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 65% 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, Southwest, and Delta 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 November 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.

$152 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.

6:00 am - 11:59 pmPWM Portland-SJU San Juan Luis Munoz Marin Intl

16h 59m1 stop Philadelphia

8:15 am - 9:43 pmSJU San Juan Luis Munoz Marin Intl-PWM Portland

14h 28m2 stops Philadelphia Washington, D.C. Reagan-National

$294American Airlines

Mon, Jan 11 - Wed, Jan 20

7:00 am - 4:57 pmPWM Portland-SJU San Juan Luis Munoz Marin Intl

8h 57m1 stop Charlotte Douglas

2:02 pm - 9:29 pmSJU San Juan Luis Munoz Marin Intl-PWM Portland

8h 27m1 stop Charlotte Douglas

$294American Airlines

Mon, Jan 11 - Wed, Jan 20

3:14 pm - 12:36 amPWM Portland-SJU San Juan Luis Munoz Marin Intl

8h 22m1 stop Newark

8:05 am - 2:33 pmSJU San Juan Luis Munoz Marin Intl-PWM Portland

7h 28m1 stop Washington, D.C. Dulles Intl

$294United Airlines

Sat, Jan 23 - Sat, Jan 30

7:10 am - 9:24 pmPWM Portland-SJU San Juan Luis Munoz Marin Intl

13h 14m2 stops Newark Houston George Bush Intcntl

2:52 pm - 11:32 pmSJU San Juan Luis Munoz Marin Intl-PWM Portland

9h 40m1 stop Newark

$294United Airlines

Wed, Feb 3 - Wed, Feb 10

6:30 am - 4:05 pmPWM Portland-SJU San Juan Luis Munoz Marin Intl

9h 35m1 stop New York John F Kennedy Intl

7:05 am - 1:53 pmSJU San Juan Luis Munoz Marin Intl-PWM Portland

6h 48m1 stop New York John F Kennedy Intl

$316Delta

Wed, Apr 28 - Fri, May 7

6:30 am - 4:05 pmPWM Portland-SJU San Juan Luis Munoz Marin Intl

9h 35m1 stop New York John F Kennedy Intl

1:15 pm - 11:49 pmSJU San Juan Luis Munoz Marin Intl-PWM Portland

10h 34m1 stop New York John F Kennedy Intl

$316Delta

Wed, Apr 28 - Tue, May 4

3:25 pm - 11:25 pmPWM Portland-SJU San Juan Luis Munoz Marin Intl

7h 00m1 stop Baltimore/Washington

5:40 am - 2:45 pmSJU San Juan Luis Munoz Marin Intl-PWM Portland

10h 05m2 stops Orlando Baltimore/Washington

$316Southwest

Mon, Dec 7 - Thu, Dec 10

5:05 am - 6:00 pmPWM Portland-SJU San Juan Luis Munoz Marin Intl

11h 55m2 stops Baltimore/Washington Orlando

5:35 am - 2:50 pmSJU San Juan Luis Munoz Marin Intl-PWM Portland

10h 15m2 stops Orlando Baltimore/Washington

$341Southwest

Sat, Jan 23 - Wed, Jan 27

12:28 pm - 2:49 amPWM Portland-SJU San Juan Luis Munoz Marin Intl

37h 21m2 stops Raleigh-Durham Miami

5:02 pm - 5:51 pmSJU San Juan Luis Munoz Marin Intl-PWM Portland

25h 49m1 stop Tampa

$378Multiple Airlines

Wed, Jan 20 - Tue, Jan 26

7:12 pm - 10:23 amPWM Portland-SJU San Juan Luis Munoz Marin Intl

14h 11m1 stop Tampa

3:28 am - 11:48 amSJU San Juan Luis Munoz Marin Intl-PWM Portland

33h 20m2 stops Miami Raleigh-Durham

$398Multiple Airlines

Sat, Dec 5 - Thu, Dec 10

Cheap last minute flights

Enter your travel dates to find the best prices.

6:00 am - 1:50 pmPWM Portland-NAS Nassau Intl

7h 50m1 stop Atlanta Hartsfield-Jackson

1:15 pm - 12:19 amNAS Nassau Intl-PWM Portland

11h 04m1 stop New York John F Kennedy Intl

$396Delta

Mon, Nov 16 - Fri, Nov 20

6:00 am - 1:50 pmPWM Portland-NAS Nassau Intl

7h 50m1 stop Atlanta Hartsfield-Jackson

1:15 pm - 12:19 amNAS Nassau Intl-PWM Portland

11h 04m1 stop New York John F Kennedy Intl

$436Delta

Mon, Nov 16 - Fri, Nov 20

5:30 am - 2:58 pmPWM Portland-NAS Nassau Intl

9h 28m2 stops Washington, D.C. Dulles Intl Chicago O'Hare Intl

2:55 pm - 11:21 pmNAS Nassau Intl-PWM Portland

8h 26m1 stop Newark

$475United Airlines

Sat, Nov 14 - Fri, Nov 20

6:00 am - 1:48 pmPWM Portland-NAS Nassau Intl

7h 48m1 stop Newark

2:55 pm - 11:21 pmNAS Nassau Intl-PWM Portland

8h 26m1 stop Newark

$475United Airlines

Sat, Nov 14 - Fri, Nov 20

7:10 am - 1:15 pmPWM Portland-NAS Nassau Intl

6h 05m1 stop Charlotte Douglas

11:49 am - 11:55 pmNAS Nassau Intl-PWM Portland

12h 06m2 stops Washington, D.C. Reagan-National Charlotte Douglas

$480American Airlines

Mon, Nov 16 - Sat, Nov 21

6:47 pm - 10:44 amPWM Portland-NAS Nassau Intl

15h 57m2 stops Philadelphia Charlotte Douglas

11:49 am - 11:55 pmNAS Nassau Intl-PWM Portland

12h 06m2 stops Washington, D.C. Reagan-National Charlotte Douglas

$480American Airlines

Mon, Nov 16 - Sat, Nov 21

6:00 am - 3:33 pmPWM Portland-NAS Nassau Intl

9h 33m1 stop Atlanta Hartsfield-Jackson

3:10 pm - 9:29 pmNAS Nassau Intl-PWM Portland

6h 19m1 stop New York LaGuardia

$485Delta

Mon, Nov 16 - Sat, Nov 21

5:08 pm - 1:33 pmPWM Portland-NAS Nassau Intl

20h 25m2 stops Chicago O'Hare Intl Houston George Bush Intcntl

2:55 pm - 11:21 pmNAS Nassau Intl-PWM Portland

8h 26m1 stop Newark

$521United Airlines

Mon, Nov 16 - Fri, Nov 20

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

$1,171JetBlue

Wed, Nov 11 - Sun, Nov 15

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

6h 27m1 stop New York John F Kennedy Intl

9:25 am - 4:55 pmNAS Nassau Intl-PWM Portland

7h 30m2 stops Tampa Charleston

$1,175Multiple Airlines

Mon, Nov 16 - Fri, Nov 20

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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

Jan 11

PWM7:00 amPortland

8h 57m

1 stop

SJU4:57 pmSan Juan Luis Munoz Marin Intl

Jan 20

SJU6:20 amSan Juan Luis Munoz Marin Intl

11h 54m

2 stops

PWM5:14 pmPortland

$294

American Airlines

Jan 11

PWM7:00 amPortland

13h 11m

1 stop

SJU9:11 pmSan Juan Luis Munoz Marin Intl

Jan 20

SJU6:20 amSan Juan Luis Munoz Marin Intl

16h 09m

1 stop

PWM9:29 pmPortland

$306

American Airlines

Jan 13

PWM10:52 amPortland

9h 19m

2 stops

SJU9:11 pmSan Juan Luis Munoz Marin Intl

Jan 19

SJU2:36 pmSan Juan Luis Munoz Marin Intl

9h 08m

1 stop

PWM10:44 pmPortland

$324

United Airlines flights from Portland, Maine to Caribbean

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

United Airlines

Feb 3

PWM3:14 pmPortland

8h 22m

1 stop

SJU12:36 amSan Juan Luis Munoz Marin Intl

Feb 10

SJU2:52 pmSan Juan Luis Munoz Marin Intl

9h 40m

1 stop

PWM11:32 pmPortland

$299

United Airlines

Apr 28

PWM6:00 amPortland

14h 38m

2 stops

SJU8:38 pmSan Juan Luis Munoz Marin Intl

May 6

SJU1:00 amSan Juan Luis Munoz Marin Intl

7h 19m

1 stop

PWM8:19 amPortland

$321

United Airlines

Mar 31

PWM5:45 amPortland

14h 53m

2 stops

SJU8:38 pmSan Juan Luis Munoz Marin Intl

Apr 6

SJU1:00 amSan Juan Luis Munoz Marin Intl

7h 19m

1 stop

PWM8:19 amPortland

$332

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

Mon 1/11

6:00 am-11:59 pm

1 stop16h 59m

San Juan Luis Munoz Marin Intl

Wed 1/20

8:15 am-9:43 pm

2 stops14h 28m

$294

PortlandSan Juan

PWM Portland - SJU San Juan Luis Munoz Marin Intl

PWMSJU

Portland

Mon 1/11

7:00 am-4:57 pm

1 stop8h 57m

San Juan Luis Munoz Marin Intl

Wed 1/20

2:02 pm-9:29 pm

1 stop8h 27m

$294

Quickest round-trip

PortlandSan Juan

PWM Portland - SJU San Juan Luis Munoz Marin Intl

PWMSJU

Portland

Sat 1/23

3:14 pm-12:36 am

1 stop8h 22m

San Juan Luis Munoz Marin Intl

Sat 1/30

8:05 am-2:33 pm

1 stop7h 28m

$294

PortlandSan Juan

PWM Portland - SJU San Juan Luis Munoz Marin Intl

PWMSJU

Portland

Wed 2/3

7:10 am-9:24 pm

2 stops13h 14m

San Juan Luis Munoz Marin Intl

Wed 2/10

2:52 pm-11:32 pm

1 stop9h 40m

$294

PortlandSan Juan

PWM Portland - SJU San Juan Luis Munoz Marin Intl

PWMSJU

Portland

Wed 4/28

6:30 am-4:05 pm

1 stop9h 35m

San Juan Luis Munoz Marin Intl

Fri 5/7

7:05 am-1:53 pm

1 stop6h 48m

$316

PortlandSan Juan

PWM Portland - SJU San Juan Luis Munoz Marin Intl

PWMSJU

Portland

Wed 4/28

6:30 am-4:05 pm

1 stop9h 35m

San Juan Luis Munoz Marin Intl

Tue 5/4

1:15 pm-11:49 pm

1 stop10h 34m

$316

PortlandSan Juan

PWM Portland - SJU San Juan Luis Munoz Marin Intl

PWMSJU

Portland

Mon 12/7

3:25 pm-11:25 pm

1 stop7h 00m

San Juan Luis Munoz Marin Intl

Thu 12/10

5:40 am-2:45 pm

2 stops10h 05m

$316

PortlandSan Juan

PWM Portland - SJU San Juan Luis Munoz Marin Intl

PWMSJU

Portland

Sat 1/23

5:05 am-6:00 pm

2 stops11h 55m

San Juan Luis Munoz Marin Intl

Wed 1/27

5:35 am-2:50 pm

2 stops10h 15m

$341

PortlandSan Juan

PWM Portland - SJU San Juan Luis Munoz Marin Intl

PWMSJU

Portland

Wed 1/20

12:28 pm-2:49 am

2 stops37h 21m

San Juan Luis Munoz Marin Intl

Tue 1/26

5:02 pm-5:51 pm

1 stop25h 49m

$378

PortlandSan Juan

PWM Portland - SJU San Juan Luis Munoz Marin Intl

PWMSJU

Portland

Sat 12/5

7:12 pm-10:23 am

1 stop14h 11m

San Juan Luis Munoz Marin Intl

Thu 12/10

3:28 am-11:48 am

2 stops33h 20m

$398

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 $426. 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 $526 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 $401 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	$152
Fastest flight time	6h 30m
Direct flights	None

The best one-way flight to Caribbean from Portland, Maine in the past 72 hours is $152. The best round-trip flight deal from Portland, Maine to Caribbean found on momondo in the last 72 hours is $294.

The fastest flight from Portland, Maine to Caribbean takes 6h 30m

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 November 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
JetBlue	PriceFrom $174	Free Cancellation	Rating 7.1 3,067 reviews	Search JetBlue flights
Delta	PriceFrom $184	Free Cancellation	Rating 7.8 8,700 reviews	Search Delta flights
United Airlines	PriceFrom $247	Free Cancellation	Rating 7.3 10,474 reviews	Search United Airlines flights
American Airlines	PriceFrom $298	Free Cancellation	Rating 7.0 12,228 reviews	Search American Airlines flights
Southwest	PriceFrom $322	Free Cancellation	Rating 8.0 4,219 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.