$158+ Cheap flights from Portland, ME (PWM) to Puerto Rico
This is the cheapest round-trip flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 1/27. Fares are subject to change and may not be available on all flights or dates of travel.
PWM — SJU
Nov 8 — Nov 151
Round-trip
1 adult, Economy
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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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Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.Cheap flight deals from Portland to Puerto Rico
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Best
Last-minute
One-way
Cheapest flights from Portland to Puerto RicoExplore the most affordable flight options available from Portland to Puerto Rico. Find the lowest fares from popular airlines and budget airlines, with prices last updated on October 9, 2026.
Explore the most affordable flight options available from Portland to Puerto Rico. Find the lowest fares from popular airlines and budget airlines, with prices last updated on October 9, 2026.
This United Airlines deal was found by Cheapflights users on 10/6. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/73:41 pm -
1 stop7h 55m
Tue 11/102:05 am -
1 stop7h 55m
Deal found 10/6![United Airlines logo]()
$249
This United Airlines deal was found by Cheapflights users on 10/5. 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 11/146:00 am -
1 stop6h 32m
Thu 11/192:05 am -
2 stops13h 11m
Deal found 10/5![United Airlines logo]()
$284
This United Airlines deal was found by Cheapflights users on 10/4. 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 10/255:50 am -
1 stop7h 50m
Fri 10/301:05 am -
2 stops13h 11m
Deal found 10/4![United Airlines logo]()
$316
This United Airlines deal was found by Cheapflights users on 10/5. 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.
Tue 10/275:30 am -
1 stop6h 45m
Wed 10/281:05 am -
1 stop7h 55m
Deal found 10/5![United Airlines logo]()
$320
This United Airlines deal was found by Cheapflights users on 10/5. 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.
Sun 10/255:50 am -
1 stop7h 50m
Fri 10/304:50 pm -
1 stop7h 09m
Deal found 10/5![United Airlines logo]()
$336
This Southwest deal was found by Cheapflights users on 10/8. 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.
Thu 11/51:40 pm -
1 stop10h 30m
Thu 11/125:50 pm -
1 stop7h 05m
Deal found 10/8![Southwest logo]()
$347
This United Airlines deal was found by Cheapflights users on 10/7. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 10/255:30 am -
1 stop6h 45m
Wed 10/281:05 am -
1 stop7h 55m
Deal found 10/7![United Airlines logo]()
$356
This American Airlines deal was found by Cheapflights users on 10/7. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 10/257:24 pm -
1 stop15h 56m
Thu 10/292:18 pm -
2 stops9h 41m
Deal found 10/7![American Airlines logo]()
$371
Best flights from Portland to Puerto RicoDiscover carefully curated flight deals from Portland to Puerto Rico that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated October 9, 2026.
Discover carefully curated flight deals from Portland to Puerto Rico that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated October 9, 2026.
This United Airlines deal was found by Cheapflights users on 10/4. 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 10/255:50 am -
1 stop7h 50m
Fri 10/301:05 am -
2 stops13h 11m
Deal found 10/4![United Airlines logo]()
$316
This Southwest deal was found by Cheapflights users on 10/5. 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.
Mon 2/112:50 pm -
1 stop9h 15m
Mon 2/85:35 am -
2 stops10h 55m
Deal found 10/5![Southwest logo]()
$375
This Delta deal was found by Cheapflights users on 10/8. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 2/12:35 pm -
1 stop8h 20m
Mon 2/83:55 pm -
1 stop7h 28m
Deal found 10/8![Delta logo]()
$404
This United Airlines deal was found by Cheapflights users on 10/5. 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.
Tue 10/275:30 am -
2 stops14h 54m
Thu 10/292:35 pm -
1 stop8h 46m
Deal found 10/5![United Airlines logo]()
$320
This United Airlines deal was found by Cheapflights users on 10/6. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 1/307:30 am -
2 stops12h 30m
Fri 2/52:05 am -
2 stops13h 39m
Deal found 10/6![United Airlines logo]()
$400
This United Airlines deal was found by Cheapflights users on 10/4. 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 1/94:25 pm -
2 stops12h 50m
Sat 1/168:05 am -
1 stop7h 28m
Deal found 10/4![United Airlines logo]()
$446
Last-minute flights from Portland to Puerto RicoDiscover last-minute flight deals from Portland to Puerto Rico. Data last updated October 9, 2026 and is based on user searches.
Discover last-minute flight deals from Portland to Puerto Rico. Data last updated October 9, 2026 and is based on user searches.
This United Airlines deal was found by Cheapflights users on 10/4. 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 10/255:50 am -
1 stop7h 50m
Fri 10/304:50 pm -
1 stop7h 09m
Deal found 10/4![United Airlines logo]()
$316
This United Airlines deal was found by Cheapflights users on 10/7. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 10/255:30 am -
1 stop6h 45m
Wed 10/281:05 am -
1 stop7h 55m
Deal found 10/7![United Airlines logo]()
$356
This American Airlines deal was found by Cheapflights users on 10/7. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 10/257:24 pm -
1 stop15h 56m
Thu 10/292:18 pm -
2 stops9h 41m
Deal found 10/7![American Airlines logo]()
$371
This United Airlines deal was found by Cheapflights users on 10/5. 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.
Tue 10/275:30 am -
1 stop6h 45m
Wed 10/281:05 am -
1 stop7h 55m
Deal found 10/5![United Airlines logo]()
$320
This Southwest deal was found by Cheapflights users on 10/8. 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.
Thu 11/51:40 pm -
1 stop10h 30m
Thu 11/125:50 pm -
1 stop7h 05m
Deal found 10/8![Southwest logo]()
$347
This United Airlines deal was found by Cheapflights users on 10/6. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/73:41 pm -
1 stop7h 55m
Tue 11/102:05 am -
1 stop7h 55m
Deal found 10/6![United Airlines logo]()
$249
This United Airlines deal was found by Cheapflights users on 10/5. 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 11/146:00 am -
1 stop6h 32m
Thu 11/192:05 am -
2 stops13h 11m
Deal found 10/5![United Airlines logo]()
$284
One-way flights from Portland to Puerto RicoSearch for one-way flight options from Portland to Puerto Rico. Find affordable one-way fares based on user searches. Data last updated October 9, 2026.
Search for one-way flight options from Portland to Puerto Rico. Find affordable one-way fares based on user searches. Data last updated October 9, 2026.
This United Airlines deal was found by Cheapflights users on 10/4. 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 1/273:14 pm -
1 stop8h 22m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/4![United Airlines logo]()
$158
This American Airlines deal was found by Cheapflights users on 10/4. 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 1/275:00 am -
2 stops15h 30m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/4![American Airlines logo]()
$163
This United Airlines deal was found by Cheapflights users on 10/4. 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 10/196:00 am -
1 stop7h 45m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/4![United Airlines logo]()
$226
This American Airlines deal was found by Cheapflights users on 10/6. 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.
Fri 10/237:00 am -
1 stop15h 57m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/6![American Airlines logo]()
$241
This Kiwi.com deal was found by Cheapflights users on 10/5. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 2/1012:28 pm -
2 stops12h 43m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/5![Multiple Airlines logo]()
$249
This American Airlines deal was found by Cheapflights users on 10/5. 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 10/195:30 am -
1 stop17h 27m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/5![American Airlines logo]()
$263
This Priceline deal was found by Cheapflights users on 10/6. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 10/186:00 am -
1 stop7h 48m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/6![JetBlue logo]()
$272
This United Airlines deal was found by Cheapflights users on 10/4. 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 10/145:15 am -
1 stop7h 19m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/4![United Airlines logo]()
$276
Find flight deals from Portland to Puerto Rico
Keep the following information in mind while searching for Portland to Puerto Rico flight deals. Data was last updated October 9, 2026.
Round-trip from | $249 (United Airlines) |
|---|---|
One-way from | $158 (United Airlines) |
Popular in | April |
Cheapest in | November |
Average price | $362 |
Cheapflights Fare Finder
Customize your flight search to find flights from Portland to Puerto Rico 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 7,457,451 searches. Data last updated October 9, 2026.
Use the filters below to find and compare flights from Portland to Puerto Rico that are best for you.
Fly from
Fly to
Route
Depart
Return
Cheapest round-trip
PortlandSan Juan
PWM Portland - SJU San Juan Luis Munoz Marin Intl
PWMSJU
Portland
Wed 1/27
3:14 pm-12:36 am
1 stop8h 22m
San Juan Luis Munoz Marin Intl
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$158
PortlandSan Juan
PWM Portland - SJU San Juan Luis Munoz Marin Intl
PWMSJU
Portland
Fri 2/19
2:35 pm-11:55 pm
1 stop8h 20m
San Juan Luis Munoz Marin Intl
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$226
Quickest round-trip
PortlandSan Juan
PWM Portland - SJU San Juan Luis Munoz Marin Intl
PWMSJU
Portland
Mon 10/19
6:00 am-1:45 pm
1 stop7h 45m
San Juan Luis Munoz Marin Intl
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$226
PortlandSan Juan
PWM Portland - SJU San Juan Luis Munoz Marin Intl
PWMSJU
Portland
Wed 2/10
12:28 pm-2:11 am
2 stops12h 43m
San Juan Luis Munoz Marin Intl
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$249
PortlandSan Juan
PWM Portland - SJU San Juan Luis Munoz Marin Intl
PWMSJU
Portland
Sun 10/18
6:00 am-1:48 pm
1 stop7h 48m
San Juan Luis Munoz Marin Intl
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$272
PortlandSan Juan
PWM Portland - SJU San Juan Luis Munoz Marin Intl
PWMSJU
Portland
Fri 10/23
7:00 am-10:02 pm
2 stops15h 02m
San Juan Luis Munoz Marin Intl
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$279
PortlandSan Juan
PWM Portland - SJU San Juan Luis Munoz Marin Intl
PWMSJU
Portland
Sun 10/18
6:00 am-1:45 pm
1 stop7h 45m
San Juan Luis Munoz Marin Intl
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$288
PortlandSan Juan
PWM Portland - SJU San Juan Luis Munoz Marin Intl
PWMSJU
Portland
Sat 10/17
5:35 am-3:15 pm
2 stops9h 40m
San Juan Luis Munoz Marin Intl
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$291
PortlandSan Juan
PWM Portland - SJU San Juan Luis Munoz Marin Intl
PWMSJU
Portland
Fri 2/19
12:35 pm-12:30 am
2 stops10h 55m
San Juan Luis Munoz Marin Intl
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$298
PortlandSan Juan
PWM Portland - SJU San Juan Luis Munoz Marin Intl
PWMSJU
Portland
Sun 10/25
5:50 am-1:40 pm
1 stop7h 50m
San Juan Luis Munoz Marin Intl
Fri 10/30
1:05 am-2:16 pm
2 stops13h 11m
$316
Showing 1-10 of 15 resultsSorted by cheapest first
Best time to book a flight from Portland to Puerto Rico
Have a flexible travel schedule? Discover the best time to fly to Puerto Rico from Portland with our price prediction graph.
PWM-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 Puerto Rico
PWM-PR0
PWM-SJU
What is the cheapest month to book a flight from Portland, Maine to Puerto Rico?
Currently, November is the cheapest month in which you can book a flight from Portland, Maine to Puerto Rico (average of $322). Flying from Portland, Maine to Puerto Rico in April is currently the most expensive (average of $738). 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 far ahead should I book a flight from Portland, Maine to Puerto Rico?
The best time to book flights from Portland, Maine to Puerto Rico is 36 days before your desired departure date. The cost of your flight will likely increase significantly if you book two weeks in advance of your flight.
Reviews of airlines servicing Puerto Rico
Get insights into the airlines that provide service to Puerto Rico. 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 Puerto Rico. Reviews last updated October 9, 2026.
Read through reviews of airlines operating flights from Portland to Puerto Rico, such as Southwest,Delta, andUnited Airlines. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Crew
8.6
Boarding
8.1
Comfort
8.0
Overall
7.9
Food
7.0
Entertainment
7.4
Reviews
1 / 20
10.0
ExcellentEdward,Sep 2026
MCO - BWI
Crew
8.6
Boarding
8.1
Comfort
8.0
Overall
7.9
Food
7.0
Entertainment
7.4
Reviews
1 / 20
10.0
ExcellentEdward,Sep 2026
MCO - BWI
Crew
8.6
Boarding
8.1
Comfort
8.0
Overall
7.9
Food
7.0
Entertainment
7.4
Reviews
1 / 20
10.0
ExcellentEdward,Sep 2026
MCO - BWI
Crew
8.6
Boarding
8.1
Comfort
8.0
Overall
7.9
Food
7.0
Entertainment
7.4
Reviews
1 / 20
10.0
ExcellentEdward,Sep 2026
MCO - BWI
Crew
8.6
Boarding
8.1
Comfort
8.0
Overall
7.9
Food
7.0
Entertainment
7.4
Reviews
1 / 20
10.0
ExcellentEdward,Sep 2026
MCO - BWI
Crew
8.6
Boarding
8.1
Comfort
8.0
Overall
7.9
Food
7.0
Entertainment
7.4
Reviews
1 / 20
10.0
ExcellentEdward,Sep 2026
MCO - BWI
Related info for your journey
Find useful and relevant information for your journey from Portland to Puerto Rico. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.
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Alternative routes for Portland to Puerto Rico
See prices for flight routes from nearby airports that may be better suited for you.
Complete your trip
Complete your trip to Puerto Rico by adding a car rental and/or hotel reservation to your travel itinerary.
Search flights from Portland to Puerto Rico by cabin class
Find flights from Portland to Puerto Rico, based on your preferred cabin class, be it economy, premium economy, business, or first class.
Portland and Puerto Rico flights
Browse other Portland and Puerto Rico flight options. Last updated on October 9, 2026.
Popular flight searches
Check out other popular destinations found by fellow travelers in 2026
Top 5 airlines flying from Portland to Puerto Rico
Discover the top 5 airlines that operate flights from Portland to Puerto Rico. 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 7,457,451 searches. Data last updated October 9, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$174 | Average$515 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$232 | Average$410 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$275 | Average$363 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$296 | Average$558 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$322 | Average$589 | FlexibilityNo cancel fee | On-time63% |