What airlines fly to Caribbean Islands?

American Airlines, JetBlue and Delta 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 45% of people opting to fly with this airline when traveling to Caribbean Islands. Keep in mind that there are 6 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.

$388 Cheap Flights from Rutland to Caribbean Islands in 2025/26

1 adult

0 bags

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Find the cheapest flights from Rutland to Caribbean Islands

Round-trip

Cheap round-trip flights

Enter your travel dates to find the best prices.

3:31 pm - 11:48 pm

RUT

SJU

7h 17m1 stop

6:10 am - 3:07 pm

SJU

RUT

9h 57m1 stop

$388JetBlue

Mon, Jan 26 - Fri, Jan 30

7:15 am - 6:05 pm

RUT

SJU

9h 50m1 stop

6:10 am - 3:07 pm

SJU

RUT

9h 57m1 stop

$402JetBlue

Mon, Jan 26 - Fri, Jan 30

3:31 pm - 3:49 am

RUT

STI

12h 18m1 stop

8:30 am - 6:31 pm

STI

RUT

10h 01m1 stop

$628JetBlue

Sun, Mar 29 - Thu, Apr 2

3:31 pm - 3:49 am

RUT

STI

12h 18m1 stop

8:30 am - 6:31 pm

STI

RUT

10h 01m1 stop

$648JetBlue

Sun, Mar 29 - Thu, Apr 2

3:31 pm - 11:49 pm

RUT

SJU

7h 18m1 stop

5:15 am - 3:07 pm

SJU

RUT

9h 52m1 stop

$784JetBlue

Thu, Mar 5 - Mon, Mar 9

JetBlue flights from Rutland to Caribbean Islands

Our best JetBlue deals on Rutland to Caribbean Islands flight tickets

JetBlue

Jan 26

RUT3:31 pmRutland

7h 17m

1 stop

SJU11:48 pmSan Juan Luis Munoz Marin Intl

Jan 30

SJU6:10 amSan Juan Luis Munoz Marin Intl

9h 57m

1 stop

RUT3:07 pmRutland

$388

Find similar

JetBlue

Jan 26

RUT7:15 amRutland

9h 50m

1 stop

SJU6:05 pmSan Juan Luis Munoz Marin Intl

Jan 30

SJU6:10 amSan Juan Luis Munoz Marin Intl

9h 57m

1 stop

RUT3:07 pmRutland

$402

Find similar

JetBlue

Mar 29

RUT3:31 pmRutland

12h 18m

1 stop

STI3:49 amSantiago de los Caballeros

Apr 2

STI8:30 amSantiago de los Caballeros

10h 01m

1 stop

RUT6:31 pmRutland

$628

Find similar

momondo Fare Finder

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

RutlandSan Juan

RUT - SJU

RUTSJU

Rutland

Mon 1/26

3:31 pm-11:48 pm

1 stop7h 17m

San Juan Luis Munoz Marin Intl

Fri 1/30

6:10 am-3:07 pm

1 stop9h 57m

$388

RutlandSan Juan

RUT - SJU

RUTSJU

Rutland

Mon 1/26

7:15 am-6:05 pm

1 stop9h 50m

San Juan Luis Munoz Marin Intl

Fri 1/30

6:10 am-3:07 pm

1 stop9h 57m

$402

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

$628

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

$648

RutlandSan Juan

RUT - SJU

RUTSJU

Rutland

Thu 3/5

3:31 pm-11:49 pm

1 stop7h 18m

San Juan Luis Munoz Marin Intl

Mon 3/9

5:15 am-3:07 pm

1 stop9h 52m

$784

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

Fastest flight time	6h 14m
Direct flights	None

The fastest flight from Rutland to Caribbean Islands takes 6h 14m

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

Search flight deals

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 (26.67% of total bookings). The next most popular plane models are Airbus A320-100/200 (20.00%), Cessna light aircraft (13.33%), and Boeing 737 MAX 8 (6.67%).

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.