$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
Round-trip
1 adult, Economy
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Find cheap flights from Portland to San Juan with Cheapflights
1. Tell us where you want to go
Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”2. Select your favorite providers
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Best
Last-minute
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Cheapest flights from Portland to San JuanExplore 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.
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![Southwest logo]()
$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![Southwest logo]()
$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![American Airlines logo]()
$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![Southwest logo]()
$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![Southwest logo]()
$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![American Airlines logo]()
$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![United Airlines logo]()
$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![Southwest logo]()
$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![American Airlines logo]()
$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![Southwest logo]()
$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![Delta logo]()
$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![American Airlines logo]()
$513
Best flights from Portland to San JuanDiscover carefully curated flight deals from Portland to San Juan that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated April 10, 2026.
Discover carefully curated flight deals from Portland to San Juan that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated April 10, 2026.
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.
Wed 9/210:45 pm
PDX
- SJU
1 stop12h 45m
Southwest
Wed 9/91:45 pm
SJU
- PDX
2 stops12h 25m
Southwest
Deal found 4/8![Southwest logo]()
$498
This United Airlines 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/1910:50 pm
PDX
- SJU
1 stop10h 07m
United Airlines
Sat 9/262:00 pm
SJU
- PDX
1 stop11h 38m
United Airlines
Deal found 4/5![United Airlines logo]()
$510
This Delta 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/295:51 pm
PDX
- SJU
2 stops16h 29m
Delta
Thu 6/47:30 am
SJU
- PDX
2 stops15h 41m
Delta
Deal found 4/5![Delta logo]()
$543
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.
Fri 7/247:40 pm
PDX
- SJU
2 stops11h 50m
Southwest
Mon 8/176:30 am
SJU
- PDX
2 stops13h 05m
Southwest
Deal found 4/5![Southwest logo]()
$510
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 7/307:40 pm
PDX
- SJU
2 stops12h 05m
Southwest
Sat 8/155:05 am
SJU
- PDX
2 stops11h 55m
Southwest
Deal found 4/6![Southwest logo]()
$510
This United Airlines 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 4/275:35 pm
PDX
- SJU
2 stops17h 10m
United Airlines
Tue 4/281:00 am
SJU
- PDX
2 stops16h 30m
United Airlines
Deal found 4/5![United Airlines logo]()
$561
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.
Mon 8/2410:45 pm
PDX
- SJU
1 stop11h 05m
Southwest
Mon 8/315:30 am
SJU
- PDX
1 stop12h 30m
Southwest
Deal found 4/7![Southwest logo]()
$530
Last-minute flights from Portland to San JuanDiscover last-minute flight deals from Portland to San Juan. Data last updated April 10, 2026 and is based on user searches.
Discover last-minute flight deals from Portland to San Juan. Data last updated April 10, 2026 and is based on user searches.
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![American Airlines logo]()
$493
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![Southwest logo]()
$481
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![American Airlines logo]()
$501
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![American Airlines logo]()
$476
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![United Airlines logo]()
$496
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![American Airlines logo]()
$513
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.
Thu 4/301:09 pm
PDX
- SJU
2 stops12h 23m
American Airlines
Mon 5/45:45 am
SJU
- PDX
1 stop21h 08m
American Airlines
Deal found 4/8![American Airlines logo]()
$517
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.
Mon 5/45:10 am
PDX
- SJU
2 stops11h 50m
Southwest
Fri 5/82:00 pm
SJU
- PDX
2 stops13h 25m
Southwest
Deal found 4/7![Southwest logo]()
$446
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.
Wed 5/66:00 am
PDX
- SJU
1 stop19h 32m
American Airlines
Tue 5/1212:53 pm
SJU
- PDX
2 stops13h 55m
American Airlines
Deal found 4/6![American Airlines logo]()
$515
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![Southwest logo]()
$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.
Fri 5/298:11 pm
PDX
- SJU
2 stops14h 09m
Delta
Thu 6/47:05 am
SJU
- PDX
2 stops13h 10m
Delta
Deal found 4/6![Delta logo]()
$510
One-way flights from Portland to San JuanSearch for one-way flight options from Portland to San Juan. Find affordable one-way fares based on user searches. Data last updated April 10, 2026.
Search for one-way flight options from Portland to San Juan. Find affordable one-way fares based on user searches. Data last updated April 10, 2026.
This Kiwi.com 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 5/39:54 am
PDX
- SJU
2 stops21h 00m
Frontier
Deal found 4/8![Frontier logo]()
$156
This Kiwi.com 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/812:35 pm
PDX
- SJU
2 stops21h 40m
Frontier
Deal found 4/8![Frontier logo]()
$194
This Kiwi.com deal was found by Cheapflights users on 4/9. 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.
Mon 4/2712:45 pm
PDX
- SJU
2 stops26h 14m
Frontier
Deal found 4/9![Frontier logo]()
$202
This Kiwi.com 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/88:46 pm
PDX
- SJU
3 stops41h 06m
Multiple Airlines
Deal found 4/8![Multiple Airlines logo]()
$208
This Kiwi.com 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/158:46 pm
PDX
- SJU
3 stops37h 46m
Multiple Airlines
Deal found 4/8![Multiple Airlines logo]()
$222
This Kiwi.com 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 5/312:44 pm
PDX
- SJU
3 stops54h 57m
Multiple Airlines
Deal found 4/6![Multiple Airlines logo]()
$223
This Kiwi.com 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/1512:35 pm
PDX
- SJU
2 stops32h 24m
Frontier
Deal found 4/8![Frontier logo]()
$230
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.
Tue 5/56:30 am
PDX
- SJU
2 stops13h 10m
Southwest
Deal found 4/8![Southwest logo]()
$233
This American Airlines 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 4/2711:47 pm
PDX
- SJU
2 stops12h 05m
American Airlines
Deal found 4/5![American Airlines logo]()
$238
This Delta 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/147:00 am
PDX
- SJU
1 stop13h 44m
Delta
Deal found 4/5![Delta logo]()
$255
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 |
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
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
Showing 1-10 of 14 resultsSorted by cheapest first
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.
PDX-PR1
PDX-SJU
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
PDX-PR1
PDX-SJU
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
MediocreDominic,Mar 2026
MCO - SMF
Entertainment
7.5
Boarding
8.1
Overall
8.0
Crew
8.6
Comfort
8.0
Food
7.0
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Entertainment
7.5
Boarding
8.1
Overall
8.0
Crew
8.6
Comfort
8.0
Food
7.0
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Entertainment
7.5
Boarding
8.1
Overall
8.0
Crew
8.6
Comfort
8.0
Food
7.0
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Entertainment
7.5
Boarding
8.1
Overall
8.0
Crew
8.6
Comfort
8.0
Food
7.0
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Entertainment
7.5
Boarding
8.1
Overall
8.0
Crew
8.6
Comfort
8.0
Food
7.0
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Related info for your journey
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Portland and San Juan flights
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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.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$185 | Average$369 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$235 | Average$488 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$399 | Average$587 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$399 | Average$627 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$408 | Average$566 | FlexibilityNo cancel fee | On-time63% |