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San Juan

$124+ Cheap flights from Portland, ME (PWM) to San Juan

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 1/7. Fares are subject to change and may not be available on all flights or dates of travel.
PWM — SJU
Dec 13 — Dec 201
Sat 12/13
Sat 12/20
1 adult, Economy
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Cheapflights Tip: The best prices from Portland to San Juan are usually found in November or October, booked 32 days in advance, depart on a Wednesday or Tuesday and return on a Wednesday

Find flight deals from Portland to San Juan

Cheapest flights from Portland to San Juan
Explore the most affordable flight options available from Portland to San Juan. Find the lowest fares from popular airlines and budget airlines, with prices last updated on November 13, 2025.

This Southwest deal was found by Cheapflights users on 11/11. 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 12/1012:45 pmPWM - SJU
2 stops10h 50mSouthwest
Fri 12/126:10 amSJU - PWM
1 stop11h 40mSouthwest
Deal found 11/11$267
This American Airlines deal was found by Cheapflights users on 11/11. 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 12/105:46 amPWM - SJU
2 stops17h 06mAmerican Airlines
Fri 12/122:36 pmSJU - PWM
2 stops10h 01mAmerican Airlines
Deal found 11/11$298
This Southwest deal was found by Cheapflights users on 11/11. 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.
Thu 12/1112:45 pmPWM - SJU
2 stops10h 50mSouthwest
Thu 12/186:10 amSJU - PWM
1 stop11h 40mSouthwest
Deal found 11/11$369
This American Airlines deal was found by Cheapflights users on 11/11. 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.
Thu 12/117:11 amPWM - SJU
1 stop13h 54mAmerican Airlines
Thu 12/182:44 pmSJU - PWM
1 stop9h 07mAmerican Airlines
Deal found 11/11$378
This American Airlines deal was found by Cheapflights users on 11/11. 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.
Thu 12/45:46 amPWM - SJU
2 stops15h 19mAmerican Airlines
Mon 12/86:25 amSJU - PWM
1 stop12h 50mAmerican Airlines
Deal found 11/11$434
This United Airlines deal was found by Cheapflights users on 11/11. 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 12/106:00 amPWM - SJU
2 stops14h 00mUnited Airlines
Thu 12/112:05 amSJU - PWM
1 stop8h 05mUnited Airlines
Deal found 11/11$443
This United Airlines deal was found by Cheapflights users on 11/11. 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.
Thu 12/46:00 amPWM - SJU
2 stops14h 00mUnited Airlines
Sun 12/72:05 amSJU - PWM
1 stop8h 05mUnited Airlines
Deal found 11/11$460

Cheap flight deals from Portland to San Juan

Discover tips and strategies to find the most affordable flight options for your journey from Portland (PWM) to San Juan (PR1). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated November 13, 2025.

Round-trip from

$235
(American Airlines)

One-way from

$124
(American Airlines)

Popular in

February

Cheapest in

November

Average price

$322
From Portland to San Juan
Search Deals
One-way flight from Portland to San Juan
Search Deals
Highest demand for flights based on searches. 5% potential increase in price ($27 potential increase over avg. RT price).
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Cheapest flight prices on average. 2% potential price decrease ($11 potential savings vs. average RT price).
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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 San Juan 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 13, 2025.
Use the filters below to find and compare flights from Portland to San Juan that are best for you.

Fly from

Portland

Fly to

San Juan

Route

Depart

Return

Price

PortlandSan Juan

PWM - SJU

PWMSJU

Portland

Sun 1/11

6:00 am-4:21 pm

1 stop9h 21m

San Juan Luis Munoz Marin Intl

Sat 1/17

6:30 am-12:10 pm

1 stop6h 40m

$235

PortlandSan Juan

PWM - SJU

PWMSJU

Portland

Mon 5/4

2:35 pm-11:43 pm

1 stop9h 08m

San Juan Luis Munoz Marin Intl

Thu 5/7

7:00 am-1:54 pm

1 stop6h 54m

$275

PortlandSan Juan

PWM - SJU

PWMSJU

Portland

Mon 5/4

2:18 pm-10:50 pm

1 stop8h 32m

San Juan Luis Munoz Marin Intl

Wed 5/6

3:30 am-1:23 pm

1 stop9h 53m

$308

PortlandSan Juan

PWM - SJU

PWMSJU

Portland

Tue 2/3

3:12 pm-12:36 am

1 stop8h 24m

San Juan Luis Munoz Marin Intl

Fri 2/6

2:05 am-2:39 pm

2 stops13h 34m

$325

PortlandSan Juan

PWM - SJU

PWMSJU

Portland

Sat 1/24

12:35 pm-11:00 pm

1 stop9h 25m

San Juan Luis Munoz Marin Intl

Sun 2/1

6:10 am-12:25 pm

1 stop7h 15m

$361

PortlandSan Juan

PWM - SJU

PWMSJU

Portland

Wed 2/18

6:00 am-2:40 pm

1 stop7h 40m

San Juan Luis Munoz Marin Intl

Wed 2/25

8:35 am-11:20 pm

2 stops15h 45m

$361

PortlandSan Juan

PWM - SJU

PWMSJU

Portland

Sat 1/24

2:31 pm-6:11 am

2 stops14h 40m

San Juan Luis Munoz Marin Intl

Fri 2/6

2:05 am-2:39 pm

2 stops13h 34m

$365

PortlandSan Juan

PWM - SJU

PWMSJU

Portland

Wed 2/18

3:30 pm-11:10 pm

1 stop6h 40m

San Juan Luis Munoz Marin Intl

Wed 2/25

6:10 am-2:55 pm

1 stop9h 45m

$374

PortlandSan Juan

PWM - SJU

PWMSJU

Portland

Thu 12/11

12:45 pm-12:35 am

2 stops10h 50m

San Juan Luis Munoz Marin Intl

Thu 12/18

6:40 am-4:50 pm

2 stops11h 10m

$394

PortlandSan Juan

PWM - SJU

PWMSJU

Portland

Sat 1/24

3:05 pm-6:11 am

2 stops14h 06m

San Juan Luis Munoz Marin Intl

Sat 1/31

2:05 am-2:39 pm

2 stops13h 34m

$397

Flights are sorted by cheapest round-trip flights first.

Deals found on 11/12

Showing 1-10 of 16 results
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Best time to book a flight from Portland to San Juan

Have a flexible travel schedule? Discover the best time to fly to San Juan 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 San Juan

How far ahead should I book a flight from Portland, Maine to San Juan?

Use this chart to determine the optimal time to book a round-trip flight from Portland to San Juan. Price data was last updated on November 7, 2025.

To ensure you get the cheapest price possible for a flight from Portland, Maine to San Juan, you should look to book at least 32 days in advance of your intended travel date. The price of your flight may increase if you delay and leave booking until a week or so before departure.

What is the cheapest month to book a flight from Portland, Maine to San Juan?

Currently, February is the cheapest month in which you can book a flight from Portland, Maine to San Juan (average of $65). Flying from Portland, Maine to San Juan 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 SJU?

Find hourly flight availability from Portland to San Juan. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated November 13, 2025.

When flying from Portland, Maine to San Juan, the time of day you fly usually plays a role in the price. Save by searching for a flight in the evening, which can drop the price by up to 54% versus a flight in the afternoon.

How much does it cost to fly round-trip from Portland, Maine to San Juan?

Reviews of airlines servicing San Juan

Get insights into the airlines that provide service to San Juan. 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 San Juan. Reviews last updated November 13, 2025.
Read reviews from past customers who have flown Southwest, Delta, and United Airlines from Portland to San Juan. Users can see the overall rating for each airline as well as how each is rated in terms of entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.0
Very good
4,242 reviews

Food

7.0

Overall

8.0

Boarding

8.1

Comfort

8.0

Crew

8.6

Entertainment

7.5

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
4,242 reviews
Southwest
8.0
Very good
4,242 reviews

Food

7.0

Overall

8.0

Boarding

8.1

Comfort

8.0

Crew

8.6

Entertainment

7.5

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
8,007 reviews
Southwest
8.0
Very good
4,242 reviews

Food

7.0

Overall

8.0

Boarding

8.1

Comfort

8.0

Crew

8.6

Entertainment

7.5

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
9,017 reviews
Southwest
8.0
Very good
4,242 reviews

Food

7.0

Overall

8.0

Boarding

8.1

Comfort

8.0

Crew

8.6

Entertainment

7.5

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
11,051 reviews
Southwest
8.0
Very good
4,242 reviews

Food

7.0

Overall

8.0

Boarding

8.1

Comfort

8.0

Crew

8.6

Entertainment

7.5

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
2,907 reviews
Southwest
8.0
Very good
4,242 reviews

Food

7.0

Overall

8.0

Boarding

8.1

Comfort

8.0

Crew

8.6

Entertainment

7.5

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 San Juan. 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 San Juan?

    Portland (PWM), located 2.9 mi from the city center, is the airport you fly out of when you book flights from Portland to San Juan. 6 airlines have flights from Portland to San Juan on a regular basis. Booking flights from Portland to San Juan should not be difficult; the airport handles an average of 0 outbound flights to San Juan per day.

  • How long is the flight from Portland, Maine to San Juan?

    Airlines like American Airlines, Delta, and JetBlue fly from Portland, Maine to San Juan in about 8h 32m. The time it takes to get you to your destination can typically vary by up to 49m. Airlines will cover a distance of 1758 mi. Both multi-stop and nonstop flights can be found to your destination and back.

  • What are the cheapest airlines flying from Portland, Maine to San Juan round-trip?

    Our cheapest airline available from Portland, Maine to San Juan is Frontier. Our recent data shows that you can find tickets from as low as $145 on this airline. Additional options worth looking into are United Airlines and Delta, starting at $249 and $274 round-trip. Frontier is currently priced 68% below the average price you’ll pay for this route.

  • Can I find deals for flights from Portland to San Juan that include hotel bookings?

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

  • How can I find direct flights from Portland to San Juan?

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

  • Can I find deals for business class flights from Portland to San Juan?

    Yes. Cheapflights offers flight deals from Portland to San Juan 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 San Juan?

    Currently, February is the cheapest month in which you can book a flight from Portland, Maine to San Juan (average of $65). Flying from Portland, Maine to San Juan 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

Browse thousands of different options on Cheapflights for your next trip

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Top 6 airlines flying from Portland to San Juan

Discover the top 6 airlines that operate flights from Portland to San Juan. 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 13, 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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