What airlines fly to Caribbean Islands?

American Airlines, JetBlue and United Airlines are the top three most popular airlines that fly to Caribbean Islands from Rutland according to our data. American Airlines is the first choice among our users, with 44% of people opting to fly with this airline when traveling to Caribbean Islands. Keep in mind that there are 5 different airlines that fly to Caribbean Islands on a routine basis, so you have a few additional options to choose from.

When did momondo last update prices for flights from Rutland Airport to Caribbean Islands?

Prices for flights from Rutland Airport to Caribbean Islands refresh daily.

How old do you have to be to fly from Rutland Airport to Caribbean Islands?

The minimum age a child must be to fly alone is five but airlines that offer an unaccompanied minor (UNMR) service will have their own age restrictions, including rules around flight length, timings, and stopovers. We always recommend checking with the individual airline you are booking with to travel from Rutland Airport to Caribbean Islands.

What documentation or ID do you need to fly to Caribbean Islands?

The travel and health documents required for your trip to Caribbean Islands can vary based on your itinerary and personal situation. As a rule, consider having multiple documents such as a national ID card or driver’s license, and a passport valid for six-months after you plan to arrive at Caribbean Islands. We always recommend checking with your airline or a trusted third party such as IATA to get advice.

$715 Cheap Flights from Rutland to Caribbean Islands in 2026

Find the cheapest flights from Rutland to Caribbean Islands

Round-trip

Cheap round-trip flights

Enter your travel dates to find the best prices.

7:15 am - 7:27 pmRUT Rutland-SJU San Juan Luis Munoz Marin Intl

11h 12m1 stop Boston Logan Intl

6:01 am - 3:11 pmSJU San Juan Luis Munoz Marin Intl-RUT Rutland

10h 10m1 stop Boston Logan Intl

$715Multiple Airlines

Thu, Dec 10 - Sun, Dec 13

7:15 am - 1:34 amRUT Rutland-SJU San Juan Luis Munoz Marin Intl

17h 19m2 stops Boston Logan Intl Orlando

6:01 am - 3:11 pmSJU San Juan Luis Munoz Marin Intl-RUT Rutland

10h 10m1 stop Boston Logan Intl

$735Multiple Airlines

Thu, Dec 10 - Sun, Dec 13

7:15 am - 9:42 pmRUT Rutland-SJU San Juan Luis Munoz Marin Intl

13h 27m2 stops Boston Logan Intl Orlando

6:01 am - 3:11 pmSJU San Juan Luis Munoz Marin Intl-RUT Rutland

10h 10m1 stop Boston Logan Intl

$770Multiple Airlines

Thu, Dec 10 - Sun, Dec 13

11:33 am - 1:34 amRUT Rutland-SJU San Juan Luis Munoz Marin Intl

13h 01m2 stops Boston Logan Intl Orlando

8:10 am - 6:31 pmSJU San Juan Luis Munoz Marin Intl-RUT Rutland

11h 21m2 stops New York John F Kennedy Intl Boston Logan Intl

$887Multiple Airlines

Thu, Dec 10 - Sun, Dec 13

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Use the filters below to find and compare flights from Rutland to Caribbean Islands that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

Quickest round-trip

RutlandSan Juan

RUT Rutland - SJU San Juan Luis Munoz Marin Intl

RUTSJU

Rutland

Thu 12/10

7:15 am-7:27 pm

1 stop11h 12m

San Juan Luis Munoz Marin Intl

Sun 12/13

6:01 am-3:11 pm

1 stop10h 10m

$715

RutlandSan Juan

RUT Rutland - SJU San Juan Luis Munoz Marin Intl

RUTSJU

Rutland

Thu 12/10

7:15 am-1:34 am

2 stops17h 19m

San Juan Luis Munoz Marin Intl

Sun 12/13

6:01 am-3:11 pm

1 stop10h 10m

$735

RutlandSan Juan

RUT Rutland - SJU San Juan Luis Munoz Marin Intl

RUTSJU

Rutland

Thu 12/10

7:15 am-9:42 pm

2 stops13h 27m

San Juan Luis Munoz Marin Intl

Sun 12/13

6:01 am-3:11 pm

1 stop10h 10m

$770

RutlandSan Juan

RUT Rutland - SJU San Juan Luis Munoz Marin Intl

RUTSJU

Rutland

Thu 12/10

11:33 am-1:34 am

2 stops13h 01m

San Juan Luis Munoz Marin Intl

Sun 12/13

8:10 am-6:31 pm

2 stops11h 21m

$887

Flights are sorted by cheapest round-trip flights first.

Sorted by cheapest first

How to get the cheapest flight ticket from Rutland to Caribbean Islands

Look no further. We've gone through all the searches for this route on momondo so you have the important information and insights to find the cheapest flight ticket for your trip

Prices

Airlines

Can stopping save me money on Rutland to Caribbean Islands flights?

No. A direct flight is the cheapest option for a flight between Rutland to Caribbean Islands.

Cheap Rutland to Caribbean Islands flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Rutland to Caribbean Islands

Best Price Found	$715
Fastest flight time	16h 43m
Direct flights	None

The best flight deal from Rutland to Caribbean Islands found on momondo in the last 72 hours is $715

The fastest flight from Rutland to Caribbean Islands takes 16h 43m

There are no direct flights from Rutland to Caribbean Islands. There are no popular flight routes from Rutland to Caribbean Islands.

Search flight deals

Frequently asked questions about flying from Rutland to Caribbean Islands

When did momondo last update prices for flights from Rutland Airport to Caribbean Islands?
Prices for flights from Rutland Airport to Caribbean Islands refresh daily.
How old do you have to be to fly from Rutland Airport to Caribbean Islands?
The minimum age a child must be to fly alone is five but airlines that offer an unaccompanied minor (UNMR) service will have their own age restrictions, including rules around flight length, timings, and stopovers. We always recommend checking with the individual airline you are booking with to travel from Rutland Airport to Caribbean Islands.
What documentation or ID do you need to fly to Caribbean Islands?
The travel and health documents required for your trip to Caribbean Islands can vary based on your itinerary and personal situation. As a rule, consider having multiple documents such as a national ID card or driver’s license, and a passport valid for six-months after you plan to arrive at Caribbean Islands. We always recommend checking with your airline or a trusted third party such as IATA to get advice.
What is the most popular plane model from Rutland to Caribbean Islands?
Based on momondo bookings for this flight route, the most popular plane model on flight routes from Rutland to Caribbean Islands is Tecnam P2012 Traveler (68.75% of total bookings). The next most popular plane models are Cessna light aircraft (12.50%), Boeing 737 MAX 8 (6.25%), and Canadair (Bombardier) Regional Jet 900 (6.25%).

Why use momondo?

Why should I use momondo to find a flight deal from Rutland to Caribbean Islands?

momondo collates all your flight options in one place and lets you filter them to find the perfect flight from Rutland to Caribbean Islands. momondo saves you time and could save you money on your trip.

Can I find flights from Rutland to Caribbean Islands with flexible booking policies on momondo?

Yes. momondo enables you to select and highlight flights to Caribbean Islands from Rutland with this policy.

How can momondo help me find flights from Rutland to Caribbean Islands?

Once you have performed a search in the form on the page, momondo provides useful filters and insights. We can show you the cheapest days and times to fly as well as help filter your options to help you make an informed choice when booking flights to Caribbean Islands from Rutland.

I’m not ready to book a flight from Rutland to Caribbean Islands right now. Can momondo alert me if prices change?

Of course. momondo tracks the price of Rutland to Caribbean Islands flights. All you need is a valid email address and we will do the rest; it is that quick and easy.