$79 Find Cheap Flights from Caribbean Islands to Maryland - Compare and Save

1 adult
1 adult, Economy, 0 bags

Save 21% or more on flights. Compare deals from all over the web.

Never overpay with our price tracking tools.

Filter searches by price, airline and more to find your best flights.

Useful Info

Good to know

Low season

September

Cheapest flight

$79
Best time to beat the crowds but there is an average 3% increase in price.
Most popular time to fly and prices are also 26% lower on average.
Flight from San Juan to Philadelphia

Flights from Caribbean Islands to Maryland: the best tips from KAYAK users

Insights shared by verified travelers who flew the route from Caribbean Islands 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 Islands to Maryland

  • How does KAYAK find such low prices on flights from Caribbean Islands 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 Islands to Maryland.

  • How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from Caribbean Islands to Maryland?

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight from Caribbean Islands 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 Islands 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 Islands 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 Islands 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 Islands 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 $373.

  • 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 $360. On the other hand, the most expensive day to fly is Monday, where round-trip prices are $678 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 $386 on average. Morning departures are around 38% 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 Islands found in the last 5 days was to Baltimore, at $193 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 $193.

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

    The cheapest month for flights from Caribbean Islands to Maryland is December, when tickets cost $275 (return) on average. On the other hand, the most expensive months are August and January, when the average cost of round-trip tickets is $480 and $393 respectively.

  • How far in advance should I book a flight from Caribbean Islands to Maryland?

    To get a below average price on the flight from Caribbean Islands 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 Islands, there are direct flights to Maryland from 4 cities. The city with the most direct flights is San Juan, with 16 direct flights each week.

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

    There are around 5 direct flights from within Caribbean Islands to Maryland every day. Most flights (65%) depart in the afternoon.

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

    Each week there are around 34 direct flights from within Caribbean Islands to Maryland. The most common day for departures is Sunday, with 21% of flights taking off on this day.

  • How long is the flight to Maryland?

    An average nonstop flight from Caribbean Islands to Maryland takes 6h 41m, covering a distance of 1574 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 16 medium-haul flights (3-6 hour flight duration) and 18 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. (68% of total searches to Maryland). The next most popular destination is Philadelphia (32%).

Reviews of the top 5 airlines serving from Caribbean Islands to Maryland

 
Need help choosing which airline to fly with from Caribbean Islands 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 4190 reviews
8.0Comfort
8.1Boarding
8.6Crew
7.0Food
7.5Entertainment
Airline reviews

Trash experience on all my flights this week. Delay after delay. The flight I’m waiting for has been delayed 6 times and nearly 3 hours.

2.0 MediocrePhilip, Sep 2026
Read more Southwest reviews

Trash experience on all my flights this week. Delay after delay. The flight I’m waiting for has been delayed 6 times and nearly 3 hours.

Flights delays were communicated timely and helpfully, but there was a significant delay without any real effort to make up for that. Also, the in-flight WiFi was very spotty. That said, this was my first time with Southwest and I was quite happy with the service and staff otherwise.

Very poor service with connecting flight. I missed the connection because of a delayed flight and significant delay in getting my bags in order to make the connection. The ground staff where unhelpful and rude!

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.

The wifi was barely operable. just enough to charge me, not enough to be useful. I wasted 2 hours of time I could have been working. So now, I' have two hours of work this weekend to catch up on thanks to Delta's crappy technology. Plus I'm out the money!

got ahead of the schedule, nothing else to like. crew management of boarding when overhead bag space was virtually gone in the midst of their priority zone 3 should have been better. but they absolutely did not care. ryanair crew is better than this!

It’s a 3 hour flight with no entertainment and no WiFi due to Delta using old planes on this route and food is cold. Today we were told no potable water on the flight to even make coffee or tea. Ridiculous service in this direct route for business travelers and non business travelers

The crew was excellent but the entertainment did not work. The 3mm jack for the headphones was faulty and no sound was available for entertainment.

The number of interim flight delays has been higher than I can remember in my history of travel making any connection a mystery as to whether you will actually make it.

I love how the flight crews are now saying what the weather will be like, when we can expect to be able to get up and use the restrooms etc. I have to say also that our flight crews this trip were incredible - fast and courteous - and somehow managed to do the service even on these short flights with a few bumps. The only reason for an ok rating on entertainment was because these short flights are on planes without seatback displays but that's ok because I just download shows on my iPhone beforehand.

Flight was delayed and we were on the runway after landing for 30 mins

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.

Plane congestion resulted in a 1 hr wait from landing to arrival at the gate. This was in addition to also experiencing extreme delays on my incoming flight.

Delayed too much. 1.5 hrs in the airport and another 1 hr in the runway. Got too late in the night. There was no proper food available.

Baggage claim signs were not updated with my flight information, so I had to guess. The app wasn't updated either.

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.

KUDOS TO ALL THE CREW PROVIDING ASSISTANCE WITH PASSENGERS ON A WHEELCHAIR. ON BOTH FLIGHTS THEY HUSTLED TO TAKE MY RELATIVE TO CONNECTION ON TIME. THEY DESERVE A LOT OF CREDIT!

Good experience with this flight. Boarding was smooth with no issues. The short flight was good with quick drink & snack service. Nice easy way to get back from DC.

Staff was very responsive and nice. Long delay because of mechanical issues was a problem.

Very good flight that left on time and arrived earlier than anticipated, which was a plus! The crew members were very welcoming and helpful. However, the temperature on the flight was very cold - almost to the point of extreme discomfort. Additionally, requiring passengers to pay $8 for headphones to access the JetBlue entertainment was disappointing. Those earbud jacks are not used with most technology and would not be able to be used. There was no option to use Bluetooth for my own earbuds. Beyond those inconveniences, the flight was good.

My original flight was cancelled. My replacement flight was delayed over 2 hours. I lost my whole day in NY

Delays were crazy long (over an hour) both for boarding and baggage claim

awful expereince. boarding was a mess and not communicated, then we sat on a hot plane and were at risk of getting kicked off

2 hour delay and a lack of air conditioning on the plane. Not a good combination

It was so nice! I wish that we can have direct flights to El Salvador 😊😊

Fabulous! This was the first time we've flown with JetBlue and the entire experience was flawless!

I am absolutely furious with American. they shut the door in my face when I was trying to board the flight and kicked me off of it. They made no attempt to call my name or contact me or anything. They just said they gave my seat away. The customer service response has been atrocious. I will never fly this airline again as long as I live.

Little communication with passengers after sitting over 1 hour for a maintenance issue Then we had to deplane- no crew communication Poor gate information after deplaned WiFi would not connect AT ALL

Hey as long as you bring me back to earth in one piece I’m good! Otherwise great flight smooth take off and landing good staff Only thing is the staff at the back of the aircraft chatters a lot it’s annoying at times but I’ll let that go because they are very sweet overall.

Confusion at boarding with my seat (there wasn't one) that I had to have corrected using my status; then because of that had to check bags. And then a very long delay on the tarmac with no air conditioning on a very warm day. It was just a miserable experience all around.

Flight was delayed which isn’t the airline’s fault, but the communication around it was terrible. I left the lounge to show up at the gate to board at the time in my app, and the flight in front of mine was still boarding and the inbound plane hadn’t even taken off yet. Delays were slow to show up in my app. Improved communication could have let me have a more pleasant experience in the lounge vs waiting 1.5 hours at the gate.

We had to de-board do to maintenance and there was ZERO help with getting rebooked. The flight was delayed by over 24 hours. Quite ridiculous. When I. called Kayak to get help to rebook, they said they couldn't and that it had to be done at the American counter that didn't exist without going outside TSA security, which I did.

I spent 12 hrs getting home and had a direct flight that should have taken no more than 3 hrs. The first plane has an issue, was on the plane for over an hour before we had to deplane and move from A19 to A39 to board another plane. Boarded that plane to wait for another 45 minutes for it to also have an issue where we had to deboard. After everyone had went to get something to eat the food vouchers came out and half of us could not use. We then had to wait until 8:00 pm to board and finally got to Columbus Ohio at midnight. We were told that our luggage was on baggage 5. I waited 30 minutes to then realize my luggage was on 4. No notification sent. Horrible communication and I have a priority status.

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.

More options for your flight to Maryland

Complete your trip to Maryland with a hotel stay or car rental