$92 Find Cheap Flights from Baltimore to Caribbean Islands - Compare and Save

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Cheap Flights from Baltimore to Caribbean Islands

Cheapest round-trip prices found by our users on KAYAK in the last 5 days
Punta Cana
Punta Cana1 stop$458
Santo Domingo
Santo Domingo1 stop$350
Montego Bay
Montego Bay1 stop$332
Oranjestad
Oranjestad1 stop$394
Nassau
Nassau1 stop$402
Kingston
Kingston1 stop$548
Simpson Bay
Simpson Baynonstop$290
Providenciales
Providenciales1 stop$469
Port of Spain
Port of Spain1 stop$442
Bridgetown
Bridgetown2 stops$597
George Town
George Town1 stop$349
Willemstad
Willemstad1 stop$476
Aguadilla
Aguadilla1 stop$235
St. John's
St. John's1 stop$581
Puerto Plata
Puerto Plata1 stop$576
Punta Cana
Punta Cana1 stop$458
Santo Domingo
Santo Domingo1 stop$350
Montego Bay
Montego Bay1 stop$332
Oranjestad
Oranjestad1 stop$394
Nassau
Nassau1 stop$402
Kingston
Kingston1 stop$548
Simpson Bay
Simpson Baynonstop$290
Providenciales
Providenciales1 stop$469
Port of Spain
Port of Spain1 stop$442
Bridgetown
Bridgetown2 stops$597
George Town
George Town1 stop$349
Willemstad
Willemstad1 stop$476
Aguadilla
Aguadilla1 stop$235
St. John's
St. John's1 stop$581
Puerto Plata
Puerto Plata1 stop$576
Booking Insights

KAYAK's insights & trends for Baltimore to Caribbean Islands flights

Get data-powered insights and trends into flights from Baltimore to Caribbean Islands to help you find the cheapest flights, the best time to fly and much more.

What is the cheapest Baltimore to Caribbean Islands flight route?

The cheapest ticket to Caribbean Islands from Baltimore found in the last 5 days was to San Juan, at $200 round-trip. The most popular route is from Baltimore (BWI) to San Juan Luis Munoz Marin Intl Airport (SJU), and the cheapest round-trip airline ticket found on this route in the last 5 days was $200.

What is the cheapest time of day to fly to Caribbean Islands?

The cheapest time of day to fly to Caribbean Islands is generally in the afternoon, when round-trip flights cost $348 on average. Morning departures are around 3% more expensive than evening flights, on average. The most expensive time of day to fly to Caribbean Islands is generally in the morning, which is peak travel time and where the average cost of a ticket is $408.

Can I save money by flying with a layover from Baltimore to Caribbean Islands?

No, with an average price for the route of $428, prices are generally cheapest when you fly direct.

What is the cheapest month to fly from Baltimore to Caribbean Islands?

The cheapest month for flights from Baltimore to Caribbean Islands is January, when tickets cost $557 (return) on average. On the other hand, the most expensive months are June and December, when the average cost of round-trip tickets is $710 and $696 respectively.

What’s the cheapest day of the week to fly from Baltimore to Caribbean Islands?

Your flight ticket price will generally be cheaper if you fly to Caribbean Islands on a Monday and more expensive on a Friday. On your return trip to Baltimore, you should consider flying back on a Thursday, and avoid Sundays for better deals.

How far in advance should I book a flight from Baltimore to Caribbean Islands?

To get a below average price on the flight from Baltimore to Caribbean Islands, you should book around 1 week before departure. For the absolute cheapest price, our data suggests you should book 12 weeks before departure.

Good to know

Low season

September

Cheapest flight

$92
Best time to beat the crowds with an average 4% drop in price.
Most popular time to fly with an average 15% increase in price.
Flight from Baltimore to San Juan

FAQs - booking Caribbean Islands flights

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

    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 Baltimore to Caribbean Islands.

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

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

    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 Baltimore to Caribbean Islands 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 Baltimore to Caribbean Islands?

    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 Baltimore to Caribbean Islands up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

Top tips for finding cheap flights to Caribbean Islands

  • Looking for a cheap flight? 25% of our users found tickets from Baltimore to the following destinations at these prices or less: San Juan $148 one-way - $302 round-trip

Reviews of the top 5 airlines serving from Baltimore to Caribbean Islands

 
Need help choosing which airline to fly with from Baltimore to Caribbean Islands? 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 4190 reviews
8.6Crew
8.0Comfort
7.0Food
7.5Entertainment
8.1Boarding
Airline reviews

Nice managed … it was a smaller plane, so the seating wasn’t as comfortable.

8.0 ExcellentBobby, Sep 2026
Read more Southwest reviews

Nice managed … it was a smaller plane, so the seating wasn’t as comfortable.

Flight left on time. Seat spacing is way too small…

The entire travel day was a disaster from beginning to end. Woke up at two in the morning to make it to San Juan airport in time for a 5:30 am flight to Milwaukee which connected in Baltimore. Massive delays lead to me missing original connection out of Baltimore. Sixteen hours of delays/rebooking/layover time later, arrived in Milwaukee to find that only one of two checked bags made it there (despite the fact that Southwest brought another 737 jet to San Juan to fly us out to our original Baltimore connection—-not squeezed into another booked flight). The flight from Baltimore to Milwaukee was barely half full, so there was no logical reason to ship my bags out of Baltimore on a different flight to Chicago to then ship to Milwaukee. Southwest decided that my bags should not have been on the same connecting flight I WAS ON to Milwaukee, and then proceeded to accidentally leave my larger bag with the important items in Chicago. Terrible logic and support all around. Extremely angered and disappointed with SW. What a clownish operation your company has become!

Love them will get a Southwest card to track my points and keep flying with them. My family and I were pleased with the services.

It was canceled. Supposedly weather. But there was no snow in Baltimore. At least we found out before driving to airport

WIFI was great. My selection for seating is an aisle, but during my trip, I never had an aisle seat. If we can get that corrected, I will be thrilled. No snack or drink on this flight.

The seats were comfortable, and the boarding process was pretty smooth.

The crew canceled the complementary snack and drink in anticipation of turbulence that never materialized. I was counting on the drink (water) to take the the doses of medication - prescribed for my heart condition - that were due during the flight. Since no snack or meal was served on this flight, I cannot rate the food quality. Otherwise, this flight was excellent.

Flight was fine other than there was a gate change that I was not notified of. By chance I happened to check my phone and saw the change, otherwise, we would have missed our connecting flight.

Southwest like most American domestic airlines, is a mediocre airline. But it is among the cheapest. Oh well.

I was impressed with how quickly the baggage transfers were made.

The Airline Attendant found us in flight and moved us to seats in the front of economy due to the short time we would have to make our connecting flight. We really appreciated it.

For some reason, there was very little volume on the cabin announcements. You could not hear what the pilot or crew were saying.

Carmen was an absolute delight on the flight staff! Everyone was lovely and made it a very pleasant flight.

Flight was delayed at airport with large backlog and WiFi was spotty

I don’t like mushrooms and that’s all they had with pasta

I Love Delta but one of the flight crew training in courtesy snd hospitality.

Delta was really good about being transparent with why we were delayed it’s just that’s the plane was really old and outdated and a lot of the comfort and amenities we know Delta to have did not shine through

My sister and I paid to have our seats and have them next to each other. I heard one of the employees say to the other one that you shouldn’t have given away reserved seats away to other passengers, and so I guess that is what happened because I got the last most uncomfortable seat in the plane even though I paid to sit in the middle of the plane with my sister. Terrible Experience !!

We checked one bag. That was fast and the agent was fast and super nice. At the gate, boarding was fast and efficient. Flight was uneventful which was great because it was early in the morning and most folks were sleeping. Landing was great. Delta does a really good job of making the flying experience better all around considering you are sitting in such a small space on a plane for several hours.

Had to pay for WiFi, delayed start, and sat on the runway forever.

As with most flights these days it was delayed by about 30 min.

The airline company should manage their crew for the plane on better schedule so people don’t have to wait in the plane. And this flight that I had had no snacks offered, and if you would like a water, you had to come see somebody and ask for. If airline would let people know that they are no longer providing or offering any food. At least people could bring their own if they wish.

The flight left without us even though we were on the ground in Dallas, and American Airlines wasn't helpful or available to rebook us on another flight.

The flight crew was good. I was delayed almost 3 hours and missed my connection, had to rebook and they lost my luggage

Flight was very delayed. That made me lose the next flight. Rebooked for 23 hours later without any compensation and using a worse airline. I did not expect that from AA. Disappointing.

I would like a refund for the extra cost the seat I paid for. An oversized person sat next to me and I couldn’t fit on my seat and had to move to another seat.

Kayak boarding information contained inaccuracies that would have not existed if booked directly with American. Paid for preferential boarding, was last to board.

great experience. minimal lines at BWI. at DFW they got a long haul 787 boarded in 30 minutes

Late arrival flight arrived in BWI and I missed connecting flight in CLT to mobile. I had to wait 6.5 hours for next flight.

KUDOS TO ALL THE CREW PROVIDING ASSISTANCE WITH PASSENGERS ON A WHEELCHAIR. ON BOTH FLIGHTS THEY HUSTLED TO TAKE MY RELATIVE TO CONNECTION ON TIME. THEY DESERVE A LOT OF CREDIT!

Good experience with this flight. Boarding was smooth with no issues. The short flight was good with quick drink & snack service. Nice easy way to get back from DC.

Very good flight that left on time and arrived earlier than anticipated, which was a plus! The crew members were very welcoming and helpful. However, the temperature on the flight was very cold - almost to the point of extreme discomfort. Additionally, requiring passengers to pay $8 for headphones to access the JetBlue entertainment was disappointing. Those earbud jacks are not used with most technology and would not be able to be used. There was no option to use Bluetooth for my own earbuds. Beyond those inconveniences, the flight was good.

My original flight was cancelled. My replacement flight was delayed over 2 hours. I lost my whole day in NY

Delays were crazy long (over an hour) both for boarding and baggage claim

awful expereince. boarding was a mess and not communicated, then we sat on a hot plane and were at risk of getting kicked off

2 hour delay and a lack of air conditioning on the plane. Not a good combination

Fabulous! This was the first time we've flown with JetBlue and the entire experience was flawless!

First time flying JetBlue and my perception changed. Love it.

Delayed 4 hours because of maintenance issue they knew about all day. Get another plane. Time is precious!

Flight delayed 9 hours. On tarmac for over an hour after arrival. Will never book with Frontier under any circumstances ever again.

My ATL–CVG Frontier flight was disappointing due to both an operational issue and unprofessional customer service. After everyone had boarded and the aircraft had pushed back from the gate, we were delayed because the passenger count did not match the flight manifest. The crew counted passengers approximately six times before the aircraft returned to the gate and gate agents boarded to help resolve the discrepancy. We were ultimately advised that a family had been allowed to board but not all of their boarding passes had been properly scanned. This resulted in a departure delay of nearly an hour. I did appreciate that the pilot kept passengers informed and tried to reassure us that some of the delay could be recovered during the flight. My greater concern was the customer-service experience. I am a Frontier Elite Platinum member and was seated within the first five rows. When I boarded, the overhead bins near my seat were already closed. I opened two bins to see whether my small backpack would fit. A female flight attendant sharply told me that a closed bin meant it was full, although the second bin clearly had available space. When I tried to ask whether I could simply place my backpack in that available space, she ignored me. Later, while the gate agents were working to resolve the passenger-count problem, I heard the same flight attendant make jokes about how many gate agents it takes to count passengers. She then made unnecessary comments about the male gate agent doing the count, men thinking they can do things better than women, and women knowing better and outliving men. Later in the flight, she also commented that passengers should know that the first thing they need to do is always be nice to the flight attendants. Courtesy absolutely should go both ways. Flight attendants deserve respect from passengers, but passengers also deserve respectful and professional treatment from the crew. Joking about colleagues who were actively trying to correct an operational problem, making gender-based comments in front of passengers, and being dismissive toward a passenger asking a simple baggage question were unnecessary and unprofessional. I fly enough to understand that delays and mistakes happen. What determines the quality of the experience is how those situations are handled. Unfortunately, the customer-service attitude on this flight made an already frustrating operational delay considerably worse.

Terrible. Delayed my family flight for several hours affecting family plans

Flight was delayed and then my second leg was completely canceled. Had to get a refund

Boarding was on time and plane departed as scheduled. There are obviously no amenities (food, drink, entertainment) on Frontier, but there also didn't seem to be any issues with luggage space either.

The single worst check in experience I could imagine. I’ll never do any business with Frontier or any affiliated company

Six hour delay. Poor customer service. No voucher. Bad communication. Missed important appointments.

First time flying Frontier, I am not sure the Ala Carte menu of options is for me.

Flying frontier reminded me of flying with my family in the 80’s in all of the worst ways possible. From poor customer service to little to no technology. The plane was dirty old and also stuck in the 80’s. From their seatbelts to not having anywhere to charge our phones the seats and the equipment I wasn’t sure if I was being punked or thrown back in time. Needless to say I don’t see myself flying frontier ever again.

Beware that when flying into Atlanta with Frontier, you will wait for your checked bag for a full hour after arriving at the gate! Do NOT recommend Frontier if Atlanta is your final destination!

More options for your flight to Caribbean Islands

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