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Cheap flights from Portland, Maine to Caribbean Islands from $160

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 12/6. 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
6:00 am - 11:56 pmPWM-SJU
16h 56m1 stop
American Airlines Logo
3:49 pm - 10:07 pmSJU-PWM
7h 18m1 stop
$235American Airlines
Find Deal
Mon, Jan 12 - Fri, Jan 16
United Airlines Logo
6:00 am - 9:26 pmPWM-SJU
14h 26m2 stops
United Airlines Logo
2:05 am - 2:39 pmSJU-PWM
13h 34m2 stops
$255United Airlines
Find Deal
Tue, Jan 13 - Mon, Jan 19
American Airlines Logo
6:00 am - 11:56 pmPWM-SJU
16h 56m1 stop
American Airlines Logo
6:30 am - 12:05 pmSJU-PWM
6h 35m1 stop
$260American Airlines
Find Deal
Sun, Jan 18 - Fri, Jan 23
Delta Logo
1:25 pm - 11:13 pmPWM-SJU
8h 48m1 stop
Delta Logo
7:19 am - 1:54 pmSJU-PWM
7h 35m1 stop
$278Delta
Find Deal
Sat, Nov 15 - Thu, Dec 4
United Airlines Logo
6:00 am - 2:40 pmPWM-SJU
7h 40m1 stop
United Airlines Logo
2:05 am - 9:19 amSJU-PWM
8h 14m1 stop
$281United Airlines
Find Deal
Sat, Nov 15 - Wed, Nov 19
Southwest Logo
12:45 pm - 12:35 amPWM-SJU
10h 50m2 stops
Southwest Logo
5:40 am - 2:55 pmSJU-PWM
10h 15m2 stops
$287Southwest
Find Deal
Wed, Jan 28 - Tue, Feb 3
JetBlue Logo
3:45 pm - 12:04 amPWM-SJU
7h 19m1 stop
JetBlue Logo
6:05 am - 3:40 pmSJU-PWM
10h 35m1 stop
$300JetBlue
Find Deal
Wed, Feb 11 - Sat, Feb 21
Delta Logo
2:30 pm - 11:56 pmPWM-SJU
8h 26m1 stop
Delta Logo
1:57 pm - 10:23 pmSJU-PWM
9h 26m1 stop
$319Delta
Find Deal
Mon, Nov 17 - Wed, Dec 3
JetBlue Logo
2:20 pm - 2:55 amPWM-SJU
12h 35m1 stop
JetBlue Logo
5:40 am - 1:23 pmSJU-PWM
7h 43m1 stop
$332JetBlue
Find Deal
Fri, Apr 10 - Sat, Apr 18
Southwest Logo
5:45 am - 1:45 pmPWM-SJU
7h 00m1 stop
Southwest Logo
6:10 am - 12:10 pmSJU-PWM
7h 00m1 stop
$355Southwest
Find Deal
Wed, Jan 28 - Tue, Feb 3

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 12
PWM6:00 amPortland
16h 56m
1 stop
SJU11:56 pmSan Juan Luis Munoz Marin Intl
Jan 16
SJU3:49 pmSan Juan Luis Munoz Marin Intl
7h 18m
1 stop
PWM10:07 pmPortland
$235
Find similar
American Airlines
Jan 18
PWM6:00 amPortland
16h 56m
1 stop
SJU11:56 pmSan Juan Luis Munoz Marin Intl
Jan 23
SJU6:30 amSan Juan Luis Munoz Marin Intl
6h 35m
1 stop
PWM12:05 pmPortland
$260
Find similar
American Airlines
Jan 13
PWM5:07 pmPortland
18h 23m
2 stops
SJU12:30 pmSan Juan Luis Munoz Marin Intl
Jan 20
SJU8:20 amSan Juan Luis Munoz Marin Intl
15h 34m
2 stops
PWM10:54 pmPortland
$298
Find similar

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 13
PWM6:00 amPortland
14h 26m
2 stops
SJU9:26 pmSan Juan Luis Munoz Marin Intl
Jan 19
SJU2:05 amSan Juan Luis Munoz Marin Intl
13h 34m
2 stops
PWM2:39 pmPortland
$255
Find similar
United Airlines
Nov 15
PWM6:00 amPortland
7h 40m
1 stop
SJU2:40 pmSan Juan Luis Munoz Marin Intl
Nov 19
SJU2:05 amSan Juan Luis Munoz Marin Intl
8h 14m
1 stop
PWM9:19 amPortland
$281
Find similar
United Airlines
Nov 15
PWM9:45 amPortland
10h 15m
1 stop
SJU9:00 pmSan Juan Luis Munoz Marin Intl
Nov 18
SJU2:05 amSan Juan Luis Munoz Marin Intl
8h 14m
1 stop
PWM9:19 amPortland
$304
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 November 2, 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 1/12

6:00 am-11:56 pm

1 stop16h 56m

San Juan Luis Munoz Marin Intl

Fri 1/16

3:49 pm-10:07 pm

1 stop7h 18m

$235

PortlandSan Juan

PWM - SJU

PWMSJU

Portland

Tue 1/13

6:00 am-9:26 pm

2 stops14h 26m

San Juan Luis Munoz Marin Intl

Mon 1/19

2:05 am-2:39 pm

2 stops13h 34m

$255

PortlandSan Juan

PWM - SJU

PWMSJU

Portland

Sun 1/18

6:00 am-11:56 pm

1 stop16h 56m

San Juan Luis Munoz Marin Intl

Fri 1/23

6:30 am-12:05 pm

1 stop6h 35m

$260

PortlandSan Juan

PWM - SJU

PWMSJU

Portland

Sat 11/15

1:25 pm-11:13 pm

1 stop8h 48m

San Juan Luis Munoz Marin Intl

Thu 12/4

7:19 am-1:54 pm

1 stop7h 35m

$278

PortlandSan Juan

PWM - SJU

PWMSJU

Portland

Sat 11/15

6:00 am-2:40 pm

1 stop7h 40m

San Juan Luis Munoz Marin Intl

Wed 11/19

2:05 am-9:19 am

1 stop8h 14m

$281

PortlandSan Juan

PWM - SJU

PWMSJU

Portland

Wed 1/28

12:45 pm-12:35 am

2 stops10h 50m

San Juan Luis Munoz Marin Intl

Tue 2/3

5:40 am-2:55 pm

2 stops10h 15m

$287

PortlandSan Juan

PWM - SJU

PWMSJU

Portland

Wed 2/11

3:45 pm-12:04 am

1 stop7h 19m

San Juan Luis Munoz Marin Intl

Sat 2/21

6:05 am-3:40 pm

1 stop10h 35m

$300

PortlandSan Juan

PWM - SJU

PWMSJU

Portland

Mon 11/17

2:30 pm-11:56 pm

1 stop8h 26m

San Juan Luis Munoz Marin Intl

Wed 12/3

1:57 pm-10:23 pm

1 stop9h 26m

$319

PortlandSan Juan

PWM - SJU

PWMSJU

Portland

Fri 4/10

2:20 pm-2:55 am

1 stop12h 35m

San Juan Luis Munoz Marin Intl

Sat 4/18

5:40 am-1:23 pm

1 stop7h 43m

$332

PortlandSan Juan

PWM - SJU

PWMSJU

Portland

Wed 1/28

5:45 am-1:45 pm

1 stop7h 00m

San Juan Luis Munoz Marin Intl

Tue 2/3

6:10 am-12:10 pm

1 stop7h 00m

$355

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 September is, on average, the cheapest month to fly to Caribbean Islands from Portland, Maine, with most prices found around $360. The month of October is another great option to travel to Caribbean Islands, with average flight prices from Portland, Maine averaging around $364.

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 $479 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 $342 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

Direct flights

None
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
3,119 reviews
Search Frontier flights
United AirlinesPriceFrom $249Free CancellationRating
7.4
8,993 reviews
Search United Airlines flights
DeltaPriceFrom $275Free CancellationRating
7.9
7,995 reviews
Search Delta flights
American AirlinesPriceFrom $301Free CancellationRating
7.2
11,032 reviews
Search American Airlines flights
JetBluePriceFrom $361Free CancellationRating
7.2
2,908 reviews
Search JetBlue flights
SouthwestPriceFrom $371Free CancellationRating
8.0
4,241 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.

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