What airlines fly to Caribbean Islands?

JetBlue, Delta and American 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 69% of people opting to fly with this airline when traveling to Caribbean Islands. Keep in mind that there are 11 different airlines that fly to Caribbean Islands 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 Islands?

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

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 June 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.

$107 Cheap Flights from Portland, Maine to Caribbean Islands in 2026

Discover deals from 900+ travel sites with momondo.

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.

6:00 am - 8:38 pm

PWM

SJU

14h 38m

2 stops

4:20 pm - 11:32 pm

SJU

PWM

7h 12m

1 stop

$218United Airlines

Wed, Sep 16 - Wed, Sep 23

5:42 pm - 1:54 pm

PWM

SJU

20h 12m

2 stops

6:27 am - 11:59 pm

SJU

PWM

17h 32m

2 stops

$223American Airlines

Wed, Sep 16 - Wed, Sep 23

6:00 am - 1:45 pm

PWM

SJU

7h 45m

1 stop

4:50 pm - 11:59 pm

SJU

PWM

7h 09m

1 stop

$238United Airlines

Thu, Oct 22 - Mon, Oct 26

6:39 pm - 3:15 pm

PWM

STT

19h 36m

2 stops

6:17 pm - 12:11 pm

STT

PWM

18h 54m

2 stops

$260American Airlines

Mon, Nov 23 - Wed, Dec 2

5:19 pm - 12:07 pm

PWM

STT

17h 48m

2 stops

4:22 pm - 12:11 pm

STT

PWM

20h 49m

2 stops

$265American Airlines

Wed, Nov 25 - Wed, Dec 2

6:00 am - 1:45 pm

PWM

SJU

7h 45m

1 stop

7:25 am - 7:18 pm

SJU

PWM

11h 53m

2 stops

$270United Airlines

Tue, Oct 20 - Mon, Oct 26

6:00 am - 4:49 pm

PWM

SJU

10h 49m

1 stop

7:30 am - 3:39 pm

SJU

PWM

8h 09m

1 stop

$276Delta

Wed, Sep 16 - Wed, Sep 23

6:05 am - 11:39 am

PWM

GCM

6h 34m

1 stop

1:04 pm - 9:31 pm

GCM

PWM

7h 27m

1 stop

$351Delta

Wed, Aug 19 - Sat, Aug 29

6:41 am - 12:53 pm

PWM

PLS

6h 12m

1 stop

2:13 pm - 12:25 am

PLS

PWM

10h 12m

1 stop

$505JetBlue

Sat, Aug 29 - Wed, Sep 2

6:00 am - 4:40 pm

PWM

AUA

10h 40m

1 stop

1:40 pm - 11:52 pm

AUA

PWM

10h 12m

1 stop

$508JetBlue

Fri, Oct 2 - Tue, Oct 6

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United Airlines flights from Portland, Maine to Caribbean Islands

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

United Airlines

Sep 16

PWM6:00 amPortland

14h 38m

2 stops

SJU8:38 pmSan Juan Luis Munoz Marin Intl

Sep 23

SJU7:00 amSan Juan Luis Munoz Marin Intl

14h 23m

2 stops

PWM9:23 pmPortland

$218

United Airlines

Oct 22

PWM6:00 amPortland

7h 45m

1 stop

SJU1:45 pmSan Juan Luis Munoz Marin Intl

Oct 26

SJU4:50 pmSan Juan Luis Munoz Marin Intl

7h 09m

1 stop

PWM11:59 pmPortland

$238

United Airlines

Oct 20

PWM6:00 amPortland

7h 45m

1 stop

SJU1:45 pmSan Juan Luis Munoz Marin Intl

Oct 26

SJU7:25 amSan Juan Luis Munoz Marin Intl

11h 53m

2 stops

PWM7:18 pmPortland

$270

American Airlines flights from Portland, Maine to Caribbean Islands

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

American Airlines

Sep 16

PWM5:42 pmPortland

20h 12m

2 stops

SJU1:54 pmSan Juan Luis Munoz Marin Intl

Sep 23

SJU6:27 amSan Juan Luis Munoz Marin Intl

17h 32m

2 stops

PWM11:59 pmPortland

$223

American Airlines

Nov 23

PWM6:39 pmPortland

19h 36m

2 stops

STT3:15 pmSaint Thomas Island Cyril E King

Dec 2

STT6:17 pmSaint Thomas Island Cyril E King

18h 54m

2 stops

PWM12:11 pmPortland

$260

American Airlines

Sep 19

PWM5:06 pmPortland

17h 54m

2 stops

SJU11:00 amSan Juan Luis Munoz Marin Intl

Sep 26

SJU6:27 amSan Juan Luis Munoz Marin Intl

16h 18m

2 stops

PWM10:45 pmPortland

$295

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

PortlandSan Juan

PWM - SJU

PWMSJU

Portland

Wed 9/16

6:00 am-8:38 pm

2 stops14h 38m

San Juan Luis Munoz Marin Intl

Wed 9/23

4:20 pm-11:32 pm

1 stop7h 12m

$218

PortlandSan Juan

PWM - SJU

PWMSJU

Portland

Wed 9/16

5:42 pm-1:54 pm

2 stops20h 12m

San Juan Luis Munoz Marin Intl

Wed 9/23

6:27 am-11:59 pm

2 stops17h 32m

$223

PortlandSan Juan

PWM - SJU

PWMSJU

Portland

Thu 10/22

6:00 am-1:45 pm

1 stop7h 45m

San Juan Luis Munoz Marin Intl

Mon 10/26

4:50 pm-11:59 pm

1 stop7h 09m

$238

PortlandSaint Thomas Island

PWM - STT

PWMSTT

Portland

Mon 11/23

6:39 pm-3:15 pm

2 stops19h 36m

Saint Thomas Island Cyril E King

Wed 12/2

6:17 pm-12:11 pm

2 stops18h 54m

$260

PortlandSaint Thomas Island

PWM - STT

PWMSTT

Portland

Wed 11/25

5:19 pm-12:07 pm

2 stops17h 48m

Saint Thomas Island Cyril E King

Wed 12/2

4:22 pm-12:11 pm

2 stops20h 49m

$265

PortlandSan Juan

PWM - SJU

PWMSJU

Portland

Tue 10/20

6:00 am-1:45 pm

1 stop7h 45m

San Juan Luis Munoz Marin Intl

Mon 10/26

7:25 am-7:18 pm

2 stops11h 53m

$270

PortlandSan Juan

PWM - SJU

PWMSJU

Portland

Wed 9/16

6:00 am-4:49 pm

1 stop10h 49m

San Juan Luis Munoz Marin Intl

Wed 9/23

7:30 am-3:39 pm

1 stop8h 09m

$276

Quickest round-trip

PortlandGeorge Town

PWM - GCM

PWMGCM

Portland

Wed 8/19

6:05 am-11:39 am

1 stop6h 34m

George Town Owen Roberts Intl

Sat 8/29

1:04 pm-9:31 pm

1 stop7h 27m

$351

PortlandProvidenciales

PWM - PLS

PWMPLS

Portland

Sat 8/29

6:41 am-12:53 pm

1 stop6h 12m

Providenciales

Wed 9/2

2:13 pm-12:25 am

1 stop10h 12m

$505

PortlandOranjestad

PWM - AUA

PWMAUA

Portland

Fri 10/2

6:00 am-4:40 pm

1 stop10h 40m

Oranjestad Reina Beatrix

Tue 10/6

1:40 pm-11:52 pm

1 stop10h 12m

$508

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 June is, on average, the cheapest month to fly to Caribbean Islands from Portland, Maine, with most prices found around $118. The month of April is another great option to travel to Caribbean Islands, with average flight prices from Portland, Maine averaging around $137.

How far in advance should I book a flight from Portland, Maine 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 $471 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 $275 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 36m
Direct flights	None

The fastest flight from Portland, Maine to Caribbean Islands takes 5h 36m

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

Frequently asked questions about flying from Portland, Maine to Caribbean Islands

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 June 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 Boeing 737 MAX 8 (13.48% of total bookings). The next most popular plane models are Embraer 175 (Enhanced Winglets) (12.04%), Airbus A220-300 (11.37%), and Canadair (Bombardier) Regional Jet 900 (10.51%).

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
JetBlue	PriceFrom $156	Free Cancellation	Rating 7.1 3,012 reviews	Search JetBlue flights
Delta	PriceFrom $176	Free Cancellation	Rating 7.8 8,455 reviews	Search Delta flights
United Airlines	PriceFrom $235	Free Cancellation	Rating 7.4 9,899 reviews	Search United Airlines flights
American Airlines	PriceFrom $256	Free Cancellation	Rating 7.1 11,774 reviews	Search American Airlines flights
Southwest	PriceFrom $300	Free Cancellation	Rating 7.9 4,246 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.