

I know Frontier is a “no-frills” airline. I understand the concept. However, I jumped on some tickets for our family vacation, expecting to play a bit of a game to figure out the family bags and not over spend. In the end, I got the short end of this deal by far. 1. I did not expect them to charge the baggage fee for each direction. It makes the fee look high-ish at a glance, but reasonable. Then when you get to checkout and realize you have to pay it twice to come home with your luggage, it becomes ridiculous. 2. The low checked bag weight limit. I am used to packing a 50lb bag with my preferred airline. Frontier’s artificially low 40lb limit more quickly triggers the extra weight fee, which almost DOUBLES the price of the bag if you go over ($79 for the bag/$75 for the next 10 lbs) 3. The fee for a carry-on bag is the same as a checked bag but with a lower size and weight limit. Make it make sense! 4. The seats are terrible. My 2.5 hour flight almost had me losing my mind. I’m 6’3” and my femurs barely fit in the space provided. My knees had to wiggle just right to jam into the crack next to the armrest of the seat in front of me. The cushioning was thin and inadequate. I am tall but I’m not a freak. These seats are unacceptable. 5. I overheard the woman next to me speaking with the gate agent about being charged a $25 fee for not checking in online - she checked in at the airport counter when she arrived. That’s ridiculous. She was old and in a wheelchair. She had a paper boarding pass, and was obviously not tech savvy. She should not be punished for that. 6. They do not have good placement in the terminals. It was always out on the end or down on a subfloor, and we had to walk out on the tarmac almost every time. In Denver. Their home airport! 7. Every time I loaded a new page on the website while buying my tickets or my bags, it was constantly trying to upsell me on some esoteric bundle. Like, a pop-up every time. Very annoying. 8. No screens in the boarding area (at least where we were) to confirm you’re in the right place. Just static gate number signs. I am sure these are standard practices for Frontier, and I should have read more about them before I purchased tickets, but as a result of this single round trip, I do not plan to ever use this cut-rate airline again. I would rather pay the normal amount for a ticket and be treated like a customer instead of a mark.

Our flight was delayed 2 hours and when they changed the the time to 1 hour I wasn't alerted and when I checked the gate the plane was still there but they already shut the doors so I had to buy another flight.

Don’t even matter if I write it y'all not going to fix it

Great except upon arrival it took them a long time to open the doors

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.