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Puerto Rico

$141+ 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 4/26. Fares are subject to change and may not be available on all flights or dates of travel.
PWM — SJU
Apr 29 — May 61
Wed 4/29
Wed 5/6
1 adult, Economy
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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 March 30, 2026.

This Delta deal was found by Cheapflights users on 3/29. 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 3/29$282
This United Airlines deal was found by Cheapflights users on 3/27. 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.
Tue 11/35:06 pm
PWM
-
SJU
1 stop6h 30m
United Airlines
Wed 11/115:50 pm
SJU
-
PWM
1 stop7h 09m
United Airlines
Deal found 3/27$302
This American Airlines deal was found by Cheapflights users on 3/25. 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 8/266:00 am
PWM
-
SJU
2 stops12h 15m
American Airlines
Wed 9/26:00 am
SJU
-
PWM
1 stop13h 17m
American Airlines
Deal found 3/25$307
This United Airlines deal was found by Cheapflights users on 3/25. 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.
Mon 11/95:06 pm
PWM
-
SJU
1 stop6h 30m
United Airlines
Fri 11/135:50 pm
SJU
-
PWM
1 stop7h 09m
United Airlines
Deal found 3/25$308
This American Airlines deal was found by Cheapflights users on 3/27. 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 11/36:39 pm
PWM
-
SJU
2 stops16h 26m
American Airlines
Wed 11/116:25 am
SJU
-
PWM
1 stop12h 48m
American Airlines
Deal found 3/27$342
This Delta deal was found by Cheapflights users on 3/25. 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 9/52:35 pm
PWM
-
SJU
1 stop9h 24m
Delta
Fri 9/117:00 am
SJU
-
PWM
1 stop6h 54m
Delta
Deal found 3/25$350
This United Airlines deal was found by Cheapflights users on 3/28. 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.
Sun 4/129:49 am
PWM
-
SJU
1 stop10h 45m
United Airlines
Wed 4/151:00 am
SJU
-
PWM
1 stop8h 25m
United Airlines
Deal found 3/28$357
This United Airlines deal was found by Cheapflights users on 3/25. 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.
Tue 9/226:00 am
PWM
-
SJU
1 stop7h 45m
United Airlines
Tue 9/221:00 am
SJU
-
PWM
2 stops9h 02m
United Airlines
Deal found 3/25$367
This Kiwi.com deal was found by Cheapflights users on 3/27. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/26:18 pm
PWM
-
SJU
1 stop29h 11m
Multiple Airlines
Tue 5/123:03 am
SJU
-
PWM
2 stops13h 13m
Multiple Airlines
Deal found 3/27$368
This United Airlines deal was found by Cheapflights users on 3/29. 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 9/166:00 am
PWM
-
SJU
1 stop7h 45m
United Airlines
Tue 9/221:00 am
SJU
-
PWM
2 stops9h 02m
United Airlines
Deal found 3/29$372
This Kiwi.com deal was found by Cheapflights users on 3/27. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 5/411:29 am
PWM
-
SJU
1 stop12h 14m
Multiple Airlines
Tue 5/123:03 am
SJU
-
PWM
2 stops13h 13m
Multiple Airlines
Deal found 3/27$373
This American Airlines deal was found by Cheapflights users on 3/26. 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 5/2710:57 am
PWM
-
SJU
2 stops11h 48m
American Airlines
Wed 6/36:20 am
SJU
-
PWM
1 stop12h 09m
American Airlines
Deal found 3/26$374

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 March 30, 2026.

Round-trip from

$282
(Delta)

One-way from

$141
(Delta)

Popular in

February

Cheapest in

October

Average price

$499
From Portland to Puerto Rico
Search Deals
One-way flight from Portland to Puerto Rico
Search Deals
Highest demand for flights based on searches. 15% potential increase in price ($81 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 5% potential price decrease ($23 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in March 2026
Search Deals

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 March 30, 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

Wed 9/16

1:35 pm-10:00 pm

1 stop8h 25m

San Juan Luis Munoz Marin Intl

Wed 9/23

7:00 am-1:54 pm

1 stop6h 54m

$282

PortlandSan Juan

PWM - SJU

PWMSJU

Portland

Sun 4/12

9:49 am-8:34 pm

1 stop10h 45m

San Juan Luis Munoz Marin Intl

Wed 4/15

1:00 am-9:25 am

1 stop8h 25m

$357

PortlandSan Juan

PWM - SJU

PWMSJU

Portland

Thu 4/9

6:00 am-1:45 pm

1 stop7h 45m

San Juan Luis Munoz Marin Intl

Wed 4/15

1:00 am-9:25 am

1 stop8h 25m

$411

PortlandSan Juan

PWM - SJU

PWMSJU

Portland

Mon 9/21

6:00 am-4:31 pm

1 stop10h 31m

San Juan Luis Munoz Marin Intl

Fri 9/25

7:00 am-1:54 pm

1 stop6h 54m

$418

PortlandSan Juan

PWM - SJU

PWMSJU

Portland

Mon 8/24

5:15 am-12:54 pm

1 stop7h 39m

San Juan Luis Munoz Marin Intl

Wed 8/26

4:55 pm-11:59 pm

1 stop7h 04m

$493
Quickest round-trip

PortlandSan Juan

PWM - SJU

PWMSJU

Portland

Mon 5/25

4:50 pm-11:40 pm

1 stop6h 50m

San Juan Luis Munoz Marin Intl

Wed 5/27

3:15 pm-10:35 pm

1 stop7h 20m

$524

PortlandVieques

PWM - VQS

PWMVQS

Portland

Sat 8/22

6:00 am-5:39 pm

2 stops11h 39m

Vieques

Wed 8/26

11:40 am-11:31 pm

2 stops11h 51m

$2,364
Cheapest one-way
Quickest one-way

PortlandSan Juan

PWM - SJU

PWMSJU

Portland

Sun 4/26

5:21 am-1:25 pm

1 stop8h 04m

$141

PortlandSan Juan

PWM - SJU

PWMSJU

Portland

Sat 8/22

6:00 am-8:38 pm

2 stops14h 38m

$141

PortlandSan Juan

PWM - SJU

PWMSJU

Portland

Sat 8/22

6:00 am-11:41 pm

1 stop17h 41m

$151

Flights are sorted by cheapest round-trip flights first.

Deals found on 3/29

Showing 1-10 of 20 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

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

Currently, March is the cheapest month in which you can book a flight from Portland, Maine to Puerto Rico (average of $64). Flying from Portland, Maine to Puerto Rico in November is currently the most expensive (average of $177). 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 March 30, 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.
Southwest
8.0
Very good
4,329 reviews

Comfort

8.0

Boarding

8.1

Food

7.0

Overall

8.0

Crew

8.6

Entertainment

7.5

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.
Southwest
8.0
Very good
4,329 reviews
Southwest
8.0
Very good
4,329 reviews

Comfort

8.0

Boarding

8.1

Food

7.0

Overall

8.0

Crew

8.6

Entertainment

7.5

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.
Delta
7.9
Good
8,358 reviews
Southwest
8.0
Very good
4,329 reviews

Comfort

8.0

Boarding

8.1

Food

7.0

Overall

8.0

Crew

8.6

Entertainment

7.5

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.
United Airlines
7.4
Good
9,514 reviews
Southwest
8.0
Very good
4,329 reviews

Comfort

8.0

Boarding

8.1

Food

7.0

Overall

8.0

Crew

8.6

Entertainment

7.5

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.
JetBlue
7.2
Good
2,906 reviews
Southwest
8.0
Very good
4,329 reviews

Comfort

8.0

Boarding

8.1

Food

7.0

Overall

8.0

Crew

8.6

Entertainment

7.5

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.
American Airlines
7.1
Good
11,531 reviews
Southwest
8.0
Very good
4,329 reviews

Comfort

8.0

Boarding

8.1

Food

7.0

Overall

8.0

Crew

8.6

Entertainment

7.5

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 8h 25m. Delta provides one of the quickest options available for as low as $282. The distance from Portland, Maine to Puerto Rico is about 1758 mi. This flight may include one or multiple stops.

  • What are the cheapest airlines to fly from Portland, Maine to Puerto Rico one-way?

    $106 is the cheapest one-way deal found within the past few days, from United Airlines. You may also be able to find cheap deals on American Airlines and Southwest, with prices starting from $122 and $150, respectively.

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

    The most popular flight routes from Portland, Maine to Puerto Rico are Portland - San Juan Luis Munoz Marin Intl, Portland - Ponce Mercedita and Portland - Vieques.

  • 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, March is the cheapest month in which you can book a flight from Portland, Maine to Puerto Rico (average of $64). Flying from Portland, Maine to Puerto Rico in November is currently the most expensive (average of $177). 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

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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 March 30, 2026.
AirlineCheapestAverageFlexibilityOn-time
JetBlueCheapest$174Average$456FlexibilityNo cancel feeOn-time62%
DeltaCheapest$176Average$276FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$232Average$430FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$256Average$594FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$315Average$565FlexibilityNo cancel feeOn-time63%

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