HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
Caribbean

$463+ 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 5/7. Fares are subject to change and may not be available on all flights or dates of travel.
RUT — SJU
Apr 29 — May 61
Tue 4/29
Tue 5/6
1 adult, Economy
We work with more than 300 partners to bring you better travel deals

Find cheap flights from Rutland to Caribbean with Cheapflights

1. Tell us where you want to go

Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”

2. Select your favorite providers

We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.

3. Compare prices and book

Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.

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 April 24, 2025.

Round-trip from

$463
(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 April 24, 2025.

This JetBlue deal was found by Cheapflights users on 4/23. 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 5/712:00 pmRUT - SJU
1 stop6h 05mJetBlue
Wed 5/146:00 amSJU - RUT
1 stop8h 52mJetBlue
Deal found 4/23$463

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 April 24, 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

Wed 5/7

12:00 pm-6:05 pm

1 stop6h 05m

San Juan Luis Munoz Marin Intl

Wed 5/14

6:00 am-2:52 pm

1 stop8h 52m

$463

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/23

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, September is the cheapest month in which you can book a flight from Rutland to Caribbean (average of $254). Flying from Rutland to Caribbean in December is currently the most expensive (average of $336). 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.

Rainfall in Caribbean by month

Plan your trip to Caribbean by taking into account the average rainfall totals by month.

In terms of precipitation, rainfall in Caribbean ranges from 2.2 - 6.1 inches per month. November is typically the wettest month, when rainfall can reach 6.1 in. February is typically the driest time to visit Caribbean when rainfall is around 2.2 in.

Temperature in Caribbean by month

Plan your trip to Caribbean by taking into account the average temperature totals by month.

If weather is an important factor for your trip to Caribbean, use this chart to help with planning. For those seeking warmer temperatures, June is the ideal time of year to visit, when temperatures reach an average of 82.4 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 77.0 F).

Reviews of airlines servicing Caribbean

Get insights into the airlines that provide service to Caribbean. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Caribbean. Reviews last updated April 24, 2025.
JetBlue
7.3
Good
2,924 reviews

Overall

7.3

Boarding

7.5

Comfort

7.6

Crew

8.0

Entertainment

7.3

Food

6.7

Reviews

1 / 20
8.0
Excellent

Anonymous,Feb 2025

JFK - CHS

Boarding took a very long time, in fact we were delayed by at least 30mins. There wasn’t many options for snacks and there was only water. The pilot did an excellent job
JetBlue
7.3
Good
2,924 reviews
JetBlue
7.3
Good
2,924 reviews

Overall

7.3

Boarding

7.5

Comfort

7.6

Crew

8.0

Entertainment

7.3

Food

6.7

Reviews

1 / 20
8.0
Excellent

Anonymous,Feb 2025

JFK - CHS

Boarding took a very long time, in fact we were delayed by at least 30mins. There wasn’t many options for snacks and there was only water. The pilot did an excellent job

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.

  • 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, September is the cheapest month in which you can book a flight from Rutland to Caribbean (average of $254). Flying from Rutland to Caribbean in December is currently the most expensive (average of $336). 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

Browse thousands of different options on Cheapflights for your next trip

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

Alternative routes for Rutland to Caribbean

See prices for flight routes from nearby airports that may be better suited for you.
Hartford to Orlando flights
Hartford to Luis Munoz Marin Intl flights
Hartford to O'Hare Intl flights
Hartford to Denver flights
Albany to Orlando flights
Hartford to Tampa flights
Hartford to Las Vegas flights
Hartford to Fort Lauderdale flights
Hartford to Miami flights
Hartford to Dallas/Fort Worth flights
Hartford to Los Angeles flights
Hartford to Atlanta flights
Hartford to West Palm Beach flights
Hartford to Dulles Intl flights
Hartford to Charlotte flights
Hartford to Seattle flights
Hartford to Reagan-National flights
Hartford to Fort Myers flights
Hartford to Hobby flights
Hartford to Nashville flights
Albany to Las Vegas flights
Hartford to San Francisco flights
Hartford to Dublin flights
Hartford to Myrtle Beach flights
Hartford to Cancún flights
Burlington to Denver flights
Albany to O'Hare Intl flights
Hartford to Raleigh flights
Hartford to Detroit flights
Hartford to Baltimore flights
Hartford to Austin flights
Albany to Dulles Intl flights
Albany to Seattle flights
Albany to Denver flights
Hartford to New Orleans flights
Hartford to San Diego flights
Albany to Atlanta flights
Albany to Tampa flights
Hartford to Minneapolis flights
Burlington to O'Hare Intl flights
Albany to Fort Lauderdale flights
Hartford to Portland flights
Hartford to Midway flights
Hartford to George Bush Intcntl flights
Burlington to John F Kennedy Intl flights
Albany to Charlotte flights
Hartford to Charleston flights
Burlington to Newark flights
Burlington to Las Vegas flights
Hartford to Sky Harbor Intl flights

100% Free

Cheapflights is completely free to use, so you can start saving the moment you arrive.

Book with Flexibility

Our users can plan ahead with confidence and find flights with no change fees

Travel Smart

Millions of people come to us for their flight needs every year. We help make travel planning easy by providing useful insights and data-driven graphs that can inform your decisions.