$93+ Cheap flights from Boston (BOS) to Caribbean
This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 5/25. Fares are subject to change and may not be available on all flights or dates of travel.
Find cheap flights from Boston to Caribbean with Cheapflights
1. Tell us where you want to go
Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”2. Select your favorite providers
We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.3. Compare prices and book
Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.Cheap flight deals from Boston to Caribbean
Keep the following information in mind while searching for Boston to Caribbean flight deals. Data was last updated mai 15, 2025.
Most accurate provider | Expedia 1 star |
|---|---|
Most trusted provider | Expedia 3 stars |
Round-trip from | $150 (Kiwi.com) |
One-way from | $93 (Kiwi.com) |
Popular in | December |
Cheapest in | September |
Average price | $264 |
Good round-trip deal | $278 or less |
Good one-way deal | $143 or less |
Find flight deals from Boston to Caribbean
Cheapest flights from Boston to CaribbeanExplore the most affordable flight options available from Boston to Caribbean. Find the lowest fares from popular airlines and budget airlines, with prices last updated on mai 15, 2025.
Explore the most affordable flight options available from Boston to Caribbean. Find the lowest fares from popular airlines and budget airlines, with prices last updated on mai 15, 2025.
This Cheapflightsfares deal was found by Cheapflights users on 5/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
This JetBlue deal was found by Cheapflights users on 5/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
This United Airlines deal was found by Cheapflights users on 5/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
This American Airlines deal was found by Cheapflights users on 5/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
This Delta deal was found by Cheapflights users on 5/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
This Mytrip deal was found by Cheapflights users on 5/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
This JetBlue deal was found by Cheapflights users on 5/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
This American Airlines deal was found by Cheapflights users on 5/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
This Cheapflightsfares deal was found by Cheapflights users on 5/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
This Delta deal was found by Cheapflights users on 5/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
This Mytrip deal was found by Cheapflights users on 5/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
This American Airlines deal was found by Cheapflights users on 5/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Cheapflights Fare Finder
Customize your flight search to find flights from Boston to Caribbean that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated mai 15, 2025.
Use the filters below to find and compare flights from Boston to Caribbean that are best for you.
Fly from
Fly to
Route
Depart
Return
Price
BostonSan Juan
BOS - SJU
BOSSJU
Boston Logan Intl
mar. 6/10
5:42 pm-12:54 am
1 stop7h 12m
San Juan Luis Munoz Marin Intl
dim. 6/15
9:30 am-1:37 pm
Nonstop4h 07m
BostonSan Juan
BOS - SJU
BOSSJU
Boston Logan Intl
mer. 7/16
9:30 pm-1:31 am
Nonstop4h 01m
San Juan Luis Munoz Marin Intl
mer. 7/30
6:05 am-10:12 am
Nonstop4h 07m
BostonSan Juan
BOS - SJU
BOSSJU
Boston Logan Intl
jeu. 5/29
12:29 pm-11:57 pm
2 stops11h 28m
San Juan Luis Munoz Marin Intl
mer. 6/4
1:05 am-8:55 am
1 stop7h 50m
BostonSan Juan
BOS - SJU
BOSSJU
Boston Logan Intl
mar. 6/17
8:15 am-12:23 pm
Nonstop4h 08m
San Juan Luis Munoz Marin Intl
mer. 6/25
1:33 pm-5:44 pm
Nonstop4h 11m
BostonSaint Thomas Island
BOS - STT
BOSSTT
Boston Logan Intl
sam. 6/7
5:45 am-9:57 am
2 stops28h 12m
Saint Thomas Island Cyril E King
mer. 6/11
10:52 am-11:29 pm
1 stop12h 37m
BostonSaint Thomas Island
BOS - STT
BOSSTT
Boston Logan Intl
sam. 6/7
9:30 am-1:32 pm
Nonstop4h 02m
Saint Thomas Island Cyril E King
sam. 6/14
1:35 pm-7:24 pm
1 stop5h 49m
BostonSan Juan
BOS - SJU
BOSSJU
Boston Logan Intl
mer. 5/21
5:55 am-12:45 pm
1 stop6h 50m
San Juan Luis Munoz Marin Intl
mer. 5/28
5:25 am-7:24 pm
1 stop13h 59m
BostonSaint Thomas Island
BOS - STT
BOSSTT
Boston Logan Intl
dim. 7/20
6:05 am-12:17 pm
1 stop6h 12m
Saint Thomas Island Cyril E King
jeu. 7/31
4:10 pm-10:51 pm
1 stop6h 41m
BostonSan Juan
BOS - SJU
BOSSJU
Boston Logan Intl
jeu. 6/12
2:42 pm-6:36 pm
Nonstop3h 54m
San Juan Luis Munoz Marin Intl
lun. 6/16
12:59 am-8:06 am
1 stop7h 07m
BostonSaint Thomas Island
BOS - STT
BOSSTT
Boston Logan Intl
jeu. 5/29
6:05 am-4:20 pm
1 stop10h 15m
Saint Thomas Island Cyril E King
jeu. 6/5
5:00 pm-7:20 am
2 stops14h 20m
Best time to book a flight from Boston to Caribbean
Have a flexible travel schedule? Discover the best time to fly to Caribbean from Boston with our price prediction graph.
Cheapflights Insights
Everything you need to know about your flight from Boston to Caribbean
What is the cheapest month to book a flight from Boston to Caribbean?
Currently, September is the cheapest month in which you can book a flight from Boston to Caribbean (average of $254). Flying from Boston to Caribbean in December is currently the most expensive (average of $336). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.
What is the cheapest time of day to fly from BOS to CB?
Find hourly flight availability from Boston to Caribbean. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated mai 15, 2025.
When flying from Boston to Caribbean, the time of day you decide to fly out makes little to no difference towards the overall price you’ll pay on tickets.
Weekly flight availability from Boston to Caribbean
Explore weekly flight availability from Boston to Caribbean. Discover flights operating on different days of the week, giving you the flexibility to choose a travel day that best fits your plans. Compare info to find the most convenient option for your journey. Data last updated mai 15, 2025.
The most flights from BOS to 0CB are scheduled on a Thursday (17 on average). You will have fewer flight options on Tuesday, which is when the least amount of flights are scheduled (12 on average).
Rainfall in Caribbean by month
Plan your trip to Caribbean by taking into account the average rainfall totals by month.
In terms of precipitation, rainfall in Caribbean ranges from 2.2 - 6.1 inches per month. November is typically the wettest month, when rainfall can reach 6.1 in. February is typically the driest time to visit Caribbean when rainfall is around 2.2 in.
Temperature in Caribbean by month
Plan your trip to Caribbean by taking into account the average temperature totals by month.
If weather is an important factor for your trip to Caribbean, use this chart to help with planning. For those seeking warmer temperatures, June is the ideal time of year to visit, when temperatures reach an average of 82.4 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 77.0 F).
Reviews of airlines servicing Caribbean
Get insights into the airlines that provide service to Caribbean. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Caribbean. Reviews last updated mai 15, 2025.
Comfort
Boarding
Crew
Entertainment
Overall
Food
Reviews
Kim,May 2025
PIH - SLC
Comfort
Boarding
Crew
Entertainment
Overall
Food
Reviews
Kim,May 2025
PIH - SLC
Comfort
Boarding
Crew
Entertainment
Overall
Food
Reviews
Kim,May 2025
PIH - SLC
Comfort
Boarding
Crew
Entertainment
Overall
Food
Reviews
Kim,May 2025
PIH - SLC
Comfort
Boarding
Crew
Entertainment
Overall
Food
Reviews
Kim,May 2025
PIH - SLC
Comfort
Boarding
Crew
Entertainment
Overall
Food
Reviews
Kim,May 2025
PIH - SLC
Related info for your journey
Find useful and relevant information for your journey from Boston to Caribbean. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.
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Alternative routes for Boston to Caribbean
See prices for flight routes from nearby airports that may be better suited for you.
Top 10 airlines flying from Boston to Caribbean
Discover the top 10 airlines that operate flights from Boston to Caribbean. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated mai 15, 2025.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$76 | Average$364 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$92 | Average$463 | FlexibilityNo cancel fee | On-time65% | |
| Cheapest$142 | Average$495 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$147 | Average$532 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$156 | Average$724 | FlexibilityNo cancel fee | On-time67% | |
| Cheapest$204 | Average$544 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$282 | Average$601 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$356 | Average$518 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$364 | Average$520 | FlexibilityNo cancel fee | On-time70% | |
| Cheapest$427 | Average$783 | FlexibilityNo cancel fee | On-time63% |