What airlines fly to Caribbean?

JetBlue, Delta and Spirit Airlines are the top three most popular airlines that fly to Caribbean from Portland, Maine according to our data. JetBlue is the first choice among our users, with 64% of people opting to fly with this airline when traveling to Caribbean. Keep in mind that there are 12 different airlines that fly to Caribbean on a routine basis, so you have a few additional options to choose from.

What is the cheapest airline that flies from Portland to Caribbean?

American Airlines, JetBlue, and United Airlines are the most popular carriers operating from Portland to Caribbean

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

Prices for flights from Portland Airport to Caribbean were last updated today.

How many operators does momondo search for flights from Portland Airport to Caribbean?

There are 5 operators available for flights from Portland Airport to Caribbean as of March 2026.

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

Although the minimum age for a child to fly alone is five, airlines that offer an unaccompanied minor (UMNR) service may have their own age limits, which could be impacted by factors such as flight length, timing, and layovers. It is recommended that you verify with the airline you are booking with for travel from Portland Airport to Caribbean.

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

The travel and health documents you'll need for your trip to Caribbean may differ based on your itinerary and personal situation. Typically, you should have several documents on hand, such as a national ID card or driver's license and a passport that is valid for six months after your intended arrival at Caribbean. It is always advisable to seek advice from your airline or a trusted third party, such as IATA.

$129 Cheap Flights from Portland to Caribbean in 2026

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Find the cheapest flights from Portland, Maine to Caribbean

Round-trip

One-way

Last minute

Cheap round-trip flights

Enter your travel dates to find the best prices.

6:00 am - 12:35 pm

PWM

STT

6h 35m

1 stop

11:27 am - 11:27 pm

STT

PWM

12h 00m

1 stop

$273American Airlines

Mon, May 4 - Mon, May 11

6:00 am - 12:35 pm

PWM

STT

6h 35m

1 stop

2:05 pm - 10:23 am

STT

PWM

20h 18m

2 stops

$280American Airlines

Thu, Apr 30 - Fri, May 8

2:51 pm - 11:59 pm

PWM

SJU

9h 08m

1 stop

5:42 pm - 12:46 am

SJU

PWM

7h 04m

1 stop

$282Delta

Sat, May 2 - Wed, May 6

3:22 pm - 11:50 pm

PWM

SJU

8h 28m

1 stop

1:00 am - 8:59 am

SJU

PWM

7h 59m

1 stop

$322United Airlines

Tue, Apr 14 - Fri, Apr 17

6:00 am - 3:17 pm

PWM

STT

9h 17m

1 stop

4:38 pm - 12:43 am

STT

PWM

8h 05m

1 stop

$336Delta

Mon, May 18 - Fri, May 22

11:09 am - 9:24 pm

PWM

SJU

10h 15m

2 stops

7:20 am - 9:40 pm

SJU

PWM

14h 20m

2 stops

$339United Airlines

Tue, Apr 14 - Sat, Apr 18

7:30 am - 2:10 pm

PWM

PLS

6h 40m

1 stop

2:25 pm - 11:02 pm

PLS

PWM

8h 37m

1 stop

$347JetBlue

Tue, Apr 21 - Wed, Apr 29

7:30 am - 2:10 pm

PWM

PLS

6h 40m

1 stop

2:25 pm - 11:02 pm

PLS

PWM

8h 37m

1 stop

$359JetBlue

Mon, Apr 27 - Wed, Apr 29

6:18 pm - 11:29 pm

PWM

SJU

29h 11m

1 stop

3:03 am - 4:16 pm

SJU

PWM

13h 13m

2 stops

$368Multiple Airlines

Sat, May 2 - Tue, May 12

11:29 am - 11:43 pm

PWM

SJU

12h 14m

1 stop

3:03 am - 4:16 pm

SJU

PWM

13h 13m

2 stops

$373Multiple Airlines

Mon, May 4 - Tue, May 12

American Airlines flights from Portland, Maine to Caribbean

Our best American Airlines deals on Portland, Maine to Caribbean flight tickets

American Airlines

May 4

PWM7:23 pmPortland

16h 12m

2 stops

STT11:35 amSaint Thomas Island Cyril E King

May 11

STT2:05 pmSaint Thomas Island Cyril E King

19h 49m

2 stops

PWM9:54 amPortland

$273

American Airlines

Apr 30

PWM6:00 amPortland

6h 35m

1 stop

STT12:35 pmSaint Thomas Island Cyril E King

May 8

STT2:05 pmSaint Thomas Island Cyril E King

20h 18m

2 stops

PWM10:23 amPortland

$280

American Airlines

May 27

PWM2:24 pmPortland

8h 21m

1 stop

SJU10:45 pmSan Juan Luis Munoz Marin Intl

Jun 3

SJU6:20 amSan Juan Luis Munoz Marin Intl

15h 26m

1 stop

PWM9:46 pmPortland

$302

JetBlue flights from Portland, Maine to Caribbean

Our best JetBlue deals on Portland, Maine to Caribbean flight tickets

JetBlue

Apr 27

PWM7:30 amPortland

6h 40m

1 stop

PLS2:10 pmProvidenciales

Apr 29

PLS2:25 pmProvidenciales

8h 37m

1 stop

PWM11:02 pmPortland

$359

JetBlue

May 5

PWM7:30 amPortland

7h 19m

1 stop

PUJ2:49 pmPunta Cana

May 8

PUJ12:44 pmPunta Cana

10h 19m

1 stop

PWM11:03 pmPortland

$361

JetBlue

Jun 2

PWM6:00 amPortland

7h 54m

1 stop

SXM1:54 pmSimpson Bay Princess Juliana

Jun 6

SXM3:04 pmSimpson Bay Princess Juliana

8h 54m

1 stop

PWM11:58 pmPortland

$371

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

PortlandSaint Thomas Island

PWM - STT

PWMSTT

Portland

Mon 5/4

6:00 am-12:35 pm

1 stop6h 35m

Saint Thomas Island Cyril E King

Mon 5/11

11:27 am-11:27 pm

1 stop12h 00m

$273

PortlandSaint Thomas Island

PWM - STT

PWMSTT

Portland

Thu 4/30

6:00 am-12:35 pm

1 stop6h 35m

Saint Thomas Island Cyril E King

Fri 5/8

2:05 pm-10:23 am

2 stops20h 18m

$280

PortlandSan Juan

PWM - SJU

PWMSJU

Portland

Sat 5/2

2:51 pm-11:59 pm

1 stop9h 08m

San Juan Luis Munoz Marin Intl

Wed 5/6

5:42 pm-12:46 am

1 stop7h 04m

$282

PortlandSan Juan

PWM - SJU

PWMSJU

Portland

Tue 4/14

3:22 pm-11:50 pm

1 stop8h 28m

San Juan Luis Munoz Marin Intl

Fri 4/17

1:00 am-8:59 am

1 stop7h 59m

$322

PortlandSaint Thomas Island

PWM - STT

PWMSTT

Portland

Mon 5/18

6:00 am-3:17 pm

1 stop9h 17m

Saint Thomas Island Cyril E King

Fri 5/22

4:38 pm-12:43 am

1 stop8h 05m

$336

PortlandSan Juan

PWM - SJU

PWMSJU

Portland

Tue 4/14

11:09 am-9:24 pm

2 stops10h 15m

San Juan Luis Munoz Marin Intl

Sat 4/18

7:20 am-9:40 pm

2 stops14h 20m

$339

Quickest round-trip

PortlandProvidenciales

PWM - PLS

PWMPLS

Portland

Tue 4/21

7:30 am-2:10 pm

1 stop6h 40m

Providenciales

Wed 4/29

2:25 pm-11:02 pm

1 stop8h 37m

$347

PortlandProvidenciales

PWM - PLS

PWMPLS

Portland

Mon 4/27

7:30 am-2:10 pm

1 stop6h 40m

Providenciales

Wed 4/29

2:25 pm-11:02 pm

1 stop8h 37m

$359

PortlandSan Juan

PWM - SJU

PWMSJU

Portland

Sat 5/2

6:18 pm-11:29 pm

1 stop29h 11m

San Juan Luis Munoz Marin Intl

Tue 5/12

3:03 am-4:16 pm

2 stops13h 13m

$368

PortlandSan Juan

PWM - SJU

PWMSJU

Portland

Mon 5/4

11:29 am-11:43 pm

1 stop12h 14m

San Juan Luis Munoz Marin Intl

Tue 5/12

3:03 am-4:16 pm

2 stops13h 13m

$373

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first

How to get the cheapest flight ticket from Portland, Maine to Caribbean

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

What is the cheapest month to fly to Caribbean?

In general, October is the cheapest month to fly from Portland, Maine to Caribbean. Due to it being the ‘off-season’ during this time, you can expect flight prices to be around $265. If you don’t want to visit Caribbean in October, then you should wait until May to fly from Portland, Maine, when ticket prices are also cheap, with an average price of $302.

How far in advance should I book a flight to Caribbean?

You are more likely to see cheaper flights to Caribbean from Portland, Maine when booking weeks ahead of your departure date. In general, you can expect to find flights to Caribbean for around $442 when searching weeks out. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Caribbean from Portland, Maine for as low as $234 on momondo.

Can stopping save me money on Portland, Maine to Caribbean flights?

You could potentially save up to 13% on your flight if you consider stops on a Portland, Maine to Caribbean flight.

Cheap Portland, Maine to Caribbean flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Portland, Maine to Caribbean

Fastest flight time	5h 31m
Direct flights	None

The fastest flight from Portland, Maine to Caribbean takes 5h 31m

There are no direct flights from Portland, Maine to Caribbean. There are no popular flight routes from Portland, Maine to Caribbean.

Search flight deals

When did momondo last update prices for flights from Portland Airport to Caribbean?
Prices for flights from Portland Airport to Caribbean were last updated today.
How many operators does momondo search for flights from Portland Airport to Caribbean?
There are 5 operators available for flights from Portland Airport to Caribbean as of March 2026.
How old do you have to be to fly from Portland Airport to Caribbean?
Although the minimum age for a child to fly alone is five, airlines that offer an unaccompanied minor (UMNR) service may have their own age limits, which could be impacted by factors such as flight length, timing, and layovers. It is recommended that you verify with the airline you are booking with for travel from Portland Airport to Caribbean.
What documentation or ID do you need to fly to Caribbean?
The travel and health documents you'll need for your trip to Caribbean may differ based on your itinerary and personal situation. Typically, you should have several documents on hand, such as a national ID card or driver's license and a passport that is valid for six months after your intended arrival at Caribbean. It is always advisable to seek advice from your airline or a trusted third party, such as IATA.

Best airlines flying from Portland, Maine to Caribbean

Compare and see reviews for airlines that fly from Portland, Maine to Caribbean with momondo

Airline	Rating	Free Cancellation	Price
Delta	PriceFrom $137	Free Cancellation	Rating 7.9 8,364 reviews	Search Delta flights
JetBlue	PriceFrom $156	Free Cancellation	Rating 7.2 2,906 reviews	Search JetBlue flights
United Airlines	PriceFrom $235	Free Cancellation	Rating 7.4 9,525 reviews	Search United Airlines flights
American Airlines	PriceFrom $256	Free Cancellation	Rating 7.1 11,543 reviews	Search American Airlines flights
Southwest	PriceFrom $315	Free Cancellation	Rating 8.0 4,332 reviews	Search Southwest flights

Why use momondo?

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

momondo compares prices from hundreds of airlines and agents so you can find and book the best deal on flights from Portland to Caribbean. Millions of users trust and use momondo every year so you are in good hands.

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

All flight searches from Portland to Caribbean on momondo can be filtered to show those which offer flexible booking policies.

How can momondo help me find flights from Portland to Caribbean?

Once all potential Portland to Caribbean flight options are in front of you, momondo lets you sort and filter flights based on preferences such as airline, price and flight times amongst many other options.

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

Yes. momondo can track prices for Portland to Caribbean flights and alert you when they change. Perform a search to set up the price alert. All that is required is a valid email address.