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Cheap flights from Portland, Maine to Caribbean Islands from $116

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 1/31. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
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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.
JetBlue Logo
4:35 pm - 12:15 am
PWM
-
SJU
7h 40m1 stop
JetBlue Logo
5:05 am - 3:40 pm
SJU
-
PWM
10h 35m1 stop
$188JetBlue
Mon, Mar 9 - Wed, Mar 11
United Airlines Logo
2:31 pm - 6:11 am
PWM
-
SJU
14h 40m2 stops
United Airlines Logo
2:05 am - 9:01 am
SJU
-
PWM
7h 56m1 stop
$221United Airlines
Sat, Jan 31 - Mon, Feb 2
American Airlines Logo
6:00 am - 4:30 pm
PWM
-
SJU
9h 30m1 stop
American Airlines Logo
11:38 am - 11:43 pm
SJU
-
PWM
13h 05m2 stops
$231American Airlines
Sat, Jan 31 - Thu, Feb 5
JetBlue Logo
4:35 pm - 12:15 am
PWM
-
SJU
7h 40m1 stop
JetBlue Logo
7:10 am - 3:40 pm
SJU
-
PWM
8h 30m1 stop
$238JetBlue
Mon, Mar 9 - Wed, Mar 11
JetBlue Logo
4:35 pm - 1:15 am
PWM
-
SJU
7h 40m1 stop
JetBlue Logo
5:05 am - 3:40 pm
SJU
-
PWM
10h 35m1 stop
$253JetBlue
Wed, Mar 4 - Wed, Mar 11
United Airlines Logo
6:00 am - 9:00 pm
PWM
-
SJU
14h 00m2 stops
United Airlines Logo
2:05 am - 2:39 pm
SJU
-
PWM
13h 34m2 stops
$259United Airlines
Thu, Jan 8 - Tue, Jan 13
Delta Logo
6:18 am - 4:50 pm
PWM
-
SJU
9h 32m1 stop
Delta Logo
6:02 pm - 12:18 am
SJU
-
PWM
7h 16m1 stop
$275Delta
Thu, Feb 19 - Tue, Feb 24
JetBlue Logo
4:35 pm - 12:15 am
PWM
-
SJU
7h 40m1 stop
JetBlue Logo
5:01 am - 1:58 pm
SJU
-
PWM
8h 57m1 stop
$278JetBlue
Wed, Mar 11 - Sat, Mar 21
American Airlines Logo
3:58 pm - 1:42 pm
PWM
-
SXM
20h 44m2 stops
American Airlines Logo
3:09 pm - 10:07 pm
SXM
-
PWM
7h 58m1 stop
$298American Airlines
Wed, Jan 21 - Wed, Jan 28
Delta Logo
5:31 am - 4:22 pm
PWM
-
STT
9h 51m1 stop
Delta Logo
5:32 pm - 12:18 am
STT
-
PWM
7h 46m1 stop
$315Delta
Tue, Feb 24 - Tue, Mar 3

United Airlines flights from Portland, Maine to Caribbean Islands

Our best United Airlines deals on Portland, Maine to Caribbean Islands flight tickets
United Airlines
Jan 31
PWM2:31 pmPortland
14h 40m
2 stops
SJU6:11 amSan Juan Luis Munoz Marin Intl
Feb 2
SJU2:05 amSan Juan Luis Munoz Marin Intl
7h 56m
1 stop
PWM9:01 amPortland
$221
Find similar
United Airlines
Jan 8
PWM6:00 amPortland
14h 00m
2 stops
SJU9:00 pmSan Juan Luis Munoz Marin Intl
Jan 13
SJU2:05 amSan Juan Luis Munoz Marin Intl
13h 34m
2 stops
PWM2:39 pmPortland
$259
Find similar
United Airlines
Mar 4
PWM6:00 amPortland
14h 00m
2 stops
SJU9:00 pmSan Juan Luis Munoz Marin Intl
Mar 9
SJU1:05 amSan Juan Luis Munoz Marin Intl
9h 44m
1 stop
PWM10:49 amPortland
$292
Find similar

American Airlines flights from Portland, Maine to Caribbean Islands

Our best American Airlines deals on Portland, Maine to Caribbean Islands flight tickets
American Airlines
Jan 31
PWM3:58 pmPortland
6h 58m
1 stop
SJU11:56 pmSan Juan Luis Munoz Marin Intl
Feb 5
SJU8:20 amSan Juan Luis Munoz Marin Intl
14h 47m
1 stop
PWM10:07 pmPortland
$231
Find similar
American Airlines
Jan 21
PWM3:58 pmPortland
20h 44m
2 stops
SXM1:42 pmSimpson Bay Princess Juliana
Jan 28
SXM3:09 pmSimpson Bay Princess Juliana
7h 58m
1 stop
PWM10:07 pmPortland
$298
Find similar
American Airlines
Jan 29
PWM7:00 amPortland
12h 50m
1 stop
SJU8:50 pmSan Juan Luis Munoz Marin Intl
Feb 6
SJU2:28 pmSan Juan Luis Munoz Marin Intl
10h 15m
2 stops
PWM11:43 pmPortland
$303
Find similar

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 December 23, 2025.
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

PortlandSan Juan

PWM - SJU

PWMSJU

Portland

Mon 3/9

4:35 pm-12:15 am

1 stop7h 40m

San Juan Luis Munoz Marin Intl

Wed 3/11

5:05 am-3:40 pm

1 stop10h 35m

$188

PortlandSan Juan

PWM - SJU

PWMSJU

Portland

Sat 1/31

2:31 pm-6:11 am

2 stops14h 40m

San Juan Luis Munoz Marin Intl

Mon 2/2

2:05 am-9:01 am

1 stop7h 56m

$221

PortlandSan Juan

PWM - SJU

PWMSJU

Portland

Sat 1/31

6:00 am-4:30 pm

1 stop9h 30m

San Juan Luis Munoz Marin Intl

Thu 2/5

11:38 am-11:43 pm

2 stops13h 05m

$231

PortlandSan Juan

PWM - SJU

PWMSJU

Portland

Mon 3/9

4:35 pm-12:15 am

1 stop7h 40m

San Juan Luis Munoz Marin Intl

Wed 3/11

7:10 am-3:40 pm

1 stop8h 30m

$238

PortlandSan Juan

PWM - SJU

PWMSJU

Portland

Wed 3/4

4:35 pm-1:15 am

1 stop7h 40m

San Juan Luis Munoz Marin Intl

Wed 3/11

5:05 am-3:40 pm

1 stop10h 35m

$253

PortlandSan Juan

PWM - SJU

PWMSJU

Portland

Thu 1/8

6:00 am-9:00 pm

2 stops14h 00m

San Juan Luis Munoz Marin Intl

Tue 1/13

2:05 am-2:39 pm

2 stops13h 34m

$259

PortlandSan Juan

PWM - SJU

PWMSJU

Portland

Thu 2/19

6:18 am-4:50 pm

1 stop9h 32m

San Juan Luis Munoz Marin Intl

Tue 2/24

6:02 pm-12:18 am

1 stop7h 16m

$275

PortlandSan Juan

PWM - SJU

PWMSJU

Portland

Wed 3/11

4:35 pm-12:15 am

1 stop7h 40m

San Juan Luis Munoz Marin Intl

Sat 3/21

5:01 am-1:58 pm

1 stop8h 57m

$278

PortlandSimpson Bay

PWM - SXM

PWMSXM

Portland

Wed 1/21

3:58 pm-1:42 pm

2 stops20h 44m

Simpson Bay Princess Juliana

Wed 1/28

3:09 pm-10:07 pm

1 stop7h 58m

$298

PortlandSaint Thomas Island

PWM - STT

PWMSTT

Portland

Tue 2/24

5:31 am-4:22 pm

1 stop9h 51m

Saint Thomas Island Cyril E King

Tue 3/3

5:32 pm-12:18 am

1 stop7h 46m

$315

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.

What is the cheapest day to depart on your flight to Caribbean Islands?

The cheapest day to depart from Portland, Maine to Caribbean Islands is on a Wednesday. Travelers who choose to depart for Caribbean Islands on a Wednesday will often find tickets for as low as $334. If your travel schedule is flexible, try to avoid departing on a Sunday because tickets tend to average around $579. These prices are subject to change though, so be sure to set up a Price Alert for flights to Caribbean Islands.

What is the cheapest time of day to depart on your flight to Caribbean Islands?

According to our data, the cheapest time of day to fly to Caribbean Islands is in the evening. momondo users have found flights departing from Portland, Maine to Caribbean Islands in the evening for as low as $302. Keep in mind that these prices may fluctuate based on what airline you choose and the time of year you plan to travel. Try not to purchase tickets in the morning because they tend to be around $557. Of course, these prices can vary depending on the time of year and what airport you fly to.

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 $456 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
FrontierPriceFrom $145Free CancellationRating
5.8
3,076 reviews
Search Frontier flights
DeltaPriceFrom $188Free CancellationRating
7.9
8,014 reviews
Search Delta flights
JetBluePriceFrom $231Free CancellationRating
7.2
2,896 reviews
Search JetBlue flights
United AirlinesPriceFrom $241Free CancellationRating
7.4
9,103 reviews
Search United Airlines flights
American AirlinesPriceFrom $296Free CancellationRating
7.2
11,053 reviews
Search American Airlines flights
SouthwestPriceFrom $315Free CancellationRating
8.0
4,253 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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