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Low season

September

Cheapest flight

$94
Best time to beat the crowds with an average 18% drop in price.
Most popular time to fly with an average 2% increase in price.
Flight from San Juan to Baltimore

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.

  • Which airlines fly most frequently to Maryland?

    Caribbean and Maryland are connected by different airlines. The airlines that fly that route the most regularly are Southwest (51 flights per week), JetBlue (10 flights per week), and Frontier (2 flights per week).

  • 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 $295.

  • 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 $379. On the other hand, the most expensive day to fly is Sunday, where round-trip prices are $684 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 $377 on average. Morning departures are around 34% 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 $197 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 $197.

  • 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 $163 (return) on average. On the other hand, the most expensive months are August and January, when the average cost of round-trip tickets is $407 and $341 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 56% 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 6 cities. The city with the most direct flights is San Juan, with 27 direct flights each week.

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

    There are around 9 direct flights from within Caribbean to Maryland every day. Most flights (87%) depart in the afternoon.

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

    Each week there are around 63 direct flights from within Caribbean to Maryland. The most common day for departures is Monday, with 16% of flights taking off on this day.

  • How long is the flight to Maryland?

    An average nonstop flight from Caribbean to Maryland takes 6h 40m, covering a distance of 1566 miles. The shortest route is Nassau (NAS) to Washington, D.C. Reagan-National Airport (DCA) with an average flight time of 2h 39m.

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

    Each week, there are 34 medium-haul flights (3-6 hour flight duration) and 29 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. (67% of total searches to Maryland). The next most popular destination is Philadelphia (33%).

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 4211 reviews
7.0Food
8.1Boarding
7.5Entertainment
8.0Comfort
8.6Crew
Airline reviews

Flight was delayed out of BWI unexpectedly / without a reason given but otherwise ok.

6.0 GoodDanielle, Oct 2026
Read more Southwest reviews

Flight was delayed out of BWI unexpectedly / without a reason given but otherwise ok.

the flight itself was totally fine. The crew were great and very helpful. The flight was delayed, however, over an hour without a lot of information as to why.

You made me miss my connecting flight. I can not go to Cleveland on teh revised flight you are sending as I will the entire meeting. I have no option that to fly back. I hope you compensate me for the loss.

It was the strangest thing. The flight attendant (who was not very friendly) took our drink orders and then never brought them. I’ve never had that happen before.

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 -

Great overall experience and use of the Delta One lounge was amazing!

I used by Skymiles to upgrade to First so that I could comfortably work using my laptop. But WiFi was intermittent and unavailable for long periods. I feel like I wasted 70,000 miles :(

Great as one can be for a one connection 6 hour flight

The gate attendant was not clear w message on flight delays.

Chairs don’t recline and the ones that do recline, barely do recline. It was most uncomfortable flight i ever been on.

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.

I want much more comfortable seats on these aircraft thank you.

The boarding agent and checked bag agent were both rude. It only takes a second to be kind. However, the flight crew was amazing. I got a turkey sandwich and it wasn't bad---not great but not bad. The internet was my biggest problem. This was a work trip and I REALLY needed the internet to meet a deadline but it didn't work for 80% of the trip. Very disappointing.

I tried to check in beforehand from Ireland. The Jet Blue website sent me to the Aer Lingus website and vice versa. I tried to get a boarding pass at Dublin Airport as well, but they said they couldn't help me either. I had to wait until I arrived at the gate in Boston to secure a boarding pass...it was a bit nerve wracking.

Great flight. Best in years. Very clean craft. Easy boarding. Communicative pilot. Friendly flight attendants. Absolutely smooth take off, in flight and landing. Very comfortable seats. Smoothest flight I've experienced in years. THANK YOU JET BLUE!

I was asked to pony up an additional $239 (over the $735 paid originally) for a one way middle seat, which was very uncomfortable. Where did you expect me to sit?

Jet Blue sevice was good. Just don't understand why they charge for earphones to listen to flight entertainment. Other than that, everything was excellent.

The whole experience at the airport in Istanbul should be made known beforehand. Four passport checks and a huge check-in line as I could not check in online made it a very lengthy and frustrating experience. The flights on Turkish Airlines however were just fine.

Mostly good, flight take off in time and land earlier I can’t ask for more..

The crew was not nice this time. I asked for a drink one time and the girl didn’t say anything to me and just got me the hot drink while walking super fast to the back. We were sitting in the back and she wasn’t doing anything except socializing. She was upset I asked for something and she had to do her job. I also didn’t fully have it in my hands when she handed it to me so it was dangerous. She was abrupt and rude. She wouldn’t allow for people to spread out like previous flights we had been on if they were empty, and there were empty rows. It was strange and she enjoyed being angry at us.

The plane was FREEZING COLD. Like I was wishing I'd brought gloves. Is this how JetBlue sells more blankets? Other than that, all fine. Crew just as nice as usual. A flight attendant asked (who? The pilot?) to have the air turned down for a great number of passengers who were as cold as I was. They (again -- who is "they") did not.

The flight was delayed several times as they didn't have pilots. Then we were boarded on the plane and again waited on the tarmac for over 30-40 minutes waiting for pilots to board. The in flight entertainment was confusing at best on how to use it. It took multiple attempts to get wifi to connect and by the time it worked the flight was almost over.

The flight was delayed and gate changed so that was not fun and the flight to Dallas from LAX was very delayed on Sunday. It was just not a great experience due to the delays both ways.

Fine. No announcement for Concierge Key to board. Not a big issue just pointing it out.

Totally uninformed of the situation. Not yet sure about compensation. Highly disappointed.

Horrible. Their delay cause me to miss my connection, the the flight they rebooked was delayed over an hour because they over booked the crew. They also left my suitcase out in the rain for hours ruining items I had in the suitcase and blew off my complaint.. worst experience ever.

The flight was almost an hour delayed causing me to miss my connecting flight, then the rebooked flight was delayed a couple of hours. They also left my suitcase in the rain for hours ruining some items I had in there. They also just blew off my complaint. It was my absolute worst flight experience of all time:

Nothing available at the assigned hotel as far as brush, toothbrush, etc after forced layover with bags that departed

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.

THE BARE METAL SEATS AT THE FRONTIER GATE IN CLEVELAND HOPKINS AIRPORT ARE DISGUSTING...BUT JUST A LITTLE BETTER THAN THE SEAT MATERIALS ON THE PLANE! THE "COMMERCIAL" ANNOUNCMENT PUSHING THE CREDIT CARD DEAL IS OBNOXIOUS AND UNWELCOME! THE VOLUME OF THE OFFER ANNOUNCMENET BLARES LOUDLY AND IS FILLED WITH A HYPED UP, CANNED SCRIPT. BOTTOM LINE IS THE FLIGHT AND THE CREW WERE VERY GOOD EXCEPT FOR THE ABOVE.

Maximizing profits is one way to a healthy bottom line, the other is repeat business and referrals from satisfied customers. Frontier has clearly chosen the former. One of many examples: Family emergency required me to cut trip short. Headed to the airport to fly standby for the return trip I had already paid for (yes I understand prices vary with demand etc). Was told there is no standby and that I would need to pay for, despite what it's called by the company, what amounts to a new ticket. And surprise surprise, there turned out to be dozens of empty seats on that flight. To say nothing of the sleazy third and fourth party resellers, the flight/ticket insurance I elected and thought I had paid for that mysteriously wasn't there when I needed it before I left, and on and on with third world sleazy management decisions. The inflight coffee (that I had to pay for) was very good though.

You have to be super careful when purchasing as *everything*, a carryon or a sip of soda, has a fee. They relentlessly chip away at you with surcharges and extra costs … and it’s not always clear what you are getting when you buy your ticket. Will not fly them again. And … crew were not friendly until off boarding .. like they don’t like working for Frontier.

Air was off while waiting on the runway and the temperatures became very uncomfortably hot. Flight attendants were very loud and rude the entire flight.

I booked tickets from San Diego to Cincinnati months in advance to attend my sister’s wedding, a wedding where I was serving as the officiant. At 10:00 PM the night before my 6:00 AM flight (just 8 hours before departure), I received an alert that my first leg to Denver was delayed, causing me to miss my connecting flight to Cincinnati. When I called Frontier customer service, they informed me that they couldn't get me on any other flight that would get me there in time for the Saturday wedding, let alone the rehearsal dinner. Because I had a critical role in the wedding, I was forced to buy a last-minute ticket on another airline for three times the original price, costing me well over $1,000 extra. Even with the emergency flight, I still missed the rehearsal dinner entirely. When I spoke with Frontier, they agreed to refund my original ticket, but showed zero care or accountability for the massive financial burden and distress they caused. Their "compensation" for causing me to spend an extra $1,000+ and miss an irreplaceable family event? A $75 Frontier voucher. Frontier completely dropped the ball. Their customer service showed zero empathy, and their reliability is non-existent. I will never fly Frontier again, and no one else should either if they actually need to get where they want to go. Tip for anyone flying from Denver to Cincinnati: Avoid Frontier connecting flights or layovers at all costs, especially for time-sensitive events. Book direct flights with an airline that actually offers reliable customer support and rebooking options when delays occur.

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!!!

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