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$326+ Cheap flights from Hyannis (HYA) 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 1/26. Fares are subject to change and may not be available on all flights or dates of travel.
HYA — SJU
Nov 29 — Dec 61
Sat 11/29
Sat 12/6
1 adult, Economy
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Find flight deals from Hyannis to Caribbean

Best flights from Hyannis to Caribbean
Discover carefully curated flight deals from Hyannis to Caribbean that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated October 30, 2025.

This JetBlue deal was found by Cheapflights users on 10/28. 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.
Mon 3/237:58 amHYA - SDQ
1 stop8h 17mJetBlue
Thu 3/265:00 amSDQ - HYA
1 stop13h 39mJetBlue
Deal found 10/28$674

Cheap flight deals from Hyannis to Caribbean

Keep the following information in mind while searching for Hyannis to Caribbean flight deals. Data was last updated October 30, 2025.

Most accurate provider

Expedia
2 stars

Most trusted provider

Expedia
3 stars

Round-trip from

$674
(JetBlue)

One-way from

$326
(JetBlue)

Popular in

December

Cheapest in

January

Average price

$265
Provider with most accurate pricing for Boston Logan Intl-San Juan flight deals.
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Provider most trusted by Cheapflights users for Boston Logan Intl-San Juan flights.
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From Hyannis Barnstable to Caribbean
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One-way flight from Hyannis Barnstable to Caribbean
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High demand for flights, 0% potential price rise
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Cheapest flight prices on average. 2% potential price decrease ($8 potential savings vs. average RT price).
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Average for round-trip flights in October 2025
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Cheapflights Fare Finder

 
Customize your flight search to find flights from Hyannis 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 October 30, 2025.
Use the filters below to find and compare flights from Hyannis to Caribbean that are best for you.

Fly from

Hyannis

Fly to

Caribbean

Route

Depart

Return

Price

HyannisSanto Domingo

HYA - SDQ

HYASDQ

Hyannis Barnstable

Mon 3/23

7:58 am-4:15 pm

1 stop8h 17m

Santo Domingo Las Americas

Thu 3/26

5:00 am-6:39 pm

1 stop13h 39m

$674

HyannisSanto Domingo

HYA - SDQ

HYASDQ

Hyannis Barnstable

Mon 1/26

7:58 am-4:49 pm

1 stop7h 51m

$326

HyannisSaint Thomas Island

HYA - STT

HYASTT

Hyannis Barnstable

Sat 1/24

7:58 am-5:00 pm

1 stop8h 02m

$451

HyannisSanto Domingo

HYA - SDQ

HYASDQ

Hyannis Barnstable

Fri 12/26

2:30 pm-4:36 am

1 stop13h 06m

$564

Flights are sorted by cheapest round-trip flights first.

Deals found on 10/29

Best time to book a flight from Hyannis to Caribbean

Have a flexible travel schedule? Discover the best time to fly to Caribbean from Hyannis with our price prediction graph.
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.

Cheapflights Insights

Everything you need to know about your flight from Hyannis to Caribbean

What is the cheapest month to book a flight from Hyannis to Caribbean?

Currently, January is the cheapest month in which you can book a flight from Hyannis to Caribbean (average of $85). Flying from Hyannis to Caribbean in September is currently the most expensive (average of $147). 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.

Related info for your journey

Find useful and relevant information for your journey from Hyannis to Caribbean. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • What airport do you fly from for flights from Hyannis to Caribbean?

    Hyannis Barnstable (HYA), located 1.0 mi from the city center, is the airport you fly out of when you book flights from Hyannis to Caribbean.

  • How long is the flight from Hyannis to Caribbean?

    A quick flight from Hyannis to Caribbean can take about 8h 17m. JetBlue provides one of the quickest options available for as low as $674. The distance from Hyannis to Caribbean is about 1605 mi.

  • What are the most popular routes from Hyannis to Caribbean?

    When deciding which route to take from Hyannis to Caribbean consider Hyannis Barnstable - Port of Spain Piarco Intl, Hyannis Barnstable - Santo Domingo Las Americas or Hyannis Barnstable - Saint Thomas Island Cyril E King as they are the most popular.

  • Can I find deals for flights from Hyannis to Caribbean that include hotel bookings?

    Yes. In addition to deals on Hyannis to Caribbean flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Hyannis to Caribbean?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Hyannis to Caribbean.

  • Can I find deals for business class flights from Hyannis to Caribbean?

    Yes. Cheapflights offers flight deals from Hyannis to Caribbean by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

  • What is the cheapest month to book a flight from Hyannis to Caribbean?

    Currently, January is the cheapest month in which you can book a flight from Hyannis to Caribbean (average of $85). Flying from Hyannis to Caribbean in September is currently the most expensive (average of $147). 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.

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