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 69% of people opting to fly with this airline when traveling to Caribbean. Keep in mind that there are 11 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, United Airlines, and JetBlue 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 September 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.

$135 Cheap Flights from Portland, Maine to Caribbean in 2026/27

Discover deals from 900+ travel sites with momondo.

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.

7:26 pm - 11:31 amPWM Portland-SJU San Juan Luis Munoz Marin Intl

16h 05m2 stops Philadelphia Miami

2:18 pm - 11:59 pmSJU San Juan Luis Munoz Marin Intl-PWM Portland

9h 41m2 stops Miami Washington, D.C. Reagan-National

$316American Airlines

Tue, Oct 20 - Mon, Oct 26

7:26 pm - 11:31 amPWM Portland-SJU San Juan Luis Munoz Marin Intl

16h 05m2 stops Philadelphia Miami

12:41 pm - 10:36 pmSJU San Juan Luis Munoz Marin Intl-PWM Portland

9h 55m1 stop Charlotte Douglas

$316American Airlines

Tue, Oct 20 - Mon, Oct 26

8:47 am - 10:22 pmPWM Portland-SJU San Juan Luis Munoz Marin Intl

12h 35m2 stops Chicago O'Hare Intl Washington, D.C. Dulles Intl

2:05 am - 9:00 amSJU San Juan Luis Munoz Marin Intl-PWM Portland

7h 55m1 stop Newark

$316United Airlines

Tue, Nov 3 - Wed, Nov 4

3:15 pm - 6:15 amPWM Portland-SJU San Juan Luis Munoz Marin Intl

14h 00m2 stops Newark Houston George Bush Intcntl

2:52 pm - 9:48 pmSJU San Juan Luis Munoz Marin Intl-PWM Portland

7h 56m1 stop Newark

$316United Airlines

Sat, Jan 30 - Wed, Feb 10

2:33 pm - 12:52 amPWM Portland-SJU San Juan Luis Munoz Marin Intl

9h 19m1 stop New York John F Kennedy Intl

6:10 pm - 12:19 amSJU San Juan Luis Munoz Marin Intl-PWM Portland

7h 09m1 stop New York John F Kennedy Intl

$316Delta

Sat, Nov 7 - Wed, Nov 11

2:33 pm - 11:44 pmPWM Portland-SJU San Juan Luis Munoz Marin Intl

9h 11m1 stop New York John F Kennedy Intl

2:15 pm - 12:10 amSJU San Juan Luis Munoz Marin Intl-PWM Portland

10h 55m1 stop New York John F Kennedy Intl

$316Delta

Sat, Oct 31 - Fri, Nov 6

6:30 am - 12:57 pmPWM Portland-NAS Nassau Intl

6h 27m1 stop New York John F Kennedy Intl

2:15 pm - 11:43 pmNAS Nassau Intl-PWM Portland

9h 28m1 stop New York John F Kennedy Intl

$322JetBlue

Mon, Oct 26 - Thu, Nov 5

7:20 am - 5:50 pmPWM Portland-SJU San Juan Luis Munoz Marin Intl

10h 30m1 stop Baltimore/Washington

5:50 pm - 11:55 pmSJU San Juan Luis Munoz Marin Intl-PWM Portland

7h 05m1 stop Baltimore/Washington

$349Southwest

Sat, Oct 31 - Fri, Nov 6

12:45 pm - 12:50 amPWM Portland-SJU San Juan Luis Munoz Marin Intl

11h 05m2 stops Baltimore/Washington Orlando

6:10 am - 2:45 pmSJU San Juan Luis Munoz Marin Intl-PWM Portland

9h 35m2 stops Tampa Baltimore/Washington

$349Southwest

Wed, Dec 2 - Wed, Dec 9

6:30 am - 12:57 pmPWM Portland-NAS Nassau Intl

6h 27m1 stop New York John F Kennedy Intl

2:15 pm - 11:43 pmNAS Nassau Intl-PWM Portland

9h 28m1 stop New York John F Kennedy Intl

$443JetBlue

Fri, Nov 6 - Wed, Nov 11

Cheap last minute flights

Enter your travel dates to find the best prices.

5:30 pm - 12:05 amPWM Portland-SJU San Juan Luis Munoz Marin Intl

6h 35m1 stop Baltimore/Washington

5:30 am - 4:45 pmSJU San Juan Luis Munoz Marin Intl-PWM Portland

11h 15m1 stop Baltimore/Washington

$452Southwest

Fri, Oct 2 - Sun, Oct 4

5:15 am - 8:38 pmPWM Portland-SJU San Juan Luis Munoz Marin Intl

15h 23m2 stops Washington, D.C. Dulles Intl Houston George Bush Intcntl

1:00 am - 9:08 amSJU San Juan Luis Munoz Marin Intl-PWM Portland

8h 08m1 stop Newark

$452United Airlines

Fri, Oct 2 - Sat, Oct 3

5:15 am - 8:38 pmPWM Portland-SJU San Juan Luis Munoz Marin Intl

15h 23m2 stops Washington, D.C. Dulles Intl Houston George Bush Intcntl

1:00 am - 10:02 amSJU San Juan Luis Munoz Marin Intl-PWM Portland

9h 02m2 stops Newark Washington, D.C. Dulles Intl

$521United Airlines

Fri, Oct 2 - Sat, Oct 3

5:29 pm - 11:00 amPWM Portland-SJU San Juan Luis Munoz Marin Intl

17h 31m2 stops New York LaGuardia Miami

6:00 am - 11:45 pmSJU San Juan Luis Munoz Marin Intl-PWM Portland

17h 45m2 stops Miami Washington, D.C. Reagan-National

$602American Airlines

Mon, Sep 28 - Wed, Sep 30

5:18 pm - 1:30 pmPWM Portland-AUA Oranjestad Reina Beatrix

20h 12m2 stops Charlotte Douglas Miami

2:31 pm - 10:58 amAUA Oranjestad Reina Beatrix-PWM Portland

20h 27m2 stops Charlotte Douglas Philadelphia

$656American Airlines

Sat, Oct 3 - Sat, Oct 10

6:00 am - 4:20 pmPWM Portland-STT Saint Thomas Island Cyril E King

10h 20m2 stops Newark San Juan Luis Munoz Marin Intl

1:56 pm - 9:08 amSTT Saint Thomas Island Cyril E King-PWM Portland

19h 12m2 stops San Juan Luis Munoz Marin Intl Newark

$954Multiple Airlines

Thu, Oct 1 - Sun, Oct 4

5:15 am - 2:35 pmPWM Portland-STT Saint Thomas Island Cyril E King

9h 20m2 stops Washington, D.C. Dulles Intl San Juan Luis Munoz Marin Intl

1:56 pm - 9:08 amSTT Saint Thomas Island Cyril E King-PWM Portland

19h 12m2 stops San Juan Luis Munoz Marin Intl Newark

$1,084Multiple Airlines

Fri, Oct 2 - Sun, Oct 4

6:00 am - 1:40 pmPWM Portland-MBJ Montego Bay Sangster Intl

8h 40m1 stop New York John F Kennedy Intl

11:45 am - 11:54 pmMBJ Montego Bay Sangster Intl-PWM Portland

11h 09m1 stop New York John F Kennedy Intl

$1,113JetBlue

Sat, Oct 3 - Sat, Oct 10

6:00 am - 1:42 pmPWM Portland-STT Saint Thomas Island Cyril E King

7h 42m1 stop Atlanta Hartsfield-Jackson

2:52 pm - 11:28 pmSTT Saint Thomas Island Cyril E King-PWM Portland

8h 36m1 stop Atlanta Hartsfield-Jackson

$1,546Delta

Fri, Oct 2 - Sun, Oct 4

6:00 am - 1:42 pmPWM Portland-STT Saint Thomas Island Cyril E King

7h 42m1 stop Atlanta Hartsfield-Jackson

2:52 pm - 11:28 pmSTT Saint Thomas Island Cyril E King-PWM Portland

8h 36m1 stop Atlanta Hartsfield-Jackson

$1,792Delta

Thu, Oct 1 - Sun, Oct 4

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American Airlines flights from Portland, Maine to Caribbean

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

American Airlines

Nov 8

PWM6:47 pmPortland

19h 51m

2 stops

STT3:38 pmSaint Thomas Island Cyril E King

Nov 12

STT3:15 pmSaint Thomas Island Cyril E King

20h 22m

2 stops

PWM10:37 amPortland

$320

American Airlines

Jan 27

PWM10:52 amPortland

9h 38m

2 stops

SJU9:30 pmSan Juan Luis Munoz Marin Intl

Feb 6

SJU8:15 amSan Juan Luis Munoz Marin Intl

14h 28m

2 stops

PWM9:43 pmPortland

$321

American Airlines

Oct 26

PWM7:24 pmPortland

15h 41m

1 stop

NAS11:05 amNassau Intl

Nov 5

NAS2:18 pmNassau Intl

8h 15m

1 stop

PWM10:33 pmPortland

$336

United Airlines flights from Portland, Maine to Caribbean

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

United Airlines

Oct 20

PWM6:00 amPortland

7h 45m

1 stop

SJU1:45 pmSan Juan Luis Munoz Marin Intl

Oct 26

SJU2:35 pmSan Juan Luis Munoz Marin Intl

8h 46m

1 stop

PWM11:21 pmPortland

$316

United Airlines

Dec 2

PWM7:00 amPortland

6h 40m

1 stop

SJU2:40 pmSan Juan Luis Munoz Marin Intl

Dec 9

SJU1:00 pmSan Juan Luis Munoz Marin Intl

7h 25m

1 stop

PWM7:25 pmPortland

$332

United Airlines

Jan 27

PWM3:15 pmPortland

8h 21m

1 stop

SJU12:36 amSan Juan Luis Munoz Marin Intl

Feb 5

SJU2:05 amSan Juan Luis Munoz Marin Intl

13h 37m

2 stops

PWM2:42 pmPortland

$378

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

Cheapest round-trip

PortlandSan Juan

PWM Portland - SJU San Juan Luis Munoz Marin Intl

PWMSJU

Portland

Tue 10/20

7:26 pm-11:31 am

2 stops16h 05m

San Juan Luis Munoz Marin Intl

Mon 10/26

2:18 pm-11:59 pm

2 stops9h 41m

$316

PortlandSan Juan

PWM Portland - SJU San Juan Luis Munoz Marin Intl

PWMSJU

Portland

Tue 10/20

7:26 pm-11:31 am

2 stops16h 05m

San Juan Luis Munoz Marin Intl

Mon 10/26

12:41 pm-10:36 pm

1 stop9h 55m

$316

PortlandSan Juan

PWM Portland - SJU San Juan Luis Munoz Marin Intl

PWMSJU

Portland

Tue 11/3

8:47 am-10:22 pm

2 stops12h 35m

San Juan Luis Munoz Marin Intl

Wed 11/4

2:05 am-9:00 am

1 stop7h 55m

$316

PortlandSan Juan

PWM Portland - SJU San Juan Luis Munoz Marin Intl

PWMSJU

Portland

Sat 1/30

3:15 pm-6:15 am

2 stops14h 00m

San Juan Luis Munoz Marin Intl

Wed 2/10

2:52 pm-9:48 pm

1 stop7h 56m

$316

PortlandSan Juan

PWM Portland - SJU San Juan Luis Munoz Marin Intl

PWMSJU

Portland

Sat 11/7

2:33 pm-12:52 am

1 stop9h 19m

San Juan Luis Munoz Marin Intl

Wed 11/11

6:10 pm-12:19 am

1 stop7h 09m

$316

PortlandSan Juan

PWM Portland - SJU San Juan Luis Munoz Marin Intl

PWMSJU

Portland

Sat 10/31

2:33 pm-11:44 pm

1 stop9h 11m

San Juan Luis Munoz Marin Intl

Fri 11/6

2:15 pm-12:10 am

1 stop10h 55m

$316

Quickest round-trip

PortlandNassau

PWM Portland - NAS Nassau Intl

PWMNAS

Portland

Mon 10/26

6:30 am-12:57 pm

1 stop6h 27m

Nassau Intl

Thu 11/5

2:15 pm-11:43 pm

1 stop9h 28m

$322

PortlandSan Juan

PWM Portland - SJU San Juan Luis Munoz Marin Intl

PWMSJU

Portland

Sat 10/31

7:20 am-5:50 pm

1 stop10h 30m

San Juan Luis Munoz Marin Intl

Fri 11/6

5:50 pm-11:55 pm

1 stop7h 05m

$349

PortlandSan Juan

PWM Portland - SJU San Juan Luis Munoz Marin Intl

PWMSJU

Portland

Wed 12/2

12:45 pm-12:50 am

2 stops11h 05m

San Juan Luis Munoz Marin Intl

Wed 12/9

6:10 am-2:45 pm

2 stops9h 35m

$349

PortlandNassau

PWM Portland - NAS Nassau Intl

PWMNAS

Portland

Fri 11/6

6:30 am-12:57 pm

1 stop6h 27m

Nassau Intl

Wed 11/11

2:15 pm-11:43 pm

1 stop9h 28m

$443

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, January 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 $427. If you don’t want to visit Caribbean in January, then you should wait until September to fly from Portland, Maine, when ticket prices are also cheap, with an average price of $442.

How far in advance should I book a flight from Portland, Maine 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 $501 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 $308 on momondo.

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

You could potentially save up to 23% 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	$135
Fastest flight time	5h 59m
Direct flights	None

The best one-way flight to Caribbean from Portland, Maine in the past 72 hours is $135. The best round-trip flight deal from Portland, Maine to Caribbean found on momondo in the last 72 hours is $316.

The fastest flight from Portland, Maine to Caribbean takes 5h 59m

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

Search flight deals

Frequently asked questions about flying from Portland, Maine 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 September 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 7.8 8,610 reviews	Search Delta flights
JetBlue	PriceFrom $174	Free Cancellation	Rating 7.1 3,041 reviews	Search JetBlue flights
United Airlines	PriceFrom $247	Free Cancellation	Rating 7.4 10,243 reviews	Search United Airlines flights
American Airlines	PriceFrom $296	Free Cancellation	Rating 7.0 12,099 reviews	Search American Airlines flights
Southwest	PriceFrom $315	Free Cancellation	Rating 8.0 4,201 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.