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$464+ 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 3/9. Fares are subject to change and may not be available on all flights or dates of travel.
RUT — SJU
Dec 3 — Dec 101
Wed 12/3
Wed 12/10
1 adult, Economy
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Cheap flight deals from Rutland to Caribbean

Keep the following information in mind while searching for Rutland to Caribbean flight deals. Data was last updated November 3, 2025.

Round-trip from

$464
(JetBlue)
From Rutland to Caribbean
Search Deals

Find 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 November 3, 2025.

This JetBlue deal was found by Cheapflights users on 11/1. 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 11/174:01 pmRUT - SJU
1 stop6h 53mJetBlue
Fri 11/216:01 amSJU - RUT
1 stop9h 50mJetBlue
Deal found 11/1$471
This JetBlue deal was found by Cheapflights users on 11/2. 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.
Tue 11/411:22 amRUT - SJU
1 stop6h 35mJetBlue
Sat 11/88:00 amSJU - RUT
1 stop7h 51mJetBlue
Deal found 11/2$613

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 November 3, 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

Mon 3/9

4:01 pm-10:48 pm

1 stop6h 47m

San Juan Luis Munoz Marin Intl

Thu 3/12

5:15 am-2:51 pm

1 stop9h 36m

$464

RutlandSan Juan

RUT - SJU

RUTSJU

Rutland

Mon 11/17

4:01 pm-11:54 pm

1 stop6h 53m

San Juan Luis Munoz Marin Intl

Fri 11/21

6:01 am-2:51 pm

1 stop9h 50m

$471

RutlandSantiago de los Caballeros

RUT - STI

RUTSTI

Rutland

Mon 3/9

4:01 pm-3:55 am

1 stop11h 54m

Santiago de los Caballeros

Thu 3/12

6:00 am-2:51 pm

1 stop8h 51m

$622

Flights are sorted by cheapest round-trip flights first.

Deals found on 11/1

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 $183). Flying from Rutland to Caribbean in August is currently the most expensive (average of $337). 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 47m. JetBlue provides one of the quickest options available for as low as $464. 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 $183). Flying from Rutland to Caribbean in August is currently the most expensive (average of $337). 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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