San Juan

$156+ 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 5/3. Fares are subject to change and may not be available on all flights or dates of travel.
PDX — SJU
May 10 — May 171
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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 April 10, 2026.

This Southwest deal was found by Cheapflights users on 4/5. 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 9/2310:45 pm
PDX
-
SJU
2 stops12h 00m
Southwest
Mon 9/286:00 am
SJU
-
PDX
2 stops13h 35m
Southwest
Deal found 4/5$446
This Southwest deal was found by Cheapflights users on 4/8. 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.
Mon 5/45:10 am
PDX
-
SJU
2 stops15h 30m
Southwest
Fri 5/82:00 pm
SJU
-
PDX
2 stops13h 25m
Southwest
Deal found 4/8$466
This American Airlines deal was found by Cheapflights users on 4/6. 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 4/231:52 pm
PDX
-
SJU
1 stop11h 40m
American Airlines
Wed 4/296:45 am
SJU
-
PDX
1 stop13h 14m
American Airlines
Deal found 4/6$476
This Southwest deal was found by Cheapflights users on 4/5. 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.
Sun 9/610:45 pm
PDX
-
SJU
2 stops12h 00m
Southwest
Mon 9/145:30 am
SJU
-
PDX
1 stop12h 30m
Southwest
Deal found 4/5$478
This Southwest deal was found by Cheapflights users on 4/7. 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 4/226:30 am
PDX
-
SJU
2 stops13h 10m
Southwest
Thu 4/3010:00 am
SJU
-
PDX
2 stops15h 40m
Southwest
Deal found 4/7$481
This American Airlines deal was found by Cheapflights users on 4/6. 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.
Mon 4/2012:59 am
PDX
-
SJU
1 stop10h 43m
American Airlines
Mon 5/45:45 am
SJU
-
PDX
1 stop21h 08m
American Airlines
Deal found 4/6$493
This United Airlines deal was found by Cheapflights users on 4/8. 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 4/238:05 am
PDX
-
SJU
1 stop10h 19m
United Airlines
Wed 4/291:25 pm
SJU
-
PDX
1 stop11h 34m
United Airlines
Deal found 4/8$496
This Southwest deal was found by Cheapflights users on 4/8. 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.
Mon 8/1710:45 pm
PDX
-
SJU
1 stop11h 05m
Southwest
Sat 8/226:25 am
SJU
-
PDX
2 stops13h 25m
Southwest
Deal found 4/8$498
This American Airlines deal was found by Cheapflights users on 4/8. 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 4/2211:48 am
PDX
-
SJU
2 stops13h 44m
American Airlines
Mon 4/276:45 am
SJU
-
PDX
1 stop20h 09m
American Airlines
Deal found 4/8$501
This Southwest deal was found by Cheapflights users on 4/6. 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 5/76:10 am
PDX
-
SJU
2 stops14h 15m
Southwest
Wed 5/1311:25 am
SJU
-
PDX
2 stops14h 35m
Southwest
Deal found 4/6$506
This Delta deal was found by Cheapflights users on 4/6. 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.
Tue 6/95:50 pm
PDX
-
SJU
2 stops16h 04m
Delta
Fri 6/192:04 pm
SJU
-
PDX
1 stop10h 46m
Delta
Deal found 4/6$510
This American Airlines deal was found by Cheapflights users on 4/8. 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.
Sat 4/251:52 pm
PDX
-
SJU
1 stop11h 40m
American Airlines
Fri 5/11:31 pm
SJU
-
PDX
2 stops12h 32m
American Airlines
Deal found 4/8$513

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 April 10, 2026.

Round-trip from

$446
(Southwest)

One-way from

$156
(Kiwi.com)

Popular in

December

Cheapest in

October

Average price

$556
From Portland to San Juan
One-way flight from Portland to San Juan
Highest demand for flights based on searches. 10% potential increase in price ($67 potential increase over avg. RT price).
Cheapest flight prices on average. 2% potential price decrease ($16 potential savings vs. average RT price).
Average for round-trip flights in April 2026

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 April 10, 2026.
Use the filters below to find and compare flights from Portland to San Juan that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

PortlandSan Juan

PDX - SJU

PDXSJU

Portland

Wed 9/2

10:45 pm-2:30 pm

1 stop12h 45m

San Juan Luis Munoz Marin Intl

Wed 9/9

1:45 pm-11:10 pm

2 stops12h 25m

$498
Quickest round-trip

PortlandSan Juan

PDX - SJU

PDXSJU

Portland

Sat 9/19

10:50 pm-11:57 am

1 stop10h 07m

San Juan Luis Munoz Marin Intl

Sat 9/26

2:00 pm-10:38 pm

1 stop11h 38m

$510

PortlandSan Juan

PDX - SJU

PDXSJU

Portland

Fri 7/24

7:40 pm-10:30 am

2 stops11h 50m

San Juan Luis Munoz Marin Intl

Mon 8/17

6:30 am-4:35 pm

2 stops13h 05m

$510

PortlandSan Juan

PDX - SJU

PDXSJU

Portland

Thu 7/30

7:40 pm-10:45 am

2 stops12h 05m

San Juan Luis Munoz Marin Intl

Sat 8/15

5:05 am-2:00 pm

2 stops11h 55m

$510

PortlandSan Juan

PDX - SJU

PDXSJU

Portland

Mon 8/24

10:45 pm-12:50 pm

1 stop11h 05m

San Juan Luis Munoz Marin Intl

Mon 8/31

5:30 am-3:00 pm

1 stop12h 30m

$530

PortlandSan Juan

PDX - SJU

PDXSJU

Portland

Fri 5/29

5:51 pm-1:20 pm

2 stops16h 29m

San Juan Luis Munoz Marin Intl

Thu 6/4

7:30 am-8:11 pm

2 stops15h 41m

$543

PortlandSan Juan

PDX - SJU

PDXSJU

Portland

Mon 4/27

5:35 pm-1:45 pm

2 stops17h 10m

San Juan Luis Munoz Marin Intl

Tue 4/28

1:00 am-2:30 pm

2 stops16h 30m

$561
Cheapest one-way

PortlandSan Juan

PDX - SJU

PDXSJU

Portland

Mon 4/27

11:47 pm-2:20 pm

1 stop11h 33m

$238

PortlandSan Juan

PDX - SJU

PDXSJU

Portland

Tue 4/28

5:00 am-11:50 pm

2 stops15h 50m

$248
Quickest one-way

PortlandSan Juan

PDX - SJU

PDXSJU

Portland

Fri 5/8

11:12 pm-1:20 pm

1 stop11h 08m

$248

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/5

Showing 1-10 of 14 resultsSorted by cheapest first
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 April 3, 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 37 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 $185). Flying from Portland to San Juan in May is currently the most expensive (average of $430). 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 April 10, 2026.
Read through reviews of airlines operating flights from Portland to San Juan, such as Southwest,Delta, andUnited Airlines. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.

Entertainment

7.5

Boarding

8.1

Overall

8.0

Crew

8.6

Comfort

8.0

Food

7.0

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.

Entertainment

7.5

Boarding

8.1

Overall

8.0

Crew

8.6

Comfort

8.0

Food

7.0

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.

Entertainment

7.5

Boarding

8.1

Overall

8.0

Crew

8.6

Comfort

8.0

Food

7.0

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.

Entertainment

7.5

Boarding

8.1

Overall

8.0

Crew

8.6

Comfort

8.0

Food

7.0

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.

Entertainment

7.5

Boarding

8.1

Overall

8.0

Crew

8.6

Comfort

8.0

Food

7.0

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.

Entertainment

7.5

Boarding

8.1

Overall

8.0

Crew

8.6

Comfort

8.0

Food

7.0

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 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 5 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 07m. Your travel time can differ by up to 2h 38m. 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), Delta ($235), and American Airlines ($399) offers the cheapest pricing from Portland to San Juan. JetBlue is currently priced 67% 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 ($184), JetBlue ($185), and Southwest ($190).

  • 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 $185). Flying from Portland to San Juan in May is currently the most expensive (average of $430). 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 San Juan

See prices for flight routes from nearby airports that may be better suited for you.

Top 5 airlines flying from Portland to San Juan

Discover the top 5 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 April 10, 2026.
AirlineCheapestAverageFlexibilityOn-time
JetBlueCheapest$185Average$369FlexibilityNo cancel feeOn-time62%
DeltaCheapest$235Average$488FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$399Average$587FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$399Average$627FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$408Average$566FlexibilityNo cancel feeOn-time63%

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