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Cheap flights from Portland, Maine to Caribbean Islands from $112

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Portland, Maine to Caribbean Islands departing on 2/25. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
1 adult
0 bags

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Find the cheapest flights from Portland, Maine to Caribbean Islands

Cheap round-trip flights

Enter your travel dates to find the best prices.
American Airlines Logo
6:49 pm - 1:03 pm
PWM
-
STT
17h 14m
2 stops
American Airlines Logo
2:03 pm - 10:59 pm
STT
-
PWM
8h 56m
1 stop
$214American Airlines
Sat, Mar 7 - Wed, Mar 11
American Airlines Logo
6:36 pm - 1:23 pm
PWM
-
STT
17h 47m
1 stop
American Airlines Logo
6:25 pm - 11:59 am
STT
-
PWM
18h 34m
2 stops
$250American Airlines
Tue, Feb 24 - Tue, Mar 3
United Airlines Logo
5:20 am - 12:34 pm
PWM
-
SJU
7h 14m
1 stop
United Airlines Logo
1:25 pm - 11:50 pm
SJU
-
PWM
10h 25m
2 stops
$250United Airlines
Tue, May 26 - Fri, May 29
Delta Logo
5:31 am - 3:04 pm
PWM
-
STT
8h 33m
1 stop
Delta Logo
3:00 pm - 11:22 pm
STT
-
PWM
8h 22m
1 stop
$270Delta
Tue, Mar 3 - Mon, Mar 9
Southwest Logo
3:55 pm - 12:05 am
PWM
-
SJU
7h 10m
1 stop
Southwest Logo
6:30 am - 1:45 pm
SJU
-
PWM
8h 15m
1 stop
$276Southwest
Mon, Feb 23 - Fri, Feb 27
Delta Logo
5:31 am - 3:04 pm
PWM
-
STT
8h 33m
1 stop
Delta Logo
5:32 pm - 12:18 am
STT
-
PWM
7h 46m
1 stop
$286Delta
Sun, Feb 22 - Thu, Feb 26
JetBlue Logo
2:18 pm - 10:50 pm
PWM
-
SJU
8h 32m
1 stop
JetBlue Logo
3:30 am - 1:23 pm
SJU
-
PWM
9h 53m
1 stop
$289JetBlue
Tue, May 26 - Thu, May 28
Delta Logo
5:21 am - 2:48 pm
PWM
-
STT
9h 27m
1 stop
Delta Logo
3:59 pm - 12:46 am
STT
-
PWM
8h 47m
1 stop
$296Delta
Tue, Apr 28 - Mon, May 4
United Airlines Logo
9:39 am - 8:34 pm
PWM
-
SJU
10h 55m
1 stop
United Airlines Logo
1:00 am - 10:18 am
SJU
-
PWM
9h 18m
2 stops
$297United Airlines
Tue, May 5 - Tue, May 5
JetBlue Logo
2:18 pm - 10:09 am
PWM
-
SJU
19h 51m
2 stops
JetBlue Logo
1:50 pm - 11:36 pm
SJU
-
PWM
9h 46m
1 stop
$308JetBlue
Wed, May 27 - Wed, Jun 3

Southwest flights from Portland, Maine to Caribbean Islands

Our best Southwest deals on Portland, Maine to Caribbean Islands flight tickets
Southwest
Feb 23
PWM3:55 pmPortland
7h 10m
1 stop
SJU12:05 amSan Juan Luis Munoz Marin Intl
Feb 27
SJU6:30 amSan Juan Luis Munoz Marin Intl
8h 15m
1 stop
PWM1:45 pmPortland
$276
Southwest
Jun 3
PWM1:00 pmPortland
10h 40m
2 stops
SJU11:40 pmSan Juan Luis Munoz Marin Intl
Jun 7
SJU5:15 pmSan Juan Luis Munoz Marin Intl
6h 50m
1 stop
PWM12:05 amPortland
$392
Southwest
Jun 11
PWM3:10 pmPortland
10h 10m
2 stops
SJU1:20 amSan Juan Luis Munoz Marin Intl
Jun 15
SJU5:15 pmSan Juan Luis Munoz Marin Intl
6h 50m
1 stop
PWM12:05 amPortland
$406

JetBlue flights from Portland, Maine to Caribbean Islands

Our best JetBlue deals on Portland, Maine to Caribbean Islands flight tickets
JetBlue
May 26
PWM2:18 pmPortland
8h 32m
1 stop
SJU10:50 pmSan Juan Luis Munoz Marin Intl
May 28
SJU3:30 amSan Juan Luis Munoz Marin Intl
9h 53m
1 stop
PWM1:23 pmPortland
$289
JetBlue
May 27
PWM2:18 pmPortland
19h 51m
2 stops
SJU10:09 amSan Juan Luis Munoz Marin Intl
Jun 3
SJU1:50 pmSan Juan Luis Munoz Marin Intl
9h 46m
1 stop
PWM11:36 pmPortland
$308
JetBlue
May 27
PWM2:18 pmPortland
8h 32m
1 stop
SJU10:50 pmSan Juan Luis Munoz Marin Intl
Jun 3
SJU1:50 pmSan Juan Luis Munoz Marin Intl
9h 46m
1 stop
PWM11:36 pmPortland
$324

momondo Fare Finder

 
Customize your flight search to find flights from Portland, Maine to Caribbean Islands that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, momondo users made 832,500 searches. Data last updated February 8, 2026.
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

PortlandSaint Thomas Island

PWM - STT

PWMSTT

Portland

Sat 3/7

6:49 pm-1:03 pm

2 stops17h 14m

Saint Thomas Island Cyril E King

Wed 3/11

2:03 pm-10:59 pm

1 stop8h 56m

$214

PortlandSaint Thomas Island

PWM - STT

PWMSTT

Portland

Tue 2/24

6:36 pm-1:23 pm

1 stop17h 47m

Saint Thomas Island Cyril E King

Tue 3/3

6:25 pm-11:59 am

2 stops18h 34m

$250

PortlandSan Juan

PWM - SJU

PWMSJU

Portland

Tue 5/26

5:20 am-12:34 pm

1 stop7h 14m

San Juan Luis Munoz Marin Intl

Fri 5/29

1:25 pm-11:50 pm

2 stops10h 25m

$250

PortlandSaint Thomas Island

PWM - STT

PWMSTT

Portland

Tue 3/3

5:31 am-3:04 pm

1 stop8h 33m

Saint Thomas Island Cyril E King

Mon 3/9

3:00 pm-11:22 pm

1 stop8h 22m

$270

PortlandSan Juan

PWM - SJU

PWMSJU

Portland

Mon 2/23

3:55 pm-12:05 am

1 stop7h 10m

San Juan Luis Munoz Marin Intl

Fri 2/27

6:30 am-1:45 pm

1 stop8h 15m

$276

PortlandSaint Thomas Island

PWM - STT

PWMSTT

Portland

Sun 2/22

5:31 am-3:04 pm

1 stop8h 33m

Saint Thomas Island Cyril E King

Thu 2/26

5:32 pm-12:18 am

1 stop7h 46m

$286

PortlandSan Juan

PWM - SJU

PWMSJU

Portland

Tue 5/26

2:18 pm-10:50 pm

1 stop8h 32m

San Juan Luis Munoz Marin Intl

Thu 5/28

3:30 am-1:23 pm

1 stop9h 53m

$289

PortlandSaint Thomas Island

PWM - STT

PWMSTT

Portland

Tue 4/28

5:21 am-2:48 pm

1 stop9h 27m

Saint Thomas Island Cyril E King

Mon 5/4

3:59 pm-12:46 am

1 stop8h 47m

$296

PortlandSan Juan

PWM - SJU

PWMSJU

Portland

Tue 5/5

9:39 am-8:34 pm

1 stop10h 55m

San Juan Luis Munoz Marin Intl

Tue 5/5

1:00 am-10:18 am

2 stops9h 18m

$297

PortlandSan Juan

PWM - SJU

PWMSJU

Portland

Wed 5/27

2:18 pm-10:09 am

2 stops19h 51m

San Juan Luis Munoz Marin Intl

Wed 6/3

1:50 pm-11:36 pm

1 stop9h 46m

$308

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first
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See travel insights to Caribbean Islands from

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

What is the cheapest month to fly to Caribbean Islands?

The month of November is, on average, the cheapest month to fly to Caribbean Islands from Portland, Maine, with most prices found around $322. The month of October is another great option to travel to Caribbean Islands, with average flight prices from Portland, Maine averaging around $343.

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 $455 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 53m

Direct flights

None
The fastest flight from Portland, Maine to Caribbean Islands takes 5h 53m
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?

  • 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?

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
DeltaPriceFrom $176Free CancellationRating
7.9
8,172 reviews
Search Delta flights
JetBluePriceFrom $190Free CancellationRating
7.2
2,896 reviews
Search JetBlue flights
United AirlinesPriceFrom $241Free CancellationRating
7.4
9,254 reviews
Search United Airlines flights
American AirlinesPriceFrom $256Free CancellationRating
7.2
11,249 reviews
Search American Airlines flights
SouthwestPriceFrom $315Free CancellationRating
8.0
4,280 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.

An easier way to manage your Caribbean Islands trip

We make it super easy to schedule, organize and travel with friends or family. Trips is free — and available to use no matter where you book.
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