Find cheap flights from Maryland to Caribbean

Find cheap flights from Maryland to Caribbean

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Round-trip
Economy
Boston (BOS)
Caribbean
Wed 4/14
Wed 4/21
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Good to know

Low season

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

High season

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

Average price round-trip

$395(avg. price over the last 2 weeks)

Good deal round-trip

$128or less

Good deal one-way

$72or less

FAQs for booking flights from Maryland to Caribbean

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Top 5 airlines serving from Maryland to Caribbean

Scores according to KAYAK customer reviews

7.9
Delta
Overall score based on 29,153 reviews
8.1
Boarding
7.8
Comfort
8.5
Crew
7.8
Entertainment
7.5
Food
Airline reviews

Pros: "The space we currently have."

Pros: "Crew was friendly and engaging"
Cons: "I wiped down my seat area to clean it. It would be nice to know what Delta is doing as well."

Pros: "Pretty much everything"
Cons: "Food somewhat expensive..... boarding off the plane - ones with no baggage should get off first then more control about everybody getting in the aisles trying to get their luggage and holding everybody up"

Pros: "Crew was very friendly"
Cons: "the seats are horribly squished and uncomfortable. It’s the only thing that makes the flight not excellent"

Pros: "Thanks for the monitors."
Cons: "The crew seems tired."

Cons: "Late departure"

Pros: "It wasn’t delayed 3 hours like the first flight"
Cons: "Departing on time"

Pros: "Delta crew is always great."
Cons: "You need to update ALL of your planes to have charging at EVERY seat, not just the passengers in comfort plus or better. It’s 2019. We ALL have devices."

Pros: "Everything about delta"

Pros: "Awesome Customer Service"
Cons: "Nothing"

Cons: "Crew was grouchy and rushed past you without really trying to cater to your needs/ get you what you want."

Pros: "Airbus was nice"
Cons: "Delayed by over 1 1/2 hours"

Pros: "Efficient, cheerful crew"
Cons: "Stop making seats smaller! The added revenue from 10 squeezed seats is not worth the discomfort it causes."

Pros: "I got to board early because I volunteered to check my carry-on. Very friendly flight attendants. Love flying delta. They are always consistent and the movies they offer with the gogo in-flight app are always updated and recently released popular movies."

Pros: "The whole crew was great and very accommodating"

Pros: "Excellent"
Cons: "None"

Pros: "Seat comfortable"
Cons: "NA"

Pros: "Great crew and plane arrived on time."
Cons: "No entertainment and no place to charge devices."

Pros: "The crew was wonderful, the flight was on time."
Cons: "But the seats are so tight that we were definitely elbow to elbow and once seated I was unable to access even the purse that was at my feet. There was no entertainment and the tray table was tiny, not even an indentation for a cup!"

Pros: "Excellent"

Cons: "The seat was very uncomfortable"

Pros: "Smooth flight, on-tome departure"
Cons: "Service in business class left a little more to be desired. I had to ask for food and drinks, because I feel off to sleep in the first round. Came to Gate early, but had to wait for agent to put the jet bridge. Only one person was available."

Cons: "Hassel about getting a visa to Cambodia. Refused to give me a boarding pass for 2nd and 3 rf leg of trip. Korean Air had no problems giving me yhe passes. Otter people had Delta boarding passes shivh they traded for Korran Aiir passes but the got better seats. Food was very good"

Pros: "Great service"
Cons: "No complain"

Pros: "Great service all around. As comfortable as you can get for a domestic flight."
Cons: "Food was pretty good, but not up to their usual high standards"

Pros: "I had the opportunity to send my carry on to the final destination. The flight was overbooked and there was no place to put carry on on the top place."
Cons: "I did not have the chance to choose my seat. I traveled sandwiched by two overweighted guys. I was holding my arms and was literally compressed by the gentlemen. Horrible experience. If I had the chance to choose my seat I would pick the corridor, and had a little less embarrassment and sweating."

Cons: "Delta staff is not too friendly"

Pros: "Seating"
Cons: "The re route to MSP... Seven hour flight time for a two and half hour flight..."

Pros: "Flights were on time boarding was easy. 2nd crew from ATLANTA was friendly."
Cons: "The foldable snack tray was broken on the flight to ATL."

Pros: "This trip into Merida was amazing from start to finish. Something was lost in translation with my handicap assistance in Atlanta, but the trip was lovely nonetheless."

Pros: "I love Delta, especially their newer planes that have screens in the backs of headrests and free movies."
Cons: "Leg room is never enough. I'm 6'1"."

Pros: "The crew was very nice and attentative."
Cons: "The amount of delays causing us to miss our connection and be stuck in another city for a night before getting to our destination the next day(hopefully)."

Pros: "great staff . clean. current movies"
Cons: "n/a"

Cons: "There was a change in our flight. According to Delta you didn't confirm every leg of our flight and the plane was over booked."

Pros: "There was a threat in the airport which caused the closure of one terminal. It happened to be the one from which this flight was due to depart. The crew was calm and able to get everyone on board with a minimum delay, considering the circumstances. The flight crew made up some time in the air and we were able to land less than 30 minutes after our original ETA. Well done, Delta."

Pros: "Smooth and easy."
Cons: "Not applicable"

Pros: "People"

Pros: "Nothing"
Cons: "The staff"

Pros: "I had to take a United flight last week for a short flight and once again I was reminded why I ALWAYS fly Delta if at all possible. United crew hid in the galley the whole trip wit lititle to no interaction with passengers. My flight today on Delta was great; food really excellent (Chicken Tika) and the crew was great as usual. Delta remains the best."

Pros: "Efficient boarding. Friendly service."
Cons: "N/A"

Pros: "The leg room and freedom of not having another seat in front of me throughout this flight was great. It made getting comfortable a lot easier."
Cons: "We couldn't hear the overhead announcements at all. Seated right next to the turbine intake on the wing made the amount of ambient noise especially high, so all the in-flight announcements were pretty much unintelligible."

Pros: "Good seat, easy on and off, everything went a little ahead of schedule and smooth"

Pros: "The crew were AMAZING and made the flight so much better. Boarding was easy. I also love that the pilot acknowledged the Service men and women on our flight."
Cons: "The older plan didn't have some of the perks that I expected from Comfort +... No conformed headrest, no USB plugs... I paid extra for Comfort + and expected some of these things."

Pros: "Great plane"

Pros: "Staff were courteous. Captain explained reason for delay."
Cons: "Over 20 minute delay to begin boarding with no explanation. Boarding process very slow due to excess carry ones needing to be checked."

Pros: "Upgrading to First Class made it worthwhile."
Cons: "As a minority provider of service at BWI, the gate was the furthest from the entry. Gate security is almost always a source of delay here."

Pros: "After the extremely long wait to check bags which made us miss the flight, the date crew got us in another flight...it wasn't direct which is what I paid for, but they did get us out, but i missed an interview because of the lack of crew and a missing luggage."
Cons: "Checking a bag, delta did not have enough crew to get everyone thru to their flights. We waited for 80 minutes inline to check a bag. Then we ran to the gate inky to find the gate was closed less than 2 minutes before we arrived. At least 20 others also missed the plane because of the lack of crew and long lines checking bags. It was frustrating, irritating, uncaring crew checking in, and a bit rude. Then on of my checked luggage was lost enroute - which made getting off the flights even later which made me miss a meeting that I was scheduled to be at. All because you didn't have the crew needed to check in."

Pros: "...the fact that they got us on the plane and back to GRR even though the connecting flight from BWI was delayed and there was little time to make that last flight out of DTW..."

Pros: "The flight was smooth. Boarding was orderly and Delta personnel were considerate, friendly and efficient."
Cons: "Seats in coach were a little cramped. The guy next to me had a hard time staying in his own space."

Pros: "Seat cramped"

Cons: "It was amazing"

Cons: "Too cold"

Cons: "The layover was 40 minutes but from one gate to another takes 30 minutes, I was one of the last person aborting and the doors were about to close."

Cons: "Snack selection"

Pros: "Smooth ride"

Cons: "Feeling of being cramped"

Pros: "Fast boarding process, on time"

Cons: "Nothing you could do, it was a maintenance issue."

Cons: "Seating in Economy plus is tight. No electrical or UBS outlets for charging devices."

Pros: "everything"
Cons: "snacks"

Pros: "People were friendly"
Cons: "Broke arm off wheelchair"

Pros: "None"
Cons: "Long delay"

Pros: "Did not experience food or entertainment"

Cons: "Overbooking and worrying I would miss my trip"

Pros: "Movie options were good."
Cons: "The a/c was not working well and t"

Cons: "Mechanical delays caused me to miss my uncle's funeral."

Pros: "Not a challenging process from beginning to end."
Cons: "Nothing"

Pros: "Perfect from start to finish"

Cons: "We never took off"

Cons: "the usual garbage AA flights on CRJ's with poor on-time performance and frequent maintenance issues..."

Cons: "Seating is a bit cramped."

Pros: "Personalities...loved their job. Great to talk to."
Cons: "Bosrdunf staff at DCA. No communication in crowded area"

Pros: "Boarding process"
Cons: "Delay, no food,"

Cons: "Our audio did not work for movies. The food was super cheap"

Cons: "I was forced to check my carry on luggage. There was no problems on the way up to DC, just on the way back."

Cons: "So many different categories to board!! Same applies to all legs of this trip... it is annoying and completely inefficient."

Pros: "There was surprisingly a great amount of legroom"

Cons: "Food was not good at all."

Pros: "Lost baggage"
Cons: "They have it arriving with me. But cannot locate it. Normally they would know where it was."

Pros: "Nothing"
Cons: "Lost connection"

Cons: "Delay. Old airplane with sewer smell in back. Not a great experience."

Cons: "Completely ignored for beverage service"

Cons: "Shaky landing."

Pros: "Nothing"

Pros: "It did not crash"
Cons: "Delays, baggage loss, how the Airline dealt with both."

Cons: "I was trying to check two bags, and I get three free bags. My one bag was my wife's bike in a case and it as 60 pounds and the other was a suitcase that was only 20. They made us take stuff out of the bike case and move it to the suitcase to get it below 50 pounds. Ridiculously nitpicky. It's the same overall weight..."

Pros: "Thanks Daniel for making my trip to San Diego comfortable!"
Cons: "Didn't get to upgrade to 1st Class, but oh well :)--"

Pros: "Loved the individual seat back entertainment"

Cons: "No have owned screen TV"

Cons: "It was freezing."

Cons: "NA"

Cons: "Checkin"

Pros: "Everything"
Cons: "Nothing"

Pros: "todo muy bien"

Pros: "Comfortable seat"
Cons: "Lack of entertainment"

Pros: "All of it"

Cons: "America Airlines...worst service and just a horrible experience"

Cons: "Thrust"

Pros: "Everyone was amazing. Helpful. Kind professional"

Pros: "When the lady in the gate saw me almost dying of running all over the airport with my suitcase, she was very nice and comfort me."
Cons: "Nothing"

Pros: "Services , on time"

Pros: "Very nice breakfast provided. Staff was great."
Cons: "No media entertainment for 3.5 hour flight"

Pros: "On time and comfort"

Pros: "The personal are very amability"

Pros: "As expected."
Cons: "N/A"

Pros: "Nothing"

Cons: "The landing was rough!"

Pros: "Snack delicious"

Pros: "No Lufthansa?!"
Cons: "No Lufthansa?!"

Pros: "I felt comfortable. Staff was great."
Cons: "The cracker and cheese box. The snack wasn't worth the money."

Pros: "Easy to board and check in, good price"
Cons: "It was extra to check luggage"

Pros: "Everything"
Cons: "N/a"

Pros: "Everything"
Cons: "NA"

Pros: "Thank you for making this connection available from charlottesville to dulles. It beat driving! Everyone was helpful"

Pros: "Boarding"
Cons: "Excellent"

Pros: "This plane was smaller so I got to sit by myself so it was more comfortable for me"
Cons: "Lack of drinks/ comp snacks"

Pros: "I had to get my luggage in Frankfurt and was almost denied access to it in the airport because the airlines don't have agreement together."
Cons: "Luggage transfer"

Pros: "The service since I am handicap"

Pros: "Fine. Wish my earlier one wasn't so delayed."

Pros: "On time"
Cons: "The boarding process Boarding should start from the rear rows to the front irrespective of what group shows on your ticket.some ended up with no storage space as they are in group 4 or 5"

Pros: "It's seems like no one cares about passengers in this airline.... Rude services"

Cons: "we had to pay to watch any channel."

Pros: "The upgrade it made the all the difference in the world"
Cons: "Would not change a thing"

Pros: "Very organized . On time"

Pros: "Everything! My grandparents needed special assistance with wheelchair and the crew was very helpful! They spoke Spanish and they were able to get a crew member to translate"

Cons: "EVERYTHING WAS EXCELLENT"

Pros: "Good"

Pros: "Good trip"
Cons: "Nothing"

Pros: "Liked the upgrade to first class"

Cons: "Was asked to pay $25 extra for my luggage. That should have been disclosed up front on the ticket. Not happy"

Cons: "N/a"

Cons: "I never took this flight since the San Francisco flight got delayed that when I got to the gate to board the Washington flight. The gates closed on my face literally. Awesome trip.! (Sarcasm included)"

Cons: "When I boarded the plane, I noticed crumbs and grease marks on my seat and crackers all over the floor at my feet. Rather than clean my area, the stewardess handed me wet wipes."

Cons: "Bad"

Cons: "Long wait. Not communication between employees. Poor customer. Service"

Pros: "Everything"

Cons: "not offered any break on food or beverage, or wifi."

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

Cons: "Late departure."

Pros: "Very poor service"

Cons: "Service"

Pros: "I loved how quickly we departed and arrived at each destination!"
Cons: "The boarding process was terrible. People forgetting to even stand in line for their boarding groups getting to cut ahead of those whose group is currently in the process of boarding. That should not be allowed. It's rude and disrespectful to other passengers/customers."

Cons: "Maintenance delays and rerouting caused me to miss my reserved ground transit in LA... United claimed on the phone I would be reimbursed for a taxi, but changed their mind when I sent them a receipt a few days later."

Pros: "same comments as above"
Cons: "same comments as above"

Cons: "Tight aisle"

Pros: "Professional, friendly service."
Cons: "Nothing"

Pros: "Getting from point a to point b."
Cons: "Lack of good free snacks. Not getting free bag checked."

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

Pros: "I like free wifi, aspecial food item like middle east food"

Pros: "Check in was"

Pros: "Nothing"
Cons: "Smoother ride to location"

Cons: "Nothing because everything is good."

Pros: "En realidad nada porque desde los empleados hasta las azafatas del avión brindan muy pésimo servicio"
Cons: "Todo Check in Empleados Meriendas Entretenimiento"

Pros: "Once again everyone was so wonderful and helpful"
Cons: "Lower luggage cost. I spent $110 additional on this trip since since I wasn't well informed (my fault)"

Pros: "Nothing"
Cons: "Everything"

Pros: "Nothing"
Cons: "Staff crabage"

Pros: "Yes it was. People were very nice"

Cons: "People should be restrained from jamming entrance to aircraft BEFORE their zone is called."

Cons: "Never happened, the flight was cancelled and never rebooked."

Cons: "The flight was delayed, it was a mess."

Cons: "Boarding"

Cons: "Good"

Cons: "Tremenda porquería horrendo"

Pros: "Yes"
Cons: "Food"

Pros: "No issues"

Pros: "SEAT was comfortable"
Cons: "Service"

Pros: "Estaba todo bien."
Cons: "Pero no me gusto q havia mucha turbulencia. Y mis photos queria esplotar."

Pros: "Good"

Pros: "Liked everything just wanted a better seating choice"
Cons: "The middle seat"

Pros: "Nothing."

Pros: "Nice service. Exceptionally new plane about a year old to the month."
Cons: "Need to ask people to prepare to deplane. Perhaps use rear door to expedite process"

Pros: "Noting"

Pros: "Nada"
Cons: "Everything"

Pros: "Cheap flight"
Cons: "Bag fee"

Cons: "Terrible service, unprofessional, impractical and unreasonable airline that should never be suggested."

Pros: "I país for seat 25...$12."
Cons: "I would not FL y any more for Frontier"

Cons: "The credit card sales pitch. Too long and loud. People were trying to sleep and were rudely woken up and subjected to that !"

Pros: "Comfort"
Cons: "Don't have food free inside the fly"

Pros: "Overall service"

Cons: "The check in was soooo slow, the person who was helping did not know what she was doing."

Pros: "Poor quality airline. Will never ride the airline again."
Cons: "Frontier service."

Pros: "When all the add ons are factored it is no cheaper than delta."

Pros: "Nothing good, bad baggage handling experience, miss commitment. Overall it was pretty bad."

Pros: "Picking out seat"
Cons: "No free snacks"

Cons: "40 minutes and still no bags"

Cons: "this company does not respect the customer. For both flights delay of more than 6 hours."

Cons: "2 hours on tarmac. Yuck."

Pros: "I'd rather take a shower at auschwitz than fly frontier again"
Cons: "Everything. Literally everything"

Pros: "I didn't die."
Cons: "Terrible service. Massive delays. Will not use this airline again."

Pros: "Nothing"
Cons: "Everything"

Cons: "No entertainment and you have to pay for a soda. Really"

Pros: "That we eventually arrived"
Cons: "That we arrived 3.5 hours after we were supposed to"

Pros: "N/a"
Cons: "N/a"

Pros: "Nothing!"
Cons: "They charge $40 for carry on luggage!!? They don't tell you before only when you are ready to board!!!"

Cons: "There were too many added costs. In the end it is more expensive to fly Frontier than other airlines. The pricing is deceiving."

Pros: "I like lower charges on changing bags"

Cons: "Luggage took 45 minutes to arrive"

Cons: "It was unfair to Charged us $90 for the carry on"

Pros: "Arrived early"

Pros: "The cheap airfares, charging for carryons and food and beverages makes for much faster boarding and disembarking!"
Cons: "Staff at airport was not very friendly, charging to print boarding passes seemed to cross the line a little bit."

Pros: "Cleanliness"
Cons: "Way hostess treat people with respect"

Pros: "Nothing"
Cons: "Everything"

Pros: "It is fun and comfortable"
Cons: "The small plane"

Pros: "Its over"
Cons: "Literally the most uncomfortable fli"

Pros: "Cheap fare"
Cons: "Have to pay for anything beyond ticket"

Pros: "I don't like it"

Cons: "So just remember that while the ticket itself might not be that expensive, you'll be charged for everything other than your personal bag, which might make up for the difference in ticket cost. Both of my flights were also delayed by about a half hour, which didn't make that much difference to my trip, but could be problematic if you have a tight layover."

Pros: "Got there earlier than promise"
Cons: "Table tray was broken couldn't eat or drink without sitting it down"

Pros: "Ticket fare is low."
Cons: "Check in luggage is too expensive."

Pros: "Short flights"
Cons: "Layovers"

Pros: "I liked the timely fashion and although I arrived later that expected"

Pros: "fresh and clean, kind personnel. Informative captain"
Cons: "I didn't like how spirit tries to bait you into having to spend extra money to get an actual seat"

Pros: "The ride"

Pros: "Cost"
Cons: "Wish the people would talk slower when making announcements."

Pros: "everything"

Pros: "Boarding in group 2"
Cons: "Waiting for plane to unload before we load plane was late 45 min delay."

Pros: "Nothing was good about working with Spirit."
Cons: "Every instance of this experience was terrible. We never made it to our destination, luggage was lost and we dealt with extremely rude, unprofessional and flippant employees (in the rare opportunity you can find one or speak to one). I'd never consider booking with Spirit Air again and will do my best to save anyone and everyone I know from making the same horrible mistake I made."

Pros: "They suck"

Pros: "Smooth ride"
Cons: "Long boarding"

Cons: "Unprofessional staff, long waits for staff at bag drop despite no line."

Pros: "Nothing"
Cons: "Everything"

Pros: "I liked the comfort of the seat."
Cons: "Arrival was delayed and the subsequent delay after we boarded because of paperwork. Paperwork..."

Pros: "Location was easy to find"
Cons: "Not enough sitting in waiting area"

Cons: "Everything"

Cons: "Aircraft was cold, No blankets."

Pros: "Nothing"
Cons: "No compensation, missed first day if trip, no explanation"

Cons: "You need a bigger variety in snacks"

Cons: "All the added surcharges are rediculous."

Pros: "The fast pace lines got check in"
Cons: "Nothing"

Cons: "I missed check-in by 5 minutes and there were no available flights to Detroit, Cleveland, or the vicinity within 2 full days. So I drove instead."

Pros: "Nothing."

Cons: "Spirit Airlines owes my a carryon bag refund of $45. I ordered my bag online and went to check in but found out my computer bag was free on plane. Spirit refused to refund."

Pros: "It is cheap. It gets the job done."
Cons: "The staff really needs to go through training. Being nice does not have to cost a buck. Well if they could be nice I would actually pay for it"

Pros: "Nothing"
Cons: "Horrible servie. Just taking money for no show. Terrible system."

Cons: "I should never be charged $50 for bags. EVER!"

Cons: "If you're eager for an entirely dehumanizing, infuriating travel experience, try Spirit!"

Cons: "Legroom was ridiculously limited and I am short...only 5 foot 2 inches...can't imagine what taller people do. Couldn't believe all the add on fees...baggage cost and weight restrictions both ridiculous"

Pros: "Well kept"
Cons: "The seating is too tight!!!"

Pros: "They kept the passengers in the loop as to what was happening"
Cons: "Late noarding"

Pros: "The ticket is not expensive but the baggage costs a lot higher."
Cons: "The ticket is not expensive but the baggage costs a lot higher."

Pros: "Staff"

Pros: "Comfortable"
Cons: "Nice"

Pros: "N/a"
Cons: "N/a"

Pros: "Nothing!"
Cons: "Everything"

Pros: "Nothing"
Cons: "Don't use spirit airlines ever"

Pros: "Nothing"
Cons: "Most of everything, starting with both flights being delayed."

Pros: "Fly attendant very friendly"
Cons: "passengers did not follow airlines rules, for example they stand up when the sign of keep seat belt was on. They should not move around or stand up"

Pros: "Complete lack of communication, very uniformitive website with misleading prices on services. The attendants and counter staff were very helpful though."

Cons: "Very unprofessional and classlrss"

Read more about Delta
COVID-19 information

Safety measures for airlines flying from Maryland to Caribbean

Airlines flying from Maryland to Caribbean 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 Maryland to Caribbean

Mandatory masks

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

Social distancing seating

Middle seats unavailable to book on flights from Maryland to Caribbean

Pre-flight testing

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

Book cheap flights from Maryland to Caribbean

Recent round-trip flight deals

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5h 28m
BWI - SJU
4/18
Sun
1 stop
Spirit Airlines
16h 54m
BWI - STT
4/20
Tue
1 stop
Spirit Airlines
8h 07m
BWI - SJU
4/19
Mon
1 stop
Spirit Airlines
8h 07m
BWI - SJU
7/12
Mon
1 stop
Frontier
10h 37m
BWI - SJU
5/1
Sat
1 stop
Frontier
10h 26m
BWI - SJU
4/27
Tue
2 stops
Multiple Airlines
23h 59m
IAD - SJU
6/12
Sat
1 stop
Frontier
8h 29m
BWI - SJU
4/20
Tue
2 stops
Multiple Airlines
32h 23m
IAD - SJU
4/18
Sun
1 stop
Multiple Airlines
27h 50m
IAD - STT
5/24
Mon
1 stop
United Airlines
13h 15m
IAD - SJU
5/11
Tue
2 stops
American Airlines
14h 51m
DCA - SJU
5/4
Tue
2 stops
American Airlines
16h 49m
DCA - SJU
5/12
Wed
2 stops
Delta
10h 31m
BWI - MBJ
5/9
Sun
nonstop
JetBlue
3h 43m
DCA - SJU
5/3
Mon
1 stop
Copa Airlines
9h 08m
IAD - PUJ
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