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

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

What airlines fly to Caribbean?

JetBlue, Delta and Frontier 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 61% 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.

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 6 operators available for flights from Portland Airport to Caribbean as of August 2025.

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.

$108 Cheap Flights from Portland to Caribbean in 2025

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Find the cheapest flights from Portland, Maine to Caribbean

Round-trip

One-way

Last minute

Cheap round-trip flights

5:51 am - 11:40 pmPWM-SJU

16h 49m1 stop

5:01 pm - 10:29 pmSJU-PWM

6h 28m1 stop

$215American Airlines

Find Deal

Sat, Jan 24 - Sat, Feb 7

6:30 am - 5:10 pmPWM-SJU

9h 40m1 stop

3:30 pm - 9:59 pmSJU-PWM

7h 29m1 stop

$275Delta

Find Deal

Sun, Nov 16 - Wed, Nov 19

2:17 pm - 9:24 pmPWM-SJU

7h 07m1 stop

3:03 am - 1:22 pmSJU-PWM

10h 19m1 stop

$282JetBlue

Find Deal

Thu, Oct 2 - Sun, Oct 5

7:05 am - 11:37 pmPWM-SJU

16h 32m2 stops

7:00 pm - 11:54 amSJU-PWM

16h 54m2 stops

$300American Airlines

Find Deal

Thu, Oct 2 - Mon, Oct 6

11:50 am - 12:35 amPWM-SJU

11h 45m2 stops

4:40 pm - 10:15 pmSJU-PWM

6h 35m1 stop

$391Southwest

Find Deal

Fri, Nov 7 - Tue, Nov 11

5:30 am - 12:40 pmPWM-MBJ

7h 10m1 stop

8:00 am - 9:59 pmMBJ-PWM

13h 59m1 stop

$393Delta

Find Deal

Mon, Feb 9 - Fri, Feb 13

11:50 am - 12:35 amPWM-SJU

11h 45m2 stops

11:20 am - 10:15 pmSJU-PWM

11h 55m2 stops

$398Southwest

Find Deal

Fri, Nov 7 - Tue, Nov 11

6:00 am - 2:40 pmPWM-SJU

7h 40m1 stop

2:05 am - 2:12 pmSJU-PWM

13h 07m2 stops

$400United Airlines

Find Deal

Sun, Nov 16 - Tue, Nov 18

7:30 am - 2:05 pmPWM-NAS

6h 35m1 stop

3:10 pm - 10:01 pmNAS-PWM

6h 51m1 stop

$437JetBlue

Find Deal

Sun, Oct 19 - Wed, Oct 22

6:00 am - 2:40 pmPWM-SJU

7h 40m1 stop

2:05 am - 2:27 pmSJU-PWM

13h 22m2 stops

$451United Airlines

Find Deal

Sat, Jan 24 - Fri, Feb 6

Southwest flights from Portland, Maine to Caribbean

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

Southwest

Nov 7

PWM11:50 amPortland

11h 45m

2 stops

SJU12:35 amSan Juan Luis Munoz Marin Intl

Nov 11

SJU4:40 pmSan Juan Luis Munoz Marin Intl

6h 35m

1 stop

PWM10:15 pmPortland

$391

Find similar

Southwest

Nov 7

PWM11:50 amPortland

11h 45m

2 stops

SJU12:35 amSan Juan Luis Munoz Marin Intl

Nov 11

SJU11:20 amSan Juan Luis Munoz Marin Intl

11h 55m

2 stops

PWM10:15 pmPortland

$398

Find similar

Southwest

Nov 7

PWM5:25 pmPortland

7h 00m

1 stop

SJU1:25 amSan Juan Luis Munoz Marin Intl

Nov 11

SJU11:20 amSan Juan Luis Munoz Marin Intl

11h 55m

2 stops

PWM10:15 pmPortland

$421

Find similar

American Airlines flights from Portland, Maine to Caribbean

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

American Airlines

Jan 24

PWM5:51 amPortland

16h 49m

1 stop

SJU11:40 pmSan Juan Luis Munoz Marin Intl

Feb 7

SJU5:01 pmSan Juan Luis Munoz Marin Intl

6h 28m

1 stop

PWM10:29 pmPortland

$215

Find similar

American Airlines

Oct 2

PWM7:05 amPortland

16h 32m

2 stops

SJU11:37 pmSan Juan Luis Munoz Marin Intl

Oct 6

SJU7:00 pmSan Juan Luis Munoz Marin Intl

16h 54m

2 stops

PWM11:54 amPortland

$300

Find similar

American Airlines

Jan 24

PWM4:16 pmPortland

6h 24m

1 stop

SJU11:40 pmSan Juan Luis Munoz Marin Intl

Feb 7

SJU6:30 amSan Juan Luis Munoz Marin Intl

6h 35m

1 stop

PWM12:05 pmPortland

$310

Find similar

momondo Fare Finder

Use the filters below to find and compare flights from Portland, Maine to Caribbean that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

PortlandSan Juan

PWM - SJU

PWMSJU

Portland

Sat 1/24

5:51 am-11:40 pm

1 stop16h 49m

San Juan Luis Munoz Marin Intl

Sat 2/7

5:01 pm-10:29 pm

1 stop6h 28m

$215

PortlandSan Juan

PWM - SJU

PWMSJU

Portland

Sun 11/16

6:30 am-5:10 pm

1 stop9h 40m

San Juan Luis Munoz Marin Intl

Wed 11/19

3:30 pm-9:59 pm

1 stop7h 29m

$275

PortlandSan Juan

PWM - SJU

PWMSJU

Portland

Thu 10/2

2:17 pm-9:24 pm

1 stop7h 07m

San Juan Luis Munoz Marin Intl

Sun 10/5

3:03 am-1:22 pm

1 stop10h 19m

$282

PortlandSan Juan

PWM - SJU

PWMSJU

Portland

Thu 10/2

7:05 am-11:37 pm

2 stops16h 32m

San Juan Luis Munoz Marin Intl

Mon 10/6

7:00 pm-11:54 am

2 stops16h 54m

$300

PortlandSan Juan

PWM - SJU

PWMSJU

Portland

Fri 11/7

11:50 am-12:35 am

2 stops11h 45m

San Juan Luis Munoz Marin Intl

Tue 11/11

4:40 pm-10:15 pm

1 stop6h 35m

$391

PortlandMontego Bay

PWM - MBJ

PWMMBJ

Portland

Mon 2/9

5:30 am-12:40 pm

1 stop7h 10m

Montego Bay Sangster Intl

Fri 2/13

8:00 am-9:59 pm

1 stop13h 59m

$393

PortlandSan Juan

PWM - SJU

PWMSJU

Portland

Fri 11/7

11:50 am-12:35 am

2 stops11h 45m

San Juan Luis Munoz Marin Intl

Tue 11/11

11:20 am-10:15 pm

2 stops11h 55m

$398

PortlandSan Juan

PWM - SJU

PWMSJU

Portland

Sun 11/16

6:00 am-2:40 pm

1 stop7h 40m

San Juan Luis Munoz Marin Intl

Tue 11/18

2:05 am-2:12 pm

2 stops13h 07m

$400

PortlandNassau

PWM - NAS

PWMNAS

Portland

Sun 10/19

7:30 am-2:05 pm

1 stop6h 35m

Nassau Intl

Wed 10/22

3:10 pm-10:01 pm

1 stop6h 51m

$437

PortlandSan Juan

PWM - SJU

PWMSJU

Portland

Sat 1/24

6:00 am-2:40 pm

1 stop7h 40m

San Juan Luis Munoz Marin Intl

Fri 2/6

2:05 am-2:27 pm

2 stops13h 22m

$451

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, September 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 $275. If you don’t want to visit Caribbean in September, then you should wait until October to fly from Portland, Maine, when ticket prices are also cheap, with an average price of $364.

What is the cheapest day to depart on your flight to Caribbean?

The cheapest day to depart from Portland, Maine to Caribbean is on a Wednesday when prices can be found for as low as $334. If your travel schedule is flexible, try to avoid departing on a Sunday because tickets tend to average around $579. These prices are subject to change though, so be sure to set up a Price Alert for flights to Caribbean.

What is the cheapest time of day to depart on your flight to Caribbean?

In the evening is the cheapest time of day to fly from Portland, Maine to Caribbean when you can find flight prices for as low as $302. Flying to Caribbean in the evening is an ideal time because this is during off-peak travel hours. Flights in the morning are often more expensive with an average ticket price of $557.

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 $487 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 $359 on momondo.

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

You could potentially save up to 60% 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

Best Price Found	$108
Fastest flight time	5h 24m
Direct flights	None
Airports in Caribbean	10 airports

The best one-way flight to Caribbean from Portland, Maine in the past 72 hours is $108. The best round-trip flight deal from Portland, Maine to Caribbean found on momondo in the last 72 hours is $215.

The fastest flight from Portland, Maine to Caribbean takes 5h 24m

There are no direct flights from Portland, Maine to Caribbean. Popular non-direct routes for this connection are Portland Airport - George Town Owen Roberts Intl Airport, Portland Airport - San Juan Luis Munoz Marin Intl Airport and Portland Airport - Punta Cana Airport.

There are 10 airports near Caribbean: George Town Owen Roberts Intl (GCM), Nassau Intl (NAS), Saint Thomas Island Cyril E King (STT), Punta Cana (PUJ), Montego Bay Sangster Intl (MBJ), Castries Hewanorra (UVF), Providenciales (PLS), Simpson Bay Princess Juliana (SXM), Oranjestad Reina Beatrix (AUA), San Juan Luis Munoz Marin Intl (SJU)

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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 6 operators available for flights from Portland Airport to Caribbean as of August 2025.
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
Frontier	PriceFrom $145	Free Cancellation	Rating 5.8 3,212 reviews	Search Frontier flights
JetBlue	PriceFrom $214	Free Cancellation	Rating 7.2 2,915 reviews	Search JetBlue flights
Delta	PriceFrom $274	Free Cancellation	Rating 8.0 7,986 reviews	Search Delta flights
United Airlines	PriceFrom $285	Free Cancellation	Rating 7.4 8,925 reviews	Search United Airlines flights
American Airlines	PriceFrom $332	Free Cancellation	Rating 7.2 10,000 reviews	Search American Airlines flights
Southwest	PriceFrom $401	Free Cancellation	Rating 8.0 4,246 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.