Puerto Rico

$151+ Cheap flights from Portland, ME (PWM) to Puerto Rico

This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 8/21. Fares are subject to change and may not be available on all flights or dates of travel.
PWM — SJU
Jun 17 — Jun 241
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Cheap flight deals from Portland to Puerto Rico

Cheapest flights from Portland to Puerto Rico
Explore the most affordable flight options available from Portland to Puerto Rico. Find the lowest fares from popular airlines and budget airlines, with prices last updated on May 18, 2026.

This Delta deal was found by Cheapflights users on 5/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/192:35 pm
PWM
-
SJU
1 stop9h 09m
Delta
Sat 9/267:00 am
SJU
-
PWM
1 stop6h 54m
Delta
Deal found 5/13$302
This United Airlines deal was found by Cheapflights users on 5/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/216:00 am
PWM
-
SJU
1 stop7h 45m
United Airlines
Wed 10/287:30 am
SJU
-
PWM
1 stop7h 04m
United Airlines
Deal found 5/15$308
This American Airlines deal was found by Cheapflights users on 5/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/202:55 pm
PWM
-
SJU
1 stop8h 55m
American Airlines
Mon 10/265:25 am
SJU
-
PWM
1 stop13h 00m
American Airlines
Deal found 5/13$312
This American Airlines deal was found by Cheapflights users on 5/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/166:00 am
PWM
-
SJU
2 stops12h 10m
American Airlines
Wed 9/232:05 pm
SJU
-
PWM
2 stops9h 46m
American Airlines
Deal found 5/13$357
This Delta deal was found by Cheapflights users on 5/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/212:35 pm
PWM
-
SJU
1 stop9h 21m
Delta
Sun 10/257:00 am
SJU
-
PWM
1 stop6h 53m
Delta
Deal found 5/17$380
This Justfly.com deal was found by Cheapflights users on 5/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Justfly.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 6/132:30 pm
PWM
-
SJU
1 stop9h 02m
JetBlue
Thu 6/253:24 pm
SJU
-
PWM
1 stop9h 01m
JetBlue
Deal found 5/17$391
This United Airlines deal was found by Cheapflights users on 5/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/226:00 am
PWM
-
SJU
1 stop8h 44m
United Airlines
Wed 8/264:55 pm
SJU
-
PWM
1 stop7h 04m
United Airlines
Deal found 5/16$392
This American Airlines deal was found by Cheapflights users on 5/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/216:00 am
PWM
-
SJU
2 stops12h 05m
American Airlines
Sun 10/255:25 am
SJU
-
PWM
1 stop13h 00m
American Airlines
Deal found 5/17$397
This Southwest deal was found by Cheapflights users on 5/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/165:30 am
PWM
-
SJU
2 stops11h 00m
Southwest
Wed 10/216:10 am
SJU
-
PWM
1 stop9h 55m
Southwest
Deal found 5/15$411
This JetBlue deal was found by Cheapflights users on 5/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/222:40 pm
PWM
-
SJU
1 stop8h 49m
JetBlue
Wed 8/263:10 pm
SJU
-
PWM
1 stop9h 04m
JetBlue
Deal found 5/13$435
This Justfly.com deal was found by Cheapflights users on 5/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Justfly.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 5/316:00 am
PWM
-
SJU
1 stop16h 53m
JetBlue
Wed 6/36:30 am
SJU
-
PWM
1 stop17h 28m
JetBlue
Deal found 5/16$452
This United Airlines deal was found by Cheapflights users on 5/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/226:00 am
PWM
-
VQS
2 stops11h 39m
United Airlines
Tue 8/2511:40 am
VQS
-
PWM
2 stops11h 52m
United Airlines
Deal found 5/13$2,364

Find flight deals from Portland to Puerto Rico

Keep the following information in mind while searching for Portland to Puerto Rico flight deals. Data was last updated May 18, 2026.

Round-trip from

$302
(Delta)

One-way from

$151
(Delta)

Popular in

April

Cheapest in

October

Average price

$342
From Portland to Puerto Rico
One-way flight from Portland to Puerto Rico
Highest demand for flights based on searches. 10% potential increase in price ($53 potential increase over avg. RT price).
Cheapest flight prices on average. 5% potential price decrease ($24 potential savings vs. average RT price).
Average for round-trip flights in May 2026

Cheapflights Fare Finder

 
Customize your flight search to find flights from Portland to Puerto Rico 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, Cheapflights users made 2,558,603 searches. Data last updated May 18, 2026.
Use the filters below to find and compare flights from Portland to Puerto Rico that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

PortlandSan Juan

PWM - SJU

PWMSJU

Portland

Mon 9/21

6:00 am-1:16 pm

1 stop7h 16m

San Juan Luis Munoz Marin Intl

Fri 9/25

1:32 pm-11:59 pm

1 stop10h 27m

$302

PortlandSan Juan

PWM - SJU

PWMSJU

Portland

Sat 9/19

2:35 pm-11:44 pm

1 stop9h 09m

San Juan Luis Munoz Marin Intl

Sat 9/26

1:32 pm-11:59 pm

1 stop10h 27m

$302

PortlandSan Juan

PWM - SJU

PWMSJU

Portland

Wed 10/21

6:00 am-1:45 pm

1 stop7h 45m

San Juan Luis Munoz Marin Intl

Wed 10/28

1:20 pm-11:59 pm

2 stops10h 39m

$308
Quickest round-trip

PortlandSan Juan

PWM - SJU

PWMSJU

Portland

Sat 8/22

6:00 am-2:44 pm

1 stop8h 44m

San Juan Luis Munoz Marin Intl

Wed 8/26

4:55 pm-11:59 pm

1 stop7h 04m

$392

PortlandSan Juan

PWM - SJU

PWMSJU

Portland

Sat 8/22

2:40 pm-12:39 am

1 stop9h 59m

San Juan Luis Munoz Marin Intl

Wed 8/26

3:10 pm-12:14 am

1 stop9h 04m

$435

PortlandVieques

PWM - VQS

PWMVQS

Portland

Sat 8/22

6:00 am-5:39 pm

2 stops11h 39m

Vieques

Tue 8/25

11:40 am-11:32 pm

2 stops11h 52m

$2,364
Cheapest one-way

PortlandSan Juan

PWM - SJU

PWMSJU

Portland

Fri 8/21

6:00 am-4:33 pm

1 stop10h 33m

$151
Quickest one-way

PortlandSan Juan

PWM - SJU

PWMSJU

Portland

Sat 8/22

5:15 am-12:34 pm

1 stop7h 19m

$151

PortlandSan Juan

PWM - SJU

PWMSJU

Portland

Sun 9/6

6:00 am-4:35 pm

1 stop10h 35m

$151

PortlandSan Juan

PWM - SJU

PWMSJU

Portland

Sat 8/22

6:00 am-4:56 pm

2 stops10h 56m

$156

Flights are sorted by cheapest round-trip flights first.

Deals found on 5/14

Showing 1-10 of 13 resultsSorted by cheapest first
1
2

Best time to book a flight from Portland to Puerto Rico

Have a flexible travel schedule? Discover the best time to fly to Puerto Rico from Portland with our price prediction graph.
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.

Cheapflights Insights

Everything you need to know about your flight from Portland to Puerto Rico

How far ahead should I book a flight from Portland, Maine to Puerto Rico?

The best time to book flights from Portland, Maine to Puerto Rico is 32 days before your desired departure date. The cost of your flight will likely increase significantly if you book two weeks in advance of your flight.

What is the cheapest month to book a flight from Portland, Maine to Puerto Rico?

Currently, February is the cheapest month in which you can book a flight from Portland, Maine to Puerto Rico (average of $101). Flying from Portland, Maine to Puerto Rico in December is currently the most expensive (average of $298). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

Reviews of airlines servicing Puerto Rico

Get insights into the airlines that provide service to Puerto Rico. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Puerto Rico. Reviews last updated May 18, 2026.
Read through reviews of airlines operating flights from Portland to Puerto Rico, such as Southwest,Delta, andUnited Airlines. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.

Crew

8.6

Overall

7.9

Entertainment

7.5

Food

7.0

Comfort

8.0

Boarding

8.1

Reviews

1 / 20
2.0
Mediocre

Dominic,Mar 2026

MCO - SMF

I had to try and sleep on the floor of the Austin airport. I spent 12 hours there. The airline policies were so poor, that a near violent argument broke out between the people in front of me and the flight attendants - making for a super stressful situation at 30,000 feet. Garbage airline choice by Kayak Garbage idea to book a flight with a layover. Next time I will pay for a quality booking myself, and somehow force the company to reimburse it.

Crew

8.6

Overall

7.9

Entertainment

7.5

Food

7.0

Comfort

8.0

Boarding

8.1

Reviews

1 / 20
2.0
Mediocre

Dominic,Mar 2026

MCO - SMF

I had to try and sleep on the floor of the Austin airport. I spent 12 hours there. The airline policies were so poor, that a near violent argument broke out between the people in front of me and the flight attendants - making for a super stressful situation at 30,000 feet. Garbage airline choice by Kayak Garbage idea to book a flight with a layover. Next time I will pay for a quality booking myself, and somehow force the company to reimburse it.

Crew

8.6

Overall

7.9

Entertainment

7.5

Food

7.0

Comfort

8.0

Boarding

8.1

Reviews

1 / 20
2.0
Mediocre

Dominic,Mar 2026

MCO - SMF

I had to try and sleep on the floor of the Austin airport. I spent 12 hours there. The airline policies were so poor, that a near violent argument broke out between the people in front of me and the flight attendants - making for a super stressful situation at 30,000 feet. Garbage airline choice by Kayak Garbage idea to book a flight with a layover. Next time I will pay for a quality booking myself, and somehow force the company to reimburse it.

Crew

8.6

Overall

7.9

Entertainment

7.5

Food

7.0

Comfort

8.0

Boarding

8.1

Reviews

1 / 20
2.0
Mediocre

Dominic,Mar 2026

MCO - SMF

I had to try and sleep on the floor of the Austin airport. I spent 12 hours there. The airline policies were so poor, that a near violent argument broke out between the people in front of me and the flight attendants - making for a super stressful situation at 30,000 feet. Garbage airline choice by Kayak Garbage idea to book a flight with a layover. Next time I will pay for a quality booking myself, and somehow force the company to reimburse it.

Crew

8.6

Overall

7.9

Entertainment

7.5

Food

7.0

Comfort

8.0

Boarding

8.1

Reviews

1 / 20
2.0
Mediocre

Dominic,Mar 2026

MCO - SMF

I had to try and sleep on the floor of the Austin airport. I spent 12 hours there. The airline policies were so poor, that a near violent argument broke out between the people in front of me and the flight attendants - making for a super stressful situation at 30,000 feet. Garbage airline choice by Kayak Garbage idea to book a flight with a layover. Next time I will pay for a quality booking myself, and somehow force the company to reimburse it.

Crew

8.6

Overall

7.9

Entertainment

7.5

Food

7.0

Comfort

8.0

Boarding

8.1

Reviews

1 / 20
2.0
Mediocre

Dominic,Mar 2026

MCO - SMF

I had to try and sleep on the floor of the Austin airport. I spent 12 hours there. The airline policies were so poor, that a near violent argument broke out between the people in front of me and the flight attendants - making for a super stressful situation at 30,000 feet. Garbage airline choice by Kayak Garbage idea to book a flight with a layover. Next time I will pay for a quality booking myself, and somehow force the company to reimburse it.

Related info for your journey

Find useful and relevant information for your journey from Portland to Puerto Rico. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.
  • What airport do you fly from for flights from Portland to Puerto Rico?

    Most people fly from Portland (PWM) if they book a flight from Portland to Puerto Rico. Portland is conveniently located just 2.9 mi from Portland’s city center.

  • How long is the flight from Portland, Maine to Puerto Rico?

    A quick flight from Portland, Maine to Puerto Rico can take about 7h 16m. Delta provides one of the quickest options available for as low as $302. The distance from Portland, Maine to Puerto Rico is about 1758 mi. This flight may include one or multiple stops.

  • What are the most popular routes from Portland, Maine to Puerto Rico?

  • Can I find deals for flights from Portland to Puerto Rico that include hotel bookings?

    Yes. In addition to deals on Portland to Puerto Rico flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Portland to Puerto Rico?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Portland to Puerto Rico.

  • Can I find deals for business class flights from Portland to Puerto Rico?

    Yes. Cheapflights offers flight deals from Portland to Puerto Rico by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

  • What is the cheapest month to book a flight from Portland, Maine to Puerto Rico?

    Currently, February is the cheapest month in which you can book a flight from Portland, Maine to Puerto Rico (average of $101). Flying from Portland, Maine to Puerto Rico in December is currently the most expensive (average of $298). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

See more FAQs

Browse thousands of different options on Cheapflights for your next trip

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

Top 5 airlines flying from Portland to Puerto Rico

Discover the top 5 airlines that operate flights from Portland to Puerto Rico. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated May 18, 2026.
AirlineCheapestAverageFlexibilityOn-time
JetBlueCheapest$174Average$430FlexibilityNo cancel feeOn-time62%
DeltaCheapest$176Average$276FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$232Average$446FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$256Average$577FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$300Average$565FlexibilityNo cancel feeOn-time63%

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