$98 Find Cheap Flights from Baltimore to Caribbean - Compare and Save

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Cheap Flights from Baltimore to Caribbean

Cheapest round-trip prices found by our users on KAYAK in the last 5 days
Punta Cana
Punta Cana2 stops$501
Santo Domingo
Santo Domingo1 stop$368
Montego Bay
Montego Bay1 stop$458
Oranjestad
Oranjestad1 stop$373
Nassau
Nassau1 stop$333
Kingston
Kingston2 stops$553
Simpson Bay
Simpson Bay1 stop$275
Providenciales
Providencialesnonstop$407
Port of Spain
Port of Spain1 stop$517
Bridgetown
Bridgetown1 stop$713
George Town
George Town1 stop$342
Willemstad
Willemstad1 stop$487
Aguadilla
Aguadilla1 stop$238
Puerto Plata
Puerto Plata1 stop$616
St. John's
St. John's1 stop$578
Punta Cana
Punta Cana2 stops$501
Santo Domingo
Santo Domingo1 stop$368
Montego Bay
Montego Bay1 stop$458
Oranjestad
Oranjestad1 stop$373
Nassau
Nassau1 stop$333
Kingston
Kingston2 stops$553
Simpson Bay
Simpson Bay1 stop$275
Providenciales
Providencialesnonstop$407
Port of Spain
Port of Spain1 stop$517
Bridgetown
Bridgetown1 stop$713
George Town
George Town1 stop$342
Willemstad
Willemstad1 stop$487
Aguadilla
Aguadilla1 stop$238
Puerto Plata
Puerto Plata1 stop$616
St. John's
St. John's1 stop$578
Booking Insights

KAYAK's insights & trends for Baltimore to Caribbean flights

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

What is the cheapest Baltimore to Caribbean flight route?

The cheapest ticket to Caribbean from Baltimore found in the last 5 days was to San Juan, at $102 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 $102.

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

The cheapest time of day to fly to Caribbean is generally in the afternoon, when round-trip flights cost $362 on average. Morning departures are around 8% more expensive than evening flights, on average. The most expensive time of day to fly to Caribbean is generally in the morning, which is peak travel time and where the average cost of a ticket is $405.

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

No, with an average price for the route of $620, prices are generally cheapest when you fly direct.

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

The cheapest month for flights from Baltimore to Caribbean is February, when tickets cost $450 (return) on average. On the other hand, the most expensive months are June and July, when the average cost of round-trip tickets is $597 and $563 respectively.

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

If you are looking for a flight deal from Baltimore to Caribbean, look for departures on Sundays and avoid leaving on a Friday, as it's usually the priciest day. When flying back from Caribbean, Thursday is the cheapest day to fly and Sunday is the most expensive.

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

To get a below average price on the flight from Baltimore to Caribbean, 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

$98
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.
Flight from Baltimore to Simpson Bay

FAQs - booking Caribbean flights

  • Which are the most popular layovers for flights from Baltimore/Washington (BWI) and the Caribbean?

    Layover options between Baltimore/Washington International Airport and the Caribbean can vary based on the airline, route, and availability. Also, the popularity of layover airports can change due to factors such as airline partnerships, schedules, and customer preferences. To this end, the most common transit cities include Miami (MIA), Fort Lauderdale (FLL), Atlanta (ATL), New York (JFK), and Orlando (MCO).

  • Which airlines offer seat upgrades on flights from Baltimore/Washington and the Caribbean?

    With airlines such as American Airlines and Delta Air Lines, you can easily shift from economy to premium economy, business, or first class cabins on flights from Baltimore/Washington and the Caribbean. Some common ways to upgrade seats on these flights include using mileage points, paying in cash, bidding, or with a complimentary upgrade for elite status.

  • Which are the most eco-friendly airlines offering flights from Baltimore-Washington to the Caribbean?

    Southwest Airlines, JetBlue, and Spirit Airlines are some airlines taking steps to minimize their environmental impact on flights from Baltimore/Washington International Airport (BWI) and the Caribbean. They have invested in modern, fuel-efficient aircraft that consume less fuel and produce fewer emissions. Newer planes are designed with advanced technologies that improve fuel efficiency and reduce greenhouse gas emissions.

  • What airlines offer family services on flights from Baltimore/Washington (BWI) to the Caribbean?

    Parents often appreciate American Airways for their family-friendly services and overall travel experience between Baltimore and the Caribbean. They offer early boarding for families, in-flight entertainment options suitable for kids, and spacious seating.

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

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

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

    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 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

  • Looking for a cheap flight? 25% of our users found tickets from Baltimore to the following destinations at these prices or less: San Juan $136 one-way - $260 round-trip
  • Compared to Ronald Reagan Washington National Airport (DCA) and Washington Dulles International Airport (IAD), Baltimore/Washington International Airport (BWI) can have less congestion and shorter security lines, which can contribute to a smoother and less stressful travel experience. The layout of BWI is often considered straightforward and easy to navigate, which can benefit travelers unfamiliar with the airport.
  • Baltimore/Washington International Airport (BWI) is well connected to public transportation options, making it convenient for travelers to reach the airport from the city center. For example, the Baltimore Light RailLink directly connects downtown Baltimore to BWI Airport. The Light RailLink provides a cost-effective and efficient way to travel to the airport to catch a flight from Baltimore to the Caribbean. The BWI Business District Light Rail Station is located just outside the terminal.
  • Major carriers offering flights from Baltimore/Washington International Airport to the Caribbean, such as American and Delta Air Lines, cater to travelers with mobility limitations. Besides wheelchair assistance and priority boarding, airlines typically offer special seating arrangements for passengers with disabilities, such as bulkhead seats or seats with extra legroom to accommodate mobility aids.
  • Several Caribbean airports offer excellent business amenities and facilities for arriving on flights from Baltimore/Washington International Airport (BWI) to the Caribbean. For example, Grantley Adams International Airport (BGI) in Barbados provides VIP lounges, executive services, and meeting facilities for business travelers. The airport's proximity to Bridgetown, the capital, makes it convenient for business activities.
  • United Airlines, American Airlines, and Delta Air Lines offer services for unaccompanied minors on flights from Baltimore/Washington International Airport and various destinations in the Caribbean. These airlines supervise and assist unaccompanied minors throughout their journey, including check-in, boarding, in-flight, and arrival. In addition, parents or guardians are typically required to provide contact information for themselves and the person picking up the child at the destination.

Reviews of the top 5 airlines serving from Baltimore to Caribbean

 
Need help choosing which airline to fly with from Baltimore 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.
7.9
SouthwestOverall score based on 4220 reviews
7.4Entertainment
8.1Boarding
7.0Food
8.0Comfort
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.

Bad. Flight was delayed due to maintenance issue with Delta. Seats were small, no service, bag got broken on initial flight. Cramped and hot. Sitting inside with no ac.

Flight attendent didn't let me sit in the empty window seat literally next to me. Doors had closed already so I moved over. She came over, asked for my ticket and made me switch back to the middle. The man on the aisle and I were right on top of each other. Seemed like a real power trip for no reason at all.

The flight was delayed and passengers were told that they will miss connections as flight may get 40-55 min late.

The flight from Atlanta to Tallahassee was delayed, not such a big deal because it arrived almost the same original time. Most of my complaint is that one of the boarding agents and one of the flight attendants seemed bothered and were not very friendly.

Be on time. No issues with weather etc. entirely on airline.

Good flight — left on time due to on time arrival of Pittsburgh flight

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.

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.

Everything was great the only issue was lack of Wi-Fi

Left a bit late duee to a technical issue, but got in early

Wonderful aircraft Crew was tired,but great considering On time No complaints

I am always very pleased with the service u receive from JetBlue employees

Your Jet Blue representative at the check in desk in Boston on Sunday morning, October 13, was unkind and unhelpful. For that reason alone I will avoid JetBlue airlines in the future. No food or beverage on the flight due to turbulence (not your fault). However I paid extra to sit in the upgraded section in the front and did not benefit from most amenities.

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

Wheel Chair Access sucked. I had a guy from Bangaldesh drop me off without taking me to the gate

The amount of gate changes and delays is completely unacceptable. This has happened on 3 of 4 trips between Chicago and Dallas in 2026.

I didn't like anything about this flight. The only reason anyone drinks Jack is because you ran out of Woodford. You should know to stock more Woodford. When you wait of first class hand and foot from the minute they get on the plane 5 feet from me but then start service from the rear of the plane so main cabin plus gets the scraps, that's how you get people to stop flying your airline.

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.

I booked tickets from San Diego to Cincinnati months in advance to attend my sister’s wedding, a wedding where I was serving as the officiant. At 10:00 PM the night before my 6:00 AM flight (just 8 hours before departure), I received an alert that my first leg to Denver was delayed, causing me to miss my connecting flight to Cincinnati. When I called Frontier customer service, they informed me that they couldn't get me on any other flight that would get me there in time for the Saturday wedding, let alone the rehearsal dinner. Because I had a critical role in the wedding, I was forced to buy a last-minute ticket on another airline for three times the original price, costing me well over $1,000 extra. Even with the emergency flight, I still missed the rehearsal dinner entirely. When I spoke with Frontier, they agreed to refund my original ticket, but showed zero care or accountability for the massive financial burden and distress they caused. Their "compensation" for causing me to spend an extra $1,000+ and miss an irreplaceable family event? A $75 Frontier voucher. Frontier completely dropped the ball. Their customer service showed zero empathy, and their reliability is non-existent. I will never fly Frontier again, and no one else should either if they actually need to get where they want to go. Tip for anyone flying from Denver to Cincinnati: Avoid Frontier connecting flights or layovers at all costs, especially for time-sensitive events. Book direct flights with an airline that actually offers reliable customer support and rebooking options when delays occur.

I booked tickets from San Diego to Cincinnati months in advance to attend my sister’s wedding, a wedding where I was serving as the officiant. At 10:00 PM the night before my 6:00 AM flight (just 8 hours before departure), I received an alert that my first leg to Denver was delayed, causing me to miss my connecting flight to Cincinnati. When I called Frontier customer service, they informed me that they couldn't get me on any other flight that would get me there in time for the Saturday wedding, let alone the rehearsal dinner. Because I had a critical role in the wedding, I was forced to buy a last-minute ticket on another airline for three times the original price, it costing me well over $1,000 extra. Even with the emergency flight, I still missed the rehearsal dinner entirely. When I spoke with Frontier, they agreed to refund my original ticket, but showed zero care or accountability for the massive financial burden and distress they caused. Their "compensation” for causing me to spend an extra $1,000+ and miss an irreplaceable family event? A $75 Frontier voucher. Frontier completely dropped the ball. Their customer service showed zero empathy letting me know that it was Frontier who was the real victim by refunding my ticket price, and their reliability is non-existent. I will never fly Frontier again, and I strongly advise anyone who actually needs to arrive at their destination on time for an important event to book with literally any other airline.

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

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