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 68% 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, United Airlines, and Delta 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 August 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.

$139 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.

5:08 pm - 2:36 pmPWM Portland-STT Saint Thomas Island Cyril E King

20h 28m2 stops Washington, D.C. Reagan-National New York John F Kennedy Intl

4:46 pm - 12:05 pmSTT Saint Thomas Island Cyril E King-PWM Portland

20h 19m2 stops Miami Philadelphia

$200American Airlines

Tue, Feb 2 - Tue, Feb 9

5:08 pm - 2:36 pmPWM Portland-STT Saint Thomas Island Cyril E King

20h 28m2 stops Washington, D.C. Reagan-National New York John F Kennedy Intl

2:26 pm - 10:54 pmSTT Saint Thomas Island Cyril E King-PWM Portland

9h 28m1 stop Philadelphia

$200American Airlines

Tue, Feb 2 - Tue, Feb 9

6:00 am - 1:30 pmPWM Portland-NAS Nassau Intl

7h 30m1 stop Atlanta Hartsfield-Jackson

1:00 pm - 11:55 pmNAS Nassau Intl-PWM Portland

10h 55m1 stop New York John F Kennedy Intl

$326Delta

Mon, Nov 16 - Fri, Nov 20

6:00 am - 1:30 pmPWM Portland-NAS Nassau Intl

7h 30m1 stop Atlanta Hartsfield-Jackson

1:00 pm - 11:55 pmNAS Nassau Intl-PWM Portland

10h 55m1 stop New York John F Kennedy Intl

$346Delta

Mon, Nov 16 - Fri, Nov 20

5:50 am - 1:48 pmPWM Portland-NAS Nassau Intl

7h 58m1 stop Newark

12:55 pm - 11:21 pmNAS Nassau Intl-PWM Portland

10h 26m1 stop Newark

$357United Airlines

Fri, Nov 6 - Wed, Nov 11

8:29 am - 9:00 pmPWM Portland-SJU San Juan Luis Munoz Marin Intl

11h 31m1 stop Chicago O'Hare Intl

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

7h 55m1 stop Newark

$372United Airlines

Thu, Nov 12 - Mon, Nov 16

11:10 am - 10:55 pmPWM Portland-SJU San Juan Luis Munoz Marin Intl

10h 45m2 stops Baltimore/Washington Orlando

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

9h 35m2 stops Tampa Baltimore/Washington

$396Southwest

Thu, Nov 12 - Tue, Nov 17

1:40 pm - 12:55 amPWM Portland-SJU San Juan Luis Munoz Marin Intl

10h 15m2 stops Baltimore/Washington Orlando

6:40 am - 12:10 pmSJU San Juan Luis Munoz Marin Intl-PWM Portland

6h 30m1 stop Baltimore/Washington

$397Southwest

Fri, Nov 6 - Wed, Nov 11

6:00 am - 4:12 pmPWM Portland-SJU San Juan Luis Munoz Marin Intl

10h 12m1 stop New York John F Kennedy Intl

10:30 am - 11:54 pmSJU San Juan Luis Munoz Marin Intl-PWM Portland

13h 24m1 stop New York John F Kennedy Intl

$420JetBlue

Wed, Sep 16 - Wed, Sep 23

6:00 am - 1:49 pmPWM Portland-SJU San Juan Luis Munoz Marin Intl

7h 49m1 stop New York John F Kennedy Intl

3:00 pm - 11:43 pmSJU San Juan Luis Munoz Marin Intl-PWM Portland

8h 43m1 stop New York John F Kennedy Intl

$428JetBlue

Sat, Oct 24 - Wed, Oct 28

Cheap last minute flights

Enter your travel dates to find the best prices.

7:00 am - 11:59 pmPWM Portland-SJU San Juan Luis Munoz Marin Intl

16h 59m2 stops Akron/Canton Raleigh-Durham

5:37 pm - 5:58 pmSJU San Juan Luis Munoz Marin Intl-PWM Portland

24h 21m1 stop Tampa

$538Multiple Airlines

Thu, Aug 20 - Tue, Aug 25

1:05 pm - 11:50 pmPWM Portland-SJU San Juan Luis Munoz Marin Intl

10h 45m2 stops Baltimore/Washington Orlando

10:30 am - 10:05 pmSJU San Juan Luis Munoz Marin Intl-PWM Portland

11h 35m2 stops Orlando Chicago Midway

$562Southwest

Thu, Aug 20 - Tue, Aug 25

3:40 pm - 10:50 pmPWM Portland-SJU San Juan Luis Munoz Marin Intl

7h 10m1 stop Baltimore/Washington

2:25 pm - 9:10 pmSJU San Juan Luis Munoz Marin Intl-PWM Portland

6h 45m1 stop Baltimore/Washington

$562Southwest

Thu, Aug 20 - Tue, Aug 25

6:00 am - 2:44 pmPWM Portland-SJU San Juan Luis Munoz Marin Intl

8h 44m1 stop Chicago O'Hare Intl

4:55 pm - 11:32 pmSJU San Juan Luis Munoz Marin Intl-PWM Portland

30h 37m2 stops Washington, D.C. Dulles Intl Newark

$689United Airlines

Tue, Aug 18 - Thu, Sep 10

6:00 am - 8:38 pmPWM Portland-SJU San Juan Luis Munoz Marin Intl

14h 38m2 stops Chicago O'Hare Intl Houston George Bush Intcntl

4:55 pm - 11:32 pmSJU San Juan Luis Munoz Marin Intl-PWM Portland

30h 37m2 stops Washington, D.C. Dulles Intl Newark

$689United Airlines

Tue, Aug 18 - Thu, Sep 10

5:30 am - 1:40 pmPWM Portland-STT Saint Thomas Island Cyril E King

8h 10m1 stop Philadelphia

1:48 pm - 9:21 amSTT Saint Thomas Island Cyril E King-PWM Portland

19h 33m2 stops Miami New York LaGuardia

$985American Airlines

Sat, Aug 22 - Sun, Aug 23

6:02 am - 2:59 pmPWM Portland-STT Saint Thomas Island Cyril E King

8h 57m2 stops Washington, D.C. Reagan-National Charlotte Douglas

1:48 pm - 9:21 amSTT Saint Thomas Island Cyril E King-PWM Portland

19h 33m2 stops Miami New York LaGuardia

$985American Airlines

Sat, Aug 22 - Sun, Aug 23

7:35 pm - 12:58 pmPWM Portland-STT Saint Thomas Island Cyril E King

17h 23m1 stop Washington, D.C. Dulles Intl

5:45 pm - 9:08 amSTT Saint Thomas Island Cyril E King-PWM Portland

15h 23m2 stops San Juan Luis Munoz Marin Intl Newark

$1,058Multiple Airlines

Fri, Aug 21 - Sat, Aug 22

6:53 pm - 12:58 pmPWM Portland-STT Saint Thomas Island Cyril E King

18h 05m2 stops Newark Washington, D.C. Dulles Intl

5:45 pm - 9:08 amSTT Saint Thomas Island Cyril E King-PWM Portland

15h 23m2 stops San Juan Luis Munoz Marin Intl Newark

$1,058Multiple Airlines

Fri, Aug 21 - Sat, Aug 22

5:45 am - 1:10 pmPWM Portland-MBJ Montego Bay Sangster Intl

8h 25m2 stops Baltimore/Washington Orlando

12:15 pm - 10:25 pmMBJ Montego Bay Sangster Intl-PWM Portland

9h 10m2 stops Orlando Baltimore/Washington

$1,263Southwest

Tue, Aug 18 - Thu, Aug 20

Save money when you book flights with momondo

Big names and deals

Search 100s of travel sites to compare prices.

Filter for what you want

Free Wi-Fi? Stopover? Instantly customize your results.

Trusted and free

We’re completely free to use - no hidden charges or fees.

Price Alerts

Not ready to book? to track prices.

Search flight deals

Southwest flights from Portland, Maine to Caribbean Islands

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

Southwest

Nov 12

PWM11:10 amPortland

10h 45m

2 stops

SJU10:55 pmSan Juan Luis Munoz Marin Intl

Nov 17

SJU6:10 amSan Juan Luis Munoz Marin Intl

9h 35m

2 stops

PWM2:45 pmPortland

$396

Southwest

Nov 6

PWM1:40 pmPortland

10h 15m

2 stops

SJU12:55 amSan Juan Luis Munoz Marin Intl

Nov 11

SJU6:10 amSan Juan Luis Munoz Marin Intl

9h 35m

2 stops

PWM2:45 pmPortland

$397

Southwest

Nov 13

PWM1:40 pmPortland

10h 15m

2 stops

SJU12:55 amSan Juan Luis Munoz Marin Intl

Nov 16

SJU5:40 amSan Juan Luis Munoz Marin Intl

10h 05m

2 stops

PWM2:45 pmPortland

$400

United Airlines flights from Portland, Maine to Caribbean Islands

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

United Airlines

Nov 6

PWM5:50 amPortland

7h 58m

1 stop

NAS1:48 pmNassau Intl

Nov 11

NAS12:55 pmNassau Intl

10h 26m

1 stop

PWM11:21 pmPortland

$357

United Airlines

Sep 10

PWM3:47 pmPortland

8h 03m

1 stop

SJU11:50 pmSan Juan Luis Munoz Marin Intl

Sep 12

SJU1:00 amSan Juan Luis Munoz Marin Intl

9h 04m

2 stops

PWM10:04 amPortland

$372

United Airlines

Oct 24

PWM8:03 amPortland

29h 12m

1 stop

GCM12:15 pmGeorge Town Owen Roberts Intl

Oct 31

GCM1:25 pmGeorge Town Owen Roberts Intl

8h 56m

1 stop

PWM11:21 pmPortland

$384

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 Portland - STT Saint Thomas Island Cyril E King

PWMSTT

Portland

Tue 2/2

5:08 pm-2:36 pm

2 stops20h 28m

Saint Thomas Island Cyril E King

Tue 2/9

4:46 pm-12:05 pm

2 stops20h 19m

$200

PortlandSaint Thomas Island

PWM Portland - STT Saint Thomas Island Cyril E King

PWMSTT

Portland

Tue 2/2

5:08 pm-2:36 pm

2 stops20h 28m

Saint Thomas Island Cyril E King

Tue 2/9

2:26 pm-10:54 pm

1 stop9h 28m

$200

PortlandNassau

PWM Portland - NAS Nassau Intl

PWMNAS

Portland

Mon 11/16

6:00 am-1:30 pm

1 stop7h 30m

Nassau Intl

Fri 11/20

1:00 pm-11:55 pm

1 stop10h 55m

$326

PortlandNassau

PWM Portland - NAS Nassau Intl

PWMNAS

Portland

Mon 11/16

6:00 am-1:30 pm

1 stop7h 30m

Nassau Intl

Fri 11/20

1:00 pm-11:55 pm

1 stop10h 55m

$346

PortlandNassau

PWM Portland - NAS Nassau Intl

PWMNAS

Portland

Fri 11/6

5:50 am-1:48 pm

1 stop7h 58m

Nassau Intl

Wed 11/11

12:55 pm-11:21 pm

1 stop10h 26m

$357

PortlandSan Juan

PWM Portland - SJU San Juan Luis Munoz Marin Intl

PWMSJU

Portland

Thu 11/12

8:29 am-9:00 pm

1 stop11h 31m

San Juan Luis Munoz Marin Intl

Mon 11/16

2:05 am-9:00 am

1 stop7h 55m

$372

PortlandSan Juan

PWM Portland - SJU San Juan Luis Munoz Marin Intl

PWMSJU

Portland

Thu 11/12

11:10 am-10:55 pm

2 stops10h 45m

San Juan Luis Munoz Marin Intl

Tue 11/17

6:10 am-2:45 pm

2 stops9h 35m

$396

PortlandSan Juan

PWM Portland - SJU San Juan Luis Munoz Marin Intl

PWMSJU

Portland

Fri 11/6

1:40 pm-12:55 am

2 stops10h 15m

San Juan Luis Munoz Marin Intl

Wed 11/11

6:40 am-12:10 pm

1 stop6h 30m

$397

PortlandSan Juan

PWM Portland - SJU San Juan Luis Munoz Marin Intl

PWMSJU

Portland

Wed 9/16

6:00 am-4:12 pm

1 stop10h 12m

San Juan Luis Munoz Marin Intl

Wed 9/23

10:30 am-11:54 pm

1 stop13h 24m

$420

Quickest round-trip

PortlandSan Juan

PWM Portland - SJU San Juan Luis Munoz Marin Intl

PWMSJU

Portland

Sat 10/24

6:00 am-1:49 pm

1 stop7h 49m

San Juan Luis Munoz Marin Intl

Wed 10/28

3:00 pm-11:43 pm

1 stop8h 43m

$428

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 January is, on average, the cheapest month to fly to Caribbean Islands from Portland, Maine, with most prices found around $468. The month of May is another great option to travel to Caribbean Islands, with average flight prices from Portland, Maine averaging around $552.

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 $500 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 $287 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

Best Price Found	$139
Fastest flight time	5h 55m
Direct flights	None

The best one-way flight to Caribbean Islands from Portland, Maine in the past 72 hours is $139. The best round-trip flight deal from Portland, Maine to Caribbean Islands found on momondo in the last 72 hours is $200.

The fastest flight from Portland, Maine to Caribbean Islands takes 5h 55m

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 August 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 (14.77% of total bookings). The next most popular plane models are Embraer 175 (Enhanced Winglets) (12.69%), Embraer 170 (10.11%), and Airbus A220-300 (10.05%).

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 $174	Free Cancellation	Rating 7.1 3,032 reviews	Search JetBlue flights
Delta	PriceFrom $216	Free Cancellation	Rating 7.8 8,503 reviews	Search Delta flights
United Airlines	PriceFrom $247	Free Cancellation	Rating 7.4 10,106 reviews	Search United Airlines flights
American Airlines	PriceFrom $256	Free Cancellation	Rating 7.1 11,946 reviews	Search American Airlines flights
Southwest	PriceFrom $315	Free Cancellation	Rating 8.0 4,218 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.