Latest deals
Insights
FAQs
Reviews
Price Alerts

Cheap flights from Portland, Maine to Caribbean Islands from $121

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 10/4. 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

Discover deals from 900+ travel sites with momondo.

Save money when you book flights with momondo

Big names and deals

Big names and deals

Search 100s of travel sites to compare prices.

Filter for what you want

Filter for what you want

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

Trusted and free

Trusted and free

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

Price Alerts

Price Alerts

Not ready to book? to track prices.
Search flight deals

Find the cheapest flights from Portland, Maine to Caribbean Islands

Cheap round-trip flights

American Airlines Logo
5:51 am - 11:40 pmPWM-SJU
16h 49m1 stop
American Airlines Logo
5:01 pm - 10:29 pmSJU-PWM
6h 28m1 stop
$235American Airlines
Find Deal
Sat, Jan 24 - Sat, Feb 7
United Airlines Logo
9:45 am - 10:22 pmPWM-SJU
11h 37m2 stops
United Airlines Logo
2:05 am - 2:12 pmSJU-PWM
13h 07m2 stops
$255United Airlines
Find Deal
Sat, Nov 15 - Tue, Nov 18
United Airlines Logo
9:45 am - 12:36 amPWM-SJU
13h 51m2 stops
United Airlines Logo
8:30 am - 2:19 pmSJU-PWM
6h 49m1 stop
$267United Airlines
Find Deal
Sat, Nov 15 - Wed, Nov 19
JetBlue Logo
7:09 am - 2:54 pmPWM-SJU
7h 45m1 stop
JetBlue Logo
6:00 am - 1:22 pmSJU-PWM
7h 22m1 stop
$279JetBlue
Find Deal
Wed, Oct 8 - Wed, Oct 15
American Airlines Logo
5:51 am - 9:05 pmPWM-SJU
14h 14m2 stops
American Airlines Logo
5:01 pm - 10:29 pmSJU-PWM
6h 28m1 stop
$303American Airlines
Find Deal
Sat, Jan 24 - Sat, Feb 7
JetBlue Logo
7:09 am - 4:55 pmPWM-SJU
9h 46m1 stop
JetBlue Logo
3:03 am - 1:22 pmSJU-PWM
10h 19m1 stop
$304JetBlue
Find Deal
Wed, Oct 8 - Mon, Oct 13
Delta Logo
2:41 pm - 11:44 pmPWM-SJU
9h 03m1 stop
Delta Logo
1:32 pm - 12:34 amSJU-PWM
11h 02m1 stop
$321Delta
Find Deal
Mon, Sep 29 - Fri, Oct 3
Delta Logo
2:35 pm - 11:58 pmPWM-SJU
8h 23m1 stop
Delta Logo
5:56 pm - 11:49 pmSJU-PWM
6h 53m1 stop
$350Delta
Find Deal
Wed, Feb 25 - Wed, Mar 4
Southwest Logo
3:15 pm - 11:00 pmPWM-SJU
6h 45m1 stop
Southwest Logo
1:40 pm - 12:20 amSJU-PWM
11h 40m1 stop
$372Southwest
Find Deal
Sat, Nov 15 - Sat, Nov 22
Southwest Logo
3:15 pm - 11:00 pmPWM-SJU
6h 45m1 stop
Southwest Logo
6:15 pm - 12:05 amSJU-PWM
6h 50m1 stop
$425Southwest
Find Deal
Sat, Dec 6 - Mon, Dec 22

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 15
PWM9:45 amPortland
11h 37m
2 stops
SJU10:22 pmSan Juan Luis Munoz Marin Intl
Nov 18
SJU2:05 amSan Juan Luis Munoz Marin Intl
13h 07m
2 stops
PWM2:12 pmPortland
$255
Find similar
United Airlines
Nov 15
PWM9:45 amPortland
13h 51m
2 stops
SJU12:36 amSan Juan Luis Munoz Marin Intl
Nov 19
SJU8:30 amSan Juan Luis Munoz Marin Intl
6h 49m
1 stop
PWM2:19 pmPortland
$267
Find similar
United Airlines
Jan 24
PWM4:10 pmPortland
13h 01m
2 stops
SJU6:11 amSan Juan Luis Munoz Marin Intl
Feb 6
SJU2:05 amSan Juan Luis Munoz Marin Intl
13h 34m
2 stops
PWM2:39 pmPortland
$312
Find similar

JetBlue flights from Portland, Maine to Caribbean Islands

Our best JetBlue deals on Portland, Maine to Caribbean Islands flight tickets
JetBlue
Oct 8
PWM7:09 amPortland
7h 45m
1 stop
SJU2:54 pmSan Juan Luis Munoz Marin Intl
Oct 15
SJU6:00 amSan Juan Luis Munoz Marin Intl
7h 22m
1 stop
PWM1:22 pmPortland
$279
Find similar
JetBlue
Oct 8
PWM7:09 amPortland
9h 46m
1 stop
SJU4:55 pmSan Juan Luis Munoz Marin Intl
Oct 13
SJU3:03 amSan Juan Luis Munoz Marin Intl
10h 19m
1 stop
PWM1:22 pmPortland
$304
Find similar
JetBlue
Oct 9
PWM7:09 amPortland
7h 45m
1 stop
SJU2:54 pmSan Juan Luis Munoz Marin Intl
Oct 13
SJU3:03 amSan Juan Luis Munoz Marin Intl
20h 01m
1 stop
PWM11:04 pmPortland
$419
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 September 16, 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

Sat 1/24

5:51 am-11:40 pm

1 stop16h 49m

San Juan Luis Munoz Marin Intl

Sat 2/7

5:01 pm-10:29 pm

1 stop6h 28m

$235

PortlandSan Juan

PWM - SJU

PWMSJU

Portland

Sat 11/15

9:45 am-10:22 pm

2 stops11h 37m

San Juan Luis Munoz Marin Intl

Tue 11/18

2:05 am-2:12 pm

2 stops13h 07m

$255

PortlandSan Juan

PWM - SJU

PWMSJU

Portland

Sat 11/15

9:45 am-12:36 am

2 stops13h 51m

San Juan Luis Munoz Marin Intl

Wed 11/19

8:30 am-2:19 pm

1 stop6h 49m

$267

PortlandSan Juan

PWM - SJU

PWMSJU

Portland

Wed 10/8

7:09 am-2:54 pm

1 stop7h 45m

San Juan Luis Munoz Marin Intl

Wed 10/15

6:00 am-1:22 pm

1 stop7h 22m

$279

PortlandSan Juan

PWM - SJU

PWMSJU

Portland

Sat 1/24

5:51 am-9:05 pm

2 stops14h 14m

San Juan Luis Munoz Marin Intl

Sat 2/7

5:01 pm-10:29 pm

1 stop6h 28m

$303

PortlandSan Juan

PWM - SJU

PWMSJU

Portland

Wed 10/8

7:09 am-4:55 pm

1 stop9h 46m

San Juan Luis Munoz Marin Intl

Mon 10/13

3:03 am-1:22 pm

1 stop10h 19m

$304

PortlandSan Juan

PWM - SJU

PWMSJU

Portland

Mon 9/29

2:41 pm-11:44 pm

1 stop9h 03m

San Juan Luis Munoz Marin Intl

Fri 10/3

1:32 pm-12:34 am

1 stop11h 02m

$321

PortlandSan Juan

PWM - SJU

PWMSJU

Portland

Wed 2/25

2:35 pm-11:58 pm

1 stop8h 23m

San Juan Luis Munoz Marin Intl

Wed 3/4

5:56 pm-11:49 pm

1 stop6h 53m

$350

PortlandSan Juan

PWM - SJU

PWMSJU

Portland

Sat 11/15

3:15 pm-11:00 pm

1 stop6h 45m

San Juan Luis Munoz Marin Intl

Sat 11/22

1:40 pm-12:20 am

1 stop11h 40m

$372

PortlandSan Juan

PWM - SJU

PWMSJU

Portland

Sat 12/6

3:15 pm-11:00 pm

1 stop6h 45m

San Juan Luis Munoz Marin Intl

Mon 12/22

6:15 pm-12:05 am

1 stop6h 50m

$425

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first
1
2

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 January is, on average, the cheapest month to fly to Caribbean Islands from Portland, Maine, with most prices found around $349. The month of September is another great option to travel to Caribbean Islands, with average flight prices from Portland, Maine averaging around $360.

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 $489 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 $359 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
3,174 reviews
Search Frontier flights
DeltaPriceFrom $274Free CancellationRating
7.9
7,957 reviews
Search Delta flights
American AirlinesPriceFrom $281Free CancellationRating
7.2
10,000 reviews
Search American Airlines flights
United AirlinesPriceFrom $285Free CancellationRating
7.4
8,924 reviews
Search United Airlines flights
JetBluePriceFrom $361Free CancellationRating
7.2
2,914 reviews
Search JetBlue flights
SouthwestPriceFrom $425Free CancellationRating
8.0
4,242 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.
Start using Trips
Find my bookings

Get notified when prices go down

Daily price changes in your inbox - only with Price Alerts.
1 adult
Thu 10/16
Thu 10/23
By creating a price alert you accept our terms of use and privacy policy.

Find better results for your trip to Caribbean Islands

Popular cities in Caribbean Islands

Popular flights according to clicks in the last 7 days on momondo
Flights to New Yorkfrom $49
Flights to Londonfrom $318
Flights to Bangkokfrom $508
Flights to Tokyofrom $383
Flights to Los Angelesfrom $49
Flights to Parisfrom $360
Flights to Copenhagenfrom $369
Flights to Istanbulfrom $397
Flights to Manilafrom $516
Flights to Romefrom $340
Flights to Miamifrom $49
Flights to Chicagofrom $49