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Find cheap flights from Caribbean to Maryland from $53

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 6/4. 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.
1 adult
0 bags
Sat 6/29
Sat 7/6

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Good to know

Low season

January

High season

July

Cheapest flight

$53
Best time to beat the crowds but there is an average 47% increase in price.
Most popular time to fly with an average 6% increase in price.
Flight from San Juan Airport to Philadelphia

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 to Maryland from Caribbean 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 to Maryland with an airline and back to Caribbean 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 to Maryland from Caribbean up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

See more FAQs

Top 4 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.
7.9
Caribbean AirlinesOverall score based on 186 reviews
8.3Crew
7.6Comfort
6.7Entertainment
8.2Boarding
6.7Food
Airline reviews

There was no music on the flights unless you came with your headset.

10.0 Excellentsusan, Apr 2024MIA - POS
Read more about Caribbean Airlines reviews

There was no music on the flights unless you came with your headset.

Their bar selection could be greatly improved; they only had one spirit option

Music would have been great and information about the flight. Meaning how high and the weather conditions.

It was good but the food was small for the duration of the flight.

I wrote to the entertainment and food OK because it was non-applicable All excellent

Checking in online still requires going on the physical check in line

I enjoyed the smooth flow and well coordinated boarding and the very courteous attitude from the cabin crew We look forward to flying with ya’ll again

Pleasant experience checking in. Seating is way too tight, especially for persons who are not petite. I thought the pilot was excellent in terms of his commentary and information. Wrong gate information on boarding passes. If I was not alert I could have lined up to board the wrong plane.

The crew was excellent, check in was easy ,the food wasn't good, movies should be recent and more selections

The captain was great he made jokes and make thebflight very comfortable. Alerted us about the islands we flew over and Yolandra and her team took great care of us, very personable.

Overall fine but both ways for this trip was delayed.

Flight was delayed by almost 5 hours. Suitcase was not loaded despite the flight being near empty (my colleagues’ suitcases did reach JFK, unlike mine). Had to argue on phone to get JetBlue to deliver the case to my hotel. Never again

The flight was excellent. The crew was welcoming and attentive.

Great! I love Jet Blue. My favorite airline! Very efficient, clean and timely.

Run out of snack choices. Why are the seats not padded for your butt? Are we sitting on blocks of wood or metal for $250-300 a pop? This ain’t spirit. Let’s get it together people

We were told that our flight would be delayed for 90+ minutes because of weather, so we went to get something to eat only to have them randomly start boarding 15 minutes after the announcement, with no warning.

Entertainment... No earphones passed out. Many including me couldn't use the TV. Legroom was good. Crew was indifferent and a bit surly. Free wifi was a nice convenience. Check in desk location was unknown. Gate number on the boarding passes was wrong.

Going through JFK’s security is a mess. The TSA security said no shoes on the bins. So, we place our shoes in the belt and they came out all over the belt. Boarding was delayed and Flight as well.

Safe and on time were the positives. The plane wasn't cleaned before boarding, there was garbage and food on the floor and in the seat pocket. The TV screen was small and the picture fuzzy, audio quality was poor. Seatbelt was fraying and seat did not recline properly. No charging ports near the seats,

Confusing. Delay updates were out of whack At one point it said my flight was 25 hours. Three gate changes and two delays only to change back to original departure time. Gate announcer and on board flight attendant (Alejandro) making the announcements was impossible to understand due to accent and speed of speech. After beverage service the rear flight attendants sat back there on their phones. No refills no checking in, one sweep through for trash collection. Very impersonal. Bring back Coke products

Delay flight more than 8hours waiting and poor customer service!

Plane was extremely small so mind the size of your carry on

Other than lack of snacks, everything else went very well.

They don’t keep you updated on the flight status very well. It was late but nothing said

Pros: "Nothing!!! Horrible airline with horrible staff members."
Cons: "Everything. The staff and crew of Intercaribbean airlines are very unprofessional and not helpful at all. On top of the flight delays all the luggage for that particular flight was left in Kingston. Everybody was rather nonchalant and unapologetic about the situation. I was told I would get the the following day. The next day only two of my three bags showed up. I was not compensated for the inconvenience and was told point blank that they will only deliver one of my bags to my address even though they were the reason I had NONE of my luggage in the first place. They are disgusting!!! I would never recommend this airline to anyone."
Pros: "Nice people"
Cons: "A long walk to the D3 gate, but there were no amenities there I.e. snacks (to be fair a new terminal is under construction)"
Cons: "There was no air. I understand when you are on the ground it can be limited but even after getting to altitude there was no air conditioning."
Cons: "The flight was delayed for over three hours, apparently it is a regular occurence."
Pros: "almost nothing"
Cons: "The plane had a problem that forced us to turn around right after take off and as of this writing we still don’t know what’s going on or how long we are stuck here. Planes are old and apparently maintenance could be better."
Cons: "Was a bit difficult understanding the flight attendant, she had a thick Spanish accent"

I am very disappointed. I booked with kiwi when I got to the airport there was no reservation I had to purchase another ticket after my card was already charged for almost double the cost I payed through kiwi eight days after I went to their office in Tortola and they refuse to give me a receipt so that I can cancel the original payment. They said “ there is no record that you used silver to travel “ I know I did not swim to Puerto Rico . If someone can help me please so that I can cancel the payment the credit card company said I need it, I have less than 14 days or I will loose my money. This is terrible and there is no local number for them.

I booked because of time of the flights. I needed to be at my destination at a specific time, and missed my appointment because of your delays.Get rid of these junk planes. The ATR planes are dated old scary planes. And maybe you could actually be on time. This airlines on time record is horrible. The communications between the gate agents and this company dont exist.. They couldn't give any answers,. When trying to find out when the flight would leave, they get no response when they asked for details on flights, they receivedconflicting information. I felt bad for the gate agents having to deal with Silver's inability to communicate simple information. This is my last choice in air travel. On time flights are everywhere, and both flights I took were delayed. It's a sad company.

The flight itself was good and the flight attendant was very good.

It was awesome until we ran into some bad weather but the pilots did an amazing job getting us to safety and landed

If you take this airline, they WILL change the flight time, and make you miss your connection. It has happened every time I used it. It's so unreliable that I think it shouldn't be offered on Kayak. You will regret it!

In addition to the fact that Silver changed the flight time several days before the trip without offering any choices , I was sick with Covid and unable to go on the trip. I tried to ask Silver for a credit for a flight when I’d recooperated but they don’t do credits, even for illness. I will Never fly on Silver again

I canceled due to a 7 hour delay. Was forced to book another airline last minute , very expensive. Silver Aorways sucks

I spent hours with orbitz to get my tsa # on my ticket. They didn’t have a place to enter. I will never use orbitz again. No customer service. A number in which u press offered options and the message replays instead of getting customer to that area. Silver did not make the promised call back. Finally someone responded to my email and took care of it after I lost hours of my vacation arranging this. Staff on flight barked orders.

Our pilot and flight attendant, Desiree, were great. I always fly this route and this crew was better than most.

The worst flight ever; 1st and last flying to this airlines

Book cheap flights from Caribbean to Maryland

Recent round-trip flight deals

9/5Thu
1 stopSpirit Airlines
12h 52mSJU-PHL
9/10Tue
1 stopSpirit Airlines
13h 27mPHL-SJU
$121
8/27Tue
1 stopSpirit Airlines
13h 03mSJU-PHL
9/4Wed
1 stopSpirit Airlines
13h 27mPHL-SJU
$127
8/13Tue
nonstopFrontier
4h 10mSJU-PHL
8/17Sat
nonstopFrontier
4h 05mPHL-SJU
$152
8/26Mon
nonstopFrontier
4h 08mSJU-PHL
9/4Wed
nonstopFrontier
4h 05mPHL-SJU
$156
9/17Tue
1 stopJetBlue
7h 55mSJU-DCA
9/24Tue
nonstopJetBlue
3h 46mDCA-SJU
$269
9/17Tue
1 stopJetBlue
6h 25mSJU-DCA
9/24Tue
1 stopJetBlue
9h 07mDCA-SJU
$271
9/5Thu
1 stopAmerican Airlines
17h 08mSJU-DCA
9/8Sun
1 stopAmerican Airlines
15h 04mDCA-SJU
$283
9/19Thu
1 stopAmerican Airlines
8h 45mSJU-DCA
9/27Fri
1 stopAmerican Airlines
9h 20mDCA-SJU
$290
9/4Wed
1 stopCopa Airlines
15h 38mSDQ-IAD
9/7Sat
1 stopCopa Airlines
8h 36mIAD-SDQ
$395
9/1Sun
1 stopCopa Airlines
16h 04mSDQ-IAD
9/8Sun
1 stopCopa Airlines
12h 35mIAD-SDQ
$398

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Recent one-way flight deals

6/4Tue
1 stopSpirit Airlines
13h 03mSJU-PHL
$53
6/5Wed
1 stopSpirit Airlines
11h 54mSJU-PHL
$58
9/9Mon
nonstopFrontier
4h 08mSJU-PHL
$64
6/10Mon
nonstopFrontier
4h 04mSJU-BWI
$72
6/12Wed
1 stopJetBlue
7h 42mSJU-DCA
$127
6/6Thu
1 stopJetBlue
7h 42mSJU-DCA
$140
10/16Wed
1 stopAmerican Airlines
11h 48mSJU-IAD
$141
8/22Thu
1 stopAmerican Airlines
16h 54mSJU-IAD
$161
10/27Sun
1 stopCopa Airlines
18h 04mSDQ-IAD
$208
6/5Wed
1 stopCopa Airlines
18h 12mSDQ-IAD
$215

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Last minute flights from Caribbean to Maryland

Last minute flight, train and bus deals

6/4Tue
multi-stop
11h 53mSJU-PHL
6/10Mon
nonstop
3h 37mPHL-SJU
$130
6/4Tue
multi-stop
11h 53mSJU-PHL
6/10Mon
multi-stop
9h 16mPHL-SJU
$160
6/1Sat
nonstopFrontier
3h 46mSJU-PHL
6/4Tue
nonstopFrontier
3h 39mPHL-SJU
$173
6/4Tue
multi-stopFrontier
10h 54mSJU-PHL
6/12Wed
nonstopFrontier
3h 37mPHL-SJU
$187
6/4Tue
multi-stopJetBlue
6h 47mSJU-DCA
6/8Sat
multi-stopJetBlue
6h 05mDCA-SJU
$492
6/4Tue
nonstopJetBlue
4h 08mSJU-DCA
6/8Sat
multi-stopJetBlue
6h 05mDCA-SJU
$503
6/4Tue
multi-stopAmerican Airlines
12h 24mMBJ-BWI
6/19Wed
multi-stopAmerican Airlines
16h 35mBWI-MBJ
$529
6/3Mon
multi-stopAmerican Airlines
10h 14mSJU-DCA
6/12Wed
multi-stopAmerican Airlines
11h 15mDCA-SJU
$545
6/2Sun
multi-stopCopa Airlines
11h 22mMBJ-IAD
6/3Mon
multi-stopCopa Airlines
9h 40mIAD-MBJ
$673
6/4Tue
multi-stopCopa Airlines
17h 30mSDQ-IAD
6/6Thu
multi-stopCopa Airlines
12h 37mIAD-SDQ
$695

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