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$199+ Cheap flights from Rutland (RUT) 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 1/6. Fares are subject to change and may not be available on all flights or dates of travel.
RUT — SJU
Jan 22 — Jan 291
Thu 1/22
Thu 1/29
1 adult, Economy
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Cheap flight deals from Rutland to Caribbean

Cheapest flights from Rutland to Caribbean
Explore the most affordable flight options available from Rutland to Caribbean. Find the lowest fares from popular airlines and budget airlines, with prices last updated on December 23, 2025.

This Kiwi.com deal was found by Cheapflights users on 12/21. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/2711:19 amRUT - SJU
1 stop12h 22mMultiple Airlines
Tue 1/62:59 amSJU - RUT
2 stops32h 19mMultiple Airlines
Deal found 12/21$673
This Kiwi.com deal was found by Cheapflights users on 12/21. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/2711:19 amRUT - SJU
1 stop12h 22mMultiple Airlines
Tue 1/68:20 amSJU - RUT
1 stop26h 58mMultiple Airlines
Deal found 12/21$702
This Kiwi.com deal was found by Cheapflights users on 12/21. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/2711:19 amRUT - SJU
1 stop12h 22mMultiple Airlines
Thu 1/12:44 pmSJU - RUT
2 stops28h 47mMultiple Airlines
Deal found 12/21$729
This Kiwi.com deal was found by Cheapflights users on 12/21. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/247:15 amRUT - SJU
2 stops15h 39mMultiple Airlines
Tue 1/68:20 amSJU - RUT
1 stop26h 58mMultiple Airlines
Deal found 12/21$738
This JetBlue deal was found by Cheapflights users on 12/21. 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.
Wed 12/243:31 pmRUT - SJU
1 stop7h 25mJetBlue
Thu 1/16:01 amSJU - RUT
1 stop10h 06mJetBlue
Deal found 12/21$784
This Kiwi.com deal was found by Cheapflights users on 12/21. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/247:15 amRUT - SJU
2 stops15h 39mMultiple Airlines
Thu 1/18:00 amSJU - RUT
1 stop27h 18mMultiple Airlines
Deal found 12/21$794
This Kiwi.com deal was found by Cheapflights users on 12/21. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/2711:19 amRUT - SJU
1 stop12h 22mMultiple Airlines
Fri 1/29:37 pmSJU - RUT
2 stops18h 30mMultiple Airlines
Deal found 12/21$807
This Kiwi.com deal was found by Cheapflights users on 12/21. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/253:31 pmRUT - SJU
2 stops33h 41mMultiple Airlines
Tue 1/68:20 amSJU - RUT
1 stop26h 58mMultiple Airlines
Deal found 12/21$878
This Kiwi.com deal was found by Cheapflights users on 12/21. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/2711:19 amRUT - SJU
1 stop12h 22mMultiple Airlines
Fri 1/22:59 amSJU - RUT
2 stops13h 08mMultiple Airlines
Deal found 12/21$920
This Kiwi.com deal was found by Cheapflights users on 12/21. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/2711:19 amRUT - SJU
1 stop12h 22mMultiple Airlines
Sun 1/42:44 pmSJU - RUT
2 stops20h 34mMultiple Airlines
Deal found 12/21$932

Find flight deals from Rutland to Caribbean

Keep the following information in mind while searching for Rutland to Caribbean flight deals. Data was last updated December 23, 2025.

Round-trip from

$393
(JetBlue)

One-way from

$199
(JetBlue)
From Rutland to Caribbean
Search Deals
One-way flight from Rutland to Caribbean
Search Deals

Cheapflights Fare Finder

 
Customize your flight search to find flights from Rutland 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 December 23, 2025.
Use the filters below to find and compare flights from Rutland to Caribbean that are best for you.

Fly from

Rutland

Fly to

Caribbean

Route

Depart

Return

Price

RutlandSan Juan

RUT - SJU

RUTSJU

Rutland

Sat 1/31

3:31 pm-10:55 pm

1 stop6h 24m

San Juan Luis Munoz Marin Intl

Wed 2/4

6:15 am-3:07 pm

1 stop9h 52m

$393

RutlandSan Juan

RUT - SJU

RUTSJU

Rutland

Wed 1/7

3:31 pm-1:22 am

1 stop8h 51m

San Juan Luis Munoz Marin Intl

Sun 1/11

6:15 am-3:07 pm

1 stop9h 52m

$584

RutlandSan Juan

RUT - SJU

RUTSJU

Rutland

Tue 1/6

7:15 am-6:05 pm

1 stop9h 50m

$199

RutlandSan Juan

RUT - SJU

RUTSJU

Rutland

Mon 1/5

11:19 am-7:25 pm

1 stop7h 06m

$199

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/21

Best time to book a flight from Rutland to Caribbean

Have a flexible travel schedule? Discover the best time to fly to Caribbean from Rutland 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 Rutland to Caribbean

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

Currently, February is the cheapest month in which you can book a flight from Rutland to Caribbean (average of $179). Flying from Rutland to Caribbean in August is currently the most expensive (average of $346). 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 Rutland 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 Rutland to Caribbean?

    Most people fly from Rutland (RUT) if they book a flight from Rutland to Caribbean. Rutland is conveniently located just 5.9 mi from Rutland’s city center.

  • How long is the flight from Rutland to Caribbean?

    A quick flight from Rutland to Caribbean can take about 6h 24m. JetBlue provides one of the quickest options available for as low as $393. Airlines will cover a distance of 1779 mi.

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

    The most popular flight routes from Rutland to Caribbean are Rutland - San Juan Luis Munoz Marin Intl, Rutland - Santiago de los Caballeros and Rutland - Christiansted Henry Rohlsen.

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

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

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

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

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

    Yes. Cheapflights offers flight deals from Rutland 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 Rutland to Caribbean?

    Currently, February is the cheapest month in which you can book a flight from Rutland to Caribbean (average of $179). Flying from Rutland to Caribbean in August is currently the most expensive (average of $346). 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.

See more FAQs

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