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San Juan

$185+ Cheap flights from Portland (PDX) 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 3/3. Fares are subject to change and may not be available on all flights or dates of travel.
PDX — SJU
Feb 20 — Feb 271
Fri 2/20
Fri 2/27
1 adult, Economy
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Cheap 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 January 21, 2026.

This Southwest deal was found by Cheapflights users on 1/20. 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 4/296:30 am
PDX
-
SJU
2 stops13h 10m
Southwest
Tue 5/55:05 am
SJU
-
PDX
2 stops18h 55m
Southwest
Deal found 1/20$397
This Southwest deal was found by Cheapflights users on 1/21. 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 4/77:25 pm
PDX
-
SJU
2 stops12h 10m
Southwest
Thu 4/96:50 am
SJU
-
PDX
2 stops16h 20m
Southwest
Deal found 1/21$405
This Southwest deal was found by Cheapflights users on 1/20. 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 5/811:55 pm
PDX
-
SJU
1 stop10h 25m
Southwest
Thu 5/1410:00 am
SJU
-
PDX
2 stops13h 10m
Southwest
Deal found 1/20$432
This Delta deal was found by Cheapflights users on 1/19. 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.
Fri 10/307:40 pm
PDX
-
SJU
2 stops15h 31m
Delta
Tue 11/103:10 pm
SJU
-
PDX
1 stop10h 43m
Delta
Deal found 1/19$440
This American Airlines deal was found by Cheapflights users on 1/19. 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 2/179:44 pm
PDX
-
SJU
1 stop18h 55m
American Airlines
Tue 2/2410:50 am
SJU
-
PDX
1 stop17h 00m
American Airlines
Deal found 1/19$442
This American Airlines deal was found by Cheapflights users on 1/20. 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 4/15:40 am
PDX
-
SJU
1 stop13h 51m
American Airlines
Wed 4/151:31 pm
SJU
-
PDX
2 stops13h 10m
American Airlines
Deal found 1/20$450
This United Airlines deal was found by Cheapflights users on 1/20. 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 12/210:00 am
PDX
-
SJU
1 stop10h 36m
United Airlines
Thu 12/172:25 pm
SJU
-
PDX
1 stop12h 13m
United Airlines
Deal found 1/20$468
This Southwest deal was found by Cheapflights users on 1/20. 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 2/196:45 am
PDX
-
SJU
2 stops13h 55m
Southwest
Thu 2/263:15 pm
SJU
-
PDX
2 stops12h 50m
Southwest
Deal found 1/20$470
This United Airlines deal was found by Cheapflights users on 1/20. 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 2/157:10 am
PDX
-
SJU
1 stop10h 16m
United Airlines
Fri 2/208:05 am
SJU
-
PDX
2 stops14h 44m
United Airlines
Deal found 1/20$472
This United Airlines deal was found by Cheapflights users on 1/21. 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 5/205:00 am
PDX
-
SJU
1 stop9h 38m
United Airlines
Mon 5/251:05 am
SJU
-
PDX
1 stop11h 16m
United Airlines
Deal found 1/21$476

Find flight deals from Portland to San Juan

Discover tips and strategies to find the most affordable flight options for your journey from Portland (PDX) 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 January 21, 2026.

Round-trip from

$397
(Southwest)

One-way from

$185
(Southwest)

Popular in

December

Cheapest in

October

Average price

$554
From Portland to San Juan
Search Deals
One-way flight from Portland to San Juan
Search Deals
Highest demand for flights based on searches. 11% potential increase in price ($76 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 3% potential price decrease ($19 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in January 2026
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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 January 21, 2026.
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

PDX - SJU

PDXSJU

Portland

Wed 4/29

6:30 am-10:40 pm

2 stops13h 10m

San Juan Luis Munoz Marin Intl

Tue 5/5

5:05 am-9:00 pm

2 stops18h 55m

$397

PortlandSan Juan

PDX - SJU

PDXSJU

Portland

Sun 4/19

7:00 am-8:38 pm

1 stop10h 38m

San Juan Luis Munoz Marin Intl

Tue 4/21

1:00 am-11:46 am

2 stops13h 46m

$440

PortlandSan Juan

PDX - SJU

PDXSJU

Portland

Sun 4/26

5:59 pm-12:50 pm

2 stops15h 51m

San Juan Luis Munoz Marin Intl

Tue 5/5

2:34 pm-11:53 pm

2 stops12h 19m

$440

PortlandSan Juan

PDX - SJU

PDXSJU

Portland

Sat 4/25

5:00 am-8:34 pm

2 stops12h 34m

San Juan Luis Munoz Marin Intl

Fri 5/1

1:00 am-11:37 am

2 stops13h 37m

$440

PortlandSan Juan

PDX - SJU

PDXSJU

Portland

Wed 3/11

7:00 am-11:59 pm

1 stop13h 59m

San Juan Luis Munoz Marin Intl

Sat 5/2

7:00 am-10:21 pm

2 stops18h 21m

$440

PortlandSan Juan

PDX - SJU

PDXSJU

Portland

Sat 2/21

1:40 pm-6:11 am

2 stops12h 31m

San Juan Luis Munoz Marin Intl

Wed 2/25

2:25 pm-9:15 pm

1 stop10h 50m

$440

PortlandSan Juan

PDX - SJU

PDXSJU

Portland

Thu 5/28

5:15 am-8:38 pm

2 stops12h 23m

San Juan Luis Munoz Marin Intl

Sun 5/31

1:05 am-9:21 am

1 stop11h 16m

$483

PortlandSan Juan

PDX - SJU

PDXSJU

Portland

Sun 2/1

5:30 am-11:57 pm

2 stops14h 27m

San Juan Luis Munoz Marin Intl

Thu 3/12

2:07 pm-9:53 pm

1 stop10h 46m

$503

PortlandSan Juan

PDX - SJU

PDXSJU

Portland

Wed 2/4

7:00 am-12:36 am

2 stops13h 36m

San Juan Luis Munoz Marin Intl

Tue 2/10

2:05 am-2:46 pm

2 stops16h 41m

$503

PortlandSan Juan

PDX - SJU

PDXSJU

Portland

Mon 2/2

5:00 am-6:25 pm

1 stop9h 25m

San Juan Luis Munoz Marin Intl

Tue 2/10

3:46 pm-10:53 pm

1 stop11h 07m

$503

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/20

Showing 1-10 of 20 results
1
2

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 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 January 16, 2026.

The price you pay for your flight from Portland to San Juan may vary depending on when you book. For the best chance of a lower fare, look to book 49 days in advance of your trip. Fares are likely to increase a fortnight or so before your departure date.

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

Currently, August is the cheapest month in which you can book a flight from Portland to San Juan (average of $188). Flying from Portland to San Juan in January is currently the most expensive (average of $400). 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.

How much does it cost to fly round-trip from Portland 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 January 21, 2026.
Read through reviews of airlines operating flights from Portland to San Juan, 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
4,266 reviews

Crew

8.6

Food

7.0

Overall

8.0

Boarding

8.1

Comfort

8.0

Entertainment

7.5

Reviews

1 / 20
2.0
Mediocre

Thomas,Dec 2025

SEA - DEN

Plane two hours late in leaving 1:00 pm west coat time got home next day at 2:45am most car rental places are closed and don’t open till 5am
Southwest
8.0
Very good
4,266 reviews
Southwest
8.0
Very good
4,266 reviews

Crew

8.6

Food

7.0

Overall

8.0

Boarding

8.1

Comfort

8.0

Entertainment

7.5

Reviews

1 / 20
2.0
Mediocre

Thomas,Dec 2025

SEA - DEN

Plane two hours late in leaving 1:00 pm west coat time got home next day at 2:45am most car rental places are closed and don’t open till 5am
Delta
7.9
Good
8,089 reviews
Southwest
8.0
Very good
4,266 reviews

Crew

8.6

Food

7.0

Overall

8.0

Boarding

8.1

Comfort

8.0

Entertainment

7.5

Reviews

1 / 20
2.0
Mediocre

Thomas,Dec 2025

SEA - DEN

Plane two hours late in leaving 1:00 pm west coat time got home next day at 2:45am most car rental places are closed and don’t open till 5am
United Airlines
7.4
Good
9,191 reviews
Southwest
8.0
Very good
4,266 reviews

Crew

8.6

Food

7.0

Overall

8.0

Boarding

8.1

Comfort

8.0

Entertainment

7.5

Reviews

1 / 20
2.0
Mediocre

Thomas,Dec 2025

SEA - DEN

Plane two hours late in leaving 1:00 pm west coat time got home next day at 2:45am most car rental places are closed and don’t open till 5am
American Airlines
7.2
Good
11,174 reviews
Southwest
8.0
Very good
4,266 reviews

Crew

8.6

Food

7.0

Overall

8.0

Boarding

8.1

Comfort

8.0

Entertainment

7.5

Reviews

1 / 20
2.0
Mediocre

Thomas,Dec 2025

SEA - DEN

Plane two hours late in leaving 1:00 pm west coat time got home next day at 2:45am most car rental places are closed and don’t open till 5am
Spirit Airlines
6.3
Okay
8,364 reviews
Southwest
8.0
Very good
4,266 reviews

Crew

8.6

Food

7.0

Overall

8.0

Boarding

8.1

Comfort

8.0

Entertainment

7.5

Reviews

1 / 20
2.0
Mediocre

Thomas,Dec 2025

SEA - DEN

Plane two hours late in leaving 1:00 pm west coat time got home next day at 2:45am most car rental places are closed and don’t open till 5am

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?

    Located just 6.0 mi from the city center, Portland is the airport most travelers will use when flying to San Juan from Portland. Booking flights from Portland (PDX) to San Juan should be relatively easy as there are 0 daily outbound flights to San Juan from 6 different airlines.

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

    Southwest and United Airlines can get you from Portland to San Juan in just under 10h 38m. Your travel time can differ by up to 2h 32m. Portland and San Juan are separated by a distance of 3710 mi. Both multi-stop and nonstop flights can be found to your destination and back.

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

    According to our current data, JetBlue ($185), Spirit Airlines ($243), and Delta ($272) offers the cheapest pricing from Portland to San Juan. JetBlue is currently priced 68% below the average price you’ll pay for this route.

  • What are the cheapest airlines to fly from Portland to San Juan one-way?

    The cheapest airlines for a one-way flight from Portland to San Juan are Delta ($150), American Airlines ($184), and JetBlue ($185).

  • 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 to San Juan?

    Currently, August is the cheapest month in which you can book a flight from Portland to San Juan (average of $188). Flying from Portland to San Juan in January is currently the most expensive (average of $400). 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 January 21, 2026.
AirlineCheapestAverageFlexibilityOn-time
JetBlueCheapest$185Average$371FlexibilityNo cancel feeOn-time62%
Spirit AirlinesCheapest$243Average$382FlexibilityNo cancel feeOn-time65%
DeltaCheapest$272Average$510FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$359Average$605FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$401Average$595FlexibilityNo cancel feeOn-time69%
SouthwestCheapest$454Average$635FlexibilityNo cancel feeOn-time63%

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