Find cheap flights from Caribbean to Maryland

Find cheap flights from Caribbean to Maryland

Round-trip
Economy
Boston (BOS)
Maryland
Fri 3/5
Fri 3/12
Any month
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Good to know

Low season

FebruaryBest time to beat the crowds with an average 5% drop in price.

High season

OctoberMost popular time to fly with an average 13% increase in price.

Average price round-trip

$375(avg. price over the last 2 weeks)

Good deal round-trip

$199or less

Good deal one-way

$153or less

FAQs for booking flights from Caribbean to Maryland

Which airlines have a flexible cancellation policy for flights from Caribbean to Maryland due to COVID-19?

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What is the Hacker Fare option on flights from Caribbean to Maryland?

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Top 4 airlines serving from Caribbean to Maryland

Scores according to KAYAK customer reviews

7.2
American Airlines
Overall score based on 45,168 reviews
7.5
Boarding
7.1
Comfort
7.8
Crew
6.8
Entertainment
6.7
Food
Airline reviews

Cons: "Wifi didn’t work."

Cons: "Nothing, great job"

Pros: "Seats were not too cramped."
Cons: "Wifi that actually worked."

Cons: "O prematurely had to check my carry on when there was room to bring it on board with me"

Pros: "Free movies on the included display and electric outlets are top notch."
Cons: "I wish they would offer food service more in the middle as we just ate before boarding."

Cons: "Baggage lost."

Pros: "The free entertainment."
Cons: "Everything was great."

Pros: "Ease of boarding with the group numbers"

Cons: "Nickel and diming people for every little thing. I didn't mean to select a paid seat upon making my reservation on-line, and I couldn't get it to come off. Had to pay anyway."

Cons: "Very inefficient that all bags had to be checked on the jet way and then picked up on the jet way. The picking up on the jet way turned into a cluster F."

Pros: "Very helpful and kind staff. Everything was on time and made for a great travel experience."

Pros: "Arrived 30 minutes early"
Cons: "We had to wait 40 minutes in the runway before parking at the gate."

Pros: "Shabby Cramped"
Cons: "Cramped Uncomfortable"

Cons: "The aircraft was hot. Barely any A/C. It felt like 78 degrees. Uncomfortably hot."

Pros: "Good meals"
Cons: "Not much legroom. Good movie shown but would have like personal options like other airlines."

Pros: "Quick boarding and luggage pickup."
Cons: "Mediocre staff. In my experience United is more friendly and welcoming."

Cons: "At 6'1" the seats are too small and close together."

Pros: "That I arrived at my destination"
Cons: "Everything"

Pros: "Boarding was quick."
Cons: "1. No individual monitors. The pull down shared monitors are antiquated and not the standard now. 2. Would not fly AA from SJU again because of this. Unless I preloaded my iPad with movies."

Pros: "Small airport"
Cons: "Service and flexibility, needed to call online for assistance"

Cons: "ATC delay on take off and then a 10 min wait for a gate a DCA. Just disappointing in adding delays."

Pros: "On time departure"
Cons: "Please use the A330 for the return trip..."

Pros: "Quick boarding and on time departure"

Cons: "It was one hour late."

Pros: "I had a great experience overall. I don't give 5 stars because there is always room for improvement no matter how good your service is."
Cons: "Size of the snacks"

Pros: "Great steward with fabulous sense of humor"

Pros: "todo me gusto"

Pros: "Good view"
Cons: "Breakfast does not have good things to eat. Too cheap ones.."

Pros: "Not applicable"

Pros: "Todo muy bueno"

Cons: "No tv/movies."

Pros: "More confortable seats."

Cons: "It was a headache!"

Pros: "Easy connections"

Cons: "20 min delay at Dallas International"

Cons: "No"

Cons: "Food choices are pretzels or crackers."

Pros: "It was great."
Cons: "Everything was good."

Pros: "Todo estubo muy bien"

Pros: "Easy booking, Great prices"

Pros: "All great."

Pros: "That I got a soda"
Cons: "Delayed at Ohare by an hour. Sitting on the Tarmac for a half hour in Reagan, waiting for a gate. This was our leg back to DC, after our leg to Chicago four days previously. On that trip I did a review and gave the whole trip a 1 out of 5 stars. That trip was the trip from hell, with delays, waiting on the Tarmac, deplaning, almost cancelled, more waiting on the Tarmac, wheels up in Reagan, wheels down in ORD, and then more Tarmac waiting for a gate. So I was already more than perturbed when this trip had similar outcomes."

Pros: "We arrived earlier that predicted. I liked it."
Cons: "They gave us just 2 small snack"

Cons: "No entertainment, no food."

Pros: "On time and smooth"

Pros: "I like your update e-mail. Every thing was so perfect. Good luck in your business(: Sincerely, Parvin Haji-Djafari"

Pros: "Nothing"
Cons: "Everything"

Cons: "Delayed as well!!!"

Pros: "Was fine."
Cons: "At FJK the air train signs need to be more visual."

Pros: "Nice crew, clean plane, and they had soda and coffee!!!"
Cons: "Full flight, not spaced out like I thought it would be."

Pros: "Crew was nice friendly and helpful."
Cons: "Free food. This was a three hour and 55 minute flight. You could at least give a sandwich. I don’t fly often but, I was with a group of us. I take snacks everywhere I go so I was not humbug it would have been nice."

Cons: "Cabin felt quite warm"

Cons: "Seats too small. Guy next to me was practically in my seat."

Pros: "Basically realized that I won’t fly again if it’s not first class ."
Cons: "When the flight attendant was serving the food, he hit my knee with the cart, I got mad of course because it made no sense that he was pushing the car from behind towards he back of a plane. That can’t happen. I can’t “seat back and relax “ if I need to be worried about getting my knee hurt."

Pros: "The respect for the time and the organization to boarding"
Cons: "My baggage did not arrive to my destination"

Pros: "Staff was courteous polite. Pilot kept everyone informed. Smooth, relaxing flight!"

Pros: "Crew was nice and very helpful."

Pros: "Free dish movies provided due to flight delays"
Cons: "Flight delayed over 5 hours."

Pros: "Great experience"

Cons: "The flight was delayed and we have to pay for the entertainment what it's that One of flight attendant was getto, saying bad words and unhelpful The guy at the gate unhelpful in other airlines if my family and I have seats away from each other they will help you to be together specially if you have children. In united the guy didn't even bother to look in the system and just told me that that's the only thing he has I asked again and he's told me no because if he help me the flight will be delayed and I laugh and then I said are u serious so I told him that the only thing that he needs to do it's to call the person that has the seat next to my family and ask if he or she can switch seats with me that's all and he just walked away. Very unprofessional most of the staff. I'm a ARMY VETERAN 90% disabled and my wife ssg Ayala active duty the flights that we took on our deployments were smoother than the united airlines flights"

Cons: "I did not like the seats. I was unable to recline and rest the way I wanted and did not like having to wait 45 minutes for baggage claim to drop my bags"

Pros: "Food was good service was great"

Cons: "I was upgraded to first class. This was the first time this has happened to me, and I was excited. I had a great experience there and am grateful for it! The trip was quick, with low turbulence and no air pockets. I felt good. Thanks."

Pros: "seats aren't so cramped."
Cons: "too cold. could have a few blankets on hand.."

Pros: "Everything went to well."
Cons: "Couldn't be more better."

Pros: "Smooth ride"
Cons: "No drinks or snacks Well think it was only water or orange juice available"

Pros: "Good price. Good service."
Cons: "Nothing."

Pros: "Nothing at all. Delta is the best I've been with."
Cons: "The attendant were the wrort I've ever. Continue to hit arms s d was very rude to passenger. One didn't close the over head bin while in sever tubulance."

Pros: "They did not care"
Cons: "Bad"

Pros: "Nothing"
Cons: "Being stuck in DC"

Cons: "Sound was not working in my seat. Food was awful."

Pros: "On time bags made connection"

Cons: "Bad Service over all."

Cons: "Small loud plane"

Pros: "Everything"
Cons: "Nothing"

Cons: "The seats were cramped. Many people carried on extra bags as the price per bag checked was $25.00 a bag -- so there was a lot of bags carried on and delayed the process."

Cons: "need to do pre assigned seating during the purchase of the tickets"

Cons: "The worst part was the new seats are the smallest ever. I could not sit without my knees jammed into the seat in front of me, and on both legs, Ithe seats were narrow that the people next to me and I were overlapping shoulders - that was a first. Unless its flights in the future are significantly advantageous, United's losing my business. It's not worth saving a few bucks to me to be so uncomfortable."

Pros: "United crews use to tell me you couldn't preboard with children but they must have changed that policy because they allowed it this time."
Cons: "They always ask a second time for the boarding pass after the first agent scans it. They should tell you to keep it out if they are going to review it a second time."

Cons: "It was late boarding and landing. Our bags were sitting in the rain."

Cons: "No TV"

Pros: "Got there."
Cons: "Small, cramped seating. Outdoor jetway upon arrival."

Pros: "Fast, friendly, on time"
Cons: "None"

Cons: "Nothing"

Cons: "Broken WiFi"

Pros: "I liked that your beverages are complimentary"
Cons: "1 ply toilet paper is unexeptable"

Pros: "Getting off the plane!"
Cons: "Both planes were late, stewardess was extremely rude. My son was having an emergency heart surgery and I literally would have made the 15hr drive faster. Thanks for nothing"

Pros: "Zooooooommm"
Cons: "Where the asciago?"

Cons: "Long layovers, could have been shorter. Also not a huge fan of the tiny bag of snacks."

Cons: "Complimentary wifi was on the fritz"

Cons: "Seats were very uncomfortable"

Pros: "Liked that the airline paid the Hotel expense"
Cons: "Flight got cancelled for maintenance reasons but many other airlines did the flights that night"

Cons: "It was snowing and we disembarked on tarman"

Cons: "Checked luggage took close to 45 mins to arrive"

Pros: "Great service. ...communicate with customers about changes at all times."

Pros: "The service for wheel chair people was excellent"

Pros: "The flights were on time."
Cons: "A little bit more legroom."

Pros: "United gave us maximum vouchers for bumping us involuntarily."
Cons: "Our return home from a holiday family visit was oversold causing much stress for my family/small child. Our luggage went but we DID NOT."

Pros: "Terrible. Not happy."

Pros: "Crew was amazing!"
Cons: "Social Distancing"

Pros: "Fast easy boarding and direct non stop flight"
Cons: "Explain works and perks better."

Pros: "Inexpensive, direct flight. Very friendly flight crew."
Cons: "Works, Perks explanation. Misleading buy one covers all whennavtually buy one means everyone has to buy it"

Pros: "Nothing. Not clean at all."
Cons: "Clean the plane. Space people out. Passengers were bunched together while other spaces were wide open. Not cool"

Pros: "Ok."
Cons: "Nothinh"

Pros: "Yes"
Cons: "No"

Pros: "nothing, I was trying and calling Fortine Airlines to change the flight because the situation of coronavirus and I didn't get answer ...Calling more that 500 times ... This is a scam"
Cons: "nothing, I was trying and calling Fortine Airlines to change the flight because the situation of coronavirus and I didn't get answer ...Calling more that 500 times ... This is a scam"

Pros: "Crew was friendly and amazing"
Cons: "Seats recline. At least free water/coffee for refreshment."

Cons: "Los precios son muy populares por lo que la incomodidad de los asientos se te olvida. En general todo es bueno. Aparentaba estar limpio y el servicio fue excelente."

Pros: "Nothing, 2 hrs delay waiting for a crew member and plane was ~25% full, no snacks or beverages"

Pros: "The softest landing on our whole trip!"

Pros: "Maria at the San Juan counter was very nice and helpful. I recently widowed and was very nervous about flying with Frontier. She put me at ease."
Cons: "I have nothing to add here"

Pros: "Seats are not that small . It’s comfortable"

Pros: "Nothing"
Cons: "Everything"

Pros: "The guy at the front desk was awesome. Friendly and very helpful."
Cons: "We were delayed for 2 hours with little to no notification or accommodation"

Pros: "Crew it was really nice"

Pros: "An itenirary update ahead of time. We missed our flight."
Cons: "Send us an update the day before about upcoming flight."

Pros: "On time departure, early arrival. Lead crew member helped me find a trading card Frontier does with all their animal mascots I use for scrapbooking my trip. She took the extra time to find one in a kid snack pack and gave me whole thing! Made my day."
Cons: "Plane was a bit dirty from quick turnaround service. Crumbs on all my row, window smudged with who knows what. My Lysol wipe came in handy."

Pros: "Good"

Pros: "Great customer service. Bag drop is super easy and fast."
Cons: "No WiFi."

Pros: "2 hours waiting in the airport inside the plane"
Cons: "Notify what happen..."

Cons: "Some free snack and soda or water"

Pros: "Yea"

Cons: "Crew pretty lazy.. sat most of flight talking"

Cons: "Seats didn’t recline, it was a bumpy ride nothing was free! That’s what we (didn’t) pay for!"

Pros: "Nothing in particular"
Cons: "Frontier has issues with maintaining schedules. Also, the aircraft are too basic."

Cons: "No dieron gratis nada de café ni agua .y las azafatas estaban burlándose de los pasajeros es una falta de respeto"

Cons: "Tickets were purchased together but yet one ticket was zone 1 and the other two were zone 3"

Pros: "Crew was fine, there need to be a great improvement on the seats"
Cons: "Seats"

Cons: "Make seats recline"

Cons: "No TV no music not entertaining"

Pros: "I live in Orlando. I made a mistake. The travel was supoused to be from Orlando to San Juan ."

Cons: "I believe the pilot flew to high. Me and my friends ears popped severely and caused pain."

Pros: "Price, on time and cleaness."
Cons: "No entertainment (magazines, movie, tv) and seats a little uncomfortable."

Pros: "Quick and easy"
Cons: "I’m a small person.... and i barely had room sitting inside the aircraft"

Pros: "Seats are just not made for trips longer than 2hrs"

Cons: "Flight from sju to mco was delay 3 times. Lost my mco to pvd flight. And then i was send from mco to raleigh and another delay. Then raleigh to pvd with one more delay and loss bags. All frontier gave me was $50voucher when i lost hundreds in hotel and car and taxi and my time. The depart time for the sju flight was 3am i have to be in the airport 2hrs before so this was a allmost 24hrs flight for me because i reach my destination at 4pm. I expect comunication from you."

Pros: "Nothing. The only thing that was good it was that it was a direct flight, however with the delay it make it longer than other flights with stops"
Cons: "Will not use your airline in the future due unreliable flights. Never experienced this with any other airline"

Pros: "The price is good"
Cons: "I don’t like the chairs"

Cons: "I don't like the seats, they have no cushion and they don't recline. Plus the tray table is super small. Also you pay for all drinks. Another thing the pressure is horrible in these planes. It seems they try to cut down on cost so the cabin is not pressurized right to reduced your ears from getting the over pressure from the ascend and descent of the plane."

Pros: "The crew personnel aboard the plane was friendly and the seats confortable."
Cons: "They made me pay $45 for a 16 inches carry on back that I have as my only luggage , because according to the counter employee, my handbag (purse) was too big so it was considered as a second carry on. I requested a waiver, because I’m an Army Veteran, a senior citizen, but it was denied by the counter employee."

Pros: "The atendance and organisation"
Cons: "The seats. They shoul recline and not be steady in one position"

Pros: "Quick Price Nice attendants"
Cons: "Seats don’t lean back. But not bad."

Pros: "I really liked how amazingly friendly all the crew were. They all had a real smile and tried to help every costumer Kindly. Never saw this from ANY airline. They are EXCELLENT!"
Cons: "Many crying babies, most but that's nothing you could do LOL!"

Pros: "Cheap flight"
Cons: "No complimentary snacks at all. I paid $3 for a coke, very little seats with no elbow or leg room nor to lean back. I felt like i was in a can."

Pros: "Fast luggage checking"
Cons: "No cash accepted for overweight baggage"

Pros: "Check in online was easy and gate boarding a breeze, and even got a seat upgrade... THANK YOU!!!"
Cons: "Having to wait to drop off bags in terminal counter rather than curb drop off for those that have the online check in"

Pros: "Best treatment of military personal."
Cons: "Boarding was a bit chaotic."

Pros: "Good price"
Cons: "Worst trip ever"

Pros: "Flight got cancelled at the last minute and they didnt try to communic"
Cons: "Still waiting for my refund"

Cons: "Make seats reclinable!"

Pros: "The fleet has newer planes and the seats were relatively comfortable given the space."
Cons: "They cancelled our return flight for no reason. Two hours in, the front desk had only managed to accommodate 2 families. We were in San Juan at peak season, so all hotels were full. We were eventually put on a connection to Miami, had to wait a few hours in that airport for our next flight, a multi- stop Southwest flight to Richmond, Atlanta and finally Baltimore. it took us 24 h to get home, instead of a direct flight of 3h. Just because the comoany decided we were not worth serving"

Pros: "No seats need more cushion"
Cons: "Better stuff on the menu"

Pros: "The crew was average and the seat was super uncomfortable."
Cons: "Give food to the passengers and not sell it."

Pros: "flight was on-time, maybe even a little early, the plane was clean, the boarding process was simple and smooth, the flight attendants were welcoming when getting on the plane."
Cons: "The crew on the flight was just okay, including the flight attendants and pilots, I don't know if they were near the end of their shifts for the day but everything seemed so rushed, they talked very fast, to the point that sometimes it was even difficult to understand."

Pros: "We paid more for extra space and the seats were big. Nice. But the back was so upright and you couldn’t adjust it back. Super uncomfortable."
Cons: "The crew is rather blah. It’s clearly a j-o-b."

Pros: "Hope it's not late too"

Pros: "Good service"

Pros: "Everything was great"
Cons: "No complaints"

Pros: "Bad"
Cons: "Bad"

Cons: "Delayed both ways"

Pros: "My bag came out really fast. Boarding on and off was a breeze."
Cons: "Paying for baggage when I could have just carried on."

Pros: "Nothing"
Cons: "I was trying to save money for the church , but it cost me more then I had budget for"

Cons: "Check in staff was very unprofessional. 3 delays!"

Cons: "Everything niot good that all"

Pros: "One associate tells me my bag is ok no problem I get to the gate and I got charge 65$ , so for more comfort and space I will fly jetbue ty but no ty."

Cons: "They charged me three times"

Pros: "It sucked"

Pros: "Cheap"
Cons: "Uncomfortable"

Cons: "The 'low' fare is a fraud, you can't actually get a seat at that price. I checked there was one row, adjacent to the toilets at the back of the plane, and it was booked. Rather, you're going to pay $40-100 RT to actually sit down on the plane. And $50 for a carry-on bag?? Seriously??? I won't fly with them anymore."

Cons: "Undisclosed information about extent of charge for luggage"

Pros: "Nothing"
Cons: "Cancelled."

Pros: "Everything!"

Cons: "Both flights were delayed"

Pros: "Nothing"
Cons: "It got canceled on my way to the airport"

Cons: "Comfort"

Cons: "Terrible"

Cons: "cancelled after 4 gate changes and beginning boarding. no rebooking."

Cons: "Everything"

Pros: "Nothing"
Cons: "Outragious charges for carry-on and checked luggage. Misleading information regarding seat pitch on website. Charged for extra legroom. Didn't get extra legroom. Refusal to refund charge for extra legroom."

Cons: "Hour long delay"

Pros: "Plane was very clean. Attendants were delightful. Pilots were informative."
Cons: "Checki in people at counter were not very friendly."

Cons: "I NEVER EVER FLY WITH THEM , AND I WILL TELL EVERY ONE NOT TO FLY."

Pros: "Everything"
Cons: "Spirit!"

Pros: "Great savings at the cost of comfort, entertainment and happiness."

Pros: "Reshedule"
Cons: "Poor services"

Pros: "Don't recall"
Cons: "Discomfort in middle seat. Neck ache."

Cons: "Late, late, late. DISORGANIZED."

Pros: "Nothing at all, was very upset, traveling on emerg to a family member"
Cons: "Paying for carryon m my funds was very minimum, going to cate for a sick family member"

Pros: "Ihate the way the charger laggage"

Pros: "Luckily sitting by good people"
Cons: "Beer was warm and $7"

Pros: "Everything was great"
Cons: "N/A"

Cons: "I had a pocketbook and a carry on which I have taken on many other flights. They took the carry on away from me and charged me $55.00."

Pros: "Cleaning"

Cons: "Na"

Pros: "Price"
Cons: "Seating comfort was poor"

Pros: "Could have flown Southwest $70 cheaper"
Cons: "Baggage fee"

Pros: "Nothing"
Cons: "Everything"

Pros: "Everything from the economy parking to boarding was fast. The airport isn't overly full and security check was fast."

Pros: "Nothing"
Cons: "Boarding was very late. They had no schedule. Baggage charge is excessive & a ripoff."

Read more about American Airlines
COVID-19 information

Safety measures for airlines flying from Caribbean to Maryland

Airlines flying from Caribbean to Maryland have enacted additional safety measures and adjusted policies to better accommodate travelers. Policies vary by airline.

Heightened sanitation

Daily cleaning, installation of cabin HEPA filters on flights from Caribbean to Maryland

Mandatory masks

Masks required on board, masks provided on flights from Caribbean to Maryland

Social distancing seating

Middle seats unavailable to book on flights from Caribbean to Maryland

Pre-flight testing

Testing for antibodies, testing for symptoms for flights from Caribbean to Maryland

Book cheap flights from Caribbean to Maryland

Recent round-trip flight deals

4/23
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Spirit Airlines
10h 39m
SJU - BWI
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Spirit Airlines
11h 27m
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Recent one-way flight deals

3/12
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