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

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

What airlines fly to Caribbean Islands?

JetBlue, Delta and Spirit Airlines are the top three most popular airlines that fly to Caribbean Islands 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 Islands. Keep in mind that there are 12 different airlines that fly to Caribbean Islands 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 Islands?

Prices for flights from Portland Airport to Caribbean Islands are updated daily.

How many operators does momondo search for flights from Portland Airport to Caribbean Islands?

There are 5 operators available for flights from Portland Airport to Caribbean Islands as of March 2026.

How old do you have to be to fly from Portland Airport to Caribbean Islands?

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 Islands.

What documentation or ID do you need to fly to Caribbean Islands?

The necessary travel and health documents for your Caribbean Islands trip may vary depending on your travel plans and individual circumstances. Generally, you should have various documents, such as a national ID card or driver's license and a passport that is valid for six months beyond your scheduled arrival date. We recommend seeking advice from your airline or a trusted third party, such as IATA.

$99 Cheap Flights from Portland to Caribbean Islands in 2026

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Find the cheapest flights from Portland, Maine to Caribbean Islands

Round-trip

One-way

Last minute

Cheap round-trip flights

Enter your travel dates to find the best prices.

7:23 pm - 11:35 am

PWM

STT

16h 12m

2 stops

2:30 pm - 10:18 am

STT

PWM

19h 48m

2 stops

$202American Airlines

Tue, May 5 - Tue, May 12

7:23 pm - 11:35 am

PWM

STT

16h 12m

2 stops

2:05 pm - 9:54 am

STT

PWM

19h 49m

2 stops

$273American Airlines

Mon, May 4 - Mon, May 11

6:00 am - 12:35 pm

PWM

STT

6h 35m

1 stop

2:05 pm - 10:23 am

STT

PWM

20h 18m

2 stops

$280American Airlines

Thu, Apr 30 - Fri, May 8

2:35 pm - 11:44 pm

PWM

SJU

9h 09m

1 stop

7:00 am - 1:54 pm

SJU

PWM

6h 54m

1 stop

$282Delta

Sat, Sep 19 - Sat, Sep 26

5:21 am - 2:48 pm

PWM

STT

9h 27m

1 stop

3:59 pm - 12:46 am

STT

PWM

8h 47m

1 stop

$318Delta

Wed, Apr 22 - Wed, Apr 29

6:00 am - 1:58 pm

PWM

SXM

7h 58m

1 stop

12:31 pm - 11:58 pm

SXM

PWM

11h 27m

1 stop

$327JetBlue

Sat, May 30 - Wed, Jun 3

6:00 am - 1:24 pm

PWM

PLS

7h 24m

1 stop

2:29 pm - 11:58 pm

PLS

PWM

9h 29m

1 stop

$347JetBlue

Mon, May 25 - Fri, May 29

9:49 am - 8:34 pm

PWM

SJU

10h 45m

1 stop

1:00 am - 9:25 am

SJU

PWM

8h 25m

1 stop

$357United Airlines

Sun, Apr 12 - Wed, Apr 15

6:00 am - 1:45 pm

PWM

SJU

7h 45m

1 stop

1:00 am - 10:02 am

SJU

PWM

9h 02m

2 stops

$367United Airlines

Tue, Sep 22 - Tue, Sep 22

6:18 pm - 11:29 pm

PWM

SJU

29h 11m

1 stop

3:03 am - 4:16 pm

SJU

PWM

13h 13m

2 stops

$368Multiple Airlines

Sat, May 2 - Tue, May 12

American Airlines flights from Portland, Maine to Caribbean Islands

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

American Airlines

May 5

PWM7:23 pmPortland

16h 12m

2 stops

STT11:35 amSaint Thomas Island Cyril E King

May 12

STT2:30 pmSaint Thomas Island Cyril E King

19h 48m

2 stops

PWM10:18 amPortland

$202

American Airlines

May 4

PWM7:23 pmPortland

16h 12m

2 stops

STT11:35 amSaint Thomas Island Cyril E King

May 11

STT2:05 pmSaint Thomas Island Cyril E King

19h 49m

2 stops

PWM9:54 amPortland

$273

American Airlines

Apr 30

PWM6:00 amPortland

6h 35m

1 stop

STT12:35 pmSaint Thomas Island Cyril E King

May 8

STT2:05 pmSaint Thomas Island Cyril E King

20h 18m

2 stops

PWM10:23 amPortland

$280

Southwest flights from Portland, Maine to Caribbean Islands

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

Southwest

May 4

PWM2:50 pmPortland

8h 50m

1 stop

SJU11:40 pmSan Juan Luis Munoz Marin Intl

May 11

SJU5:05 amSan Juan Luis Munoz Marin Intl

9h 05m

2 stops

PWM2:10 pmPortland

$387

Southwest

Sep 21

PWM5:55 amPortland

8h 35m

1 stop

SJU2:30 pmSan Juan Luis Munoz Marin Intl

Sep 25

SJU6:00 amSan Juan Luis Munoz Marin Intl

9h 00m

2 stops

PWM3:00 pmPortland

$389

Southwest

Sep 7

PWM5:55 amPortland

8h 35m

1 stop

SJU2:30 pmSan Juan Luis Munoz Marin Intl

Sep 11

SJU5:30 amSan Juan Luis Munoz Marin Intl

9h 30m

1 stop

PWM3:00 pmPortland

$417

momondo Fare Finder

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

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

PortlandSaint Thomas Island

PWM - STT

PWMSTT

Portland

Tue 5/5

7:23 pm-11:35 am

2 stops16h 12m

Saint Thomas Island Cyril E King

Tue 5/12

2:30 pm-10:18 am

2 stops19h 48m

$202

PortlandSaint Thomas Island

PWM - STT

PWMSTT

Portland

Mon 5/4

7:23 pm-11:35 am

2 stops16h 12m

Saint Thomas Island Cyril E King

Mon 5/11

2:05 pm-9:54 am

2 stops19h 49m

$273

PortlandSaint Thomas Island

PWM - STT

PWMSTT

Portland

Thu 4/30

6:00 am-12:35 pm

1 stop6h 35m

Saint Thomas Island Cyril E King

Fri 5/8

2:05 pm-10:23 am

2 stops20h 18m

$280

Quickest round-trip

PortlandSan Juan

PWM - SJU

PWMSJU

Portland

Sat 9/19

2:35 pm-11:44 pm

1 stop9h 09m

San Juan Luis Munoz Marin Intl

Sat 9/26

7:00 am-1:54 pm

1 stop6h 54m

$282

PortlandSaint Thomas Island

PWM - STT

PWMSTT

Portland

Wed 4/22

5:21 am-2:48 pm

1 stop9h 27m

Saint Thomas Island Cyril E King

Wed 4/29

3:59 pm-12:46 am

1 stop8h 47m

$318

PortlandSimpson Bay

PWM - SXM

PWMSXM

Portland

Sat 5/30

6:00 am-1:58 pm

1 stop7h 58m

Simpson Bay Princess Juliana

Wed 6/3

12:31 pm-11:58 pm

1 stop11h 27m

$327

PortlandProvidenciales

PWM - PLS

PWMPLS

Portland

Mon 5/25

6:00 am-1:24 pm

1 stop7h 24m

Providenciales

Fri 5/29

2:29 pm-11:58 pm

1 stop9h 29m

$347

PortlandSan Juan

PWM - SJU

PWMSJU

Portland

Sun 4/12

9:49 am-8:34 pm

1 stop10h 45m

San Juan Luis Munoz Marin Intl

Wed 4/15

1:00 am-9:25 am

1 stop8h 25m

$357

PortlandSan Juan

PWM - SJU

PWMSJU

Portland

Tue 9/22

6:00 am-1:45 pm

1 stop7h 45m

San Juan Luis Munoz Marin Intl

Tue 9/22

1:00 am-10:02 am

2 stops9h 02m

$367

PortlandSan Juan

PWM - SJU

PWMSJU

Portland

Sat 5/2

6:18 pm-11:29 pm

1 stop29h 11m

San Juan Luis Munoz Marin Intl

Tue 5/12

3:03 am-4:16 pm

2 stops13h 13m

$368

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 Islands

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 Islands?

The month of October is, on average, the cheapest month to fly to Caribbean Islands from Portland, Maine, with most prices found around $265. The month of May is another great option to travel to Caribbean Islands, with average flight prices from Portland, Maine averaging around $302.

How far in advance should I book a flight to Caribbean Islands?

You are more likely to see cheaper flights to Caribbean Islands from Portland, Maine when booking weeks ahead of your departure date. In general, you can expect to find flights to Caribbean Islands for around $442 when searching weeks out. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Caribbean Islands from Portland, Maine for as low as $234 on momondo.

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

No. A direct flight is the cheapest option for a flight between Portland, Maine to Caribbean Islands.

Cheap Portland, Maine to Caribbean Islands flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Portland, Maine to Caribbean Islands

Fastest flight time	5h 57m
Direct flights	None

The fastest flight from Portland, Maine to Caribbean Islands takes 5h 57m

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

Search flight deals

When did momondo last update prices for flights from Portland Airport to Caribbean Islands?
Prices for flights from Portland Airport to Caribbean Islands are updated daily.
How many operators does momondo search for flights from Portland Airport to Caribbean Islands?
There are 5 operators available for flights from Portland Airport to Caribbean Islands as of March 2026.
How old do you have to be to fly from Portland Airport to Caribbean Islands?
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 Islands.
What documentation or ID do you need to fly to Caribbean Islands?
The necessary travel and health documents for your Caribbean Islands trip may vary depending on your travel plans and individual circumstances. Generally, you should have various documents, such as a national ID card or driver's license and a passport that is valid for six months beyond your scheduled arrival date. We recommend seeking advice from your airline or a trusted third party, such as IATA.
What is the most popular plane model from Portland, Maine to Caribbean Islands?
Based on momondo bookings for this flight route, the most popular plane model on flight routes from Portland, Maine to Caribbean Islands is Airbus A220-300 (20.68% of total bookings). The next most popular plane models are Canadair (Bombardier) Regional Jet 900 (11.16%), Embraer 175 (10.23%), and Embraer 175 (Enhanced Winglets) (9.69%).

Best airlines flying from Portland, Maine to Caribbean Islands

Compare and see reviews for airlines that fly from Portland, Maine to Caribbean Islands with momondo

Airline	Rating	Free Cancellation	Price
Delta	PriceFrom $137	Free Cancellation	Rating 7.9 8,359 reviews	Search Delta flights
JetBlue	PriceFrom $156	Free Cancellation	Rating 7.2 2,908 reviews	Search JetBlue flights
United Airlines	PriceFrom $241	Free Cancellation	Rating 7.4 9,509 reviews	Search United Airlines flights
American Airlines	PriceFrom $281	Free Cancellation	Rating 7.1 11,521 reviews	Search American Airlines flights
Southwest	PriceFrom $315	Free Cancellation	Rating 8.0 4,331 reviews	Search Southwest flights

Why use momondo?

Why should I use momondo to find a flight deal from Portland to Caribbean Islands?

To find the flight that best suits your needs, momondo gathers a range of flights from a large pool of different airlines and agents; you can then use our insights and filters to find and book the right flight to Caribbean Islands from Portland.

Can I find flights from Portland to Caribbean Islands with flexible booking policies on momondo?

All flight searches from Portland to Caribbean Islands on momondo can be filtered to show those which offer flexible booking policies.

How can momondo help me find flights from Portland to Caribbean Islands?

Once all potential Portland to Caribbean Islands 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 Islands right now. Can momondo alert me if prices change?

Yes momondo offers price alerts on flights to Caribbean Islands from Portland. After performing a search on this page you should be able to see the price alert set up feature. Simply provide a valid email address and momondo will instantly alert you when prices change.