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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$504
Santo Domingo
Santo Domingo1 stop$310
Montego Bay
Montego Bay1 stop$453
Oranjestad
Oranjestad1 stop$411
Nassau
Nassau1 stop$331
Kingston
Kingston1 stop$530
Simpson Bay
Simpson Baynonstop$271
Providenciales
Providenciales1 stop$429
Port of Spain
Port of Spain1 stop$523
Bridgetown
Bridgetown1 stop$671
George Town
George Town1 stop$379
Willemstad
Willemstad1 stop$487
Aguadilla
Aguadilla1 stop$240
Puerto Plata
Puerto Plata1 stop$616
St. John's
St. John's1 stop$571
Punta Cana
Punta Cana1 stop$504
Santo Domingo
Santo Domingo1 stop$310
Montego Bay
Montego Bay1 stop$453
Oranjestad
Oranjestad1 stop$411
Nassau
Nassau1 stop$331
Kingston
Kingston1 stop$530
Simpson Bay
Simpson Baynonstop$271
Providenciales
Providenciales1 stop$429
Port of Spain
Port of Spain1 stop$523
Bridgetown
Bridgetown1 stop$671
George Town
George Town1 stop$379
Willemstad
Willemstad1 stop$487
Aguadilla
Aguadilla1 stop$240
Puerto Plata
Puerto Plata1 stop$616
St. John's
St. John's1 stop$571
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 $95 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 $95.

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 $364 on average. Morning departures are around 5% 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 $403.

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

No, with an average price for the route of $429, 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 $567 (return) on average. On the other hand, the most expensive months are December and June, when the average cost of round-trip tickets is $753 and $710 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 Sunday 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
Best time to beat the crowds with an average 3% drop in price.
Most popular time to fly with an average 16% increase in price.

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 $132 one-way - $255 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 4219 reviews
8.1Boarding
7.5Entertainment
8.0Comfort
7.0Food
8.6Crew
Airline reviews

Wifi was terrible. I couldn't get any work done on the long flight

4.0 OkayMichael, Sep 2026
Read more Southwest reviews

Wifi was terrible. I couldn't get any work done on the long flight

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.

Chairs don’t recline and the ones that do recline, barely do recline. It was most uncomfortable flight i ever been on.

Good but not on par when compared with foreign flag carriers.

Good service but not on par when compared to foreign flag carriers.

Mechanical delay of 2 hours without telling us Canadians of the potential compensation for this delay. As this caused 2 out of three people in our travelling party to miss their connecting flights until the next day.

Travelling with 2 others for work. Delta asked to check their carry ons due to the fullness of the plane. This was all good until the next leg of the flight. One of the 3 had their carry on checked through to the final destination but their passport on in their checked bag. Which they could not get to and he was not allowed on to the plane. Even though Delta had to retrieve his bag, because he was not allowed on. So they got his bag and he was in the terminal, but even when the flight was delayed, due to mechanical issues, he was not allowed to come onto the plane. Since the delay was nearly 2 hours, he was finally allowed back on the plane.

good in general food is just snack and beverages (same snacks all the time) could you try to change them?

got ahead of the schedule, nothing else to like. crew management of boarding when overhead bag space was virtually gone in the midst of their priority zone 3 should have been better. but they absolutely did not care. ryanair crew is better than this!

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.

The boarding agent and checked bag agent were both rude. It only takes a second to be kind. However, the flight crew was amazing. I got a turkey sandwich and it wasn't bad---not great but not bad. The internet was my biggest problem. This was a work trip and I REALLY needed the internet to meet a deadline but it didn't work for 80% of the trip. Very disappointing.

I tried to check in beforehand from Ireland. The Jet Blue website sent me to the Aer Lingus website and vice versa. I tried to get a boarding pass at Dublin Airport as well, but they said they couldn't help me either. I had to wait until I arrived at the gate in Boston to secure a boarding pass...it was a bit nerve wracking.

Great flight. Best in years. Very clean craft. Easy boarding. Communicative pilot. Friendly flight attendants. Absolutely smooth take off, in flight and landing. Very comfortable seats. Smoothest flight I've experienced in years. THANK YOU JET BLUE!

I was asked to pony up an additional $239 (over the $735 paid originally) for a one way middle seat, which was very uncomfortable. Where did you expect me to sit?

Jet Blue sevice was good. Just don't understand why they charge for earphones to listen to flight entertainment. Other than that, everything was excellent.

Mostly good, flight take off in time and land earlier I can’t ask for more..

The crew was not nice this time. I asked for a drink one time and the girl didn’t say anything to me and just got me the hot drink while walking super fast to the back. We were sitting in the back and she wasn’t doing anything except socializing. She was upset I asked for something and she had to do her job. I also didn’t fully have it in my hands when she handed it to me so it was dangerous. She was abrupt and rude. She wouldn’t allow for people to spread out like previous flights we had been on if they were empty, and there were empty rows. It was strange and she enjoyed being angry at us.

The plane was FREEZING COLD. Like I was wishing I'd brought gloves. Is this how JetBlue sells more blankets? Other than that, all fine. Crew just as nice as usual. A flight attendant asked (who? The pilot?) to have the air turned down for a great number of passengers who were as cold as I was. They (again -- who is "they") did not.

Flight was fine, but I was annoyed to have to pay for luggage again. We had paid for our luggage on our first two connecting flights with SATA Azores Airlines, but had to pay for luggage again with JetBlue at JFK airport. For one trip we paid over $500 for two suitcases to travel from Azores to San Francisco.

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

AC wasn't working properly and the WiFi was also not working properly for stretches.

Flight was fine. Just delays leaving due to mechanical issues. But flight crew were kind and professional. Seats were spacious. American doesn't need to have 9 groups for boarding.

Both flights were late leaving due to repairs/switching gates. The crew and pilots, however, were professional and courteous. Most importantly, we arrived at our destination safely. The seats were comforable. That size should be standard for all economy class. American could improve its boarding process. I am not sure why you need 9 groups for a small regional plane.

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.

You have to be super careful when purchasing as *everything*, a carryon or a sip of soda, has a fee. They relentlessly chip away at you with surcharges and extra costs … and it’s not always clear what you are getting when you buy your ticket. Will not fly them again. And … crew were not friendly until off boarding .. like they don’t like working for Frontier.

Air was off while waiting on the runway and the temperatures became very uncomfortably hot. Flight attendants were very loud and rude the entire flight.

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

Complete your trip to Caribbean Islands with a hotel stay or car rental