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$121+ 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 10/16. Fares are subject to change and may not be available on all flights or dates of travel.
PWM — SJU
ago. 19 — ago. 261
mar. 8/19
mar. 8/26
1 adult, Economy
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Cheapflights Tip: The best prices from Portland to San Juan are usually found in September or October, booked 32 days in advance, depart on a Wednesday or Tuesday and return on a Wednesday

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 agosto 14, 2025.

Round-trip from

$210
(American Airlines)

One-way from

$121
(Trip.com)

Popular in

December

Cheapest in

September

Average price

$589
From Portland to San Juan
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One-way flight from Portland to San Juan
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Highest demand for flights based on searches. 3% potential increase in price ($19 potential increase over avg. RT price).
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Cheapest flight prices on average. 3% potential price decrease ($18 potential savings vs. average RT price).
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Average for round-trip flights in August 2025
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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 agosto 14, 2025.

This American Airlines deal was found by Cheapflights users on 8/14. 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.
mié. 10/154:15 pmPWM - SJU
1 stop7h 44mAmerican Airlines
jue. 10/165:30 amSJU - PWM
1 stop17h 18mAmerican Airlines
Deal found 8/14$210
This American Airlines deal was found by Cheapflights users on 8/12. 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.
mié. 10/157:44 amPWM - SJU
1 stop16h 15mAmerican Airlines
sáb. 10/185:30 amSJU - PWM
2 stops15h 51mAmerican Airlines
Deal found 8/12$215
This Delta deal was found by Cheapflights users on 8/12. 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.
dom. 11/165:40 amPWM - SJU
1 stop10h 35mDelta
mié. 11/193:30 pmSJU - PWM
1 stop7h 29mDelta
Deal found 8/12$275
This JetBlue deal was found by Cheapflights users on 8/14. 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.
jue. 10/22:17 pmPWM - SJU
1 stop7h 07mJetBlue
lun. 10/66:00 amSJU - PWM
1 stop7h 22mJetBlue
Deal found 8/14$282
This JetBlue deal was found by Cheapflights users on 8/12. 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.
mié. 10/152:17 pmPWM - SJU
1 stop7h 07mJetBlue
vie. 10/173:03 amSJU - PWM
1 stop10h 19mJetBlue
Deal found 8/12$294
This American Airlines deal was found by Cheapflights users on 8/14. 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.
jue. 10/27:05 amPWM - SJU
2 stops16h 32mAmerican Airlines
lun. 10/67:00 pmSJU - PWM
2 stops16h 54mAmerican Airlines
Deal found 8/14$300
This Southwest deal was found by Cheapflights users on 8/12. 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.
dom. 11/165:30 amPWM - SJU
2 stops10h 35mSouthwest
mié. 11/196:40 amSJU - PWM
1 stop9h 15mSouthwest
Deal found 8/12$310
This United Airlines deal was found by Cheapflights users on 8/14. 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.
mié. 10/156:00 amPWM - SJU
1 stop7h 45mUnited Airlines
mié. 10/151:05 amSJU - PWM
1 stop8h 06mUnited Airlines
Deal found 8/14$346
This Southwest deal was found by Cheapflights users on 8/12. 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.
jue. 11/133:00 pmPWM - SJU
1 stop9h 25mSouthwest
lun. 11/176:40 amSJU - PWM
1 stop6h 30mSouthwest
Deal found 8/12$359
This United Airlines deal was found by Cheapflights users on 8/12. 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.
mié. 10/156:00 amPWM - SJU
1 stop7h 45mUnited Airlines
vie. 10/171:05 amSJU - PWM
2 stops13h 28mUnited Airlines
Deal found 8/12$363

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 agosto 14, 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

mié. 10/15

4:15 pm-11:59 pm

1 stop7h 44m

San Juan Luis Munoz Marin Intl

jue. 10/16

5:30 am-10:48 pm

1 stop17h 18m

$210

PortlandSan Juan

PWM - SJU

PWMSJU

Portland

mié. 10/15

4:15 pm-11:59 pm

1 stop7h 44m

San Juan Luis Munoz Marin Intl

sáb. 10/18

5:30 am-3:10 pm

1 stop9h 40m

$215

PortlandSan Juan

PWM - SJU

PWMSJU

Portland

dom. 10/5

6:35 am-4:20 pm

1 stop9h 45m

San Juan Luis Munoz Marin Intl

jue. 10/9

1:06 pm-12:05 am

1 stop10h 59m

$275

PortlandSan Juan

PWM - SJU

PWMSJU

Portland

jue. 10/2

7:30 am-4:55 pm

1 stop9h 25m

San Juan Luis Munoz Marin Intl

dom. 10/5

3:03 am-1:22 pm

1 stop10h 19m

$282

PortlandSan Juan

PWM - SJU

PWMSJU

Portland

mié. 10/15

2:17 pm-9:24 pm

1 stop7h 07m

San Juan Luis Munoz Marin Intl

vie. 10/17

3:03 am-1:22 pm

1 stop10h 19m

$294

PortlandSan Juan

PWM - SJU

PWMSJU

Portland

jue. 10/2

7:05 am-11:37 pm

2 stops16h 32m

San Juan Luis Munoz Marin Intl

lun. 10/6

7:00 pm-11:54 am

2 stops16h 54m

$300

PortlandSan Juan

PWM - SJU

PWMSJU

Portland

mié. 10/15

6:00 am-1:45 pm

1 stop7h 45m

San Juan Luis Munoz Marin Intl

mié. 10/15

1:05 am-9:11 am

1 stop8h 06m

$346

PortlandSan Juan

PWM - SJU

PWMSJU

Portland

mié. 10/15

6:00 am-1:45 pm

1 stop7h 45m

San Juan Luis Munoz Marin Intl

vie. 10/17

1:05 am-2:33 pm

2 stops13h 28m

$363

PortlandSan Juan

PWM - SJU

PWMSJU

Portland

jue. 10/16

2:17 pm-9:24 pm

1 stop7h 07m

$121

PortlandSan Juan

PWM - SJU

PWMSJU

Portland

jue. 10/16

7:00 am-3:54 pm

2 stops8h 54m

$261

Flights are sorted by cheapest round-trip flights first.

Deals found on 8/12

Showing 1-10 of 11 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 August 8, 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, September is the cheapest month in which you can book a flight from Portland, Maine to San Juan (average of $254). Flying from Portland, Maine to San Juan in June is currently the most expensive (average of $339). 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 agosto 14, 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 46% versus a flight in the morning.

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 agosto 14, 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
4,244 reviews

Boarding

8.1

Entertainment

7.5

Comfort

8.0

Overall

8.0

Crew

8.6

Food

7.0

Reviews

1 / 20
8.0
Excellent

Walter,Aug 2025

OAK - SAN

Dozens of flights and I've never seen a row's beverages forgotten. I even went back and asked the attendant to check on them and nothing. I really hope it didn't have something to do with the Black mother with her kid in the row. Otherwise it was a typical Southwest flight, rapid boarding, tolerable leg room.
Southwest
8.0
Very good
4,244 reviews
Southwest
8.0
Very good
4,244 reviews

Boarding

8.1

Entertainment

7.5

Comfort

8.0

Overall

8.0

Crew

8.6

Food

7.0

Reviews

1 / 20
8.0
Excellent

Walter,Aug 2025

OAK - SAN

Dozens of flights and I've never seen a row's beverages forgotten. I even went back and asked the attendant to check on them and nothing. I really hope it didn't have something to do with the Black mother with her kid in the row. Otherwise it was a typical Southwest flight, rapid boarding, tolerable leg room.
Delta
8.0
Very good
7,980 reviews
Southwest
8.0
Very good
4,244 reviews

Boarding

8.1

Entertainment

7.5

Comfort

8.0

Overall

8.0

Crew

8.6

Food

7.0

Reviews

1 / 20
8.0
Excellent

Walter,Aug 2025

OAK - SAN

Dozens of flights and I've never seen a row's beverages forgotten. I even went back and asked the attendant to check on them and nothing. I really hope it didn't have something to do with the Black mother with her kid in the row. Otherwise it was a typical Southwest flight, rapid boarding, tolerable leg room.
United Airlines
7.4
Good
8,916 reviews
Southwest
8.0
Very good
4,244 reviews

Boarding

8.1

Entertainment

7.5

Comfort

8.0

Overall

8.0

Crew

8.6

Food

7.0

Reviews

1 / 20
8.0
Excellent

Walter,Aug 2025

OAK - SAN

Dozens of flights and I've never seen a row's beverages forgotten. I even went back and asked the attendant to check on them and nothing. I really hope it didn't have something to do with the Black mother with her kid in the row. Otherwise it was a typical Southwest flight, rapid boarding, tolerable leg room.
American Airlines
7.2
Good
10,000 reviews
Southwest
8.0
Very good
4,244 reviews

Boarding

8.1

Entertainment

7.5

Comfort

8.0

Overall

8.0

Crew

8.6

Food

7.0

Reviews

1 / 20
8.0
Excellent

Walter,Aug 2025

OAK - SAN

Dozens of flights and I've never seen a row's beverages forgotten. I even went back and asked the attendant to check on them and nothing. I really hope it didn't have something to do with the Black mother with her kid in the row. Otherwise it was a typical Southwest flight, rapid boarding, tolerable leg room.
JetBlue
7.2
Good
2,913 reviews
Southwest
8.0
Very good
4,244 reviews

Boarding

8.1

Entertainment

7.5

Comfort

8.0

Overall

8.0

Crew

8.6

Food

7.0

Reviews

1 / 20
8.0
Excellent

Walter,Aug 2025

OAK - SAN

Dozens of flights and I've never seen a row's beverages forgotten. I even went back and asked the attendant to check on them and nothing. I really hope it didn't have something to do with the Black mother with her kid in the row. Otherwise it was a typical Southwest flight, rapid boarding, tolerable leg room.

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.

  • 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 JetBlue and Delta, starting at $214 and $274 round-trip. Frontier is currently priced 70% 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, September is the cheapest month in which you can book a flight from Portland, Maine to San Juan (average of $254). Flying from Portland, Maine to San Juan in June is currently the most expensive (average of $339). 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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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 agosto 14, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$145Average$229FlexibilityNo cancel feeOn-time62%
JetBlueCheapest$214Average$495FlexibilityNo cancel feeOn-time62%
DeltaCheapest$274Average$393FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$285Average$651FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$332Average$583FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$401Average$656FlexibilityNo cancel feeOn-time63%

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