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$391+ Cheap flights from Rutland (RUT) to Caribbean

This is the cheapest round-trip flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 3/4. Fares are subject to change and may not be available on all flights or dates of travel.
RUT — SJU
Mar 15 — Mar 221
Sun 3/15
Sun 3/22
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 February 13, 2026.

This Kiwi.com deal was found by Cheapflights users on 2/10. 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 3/411:19 am
RUT
-
SJU
1 stop12h 49m
Multiple Airlines
Mon 3/92:30 pm
SJU
-
RUT
1 stop24h 37m
Multiple Airlines
Deal found 2/10$391
This Kiwi.com deal was found by Cheapflights users on 2/12. 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 2/253:31 pm
RUT
-
SJU
1 stop27h 35m
Multiple Airlines
Mon 3/211:22 am
SJU
-
RUT
1 stop8h 09m
Multiple Airlines
Deal found 2/12$402
This Kiwi.com deal was found by Cheapflights users on 2/11. 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 2/267:15 am
RUT
-
SJU
1 stop6h 45m
Multiple Airlines
Sun 3/16:00 am
SJU
-
RUT
1 stop10h 07m
Multiple Airlines
Deal found 2/11$414
This KAYAK deal was found by Cheapflights users on 2/12. 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 KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 7/204:05 pm
RUT
-
SJU
1 stop9h 23m
JetBlue
Wed 7/296:00 am
SJU
-
RUT
1 stop8h 55m
JetBlue
Deal found 2/12$467
This JetBlue deal was found by Cheapflights users on 2/11. 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.
Fri 5/13:31 pm
RUT
-
SJU
1 stop6h 41m
JetBlue
Fri 5/85:01 am
SJU
-
RUT
1 stop10h 06m
JetBlue
Deal found 2/11$471
This Kiwi.com deal was found by Cheapflights users on 2/12. 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 2/253:31 pm
RUT
-
SJU
1 stop8h 37m
Multiple Airlines
Sun 3/16:00 am
SJU
-
RUT
1 stop10h 07m
Multiple Airlines
Deal found 2/12$521
This JetBlue deal was found by Cheapflights users on 2/11. 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.
Sun 3/293:31 pm
RUT
-
STI
1 stop12h 18m
JetBlue
Thu 4/28:30 am
STI
-
RUT
1 stop10h 01m
JetBlue
Deal found 2/11$646

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 February 13, 2026.

Round-trip from

$391
(Kiwi.com)
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 February 13, 2026.
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

Thu 3/5

11:19 am-1:08 am

1 stop12h 49m

San Juan Luis Munoz Marin Intl

Mon 3/9

10:22 am-10:18 am

1 stop23h 56m

$391

RutlandSan Juan

RUT - SJU

RUTSJU

Rutland

Wed 3/4

11:19 am-1:08 am

1 stop12h 49m

San Juan Luis Munoz Marin Intl

Mon 3/9

2:30 pm-3:07 pm

1 stop24h 37m

$391

RutlandSan Juan

RUT - SJU

RUTSJU

Rutland

Wed 2/25

3:31 pm-8:06 pm

1 stop27h 35m

San Juan Luis Munoz Marin Intl

Mon 3/2

11:22 am-6:31 pm

1 stop8h 09m

$402

RutlandSan Juan

RUT - SJU

RUTSJU

Rutland

Thu 2/26

7:15 am-3:00 pm

1 stop6h 45m

San Juan Luis Munoz Marin Intl

Sun 3/1

6:00 am-3:07 pm

1 stop10h 07m

$414

RutlandSan Juan

RUT - SJU

RUTSJU

Rutland

Mon 7/20

4:05 pm-1:28 am

1 stop9h 23m

San Juan Luis Munoz Marin Intl

Wed 7/29

6:00 am-2:55 pm

1 stop8h 55m

$467

RutlandSan Juan

RUT - SJU

RUTSJU

Rutland

Fri 5/1

3:31 pm-10:12 pm

1 stop6h 41m

San Juan Luis Munoz Marin Intl

Fri 5/8

5:01 am-3:07 pm

1 stop10h 06m

$471

RutlandSan Juan

RUT - SJU

RUTSJU

Rutland

Sat 8/1

4:05 pm-1:28 am

1 stop9h 23m

San Juan Luis Munoz Marin Intl

Fri 8/7

8:30 am-2:55 pm

1 stop6h 25m

$526

RutlandSantiago de los Caballeros

RUT - STI

RUTSTI

Rutland

Sun 3/29

3:31 pm-3:49 am

1 stop12h 18m

Santiago de los Caballeros

Thu 4/2

8:30 am-6:31 pm

1 stop10h 01m

$646

Flights are sorted by cheapest round-trip flights first.

Deals found on 2/11

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 $139). Flying from Rutland to Caribbean in June is currently the most expensive (average of $307). 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 12h 18m. JetBlue provides one of the quickest options available for as low as $646. Airlines will cover a distance of 1671 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 $139). Flying from Rutland to Caribbean in June is currently the most expensive (average of $307). 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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