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$135+ Cheap flights from Portland (PDX) to Caribbean

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 12/10. Fares are subject to change and may not be available on all flights or dates of travel.
PDX — SJU
Nov 25 — Dec 21
Mon 11/25
Mon 12/2
1 adult, Economy
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Cheap flight deals from Portland to Caribbean

Discover tips and strategies to find the most affordable flight options for your journey from Portland (PDX) to Caribbean (0CB). 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 November 20, 2024.

Find flight deals from Portland to Caribbean

Cheapest flights from Portland to Caribbean
Explore the most affordable flight options available from Portland to Caribbean. Find the lowest fares from popular airlines and budget airlines, with prices last updated on November 20, 2024.

This FlightHub deal was found by Cheapflights users on 11/19. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/117:16 pmPDX - STT
2 stops14h 07mSpirit Airlines
Thu 12/1911:44 amSTT - PDX
2 stops15h 50mSpirit Airlines
Deal found 11/19$331
This FlightHub deal was found by Cheapflights users on 11/19. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/107:16 pmPDX - SJU
2 stops18h 27mSpirit Airlines
Wed 1/84:14 pmSJU - PDX
2 stops21h 07mSpirit Airlines
Deal found 11/19$412
This Kiwi.com deal was found by Cheapflights users on 11/20. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/55:00 amPDX - PUJ
2 stops30h 45mMultiple Airlines
Fri 12/134:05 pmPUJ - PDX
1 stop29h 13mMultiple Airlines
Deal found 11/20$424
This Delta deal was found by Cheapflights users on 11/20. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/1011:13 pmPDX - SJU
1 stop11h 01mDelta
Tue 12/177:30 amSJU - PDX
2 stops17h 00mDelta
Deal found 11/20$434
This Mytrip deal was found by Cheapflights users on 11/19. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/52:52 pmPDX - SJU
3 stops30h 57mMultiple Airlines
Sat 12/73:20 amSJU - PDX
2 stops18h 18mMultiple Airlines
Deal found 11/19$475
This United Airlines deal was found by Cheapflights users on 11/20. 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 12/89:55 pmPDX - SJU
1 stop10h 52mUnited Airlines
Wed 12/112:05 amSJU - PDX
2 stops17h 15mUnited Airlines
Deal found 11/20$491
This FlightHub deal was found by Cheapflights users on 11/20. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 12/82:52 pmPDX - AUA
2 stops44h 48mSpirit Airlines
Sun 12/154:40 pmAUA - PDX
2 stops53h 41mSpirit Airlines
Deal found 11/20$512
This United Airlines deal was found by Cheapflights users on 11/19. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/119:55 pmPDX - STT
1 stop10h 05mUnited Airlines
Thu 12/193:00 pmSTT - PDX
1 stop11h 45mUnited Airlines
Deal found 11/19$532
This American Airlines deal was found by Cheapflights users on 11/18. 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 12/310:45 pmPDX - NAS
1 stop18h 20mAmerican Airlines
Fri 12/131:06 pmNAS - PDX
1 stop13h 18mAmerican Airlines
Deal found 11/18$573
This Delta deal was found by Cheapflights users on 11/18. 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 12/310:55 pmPDX - NAS
1 stop11h 21mDelta
Fri 12/131:21 pmNAS - PDX
2 stops14h 07mDelta
Deal found 11/18$578
This American Airlines deal was found by Cheapflights users on 11/20. 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.
Mon 11/2510:45 pmPDX - SJU
1 stop19h 11mAmerican Airlines
Wed 11/277:12 amSJU - PDX
2 stops14h 28mAmerican Airlines
Deal found 11/20$583
This United Airlines deal was found by Cheapflights users on 11/20. 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 12/43:30 pmPDX - NAS
2 stops17h 23mUnited Airlines
Wed 12/112:35 pmNAS - PDX
1 stop11h 25mUnited Airlines
Deal found 11/20$603

Find flights from Portland to Caribbean within your budget

Customize your flight search to find flights from Portland to Caribbean 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 2,629,791 searches. Data last updated November 20, 2024.

Fly from

Any airport

Fly to

Any airport

Route

Depart

Return

Price

PortlandSaint Thomas Island

PDX - STT

PDXSTT

Portland

Wed 12/11

7:16 pm-1:23 pm

2 stops14h 07m

Saint Thomas Island Cyril E King

Thu 12/19

11:44 am-11:34 pm

2 stops15h 50m

$331

PortlandSan Juan

PDX - SJU

PDXSJU

Portland

Sat 1/11

9:41 pm-5:29 pm

2 stops39h 48m

San Juan Luis Munoz Marin Intl

Tue 1/21

7:00 am-8:46 pm

2 stops17h 46m

$408

PortlandSan Juan

PDX - SJU

PDXSJU

Portland

Mon 1/13

7:30 pm-12:47 pm

2 stops13h 17m

San Juan Luis Munoz Marin Intl

Fri 1/24

2:05 am-1:50 pm

2 stops15h 45m

$418

PortlandPunta Cana

PDX - PUJ

PDXPUJ

Portland

Thu 12/5

5:00 am-3:45 pm

2 stops30h 45m

Punta Cana

Fri 12/13

4:05 pm-5:18 pm

1 stop29h 13m

$424

PortlandSan Juan

PDX - SJU

PDXSJU

Portland

Mon 1/20

12:45 am-5:07 pm

2 stops12h 22m

San Juan Luis Munoz Marin Intl

Fri 1/31

2:02 pm-9:55 pm

1 stop11h 53m

$424

PortlandNassau

PDX - NAS

PDXNAS

Portland

Sun 3/16

5:15 pm-7:59 pm

2 stops23h 44m

Nassau Intl

Tue 3/18

11:00 am-11:53 pm

1 stop15h 53m

$441

PortlandSaint Thomas Island

PDX - STT

PDXSTT

Portland

Thu 1/30

6:15 pm-11:50 am

2 stops13h 35m

Saint Thomas Island Cyril E King

Sun 2/9

6:31 pm-11:06 am

2 stops20h 35m

$448

PortlandSan Juan

PDX - SJU

PDXSJU

Portland

Tue 4/15

5:20 am-8:15 pm

2 stops11h 55m

San Juan Luis Munoz Marin Intl

Fri 4/25

7:40 am-6:35 pm

2 stops13h 55m

$448

PortlandSan Juan

PDX - SJU

PDXSJU

Portland

Thu 1/9

11:59 pm-5:30 pm

2 stops13h 31m

San Juan Luis Munoz Marin Intl

Sat 1/18

12:50 pm-11:36 pm

1 stop14h 46m

$461

PortlandSan Juan

PDX - SJU

PDXSJU

Portland

Thu 12/5

2:52 pm-1:49 am

3 stops30h 57m

San Juan Luis Munoz Marin Intl

Sat 12/7

3:20 am-5:38 pm

2 stops18h 18m

$475

Flights are sorted by cheapest round-trip flights first.

Deals found on 11/19

Showing 1-10 of 54 results
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Best time to book a flight from Portland to Caribbean

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

Travel insights for flights from Portland to Caribbean

Get recent, data-driven insights about flights from Portland to Caribbean including ideal travel times, pricing trends, and more.

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

Currently, September is the cheapest month in which you can book a flight from Portland to Caribbean (average of $254). Flying from Portland to Caribbean in March is currently the most expensive (average of $335). 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 CB?

Find hourly flight availability from Portland to Caribbean. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated November 20, 2024.

When flying from Portland to Caribbean, the time of day you decide to fly out makes little to no difference towards the overall price you’ll pay on tickets.

Rainfall in Caribbean by month

Plan your trip to Caribbean by taking into account the average rainfall totals by month.

In terms of precipitation, rainfall in Caribbean ranges from 2.2 - 6.1 inches per month. November is typically the wettest month, when rainfall can reach 6.1 in. February is typically the driest time to visit Caribbean when rainfall is around 2.2 in.

Temperature in Caribbean by month

Plan your trip to Caribbean by taking into account the average temperature totals by month.

If weather is an important factor for your trip to Caribbean, use this chart to help with planning. For those seeking warmer temperatures, June is the ideal time of year to visit, when temperatures reach an average of 82.4 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 77.0 F).

Reviews of airlines servicing Caribbean

Get insights into the airlines that provide service to Caribbean. 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. Reviews last updated November 20, 2024.
Southwest
8.1
Very good
5,014 reviews

Entertainment

7.7

Comfort

8.1

Overall

8.1

Food

7.2

Boarding

8.2

Crew

8.7

Reviews

1 / 10

Great service throughout our flight. Easy boarding with early bird check in

Southwest
8.1
Very good
5,014 reviews
Southwest
8.1
Very good
5,014 reviews

Entertainment

7.7

Comfort

8.1

Overall

8.1

Food

7.2

Boarding

8.2

Crew

8.7

Reviews

1 / 10

Great service throughout our flight. Easy boarding with early bird check in

Alaska Airlines
8.0
Very good
9,461 reviews
Southwest
8.1
Very good
5,014 reviews

Entertainment

7.7

Comfort

8.1

Overall

8.1

Food

7.2

Boarding

8.2

Crew

8.7

Reviews

1 / 10

Great service throughout our flight. Easy boarding with early bird check in

Delta
8.0
Very good
8,756 reviews
Southwest
8.1
Very good
5,014 reviews

Entertainment

7.7

Comfort

8.1

Overall

8.1

Food

7.2

Boarding

8.2

Crew

8.7

Reviews

1 / 10

Great service throughout our flight. Easy boarding with early bird check in

United Airlines
7.4
Good
9,171 reviews
Southwest
8.1
Very good
5,014 reviews

Entertainment

7.7

Comfort

8.1

Overall

8.1

Food

7.2

Boarding

8.2

Crew

8.7

Reviews

1 / 10

Great service throughout our flight. Easy boarding with early bird check in

WestJet
7.3
Good
2,811 reviews
Southwest
8.1
Very good
5,014 reviews

Entertainment

7.7

Comfort

8.1

Overall

8.1

Food

7.2

Boarding

8.2

Crew

8.7

Reviews

1 / 10

Great service throughout our flight. Easy boarding with early bird check in

Related info for your journey

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

    For a flight from Portland to Caribbean, you will be flying from Portland. Portland (PDX) is just 6.0 mi from the center of the city.

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

    For one-way options, check prices for Spirit Airlines. According to our data, you can fly for as low as $135. Users have also found prices from $169 and $214 on American Airlines and United Airlines, respectively.

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

    The most popular flight routes from Portland to Caribbean are Portland - San Juan Luis Munoz Marin Intl, Portland - Saint Thomas Island Cyril E King and Portland - Punta Cana.

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

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

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

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

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

    Yes. Cheapflights offers flight deals from Portland to Caribbean 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?

    Currently, September is the cheapest month in which you can book a flight from Portland to Caribbean (average of $254). Flying from Portland to Caribbean in March is currently the most expensive (average of $335). 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

See prices for flight routes from nearby airports that may be better suited for you.
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Top 9 airlines flying from Portland to Caribbean

Discover the top 9 airlines that operate flights from Portland to Caribbean. 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 2,629,791 searches. Data last updated November 20, 2024.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$145Average$346FlexibilityNo cancel feeOn-time62%
Alaska AirlinesCheapest$217Average$826FlexibilityNo cancel feeOn-time75%
DeltaCheapest$237Average$646FlexibilityNo cancel feeOn-timeN/A
Spirit AirlinesCheapest$239Average$357FlexibilityNo cancel feeOn-time65%
United AirlinesCheapest$298Average$662FlexibilityNo cancel feeOn-time69%
JetBlueCheapest$298Average$585FlexibilityNo cancel feeOn-time62%
American AirlinesCheapest$312Average$659FlexibilityNo cancel feeOn-time71%
Sun Country AirCheapest$350Average$717FlexibilityNo cancel feeOn-time83%
SouthwestCheapest$504Average$733FlexibilityNo cancel feeOn-time63%
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