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Find cheap flights from Maryland to Caribbean from $71

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight from Maryland to Caribbean departing on 6/10. 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
Thu 6/27
Thu 7/4

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Good to know

Low season

September

High season

December

Cheapest flight

$71
Best time to beat the crowds with an average 15% drop in price.
Most popular time to fly with an average 24% increase in price.
Flight from Baltimore to San Juan

FAQs for booking flights from Maryland to Caribbean

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

    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 Maryland to Caribbean.

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

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Caribbean from 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 Maryland to Caribbean?

    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 Caribbean with an airline and back to Maryland with another airline.

  • What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from Maryland to Caribbean?

    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 Caribbean from Maryland 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 Maryland to Caribbean

 
Need help choosing which airline to fly with from Maryland to Caribbean? 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.
9.0
Cape AirOverall score based on 53 reviews
8.8Boarding
8.4Comfort
9.0Entertainment
8.7Food
9.4Crew
Airline reviews

It’s less complicated from Culebra to SJU airport. Next time I will prefer to leave from Isla Grande airport to Culebra !!

10.0 ExcellentSonia, Apr 2023CPX - SJU
Read more about Cape Air reviews

It’s less complicated from Culebra to SJU airport. Next time I will prefer to leave from Isla Grande airport to Culebra !!

10 seat Cesna. Equal parts transportation and adventure. 20 minute hop at 10000 feet and 160 mph, sitting 10 feet from the pilot. Panoramic views of the island. Very simple boarding, very low stress. VQS airport tiny, undeveloped. Highly recommended flight, Cape Air doing a great job here.

We traveled in a small Cesna so there was no food or entertainment. The pilot was excellent enjoy being able to see the places we were flying above. It was an OK flight.

Very smooth flight and landing. Pilot delivered his safety instruction in such a monotone that it wasn’t easily understandable. Words were said but he didn't communicate to us. If he was communicating to someone he cared about, he would have used inflection and other nuances of speaking. Virtually all emphasis was removed so it was just blah blah blah (really fast, like the end of a Pharma commercial)

My pilot on Cape Air was AMAZING!!!! I hoping that next time I fly I have him as my pilot. He made me feel safe and secure in his skills.

I so appreciate this service into and out of Glendive. Always a good experience with crew and support team.

It was not what I had expected but it was a great way to see the landscape.

Pros: "ground crew, pilot, flight was smooth and gate connections to Jet Blue in Boston were fantastic!"
Cons: "leg room"
Pros: "The pilot was kind and to the point."
Cons: "The guy who boarded us told me to wait as his computer could not check me in. 10min later he is rushing me to get on the runway. It was 30min before scheduled take off. I had ordered food and had to cancel my order before the café had finished, so he wasted food and did not get paid and I was hurried and boarded the plane hungry. I probably won't use Cape Air again unless it's an emergency situation"
Cons: "Boarded half hour late. No explanation. Pretty standard on Cape Air these days"

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 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

Easy boarding and deplaning. Short flight. Water was given but that was it.

Friendly staff, easy, and on time. Needs improvement on booking directly. Also

No comments, the complete handling and flying was excellent,keep up the good works.

Book cheap flights from Maryland to Caribbean

Recent round-trip flight deals

6/5Wed
nonstopSpirit Airlines
4h 05mBWI-SJU
6/12Wed
nonstopSpirit Airlines
4h 04mSJU-BWI
$124
6/4Tue
2 stopsSpirit Airlines
18h 10mBWI-SJU
6/11Tue
1 stopSpirit Airlines
16h 56mSJU-BWI
$125
6/11Tue
1 stopJetBlue
8h 43mDCA-SJU
6/12Wed
1 stopJetBlue
7h 42mSJU-DCA
$248
6/11Tue
1 stopJetBlue
8h 43mDCA-SJU
6/18Tue
nonstopJetBlue
4h 02mSJU-DCA
$264
9/18Wed
1 stopAvianca
19h 05mIAD-AUA
9/26Thu
2 stopsAvianca
15h 30mAUA-IAD
$316
9/16Mon
1 stopCopa Airlines
9h 32mIAD-AUA
9/25Wed
1 stopCopa Airlines
15h 09mAUA-IAD
$321
10/2Wed
1 stopAvianca
19h 05mIAD-AUA
10/6Sun
1 stopAvianca
20h 05mAUA-IAD
$327
9/25Wed
1 stopCopa Airlines
9h 32mIAD-AUA
9/30Mon
1 stopCopa Airlines
15h 09mAUA-IAD
$337
7/31Wed
1 stopAmerican Airlines
7h 20mDCA-SJU
8/6Tue
1 stopAmerican Airlines
5h 53mSJU-DCA
$416
6/11Tue
1 stopAmerican Airlines
9h 17mIAD-SJU
6/12Wed
1 stopAmerican Airlines
15h 59mSJU-IAD
$475

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Recent one-way flight deals

6/10Mon
1 stopSpirit Airlines
28h 26mBWI-SJU
$71
8/24Sat
1 stopSpirit Airlines
10h 56mBWI-SJU
$74
8/27Tue
1 stopCopa Airlines
9h 32mIAD-AUA
$137
7/15Mon
nonstopJetBlue
3h 52mDCA-SJU
$138
6/11Tue
1 stopJetBlue
8h 16mDCA-SJU
$147
8/28Wed
1 stopCopa Airlines
12h 16mIAD-AUA
$153
7/6Sat
1 stopAmerican Airlines
18h 20mIAD-SJU
$162
9/12Thu
2 stopsAvianca
23h 10mIAD-AUA
$182
8/28Wed
2 stopsAvianca
27h 55mIAD-AUA
$183
7/30Tue
1 stopAmerican Airlines
7h 26mIAD-PUJ
$230

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Last minute flights from Maryland to Caribbean

Last minute flight, train and bus deals

6/1Sat
nonstop
3h 39mPHL-SJU
6/4Tue
multi-stop
13h 03mSJU-PHL
$143
6/1Sat
nonstopSpirit Airlines
3h 50mPHL-SJU
6/5Wed
multi-stopSpirit Airlines
7h 59mSJU-PHL
$148
6/1Sat
multi-stopJetBlue
7h 20mDCA-SJU
6/12Wed
multi-stopJetBlue
7h 42mSJU-DCA
$437
6/2Sun
multi-stopCopa Airlines
12h 22mIAD-AUA
6/12Wed
multi-stopCopa Airlines
11h 16mAUA-IAD
$445
6/1Sat
multi-stopJetBlue
8h 20mDCA-SJU
6/18Tue
nonstopJetBlue
4h 02mSJU-DCA
$448
6/2Sun
multi-stopCopa Airlines
12h 22mIAD-AUA
6/13Thu
multi-stopCopa Airlines
8h 48mAUA-IAD
$492
6/1Sat
multi-stopAvianca
19h 05mIAD-AUA
6/4Tue
multi-stopAvianca
12h 45mAUA-IAD
$517
6/1Sat
multi-stopAvianca
17h 10mIAD-AUA
6/4Tue
multi-stopAvianca
19h 10mAUA-IAD
$551
5/30Thu
multi-stopAmerican Airlines
8h 27mIAD-SJU
6/6Thu
multi-stopAmerican Airlines
9h 13mSJU-IAD
$576
5/30Thu
multi-stopAmerican Airlines
6h 45mDCA-SJU
6/6Thu
multi-stopAmerican Airlines
9h 12mSJU-DCA
$578

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Flights to Caribbean

Return flight deals:

Caribbean - Maryland

Cabin classes:

$94