$108 Find Cheap Flights from Baltimore to Caribbean Islands - Compare and Save

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight from Baltimore to Caribbean Islands departing on 8/31. 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
1 adult, Economy, 0 bags

Save 20% or more on flights. Compare deals from all over the web.

Never overpay with our price tracking tools.

Filter searches by price, airline and more to find your best flights.

Flight Deals
Booking Insights
Flight Deals

Cheap Flights from Baltimore to Caribbean Islands

Cheapest round-trip prices found by our users on KAYAK in the last 72 hours
Punta Cana
Punta Cana1 stop$468
Santo Domingo
Santo Domingo1 stop$404
Montego Bay
Montego Bay2 stops$479
Oranjestad
Oranjestad1 stop$341
Nassau
Nassau1 stop$371
Kingston
Kingston1 stop$456
Simpson Bay
Simpson Bay2 stops$296
Providenciales
Providenciales1 stop$405
Port of Spain
Port of Spain1 stop$464
Bridgetown
Bridgetown1 stop$614
George Town
George Town1 stop$321
Willemstad
Willemstad1 stop$498
Castries
Castries3 stops$2,542
Aguadilla
Aguadilla1 stop$299
St. John's
St. John's1 stop$630
Puerto Plata
Puerto Plata1 stop$548
Punta Cana
Punta Cana1 stop$468
Santo Domingo
Santo Domingo1 stop$404
Montego Bay
Montego Bay2 stops$479
Oranjestad
Oranjestad1 stop$341
Nassau
Nassau1 stop$371
Kingston
Kingston1 stop$456
Simpson Bay
Simpson Bay2 stops$296
Providenciales
Providenciales1 stop$405
Port of Spain
Port of Spain1 stop$464
Bridgetown
Bridgetown1 stop$614
George Town
George Town1 stop$321
Willemstad
Willemstad1 stop$498
Castries
Castries3 stops$2,542
Aguadilla
Aguadilla1 stop$299
St. John's
St. John's1 stop$630
Puerto Plata
Puerto Plata1 stop$548

Book Cheap Baltimore to Caribbean Islands Plane Tickets

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Baltimore to Caribbean Islands that are departing in the next months. While these flights were available on KAYAK in the last 72 hours, prices and availability are subject to change and deals may expire.
Discover the best prices for you by selecting your travel dates on KAYAK.

Recent round-trip flight deals from Baltimore to Caribbean Islands

Mon, Jan 18 - Mon, Jan 25
Delta Logo
8:10 am - 4:15 pm
BWI
-
STT
7h 05m
1 stop
Delta Logo
1:50 pm - 10:37 pm
STT
-
BWI
9h 47m
1 stop
$230Delta
Mon, Jan 18 - Tue, Jan 26
Delta Logo
8:10 am - 4:15 pm
BWI
-
STT
7h 05m
1 stop
Delta Logo
1:50 pm - 12:26 am
STT
-
BWI
11h 36m
1 stop
$230Delta
Thu, Sep 10 - Wed, Sep 16
Frontier Logo
9:32 pm - 9:35 am
BWI
-
SJU
12h 03m
1 stop
Frontier Logo
3:08 am - 10:03 am
SJU
-
BWI
6h 55m
1 stop
$260Frontier
Thu, Oct 22 - Sun, Oct 25
Frontier Logo
1:55 pm - 11:38 pm
BWI
-
SJU
9h 43m
1 stop
Frontier Logo
4:30 pm - 8:26 pm
SJU
-
BWI
3h 56mnonstop
$260Frontier
Mon, Jan 18 - Wed, Jan 27
American Airlines Logo
6:00 am - 3:56 pm
BWI
-
STT
8h 56m
1 stop
American Airlines Logo
4:46 pm - 9:19 am
STT
-
BWI
17h 33m
1 stop
$261American Airlines
Sat, Aug 22 - Fri, Aug 28
Multiple Airlines Logo
6:09 am - 2:48 pm
BWI
-
SJU
8h 39m
1 stop
Multiple Airlines Logo
2:14 pm - 6:23 pm
SJU
-
BWI
4h 09mnonstop
$261Multiple Airlines
Wed, Aug 19 - Wed, Aug 26
Multiple Airlines Logo
3:49 pm - 11:20 pm
BWI
-
SJU
7h 31m
1 stop
Multiple Airlines Logo
2:14 pm - 6:23 pm
SJU
-
BWI
4h 09mnonstop
$266Multiple Airlines
Sat, Aug 22 - Sun, Aug 23
American Airlines Logo
6:35 pm - 9:43 am
BWI
-
SJU
15h 08m
1 stop
American Airlines Logo
5:47 pm - 9:49 am
SJU
-
BWI
16h 02m
1 stop
$291American Airlines
Mon, Nov 9 - Thu, Nov 12
JetBlue Logo
5:10 pm - 10:20 pm
BWI
-
SJU
4h 10mnonstop
JetBlue Logo
1:00 pm - 4:15 pm
SJU
-
BWI
4h 15mnonstop
$292JetBlue
Wed, Nov 4 - Wed, Nov 11
JetBlue Logo
5:10 pm - 10:20 pm
BWI
-
SJU
4h 10mnonstop
JetBlue Logo
1:00 pm - 4:15 pm
SJU
-
BWI
4h 15mnonstop
$292JetBlue
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?

Data is based on round-trip flight searches on KAYAK over the past month.

The cheapest ticket to Caribbean Islands from Baltimore found in the last 5 days was to San Juan, at $232 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 $232.

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

The average price for all round-trip flights from Baltimore to Caribbean Islands depending on the time of departure, clicked by users on KAYAK in the last 2 weeks.

The cheapest time of day to fly to Caribbean Islands is generally in the afternoon, when round-trip flights cost $338 on average. Morning departures are around 4% 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 $400.

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

The average round-trip price for all non-stop flights, flights with one layover, and flights with two layovers for the route found by users searching on KAYAK in the last 2 weeks.

No, with an average price for the route of $414, prices are generally cheapest when you fly direct.

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

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for round-trip flights from Baltimore to Caribbean Islands, removes the top 0.1% to account for outliers, and then takes the median of all values for each month.

The cheapest month for flights from Baltimore to Caribbean Islands is September, when tickets cost $533 (return) on average. On the other hand, the most expensive months are June and July, when the average cost of round-trip tickets is $706 and $675 respectively.

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

The average price of all round-trip flights from Baltimore to Caribbean Islands clicked on KAYAK for each day over the last 12 months.

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 calculate weekly average prices, KAYAK takes all prices for each week before departure over the last year for round-trip flights from Baltimore to Caribbean Islands, removes the top 0.1% to account for outliers, and then takes the average of all the values for each week.

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

$108
Best time to beat the crowds with an average 12% drop in price.
Most popular time to fly with an average 15% increase in price.
Flight from Baltimore to Simpson Bay

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 $156 one-way - $313 round-trip

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

 
See real verified KAYAK customer reviews for airlines flying from Baltimore to Caribbean Islands. Airline scores are aggregated from all reviews left by passengers on KAYAK after flying with an airline. KAYAK doesn’t show reviews that are older than 5 years. Learn how KAYAK collects reviews.
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 4227 reviews
7.5Entertainment
8.6Crew
8.0Comfort
7.0Food
8.1Boarding
Airline reviews

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!

2.0 MediocreAnonymous, Apr 2026
BWI - MKE
Read more Southwest reviews

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.

Other than a bit of a delay, everything was good. Again, the boarding process and picking seats is the only thing I don't enjoy.

The quality of Southwest Airlines continues to degrade each time I fly with them. If it were not for the free luggage, I would probably choose another airline. Their prices are a little bit competitive, but way too high for the quality of the service. Southwest is not unique in this way. Domestic flight in the United States of America has continued to be a lower and lower quality product. Very sad when you compare the quality of domestic airlines to that of many international airlines around the world.

The ac must have died, it was way to hot on this flight. Boarding g was chaotic. The flight was delayed for boarding. Not a great experience.

Comfortable seats. Nice service online. Short flight, so not a lot of time to enjoy.

Awful. There was an unexpected delay of nearly three hours because there were not enough flight attendants. I understand this is likely due to FAA regulations; but in that case, Delta should coordinate with smaller airports such as RDU to have extra flight attendants on the ground and "on call". In addition, this was the second 2-hour+ delay to Boston on this route in one week.

It was strange that the flight attendant was so adamant about having phones turned to airplane mode that he was calling out names from networks shown and waiting until they were all gone. I've never experienced that before, and after already working through an hour+ delay, it felt tone deaf. I take dozens of flights per year and have never experienced anything similar.

The flight was done by SkyWest only WIFI no entertainment center are available on the CRJ

Your survey needs a N/A option. I didn’t use the entertainment or eat food.

The flight was over 2 hours late.. once we finally got boarded things were fine

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.

A more comfortable seat. Padding would be really helpful but I've read the airlines don't want customers to be satisfied with economy seats.

When I booked, I included my checked luggage and when the bill was sent there was no record of this. Its was costly since I am from Trinidad amd Tobago. Exchange rate over seven dollars to one US dollar.

Everything was good except checking bags . I had paid for two bags but it didn’t show so we had to do it again while people waited and we were struggling to get to our flight

Flight delayed 4 times on a non-stop from BOS to SFO. Then when landed in SFO had to wait for 30 mins for a gate AT 3:30AM.

Plane was delayed multiple times. I would like to request a refund. Was due to arrive Thursday evening ended up arriving Friday morning.

The seats were roomier than other airplanes I’ve been on.

The crew and the pilots. The pilots were amazing. The landing in Cancun was excellent.

The security line at JFK was one of the longest I’ve ever experienced - probably 45 minutes. I don’t know if JetBlue has control over it, but it detracted from the overall experience. Entertainment had good options, but the volume control was a bit small to tap on and the screen had a fair amount of interference blips. Clearer picture would have been better.

I liked the entertainment on JetBlue, the service from JFK to JAX was terrible at best

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

Great. Clean. Seats comfortable. Food was free. Had new release movies.

The airplane I love and I love I came back safe thank you American airlines

Although there were two delays, they were communicated clearly and the boarding process was expedited. The crew was pleasant and efficient.

The flight I booked was conveniently timed, had one brief stop and was going to be quick. The flight I ended up getting was delayed, took longer, had a far longer layover and arrived hours later than planned. Thanks for nothing.

Flight attendant made the flight very enjoyable. He was courteous and gave great care to the passengers

Everything was done like clockwork and I find no fault with the airline.

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.

Great except upon arrival it took them a long time to open the doors

Frontier feels like a family I Worked for Eastern Airlines back in the day and I felt the family vibe that I had then. Thank you

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!

Everything you need to know for your flight to Caribbean Islands

Information on your arrival and departure airports