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Puerto Rico

$160+ 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 12/6. Fares are subject to change and may not be available on all flights or dates of travel.
PWM — SJU
Dec 4 — Dec 111
Thu 12/4
Thu 12/11
1 adult, Economy
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Find 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 November 4, 2025.

This American Airlines deal was found by Cheapflights users on 11/3. 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.
Sun 12/77:11 amPWM - SJU
1 stop13h 54mAmerican Airlines
Wed 12/104:50 pmSJU - PWM
1 stop7h 02mAmerican Airlines
Deal found 11/3$235
This United Airlines deal was found by Cheapflights users on 11/1. 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 11/156:00 amPWM - SJU
1 stop7h 40mUnited Airlines
Wed 11/192:05 amSJU - PWM
2 stops13h 07mUnited Airlines
Deal found 11/1$281
This Delta deal was found by Cheapflights users on 11/1. 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 11/151:25 pmPWM - SJU
1 stop8h 48mDelta
Thu 11/207:15 amSJU - PWM
1 stop7h 35mDelta
Deal found 11/1$322
This United Airlines deal was found by Cheapflights users on 11/3. 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 12/76:00 amPWM - SJU
1 stop7h 40mUnited Airlines
Tue 12/92:05 amSJU - PWM
1 stop8h 05mUnited Airlines
Deal found 11/3$329
This Southwest deal was found by Cheapflights users on 11/2. 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.
Tue 12/212:45 pmPWM - SJU
2 stops10h 50mSouthwest
Tue 12/96:40 amSJU - PWM
1 stop6h 30mSouthwest
Deal found 11/2$337
This Southwest deal was found by Cheapflights users on 11/2. 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.
Wed 12/312:45 pmPWM - SJU
2 stops10h 50mSouthwest
Tue 12/96:40 amSJU - PWM
1 stop9h 15mSouthwest
Deal found 11/2$372
This Kiwi.com deal was found by Cheapflights users on 11/3. 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 11/2211:16 amPWM - SJU
1 stop12h 08mMultiple Airlines
Wed 11/267:11 amSJU - PWM
2 stops32h 19mMultiple Airlines
Deal found 11/3$377

Cheap 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 November 4, 2025.

Round-trip from

$235
(American Airlines)

One-way from

$160
(Kiwi.com)

Popular in

February

Cheapest in

September

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. 6% potential increase in price ($34 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 3% potential price decrease ($15 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in November 2025
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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 November 4, 2025.
Use the filters below to find and compare flights from Portland to Puerto Rico that are best for you.

Fly from

Portland

Fly to

Puerto Rico

Route

Depart

Return

Price

PortlandSan Juan

PWM - SJU

PWMSJU

Portland

Thu 2/5

6:00 am-9:00 pm

2 stops14h 00m

San Juan Luis Munoz Marin Intl

Tue 2/10

2:05 am-9:01 am

1 stop7h 56m

$266

PortlandSan Juan

PWM - SJU

PWMSJU

Portland

Mon 1/12

8:40 am-9:00 pm

2 stops11h 20m

San Juan Luis Munoz Marin Intl

Fri 1/16

8:10 am-2:31 pm

1 stop7h 21m

$272

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

Tue 2/3

5:20 am-6:22 pm

2 stops12h 02m

San Juan Luis Munoz Marin Intl

Wed 2/11

6:00 am-3:31 pm

2 stops10h 31m

$298

PortlandSan Juan

PWM - SJU

PWMSJU

Portland

Sun 2/22

4:50 pm-1:05 am

1 stop7h 15m

San Juan Luis Munoz Marin Intl

Thu 2/26

3:15 pm-11:50 pm

2 stops9h 35m

$299

PortlandSan Juan

PWM - SJU

PWMSJU

Portland

Tue 2/3

5:45 am-1:45 pm

1 stop7h 00m

San Juan Luis Munoz Marin Intl

Wed 2/11

6:10 am-12:10 pm

1 stop7h 00m

$299

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

Sat 11/15

1:25 pm-11:13 pm

1 stop8h 48m

San Juan Luis Munoz Marin Intl

Thu 11/20

7:15 am-1:50 pm

1 stop7h 35m

$322

PortlandSan Juan

PWM - SJU

PWMSJU

Portland

Sat 2/21

3:20 pm-12:40 am

1 stop8h 20m

San Juan Luis Munoz Marin Intl

Wed 2/25

6:10 am-12:10 pm

1 stop7h 00m

$324

PortlandVieques

PWM - VQS

PWMVQS

Portland

Tue 2/24

9:40 am-3:53 pm

2 stops29h 13m

Vieques

Thu 2/26

11:44 am-8:28 pm

2 stops9h 44m

$5,529

Flights are sorted by cheapest round-trip flights first.

Deals found on 11/2

Showing 1-10 of 19 results
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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, February is the cheapest month in which you can book a flight from Portland, Maine to Puerto Rico (average of $65). Flying from Portland, Maine to Puerto Rico in September is currently the most expensive (average of $147). 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.

What is the cheapest time of day to fly from PWM to PR?

Find hourly flight availability from Portland to Puerto Rico. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated November 4, 2025.

Unlike in the afternoon, when flights are generally more expensive, you can save up to 49% on flights from Portland, Maine to Puerto Rico by exploring options for tickets at noon.

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 November 4, 2025.
Read through reviews of airlines operating flights from Portland to Puerto Rico, such as Southwest, Delta, and United Airlines. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.0
Very good
4,239 reviews

Crew

8.6

Comfort

8.0

Boarding

8.1

Entertainment

7.5

Food

7.0

Overall

8.0

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
Southwest
8.0
Very good
4,239 reviews
Southwest
8.0
Very good
4,239 reviews

Crew

8.6

Comfort

8.0

Boarding

8.1

Entertainment

7.5

Food

7.0

Overall

8.0

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
Delta
7.9
Good
8,003 reviews
Southwest
8.0
Very good
4,239 reviews

Crew

8.6

Comfort

8.0

Boarding

8.1

Entertainment

7.5

Food

7.0

Overall

8.0

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
United Airlines
7.4
Good
9,002 reviews
Southwest
8.0
Very good
4,239 reviews

Crew

8.6

Comfort

8.0

Boarding

8.1

Entertainment

7.5

Food

7.0

Overall

8.0

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
American Airlines
7.2
Good
11,040 reviews
Southwest
8.0
Very good
4,239 reviews

Crew

8.6

Comfort

8.0

Boarding

8.1

Entertainment

7.5

Food

7.0

Overall

8.0

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
JetBlue
7.2
Good
2,908 reviews
Southwest
8.0
Very good
4,239 reviews

Crew

8.6

Comfort

8.0

Boarding

8.1

Entertainment

7.5

Food

7.0

Overall

8.0

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines

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 14h. United Airlines provides one of the quickest options available for as low as $266. The distance from Portland, Maine to Puerto Rico is about 1758 mi.

  • 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 - Vieques and Portland - Ponce Mercedita.

  • 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 $65). Flying from Portland, Maine to Puerto Rico in September is currently the most expensive (average of $147). 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

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Alternative routes for Portland to Puerto Rico

See prices for flight routes from nearby airports that may be better suited for you.
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Top 6 airlines flying from Portland to Puerto Rico

Discover the top 6 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 November 4, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$145Average$228FlexibilityNo cancel feeOn-time62%
United AirlinesCheapest$249Average$588FlexibilityNo cancel feeOn-time69%
DeltaCheapest$274Average$382FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$301Average$577FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$348Average$607FlexibilityNo cancel feeOn-time63%
JetBlueCheapest$361Average$508FlexibilityNo cancel feeOn-time62%

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