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

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

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.

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 May 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, Maine 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 - 1:35 pm

PWM

SJU

7h 35m

1 stop

5:25 am - 7:16 pm

SJU

PWM

13h 51m

1 stop

$302American Airlines

Tue, Oct 20 - Mon, Oct 26

2:55 pm - 11:50 pm

PWM

SJU

8h 55m

1 stop

5:25 am - 6:25 pm

SJU

PWM

13h 00m

1 stop

$312American Airlines

Tue, Oct 20 - Mon, Oct 26

6:00 am - 11:54 am

PWM

GCM

6h 54m

1 stop

1:19 pm - 11:09 pm

GCM

PWM

8h 50m

1 stop

$321Delta

Thu, May 28 - Tue, Jun 2

2:38 pm - 11:54 am

PWM

GCM

22h 16m

2 stops

1:19 pm - 12:43 am

GCM

PWM

10h 24m

2 stops

$326Delta

Fri, May 29 - Tue, Jun 2

6:00 am - 2:23 pm

PWM

STT

8h 23m

1 stop

4:31 pm - 12:59 am

STT

PWM

8h 28m

1 stop

$333Delta

Thu, Jul 9 - Wed, Jul 15

6:00 am - 3:25 pm

PWM

NAS

9h 25m

1 stop

2:55 pm - 10:23 pm

NAS

PWM

7h 28m

1 stop

$340Delta

Sat, Nov 7 - Tue, Nov 10

6:00 am - 12:49 pm

PWM

PUJ

6h 49m

1 stop

11:56 am - 11:59 pm

PUJ

PWM

12h 03m

1 stop

$352United Airlines

Wed, Oct 28 - Sat, Oct 31

6:00 am - 12:49 pm

PWM

PUJ

6h 49m

1 stop

11:56 am - 10:57 pm

PUJ

PWM

11h 01m

2 stops

$357United Airlines

Wed, Oct 28 - Sat, Oct 31

2:37 pm - 10:48 pm

PWM

KIN

9h 11m

1 stop

11:59 pm - 1:35 pm

KIN

PWM

12h 36m

1 stop

$581JetBlue

Mon, Jun 1 - Fri, Jun 5

2:37 pm - 12:43 pm

PWM

STT

22h 06m

2 stops

2:00 pm - 12:30 pm

STT

PWM

22h 30m

3 stops

$585JetBlue

Fri, Jun 5 - Sat, Jun 13

Southwest flights from Portland, Maine to Caribbean

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

Southwest

Aug 17

PWM5:55 amPortland

8h 35m

1 stop

SJU2:30 pmSan Juan Luis Munoz Marin Intl

Aug 20

SJU3:20 pmSan Juan Luis Munoz Marin Intl

7h 05m

1 stop

PWM10:25 pmPortland

$437

Southwest

Sep 25

PWM3:40 pmPortland

7h 10m

1 stop

SJU10:50 pmSan Juan Luis Munoz Marin Intl

Sep 27

SJU6:00 amSan Juan Luis Munoz Marin Intl

10h 35m

2 stops

PWM4:35 pmPortland

$456

Southwest

Oct 2

PWM5:30 amPortland

11h 00m

2 stops

SJU4:30 pmSan Juan Luis Munoz Marin Intl

Oct 4

SJU6:00 amSan Juan Luis Munoz Marin Intl

10h 30m

2 stops

PWM4:30 pmPortland

$457

JetBlue flights from Portland, Maine to Caribbean

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

JetBlue

Aug 22

PWM2:40 pmPortland

8h 49m

1 stop

SJU11:29 pmSan Juan Luis Munoz Marin Intl

Aug 26

SJU5:01 amSan Juan Luis Munoz Marin Intl

8h 44m

1 stop

PWM1:45 pmPortland

$450

JetBlue

Jul 4

PWM2:30 pmPortland

10h 12m

1 stop

SJU12:42 amSan Juan Luis Munoz Marin Intl

Jul 9

SJU5:01 amSan Juan Luis Munoz Marin Intl

8h 44m

1 stop

PWM1:45 pmPortland

$460

JetBlue

May 28

PWM2:36 pmPortland

8h 17m

1 stop

SJU10:53 pmSan Juan Luis Munoz Marin Intl

Jun 6

SJU3:30 amSan Juan Luis Munoz Marin Intl

10h 00m

1 stop

PWM1:30 pmPortland

$468

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

PortlandSan Juan

PWM - SJU

PWMSJU

Portland

Tue 10/20

6:00 am-1:35 pm

1 stop7h 35m

San Juan Luis Munoz Marin Intl

Mon 10/26

5:25 am-7:16 pm

1 stop13h 51m

$302

PortlandSan Juan

PWM - SJU

PWMSJU

Portland

Tue 10/20

2:55 pm-11:50 pm

1 stop8h 55m

San Juan Luis Munoz Marin Intl

Mon 10/26

5:25 am-6:25 pm

1 stop13h 00m

$312

Quickest round-trip

PortlandGeorge Town

PWM - GCM

PWMGCM

Portland

Thu 5/28

6:00 am-11:54 am

1 stop6h 54m

George Town Owen Roberts Intl

Tue 6/2

1:19 pm-11:09 pm

1 stop8h 50m

$321

PortlandGeorge Town

PWM - GCM

PWMGCM

Portland

Fri 5/29

2:38 pm-11:54 am

2 stops22h 16m

George Town Owen Roberts Intl

Tue 6/2

1:19 pm-12:43 am

2 stops10h 24m

$326

PortlandSaint Thomas Island

PWM - STT

PWMSTT

Portland

Thu 7/9

6:00 am-2:23 pm

1 stop8h 23m

Saint Thomas Island Cyril E King

Wed 7/15

4:31 pm-12:59 am

1 stop8h 28m

$333

PortlandNassau

PWM - NAS

PWMNAS

Portland

Sat 11/7

6:00 am-3:25 pm

1 stop9h 25m

Nassau Intl

Tue 11/10

2:55 pm-10:23 pm

1 stop7h 28m

$340

PortlandPunta Cana

PWM - PUJ

PWMPUJ

Portland

Wed 10/28

6:00 am-12:49 pm

1 stop6h 49m

Punta Cana

Sat 10/31

11:56 am-11:59 pm

1 stop12h 03m

$352

PortlandPunta Cana

PWM - PUJ

PWMPUJ

Portland

Wed 10/28

6:00 am-12:49 pm

1 stop6h 49m

Punta Cana

Sat 10/31

11:56 am-10:57 pm

2 stops11h 01m

$357

PortlandKingston

PWM - KIN

PWMKIN

Portland

Mon 6/1

2:37 pm-10:48 pm

1 stop9h 11m

Kingston Norman Manley

Fri 6/5

11:59 pm-1:35 pm

1 stop12h 36m

$581

PortlandSaint Thomas Island

PWM - STT

PWMSTT

Portland

Fri 6/5

2:37 pm-12:43 pm

2 stops22h 06m

Saint Thomas Island Cyril E King

Sat 6/13

2:00 pm-12:30 pm

3 stops22h 30m

$585

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, February 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 $101. If you don’t want to visit Caribbean in February, then you should wait until April to fly from Portland, Maine, when ticket prices are also cheap, with an average price of $137.

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 $448 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 20% 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	6h 26m
Direct flights	None

The fastest flight from Portland, Maine to Caribbean takes 6h 26m

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 May 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 $156	Free Cancellation	Rating 7.1 2,973 reviews	Search JetBlue flights
Delta	PriceFrom $176	Free Cancellation	Rating 7.9 8,450 reviews	Search Delta flights
United Airlines	PriceFrom $235	Free Cancellation	Rating 7.4 9,706 reviews	Search United Airlines flights
American Airlines	PriceFrom $256	Free Cancellation	Rating 7.1 11,662 reviews	Search American Airlines flights
Southwest	PriceFrom $300	Free Cancellation	Rating 7.9 4,296 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.