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Caribbean Islands

$178+ Cheap flights from Portland (PDX) to Caribbean Islands

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 8/31. Fares are subject to change and may not be available on all flights or dates of travel.
PDX — SJU
Aug 10 — Aug 171
Sun 8/10
Sun 8/17
1 adult, Economy
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Cheap flight deals from Portland to Caribbean Islands

Keep the following information in mind while searching for Portland to Caribbean Islands flight deals. Data was last updated August 5, 2025.

Round-trip from

$359
(Mytrip)

One-way from

$178
(Cheapflightsfares)

Popular in

March

Cheapest in

October

Average price

$494
From Portland to Caribbean Islands
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One-way flight from Portland to Caribbean Islands
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Highest demand for flights based on searches. 8% potential increase in price ($53 potential increase over avg. RT price).
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Cheapest flight prices on average. 3% potential price decrease ($19 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 Caribbean Islands

Cheapest flights from Portland to Caribbean Islands
Explore the most affordable flight options available from Portland to Caribbean Islands. Find the lowest fares from popular airlines and budget airlines, with prices last updated on August 5, 2025.

This Mytrip deal was found by Cheapflights users on 8/5. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/2412:07 pmPDX - SJU
2 stops22h 36mSpirit Airlines
Sun 9/2811:59 amSJU - PDX
3 stops34h 24mSpirit Airlines
Deal found 8/5$359
This Mytrip deal was found by Cheapflights users on 8/4. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/218:04 pmPDX - SJU
3 stops26h 39mSpirit Airlines
Tue 10/283:19 pmSJU - PDX
3 stops30h 45mSpirit Airlines
Deal found 8/4$369
This Mytrip deal was found by Cheapflights users on 8/5. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/2512:07 pmPDX - SJU
3 stops23h 04mSpirit Airlines
Sun 9/2811:59 amSJU - PDX
3 stops34h 24mSpirit Airlines
Deal found 8/5$370
This Delta deal was found by Cheapflights users on 8/3. 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.
Sun 9/287:15 amPDX - SJU
1 stop13h 32mDelta
Wed 10/11:32 pmSJU - PDX
2 stops13h 20mDelta
Deal found 8/3$399
This Mytrip deal was found by Cheapflights users on 8/3. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/812:07 pmPDX - SJU
3 stops23h 04mSpirit Airlines
Mon 9/156:44 amSJU - PDX
3 stops31h 27mSpirit Airlines
Deal found 8/3$418
This Mytrip deal was found by Cheapflights users on 8/3. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/68:18 pmPDX - SJU
2 stops14h 59mSpirit Airlines
Sun 9/142:38 pmSJU - PDX
3 stops31h 45mSpirit Airlines
Deal found 8/3$419
This Mytrip deal was found by Cheapflights users on 8/5. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/112:07 pmPDX - SJU
2 stops22h 36mSpirit Airlines
Sun 11/28:40 pmSJU - PDX
2 stops26h 24mSpirit Airlines
Deal found 8/5$423
This United Airlines deal was found by Cheapflights users on 8/4. 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 10/1110:32 pmPDX - SJU
1 stop12h 13mUnited Airlines
Fri 10/171:05 amSJU - PDX
2 stops13h 36mUnited Airlines
Deal found 8/4$429
This United Airlines deal was found by Cheapflights users on 8/5. 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 9/157:35 pmPDX - NAS
2 stops14h 56mUnited Airlines
Fri 9/192:33 pmNAS - PDX
1 stop10h 04mUnited Airlines
Deal found 8/5$439
This American Airlines deal was found by Cheapflights users on 8/5. 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.
Tue 12/911:08 pmPDX - NAS
1 stop11h 17mAmerican Airlines
Tue 12/167:40 amNAS - PDX
2 stops12h 04mAmerican Airlines
Deal found 8/5$443
This American Airlines deal was found by Cheapflights users on 8/5. 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.
Sat 8/3011:59 pmPDX - NAS
1 stop10h 28mAmerican Airlines
Sat 9/131:16 pmNAS - PDX
1 stop10h 21mAmerican Airlines
Deal found 8/5$464
This Mytrip deal was found by Cheapflights users on 8/3. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/3012:07 pmPDX - PUJ
2 stops23h 07mMultiple Airlines
Sat 10/43:55 pmPUJ - PDX
2 stops25h 51mMultiple Airlines
Deal found 8/3$481

Cheapflights Fare Finder

 
Customize your flight search to find flights from Portland to Caribbean Islands 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 August 5, 2025.
Use the filters below to find and compare flights from Portland to Caribbean Islands that are best for you.

Fly from

Portland

Fly to

Caribbean Islands

Route

Depart

Return

Price

PortlandSan Juan

PDX - SJU

PDXSJU

Portland

Wed 9/24

12:07 pm-1:43 pm

2 stops22h 36m

San Juan Luis Munoz Marin Intl

Sun 9/28

11:59 am-7:23 pm

3 stops34h 24m

$359

PortlandSan Juan

PDX - SJU

PDXSJU

Portland

Tue 10/21

8:04 pm-1:43 am

3 stops26h 39m

San Juan Luis Munoz Marin Intl

Tue 10/28

3:19 pm-7:04 pm

3 stops30h 45m

$369

PortlandSan Juan

PDX - SJU

PDXSJU

Portland

Thu 9/25

12:07 pm-2:11 pm

3 stops23h 04m

San Juan Luis Munoz Marin Intl

Sun 9/28

11:59 am-7:23 pm

3 stops34h 24m

$370

PortlandSan Juan

PDX - SJU

PDXSJU

Portland

Sun 9/28

7:15 am-11:47 pm

1 stop13h 32m

San Juan Luis Munoz Marin Intl

Wed 10/1

1:32 pm-11:52 pm

2 stops13h 20m

$399

PortlandSan Juan

PDX - SJU

PDXSJU

Portland

Mon 9/8

12:07 pm-2:11 pm

3 stops23h 04m

San Juan Luis Munoz Marin Intl

Mon 9/15

6:44 am-11:11 am

3 stops31h 27m

$418

PortlandSan Juan

PDX - SJU

PDXSJU

Portland

Sat 9/6

8:18 pm-2:17 pm

2 stops14h 59m

San Juan Luis Munoz Marin Intl

Sun 9/14

2:38 pm-7:23 pm

3 stops31h 45m

$419

PortlandSan Juan

PDX - SJU

PDXSJU

Portland

Wed 10/1

12:07 pm-1:43 pm

2 stops22h 36m

San Juan Luis Munoz Marin Intl

Sun 11/2

8:40 pm-7:04 pm

2 stops26h 24m

$423

PortlandSan Juan

PDX - SJU

PDXSJU

Portland

Sat 10/11

10:32 pm-1:45 pm

1 stop12h 13m

San Juan Luis Munoz Marin Intl

Fri 10/17

1:05 am-11:41 am

2 stops13h 36m

$429

PortlandNassau

PDX - NAS

PDXNAS

Portland

Mon 9/15

7:35 pm-1:31 pm

2 stops14h 56m

Nassau Intl

Fri 9/19

2:33 pm-9:37 pm

1 stop10h 04m

$439

PortlandNassau

PDX - NAS

PDXNAS

Portland

Tue 12/9

6:44 pm-11:15 am

2 stops13h 31m

Nassau Intl

Tue 12/16

7:40 am-4:44 pm

2 stops12h 04m

$443

Flights are sorted by cheapest round-trip flights first.

Deals found on 8/3

Showing 1-10 of 60 results
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Best time to book a flight from Portland to Caribbean Islands

Have a flexible travel schedule? Discover the best time to fly to Caribbean Islands 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 Caribbean Islands

What is the cheapest month to book a flight from Portland to Caribbean Islands?

Currently, September is the cheapest month in which you can book a flight from Portland to Caribbean Islands (average of $254). Flying from Portland to Caribbean Islands 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 PDX to EPX?

Find hourly flight availability from Portland to Caribbean Islands. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated August 5, 2025.

Regardless of the time of day you decide to fly, the ticket price will remain around the same. Book flights from Portland to Caribbean Islands as you normally would.

Reviews of airlines servicing Caribbean Islands

Get insights into the airlines that provide service to Caribbean Islands. 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 Caribbean Islands. Reviews last updated August 5, 2025.
See what other customers who have flown with Alaska Airlines, Southwest, and Delta from Portland to Caribbean Islands have to say. Users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
Alaska Airlines
8.0
Very good
10,000 reviews

Crew

8.5

Entertainment

7.1

Boarding

8.1

Food

7.1

Overall

8.0

Comfort

7.8

Reviews

1 / 20
8.0
Excellent

Anonymous,Aug 2025

BOI - LAX

flying in first class, my husband froze the entire flight and was miserable. first class does not offer blankets or any entertainment. (TV etc)
Alaska Airlines
8.0
Very good
10,000 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Crew

8.5

Entertainment

7.1

Boarding

8.1

Food

7.1

Overall

8.0

Comfort

7.8

Reviews

1 / 20
8.0
Excellent

Anonymous,Aug 2025

BOI - LAX

flying in first class, my husband froze the entire flight and was miserable. first class does not offer blankets or any entertainment. (TV etc)
Southwest
8.0
Very good
4,246 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Crew

8.5

Entertainment

7.1

Boarding

8.1

Food

7.1

Overall

8.0

Comfort

7.8

Reviews

1 / 20
8.0
Excellent

Anonymous,Aug 2025

BOI - LAX

flying in first class, my husband froze the entire flight and was miserable. first class does not offer blankets or any entertainment. (TV etc)
Delta
8.0
Very good
7,985 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Crew

8.5

Entertainment

7.1

Boarding

8.1

Food

7.1

Overall

8.0

Comfort

7.8

Reviews

1 / 20
8.0
Excellent

Anonymous,Aug 2025

BOI - LAX

flying in first class, my husband froze the entire flight and was miserable. first class does not offer blankets or any entertainment. (TV etc)
United Airlines
7.4
Good
8,916 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Crew

8.5

Entertainment

7.1

Boarding

8.1

Food

7.1

Overall

8.0

Comfort

7.8

Reviews

1 / 20
8.0
Excellent

Anonymous,Aug 2025

BOI - LAX

flying in first class, my husband froze the entire flight and was miserable. first class does not offer blankets or any entertainment. (TV etc)
American Airlines
7.2
Good
10,000 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Crew

8.5

Entertainment

7.1

Boarding

8.1

Food

7.1

Overall

8.0

Comfort

7.8

Reviews

1 / 20
8.0
Excellent

Anonymous,Aug 2025

BOI - LAX

flying in first class, my husband froze the entire flight and was miserable. first class does not offer blankets or any entertainment. (TV etc)

Related info for your journey

Find useful and relevant information for your journey from Portland to Caribbean Islands. 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 Caribbean Islands?

    Located just 6.0 mi from the city center, Portland (PDX) is the airport most travelers will use when flying to Caribbean Islands from Portland.

  • What are the most popular routes from Portland to Caribbean Islands?

    Most travelers choose Portland - San Juan Luis Munoz Marin Intl, Portland - Punta Cana or Portland - Montego Bay Sangster Intl when deciding on the best route from Portland to Caribbean Islands.

  • Can I find deals for flights from Portland to Caribbean Islands that include hotel bookings?

    Yes. In addition to deals on Portland to Caribbean Islands flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Portland to Caribbean Islands?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Portland to Caribbean Islands.

  • Can I find deals for business class flights from Portland to Caribbean Islands?

    Yes. Cheapflights offers flight deals from Portland to Caribbean Islands 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 Caribbean Islands?

    Currently, September is the cheapest month in which you can book a flight from Portland to Caribbean Islands (average of $254). Flying from Portland to Caribbean Islands 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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Alternative routes for Portland to Caribbean Islands

See prices for flight routes from nearby airports that may be better suited for you.
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Top 7 airlines flying from Portland to Caribbean Islands

Discover the top 7 airlines that operate flights from Portland to Caribbean Islands. 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 August 5, 2025.
AirlineCheapestAverageFlexibilityOn-time
JetBlueCheapest$185Average$369FlexibilityNo cancel feeOn-time62%
DeltaCheapest$212Average$704FlexibilityNo cancel feeOn-timeN/A
Spirit AirlinesCheapest$248Average$385FlexibilityNo cancel feeOn-time65%
United AirlinesCheapest$325Average$691FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$335Average$725FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$450Average$728FlexibilityNo cancel feeOn-time63%
Alaska AirlinesCheapest$454Average$549FlexibilityNo cancel feeOn-time75%

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