What airlines fly to Caribbean Islands?

American Airlines, JetBlue and Southwest 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 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.

$525 Cheap Flights from Rutland to Caribbean Islands in 2026

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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 - 10:12 pm

RUT

SJU

6h 41m

1 stop

5:01 am - 3:07 pm

SJU

RUT

10h 06m

1 stop

$525JetBlue

Sun, Apr 26 - Thu, Apr 30

3:31 pm - 10:12 pm

RUT

SJU

6h 41m

1 stop

5:01 am - 3:07 pm

SJU

RUT

10h 06m

1 stop

$571JetBlue

Sun, Apr 26 - Thu, Apr 30

11:33 am - 9:32 pm

RUT

SJU

9h 59m

1 stop

8:30 am - 3:11 pm

SJU

RUT

6h 41m

1 stop

$603JetBlue

Tue, Jul 21 - Wed, Jul 29

3:35 pm - 1:37 am

RUT

SJU

10h 02m

1 stop

8:30 am - 3:11 pm

SJU

RUT

6h 41m

1 stop

$623JetBlue

Mon, Jul 20 - Wed, Jul 29

3:31 pm - 2:02 am

RUT

STI

10h 31m

1 stop

3:39 am - 3:07 pm

STI

RUT

11h 28m

1 stop

$629JetBlue

Wed, May 6 - Tue, May 19

7:15 am - 4:18 pm

RUT

SJU

9h 03m

1 stop

6:00 am - 3:11 pm

SJU

RUT

9h 11m

1 stop

$643JetBlue

Tue, Jul 21 - Wed, Jul 29

3:31 pm - 10:12 pm

RUT

SJU

6h 41m

1 stop

5:01 am - 3:07 pm

SJU

RUT

10h 06m

1 stop

$1,007JetBlue

Mon, Apr 20 - Fri, Apr 24

3:31 pm - 10:12 pm

RUT

SJU

6h 41m

1 stop

5:01 am - 3:07 pm

SJU

RUT

10h 06m

1 stop

$1,238JetBlue

Fri, Apr 17 - Tue, Apr 21

JetBlue flights from Rutland to Caribbean Islands

Our best JetBlue deals on Rutland to Caribbean Islands flight tickets

JetBlue

Apr 26

RUT3:31 pmRutland

6h 41m

1 stop

SJU10:12 pmSan Juan Luis Munoz Marin Intl

Apr 30

SJU5:01 amSan Juan Luis Munoz Marin Intl

10h 06m

1 stop

RUT3:07 pmRutland

$525

JetBlue

Apr 26

RUT3:31 pmRutland

6h 41m

1 stop

SJU10:12 pmSan Juan Luis Munoz Marin Intl

Apr 30

SJU5:01 amSan Juan Luis Munoz Marin Intl

10h 06m

1 stop

RUT3:07 pmRutland

$571

JetBlue

Jul 21

RUT11:33 amRutland

9h 59m

1 stop

SJU9:32 pmSan Juan Luis Munoz Marin Intl

Jul 29

SJU8:30 amSan Juan Luis Munoz Marin Intl

6h 41m

1 stop

RUT3:11 pmRutland

$603

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

RutlandSan Juan

RUT - SJU

RUTSJU

Rutland

Sun 4/26

3:31 pm-10:12 pm

1 stop6h 41m

San Juan Luis Munoz Marin Intl

Thu 4/30

5:01 am-3:07 pm

1 stop10h 06m

$525

RutlandSan Juan

RUT - SJU

RUTSJU

Rutland

Sun 4/26

3:31 pm-10:12 pm

1 stop6h 41m

San Juan Luis Munoz Marin Intl

Thu 4/30

5:01 am-3:07 pm

1 stop10h 06m

$571

Quickest round-trip

RutlandSan Juan

RUT - SJU

RUTSJU

Rutland

Tue 7/21

11:33 am-9:32 pm

1 stop9h 59m

San Juan Luis Munoz Marin Intl

Wed 7/29

8:30 am-3:11 pm

1 stop6h 41m

$603

RutlandSan Juan

RUT - SJU

RUTSJU

Rutland

Mon 7/20

3:35 pm-1:37 am

1 stop10h 02m

San Juan Luis Munoz Marin Intl

Wed 7/29

8:30 am-3:11 pm

1 stop6h 41m

$623

RutlandSantiago de los Caballeros

RUT - STI

RUTSTI

Rutland

Wed 5/6

3:31 pm-2:02 am

1 stop10h 31m

Santiago de los Caballeros

Tue 5/19

3:39 am-3:07 pm

1 stop11h 28m

$629

RutlandSan Juan

RUT - SJU

RUTSJU

Rutland

Tue 7/21

7:15 am-4:18 pm

1 stop9h 03m

San Juan Luis Munoz Marin Intl

Wed 7/29

6:00 am-3:11 pm

1 stop9h 11m

$643

RutlandSan Juan

RUT - SJU

RUTSJU

Rutland

Mon 4/20

3:31 pm-10:12 pm

1 stop6h 41m

San Juan Luis Munoz Marin Intl

Fri 4/24

5:01 am-3:07 pm

1 stop10h 06m

$1,007

RutlandSan Juan

RUT - SJU

RUTSJU

Rutland

Fri 4/17

3:31 pm-10:12 pm

1 stop6h 41m

San Juan Luis Munoz Marin Intl

Tue 4/21

5:01 am-3:07 pm

1 stop10h 06m

$1,238

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 41m
Direct flights	None

The fastest flight from Rutland to Caribbean Islands takes 6h 41m

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 (50.00% of total bookings). The next most popular plane models are Cessna light aircraft (10.00%), Airbus A320-100/200 (10.00%), and Boeing 737 MAX 8 (5.00%).

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.