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$125+ Cheap flights from Caribbean to Portland (PDX)

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 1/23. Fares are subject to change and may not be available on all flights or dates of travel.
SJU — PDX
Dec 27 — Jan 31
Fri 12/27
Fri 1/3
1 adult, Economy
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Cheap flight deals from Caribbean to Portland

Discover tips and strategies to find the most affordable flight options for your journey from Caribbean (0CB) to Portland (PDX). 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 December 22, 2024.

Round-trip from

$315
(Mytrip)

One-way from

$125
(FlightHub)
From Caribbean to Portland
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One-way flight from Caribbean to Portland
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Find flight deals from Caribbean to Portland

Cheapest flights from Caribbean to Portland
Explore the most affordable flight options available from Caribbean to Portland. Find the lowest fares from popular airlines and budget airlines, with prices last updated on December 22, 2024.

This eDestinos deal was found by Cheapflights users on 12/21. 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 eDestinos is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/235:40 pmSJU - PDX
1 stop27h 50mMultiple Airlines
Mon 1/67:19 pmPDX - SJU
2 stops36h 48mMultiple Airlines
Deal found 12/21$459
This American Airlines deal was found by Cheapflights users on 12/21. 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 12/234:10 pmSJU - PDX
1 stop10h 47mAmerican Airlines
Mon 1/61:45 pmPDX - SJU
1 stop19h 45mAmerican Airlines
Deal found 12/21$692
This Delta deal was found by Cheapflights users on 12/21. 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 12/223:13 amSJU - PDX
2 stops17h 04mDelta
Mon 1/65:15 amPDX - SJU
2 stops14h 44mDelta
Deal found 12/21$777
This American Airlines deal was found by Cheapflights users on 12/21. 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 12/263:20 pmSDQ - PDX
1 stop12h 18mAmerican Airlines
Sun 12/2910:42 pmPDX - SDQ
1 stop19h 19mAmerican Airlines
Deal found 12/21$927
This Delta deal was found by Cheapflights users on 12/21. 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.
Thu 12/262:45 pmSDQ - PDX
1 stop12h 50mDelta
Sun 12/297:20 pmPDX - SDQ
2 stops15h 09mDelta
Deal found 12/21$951
This Alaska Airlines deal was found by Cheapflights users on 12/21. 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 Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/236:25 amSJU - PDX
2 stops16h 52mAlaska Airlines
Mon 1/61:52 pmPDX - SJU
3 stops20h 53mAlaska Airlines
Deal found 12/21$3,214

Find flights from Caribbean to Portland within your budget

Customize your flight search to find flights from Caribbean to Portland 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 December 22, 2024.

Fly from

Any airport

Fly to

Any airport

Route

Depart

Return

Price

San JuanPortland

SJU - PDX

SJUPDX

San Juan Luis Munoz Marin Intl

Thu 2/20

6:00 am-9:21 am

2 stops31h 21m

Portland

Mon 2/24

10:16 am-5:01 pm

2 stops26h 45m

$315

San JuanPortland

SJU - PDX

SJUPDX

San Juan Luis Munoz Marin Intl

Wed 2/5

7:45 am-11:36 pm

1 stop19h 51m

Portland

Mon 2/10

10:45 pm-3:45 pm

1 stop13h 00m

$348

San JuanPortland

SJU - PDX

SJUPDX

San Juan Luis Munoz Marin Intl

Thu 2/6

2:11 pm-11:29 pm

1 stop13h 18m

Portland

Mon 2/10

7:35 pm-1:01 pm

2 stops13h 26m

$424

KingstonPortland

KIN - PDX

KINPDX

Kingston Norman Manley

Tue 2/4

2:38 pm-4:35 pm

3 stops28h 57m

Portland

Tue 2/11

5:30 pm-12:09 pm

3 stops15h 39m

$500

San JuanPortland

SJU - PDX

SJUPDX

San Juan Luis Munoz Marin Intl

Tue 2/4

2:05 am-7:02 pm

2 stops20h 57m

Portland

Mon 2/10

5:00 am-6:25 pm

1 stop9h 25m

$510

KingstonPortland

KIN - PDX

KINPDX

Kingston Norman Manley

Tue 2/4

9:00 am-11:51 pm

2 stops17h 51m

Portland

Tue 2/11

6:05 am-8:00 pm

2 stops10h 55m

$605

KingstonPortland

KIN - PDX

KINPDX

Kingston Norman Manley

Tue 2/4

6:48 am-11:36 pm

1 stop19h 48m

Portland

Tue 2/11

10:45 pm-12:31 pm

1 stop10h 46m

$614

Santiago de los CaballerosPortland

STI - PDX

STIPDX

Santiago de los Caballeros

Tue 1/28

6:35 am-8:12 pm

2 stops17h 37m

Portland

Tue 2/4

7:35 pm-1:05 pm

2 stops13h 30m

$658

Santo DomingoPortland

SDQ - PDX

SDQPDX

Santo Domingo Las Americas

Wed 1/15

7:30 am-11:36 pm

1 stop20h 06m

Portland

Mon 1/20

10:45 pm-2:09 pm

1 stop11h 24m

$665

Santiago de los CaballerosPortland

STI - PDX

STIPDX

Santiago de los Caballeros

Tue 1/28

12:49 pm-8:37 pm

1 stop11h 48m

Portland

Tue 2/4

10:48 pm-2:53 pm

1 stop12h 05m

$677

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/21

Showing 1-10 of 36 results
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Best time to book a flight from Caribbean to Portland

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

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

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

Currently, November is the cheapest month in which you can book a flight from Caribbean to Portland (average of $277). Flying from Caribbean to Portland in March is currently the most expensive (average of $376). 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 CB to PDX?

Find hourly flight availability from Caribbean to Portland. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated December 22, 2024.

When flying from Caribbean to Portland, 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 Portland by month

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

In terms of precipitation, rainfall in Portland ranges from 0.7 - 5.6 inches per month. November is typically the wettest month, when rainfall can reach 5.6 in. July is typically the driest time to visit Portland when rainfall is around 0.7 in.

Temperature in Portland by month

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

If weather is an important factor for your trip to Portland, use this chart to help with planning. For those seeking warmer temperatures, July is the ideal time of year to visit, when temperatures reach an average of 69.8 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 41.0 F).

Reviews of airlines servicing Portland

Get insights into the airlines that provide service to Portland. 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 Portland. Reviews last updated December 22, 2024.
Southwest
8.1
Very good
4,804 reviews

Overall

8.1

Food

7.2

Entertainment

7.7

Boarding

8.2

Crew

8.7

Comfort

8.1

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

Southwest
8.1
Very good
4,804 reviews
Southwest
8.1
Very good
4,804 reviews

Overall

8.1

Food

7.2

Entertainment

7.7

Boarding

8.2

Crew

8.7

Comfort

8.1

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

Alaska Airlines
8.0
Very good
9,537 reviews
Southwest
8.1
Very good
4,804 reviews

Overall

8.1

Food

7.2

Entertainment

7.7

Boarding

8.2

Crew

8.7

Comfort

8.1

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

Delta
8.0
Very good
8,594 reviews
Southwest
8.1
Very good
4,804 reviews

Overall

8.1

Food

7.2

Entertainment

7.7

Boarding

8.2

Crew

8.7

Comfort

8.1

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

United Airlines
7.4
Good
9,028 reviews
Southwest
8.1
Very good
4,804 reviews

Overall

8.1

Food

7.2

Entertainment

7.7

Boarding

8.2

Crew

8.7

Comfort

8.1

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

American Airlines
7.2
Good
10,000 reviews
Southwest
8.1
Very good
4,804 reviews

Overall

8.1

Food

7.2

Entertainment

7.7

Boarding

8.2

Crew

8.7

Comfort

8.1

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

Related info for your journey

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

    Portland (PDX) is the airport you will fly into if you book a flight from Caribbean to Portland. It is only a 6.0 mi journey from Portland (PDX) to Portland’s city center.

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

    One-way options have recently been found by users for as low as $125 on Spirit Airlines. Other airlines that offer cheap prices include American Airlines from $174 and Southwest from $212 one-way.

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

    When deciding which route to take from Caribbean to Portland consider San Juan Luis Munoz Marin Intl - Portland, Santo Domingo Las Americas - Portland or Kingston Norman Manley - Portland as they are the most popular.

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

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

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

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

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

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

    Currently, November is the cheapest month in which you can book a flight from Caribbean to Portland (average of $277). Flying from Caribbean to Portland in March is currently the most expensive (average of $376). 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 Caribbean to Portland

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Top 5 airlines flying from Caribbean to Portland

Discover the top 5 airlines that operate flights from Caribbean to Portland. 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 December 22, 2024.
AirlineCheapestAverageFlexibilityOn-time
JetBlueCheapest$288Average$517FlexibilityNo cancel feeOn-time62%
United AirlinesCheapest$308Average$597FlexibilityNo cancel feeOn-time69%
Spirit AirlinesCheapest$312Average$385FlexibilityNo cancel feeOn-time65%
American AirlinesCheapest$342Average$691FlexibilityNo cancel feeOn-time71%
DeltaCheapest$354Average$431FlexibilityNo cancel feeOn-timeN/A
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