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

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

What airlines fly to Caribbean?

JetBlue, Delta and American 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.

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 December 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.

$101 Cheap Flights from Portland to Caribbean in 2025/26

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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.

12:45 pm - 11:10 pmPWM-SJU

9h 25m1 stop

6:10 am - 2:55 pmSJU-PWM

9h 45m1 stop

$231Southwest

Find Deal

Tue, Jan 20 - Tue, Feb 3

4:35 pm - 1:15 amPWM-SJU

7h 40m1 stop

6:05 am - 3:40 pmSJU-PWM

10h 35m1 stop

$238JetBlue

Find Deal

Wed, Feb 25 - Wed, Mar 4

6:00 am - 9:00 pmPWM-SJU

14h 00m2 stops

8:10 am - 2:23 pmSJU-PWM

7h 13m1 stop

$262United Airlines

Find Deal

Sun, Feb 22 - Wed, Mar 4

6:00 am - 1:47 pmPWM-SJU

7h 47m1 stop

1:50 pm - 11:36 pmSJU-PWM

9h 46m1 stop

$274JetBlue

Find Deal

Sat, May 9 - Wed, May 13

2:35 pm - 11:57 pmPWM-SJU

8h 22m1 stop

6:05 pm - 12:20 amSJU-PWM

7h 15m1 stop

$275Delta

Find Deal

Sun, Jan 18 - Thu, Jan 29

4:35 pm - 12:15 amPWM-SJU

7h 40m1 stop

5:01 am - 1:58 pmSJU-PWM

8h 57m1 stop

$283JetBlue

Find Deal

Wed, Mar 11 - Sat, Mar 21

11:12 am - 10:22 pmPWM-SJU

10h 10m2 stops

8:10 am - 2:31 pmSJU-PWM

7h 21m1 stop

$285United Airlines

Find Deal

Tue, Jan 27 - Thu, Feb 5

6:00 am - 4:30 pmPWM-SJU

9h 30m1 stop

7:00 am - 10:54 pmSJU-PWM

16h 54m1 stop

$291American Airlines

Find Deal

Wed, Jan 21 - Thu, Jan 29

2:35 pm - 11:57 pmPWM-SJU

8h 22m1 stop

7:00 am - 1:45 pmSJU-PWM

7h 45m1 stop

$301Delta

Find Deal

Sun, Jan 18 - Mon, Feb 2

5:07 pm - 1:39 pmPWM-AUA

20h 32m2 stops

2:39 pm - 12:19 pmAUA-PWM

21h 40m2 stops

$304American Airlines

Find Deal

Wed, Mar 18 - Tue, Mar 24

JetBlue flights from Portland, Maine to Caribbean

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

JetBlue

Feb 25

PWM4:35 pmPortland

7h 40m

1 stop

SJU1:15 amSan Juan Luis Munoz Marin Intl

Mar 4

SJU6:05 amSan Juan Luis Munoz Marin Intl

10h 35m

1 stop

PWM3:40 pmPortland

$238

Find similar

JetBlue

May 9

PWM6:00 amPortland

7h 47m

1 stop

SJU1:47 pmSan Juan Luis Munoz Marin Intl

May 13

SJU1:50 pmSan Juan Luis Munoz Marin Intl

9h 46m

1 stop

PWM11:36 pmPortland

$274

Find similar

JetBlue

Mar 11

PWM4:35 pmPortland

7h 40m

1 stop

SJU12:15 amSan Juan Luis Munoz Marin Intl

Mar 21

SJU5:01 amSan Juan Luis Munoz Marin Intl

8h 57m

1 stop

PWM1:58 pmPortland

$283

Find similar

United Airlines flights from Portland, Maine to Caribbean

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

United Airlines

Feb 22

PWM6:00 amPortland

14h 00m

2 stops

SJU9:00 pmSan Juan Luis Munoz Marin Intl

Mar 4

SJU8:10 amSan Juan Luis Munoz Marin Intl

7h 13m

1 stop

PWM2:23 pmPortland

$262

Find similar

United Airlines

Dec 6

PWM2:13 pmPortland

7h 09m

1 stop

SJU10:22 pmSan Juan Luis Munoz Marin Intl

Dec 9

SJU8:10 amSan Juan Luis Munoz Marin Intl

11h 44m

2 stops

PWM6:54 pmPortland

$269

Find similar

United Airlines

Jan 27

PWM6:00 amPortland

7h 40m

1 stop

SJU2:40 pmSan Juan Luis Munoz Marin Intl

Feb 10

SJU2:05 amSan Juan Luis Munoz Marin Intl

7h 56m

1 stop

PWM9:01 amPortland

$285

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

Tue 1/20

12:45 pm-11:10 pm

1 stop9h 25m

San Juan Luis Munoz Marin Intl

Tue 2/3

6:10 am-2:55 pm

1 stop9h 45m

$231

PortlandSan Juan

PWM - SJU

PWMSJU

Portland

Wed 2/25

4:35 pm-1:15 am

1 stop7h 40m

San Juan Luis Munoz Marin Intl

Wed 3/4

6:05 am-3:40 pm

1 stop10h 35m

$238

PortlandSan Juan

PWM - SJU

PWMSJU

Portland

Sun 2/22

6:00 am-9:00 pm

2 stops14h 00m

San Juan Luis Munoz Marin Intl

Wed 3/4

8:10 am-2:23 pm

1 stop7h 13m

$262

PortlandSan Juan

PWM - SJU

PWMSJU

Portland

Sat 5/9

6:00 am-1:47 pm

1 stop7h 47m

San Juan Luis Munoz Marin Intl

Wed 5/13

1:50 pm-11:36 pm

1 stop9h 46m

$274

PortlandSan Juan

PWM - SJU

PWMSJU

Portland

Sun 1/18

2:35 pm-11:57 pm

1 stop8h 22m

San Juan Luis Munoz Marin Intl

Thu 1/29

6:05 pm-12:20 am

1 stop7h 15m

$275

PortlandSan Juan

PWM - SJU

PWMSJU

Portland

Wed 3/11

4:35 pm-12:15 am

1 stop7h 40m

San Juan Luis Munoz Marin Intl

Sat 3/21

5:01 am-1:58 pm

1 stop8h 57m

$283

PortlandSan Juan

PWM - SJU

PWMSJU

Portland

Tue 1/27

11:12 am-10:22 pm

2 stops10h 10m

San Juan Luis Munoz Marin Intl

Thu 2/5

8:10 am-2:31 pm

1 stop7h 21m

$285

PortlandSan Juan

PWM - SJU

PWMSJU

Portland

Wed 1/21

6:00 am-4:30 pm

1 stop9h 30m

San Juan Luis Munoz Marin Intl

Thu 1/29

7:00 am-10:54 pm

1 stop16h 54m

$291

PortlandSan Juan

PWM - SJU

PWMSJU

Portland

Sun 1/18

2:35 pm-11:57 pm

1 stop8h 22m

San Juan Luis Munoz Marin Intl

Mon 2/2

7:00 am-1:45 pm

1 stop7h 45m

$301

PortlandOranjestad

PWM - AUA

PWMAUA

Portland

Wed 3/18

5:07 pm-1:39 pm

2 stops20h 32m

Oranjestad Reina Beatrix

Tue 3/24

2:39 pm-12:19 pm

2 stops21h 40m

$304

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, November 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 $322. If you don’t want to visit Caribbean in November, then you should wait until October to fly from Portland, Maine, when ticket prices are also cheap, with an average price of $343.

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 $463 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 $275 on momondo.

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

You could potentially save up to 10% 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 53m
Direct flights	None

The fastest flight from Portland, Maine to Caribbean takes 5h 53m

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 6 operators available for flights from Portland Airport to Caribbean as of December 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 3,094 reviews	Search Frontier flights
JetBlue	PriceFrom $237	Free Cancellation	Rating 7.2 2,904 reviews	Search JetBlue flights
United Airlines	PriceFrom $249	Free Cancellation	Rating 7.4 9,063 reviews	Search United Airlines flights
Delta	PriceFrom $274	Free Cancellation	Rating 7.9 8,011 reviews	Search Delta flights
American Airlines	PriceFrom $301	Free Cancellation	Rating 7.2 11,043 reviews	Search American Airlines flights
Southwest	PriceFrom $315	Free Cancellation	Rating 8.0 4,253 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.