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Caribbean Islands

$458+ Cheap flights from Rutland (RUT) to Caribbean Islands

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 11/10. Fares are subject to change and may not be available on all flights or dates of travel.
RUT — SJU
Nov 26 — Dec 31
Wed 11/26
Wed 12/3
1 adult, Economy
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Cheap flight deals from Rutland to Caribbean Islands

Keep the following information in mind while searching for Rutland to Caribbean Islands flight deals. Data was last updated October 27, 2025.

Round-trip from

$458
(Priceline)
From Rutland to Caribbean Islands
Search Deals

Find flight deals from Rutland to Caribbean Islands

Cheapest flights from Rutland to Caribbean Islands
Explore the most affordable flight options available from Rutland to Caribbean Islands. Find the lowest fares from popular airlines and budget airlines, with prices last updated on October 27, 2025.

This Priceline deal was found by Cheapflights users on 10/26. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/107:20 amRUT - SJU
1 stop10h 37mJetBlue
Fri 11/142:33 pmSJU - RUT
1 stop25h 18mJetBlue
Deal found 10/26$458

Cheapflights Fare Finder

 
Customize your flight search to find flights from Rutland to Caribbean Islands 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 27, 2025.
Use the filters below to find and compare flights from Rutland to Caribbean Islands that are best for you.

Fly from

Rutland

Fly to

Caribbean Islands

Route

Depart

Return

Price

RutlandSan Juan

RUT - SJU

RUTSJU

Rutland

Mon 11/10

7:20 am-6:57 pm

1 stop10h 37m

San Juan Luis Munoz Marin Intl

Fri 11/14

2:33 pm-2:51 pm

1 stop25h 18m

$458

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 10/26

Best time to book a flight from Rutland to Caribbean Islands

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

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

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

    For a flight from Rutland to Caribbean Islands, you will be flying from Rutland. Rutland (RUT) is just 5.9 mi from the center of the city.

  • How long is the flight from Rutland to Caribbean Islands?

    Departing from Rutland to Caribbean Islands will take you 10h 37m. The distance between Rutland and Caribbean Islands is about 1779 mi.

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

    Most travelers choose Rutland - Santiago de los Caballeros, Rutland - San Juan Luis Munoz Marin Intl or Rutland - Christiansted Henry Rohlsen when deciding on the best route from Rutland to Caribbean Islands.

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

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

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

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

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

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

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

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