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$190+ 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 6/6. Fares are subject to change and may not be available on all flights or dates of travel.
SJU — PDX
may. 4 — may. 111
dom. 5/4
dom. 5/11
1 adult, Economy
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Cheap flight deals from Caribbean to Portland

Keep the following information in mind while searching for Caribbean to Portland flight deals. Data was last updated abril 29, 2025.

Round-trip from

$379
(Delta)

One-way from

$190
(American Airlines)

Popular in

November

Cheapest in

February

Average price

$523
From Caribbean to Portland
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One-way flight from Caribbean to Portland
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Highest demand for flights based on searches. 11% potential increase in price ($65 potential increase over avg. RT price).
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Cheapest flight prices on average. 3% potential price decrease ($17 potential savings vs. average RT price).
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Average for round-trip flights in April 2025
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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 abril 29, 2025.

This Delta deal was found by Cheapflights users on 4/29. 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.
jue. 11/63:25 pmSJU - PDX
1 stop10h 29mDelta
dom. 11/97:00 amPDX - SJU
1 stop12h 50mDelta
Deal found 4/29$379
This Mytrip deal was found by Cheapflights users on 4/29. 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.
mar. 6/106:09 amSJU - PDX
3 stops33h 33mSpirit Airlines
lun. 6/166:39 pmPDX - SJU
2 stops24h 10mSpirit Airlines
Deal found 4/29$400
This Priceline deal was found by Cheapflights users on 4/28. 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.
vie. 6/1310:15 amMBJ - PDX
2 stops27h 02mSpirit Airlines
vie. 6/2012:12 pmPDX - MBJ
2 stops20h 50mSpirit Airlines
Deal found 4/28$432
This American Airlines deal was found by Cheapflights users on 4/29. 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.
jue. 5/226:10 amSJU - PDX
1 stop19h 57mAmerican Airlines
lun. 5/2610:24 pmPDX - SJU
1 stop18h 45mAmerican Airlines
Deal found 4/29$442
This JetBlue deal was found by Cheapflights users on 4/29. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
jue. 7/1712:35 pmSJU - PDX
1 stop12h 35mJetBlue
lun. 7/2111:35 pmPDX - SJU
1 stop14h 05mJetBlue
Deal found 4/29$456
This Mytrip deal was found by Cheapflights users on 4/29. 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.
dom. 6/11:33 amSJU - PDX
2 stops38h 09mMultiple Airlines
mié. 6/114:24 pmPDX - SJU
2 stops23h 12mMultiple Airlines
Deal found 4/29$457
This United Airlines deal was found by Cheapflights users on 4/29. 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.
vie. 9/191:05 amSJU - PDX
2 stops13h 53mUnited Airlines
vie. 10/310:14 pmPDX - SJU
1 stop12h 31mUnited Airlines
Deal found 4/29$459
This Delta deal was found by Cheapflights users on 4/28. 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.
jue. 5/81:02 pmMBJ - PDX
2 stops13h 08mDelta
lun. 5/1210:55 pmPDX - MBJ
1 stop12h 03mDelta
Deal found 4/28$532
This United Airlines deal was found by Cheapflights users on 4/28. 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.
jue. 7/312:40 pmMBJ - PDX
2 stops20h 52mUnited Airlines
mié. 8/1311:59 pmPDX - MBJ
2 stops13h 11mUnited Airlines
Deal found 4/28$533
This American Airlines deal was found by Cheapflights users on 4/29. 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.
sáb. 5/1012:54 pmMBJ - PDX
2 stops11h 45mAmerican Airlines
sáb. 5/1711:59 pmPDX - MBJ
1 stop12h 36mAmerican Airlines
Deal found 4/29$566
This Southwest deal was found by Cheapflights users on 4/29. 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.
mar. 6/106:30 amSJU - PDX
1 stop11h 40mSouthwest
mar. 6/176:05 amPDX - SJU
2 stops12h 10mSouthwest
Deal found 4/29$574
This Mytrip deal was found by Cheapflights users on 4/28. 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.
vie. 6/1310:15 amMBJ - PDX
3 stops33h 29mMultiple Airlines
vie. 6/2011:59 pmPDX - MBJ
3 stops33h 03mMultiple Airlines
Deal found 4/28$585

Cheapflights Fare Finder

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 abril 29, 2025.
Use the filters below to find and compare flights from Caribbean to Portland that are best for you.

Fly from

Caribbean

Fly to

Portland

Route

Depart

Return

Price

San JuanPortland

SJU - PDX

SJUPDX

San Juan Luis Munoz Marin Intl

mié. 5/28

1:12 pm-11:15 pm

1 stop13h 03m

Portland

dom. 6/1

7:14 am-11:42 pm

1 stop13h 28m

$379

San JuanPortland

SJU - PDX

SJUPDX

San Juan Luis Munoz Marin Intl

mar. 6/10

6:09 am-12:42 pm

3 stops33h 33m

Portland

lun. 6/16

6:39 pm-9:49 pm

2 stops24h 10m

$400

Montego BayPortland

MBJ - PDX

MBJPDX

Montego Bay Sangster Intl

vie. 6/13

10:15 am-11:17 am

2 stops27h 02m

Portland

vie. 6/20

12:12 pm-11:02 am

2 stops20h 50m

$432

San JuanPortland

SJU - PDX

SJUPDX

San Juan Luis Munoz Marin Intl

jue. 5/22

6:10 am-11:07 pm

1 stop19h 57m

Portland

lun. 5/26

10:24 pm-8:09 pm

1 stop18h 45m

$442

San JuanPortland

SJU - PDX

SJUPDX

San Juan Luis Munoz Marin Intl

jue. 7/17

12:35 pm-10:10 pm

1 stop12h 35m

Portland

lun. 7/21

11:35 pm-4:40 pm

1 stop14h 05m

$456

San JuanPortland

SJU - PDX

SJUPDX

San Juan Luis Munoz Marin Intl

dom. 6/1

1:33 am-12:42 pm

2 stops38h 09m

Portland

mié. 6/11

4:24 pm-6:36 pm

2 stops23h 12m

$457

San JuanPortland

SJU - PDX

SJUPDX

San Juan Luis Munoz Marin Intl

vie. 9/19

1:05 am-11:58 am

2 stops13h 53m

Portland

vie. 10/3

10:14 pm-1:45 pm

1 stop12h 31m

$459

Montego BayPortland

MBJ - PDX

MBJPDX

Montego Bay Sangster Intl

mié. 5/28

4:12 pm-2:46 pm

2 stops24h 34m

Portland

sáb. 5/31

5:00 am-3:45 pm

1 stop8h 45m

$532

Montego BayPortland

MBJ - PDX

MBJPDX

Montego Bay Sangster Intl

sáb. 5/10

12:54 pm-10:39 pm

2 stops11h 45m

Portland

sáb. 5/17

11:59 pm-2:35 pm

1 stop12h 36m

$566

San JuanPortland

SJU - PDX

SJUPDX

San Juan Luis Munoz Marin Intl

mar. 6/10

6:30 am-3:10 pm

1 stop11h 40m

Portland

mar. 6/17

6:05 am-9:15 pm

2 stops12h 10m

$574

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/29

Showing 1-10 of 44 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.

Cheapflights Insights

Everything you need to know about your flight from Caribbean to Portland

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 $368). 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 abril 29, 2025.

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 abril 29, 2025.
Alaska Airlines
8.0
Very good
9,961 reviews

Entertainment

7.1

Comfort

7.9

Crew

8.5

Overall

8.0

Boarding

8.2

Food

7.1

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.
Alaska Airlines
8.0
Very good
9,961 reviews
Alaska Airlines
8.0
Very good
9,961 reviews

Entertainment

7.1

Comfort

7.9

Crew

8.5

Overall

8.0

Boarding

8.2

Food

7.1

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.
Southwest
8.0
Very good
4,295 reviews
Alaska Airlines
8.0
Very good
9,961 reviews

Entertainment

7.1

Comfort

7.9

Crew

8.5

Overall

8.0

Boarding

8.2

Food

7.1

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.
Delta
8.0
Very good
7,929 reviews
Alaska Airlines
8.0
Very good
9,961 reviews

Entertainment

7.1

Comfort

7.9

Crew

8.5

Overall

8.0

Boarding

8.2

Food

7.1

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.
United Airlines
7.4
Good
8,696 reviews
Alaska Airlines
8.0
Very good
9,961 reviews

Entertainment

7.1

Comfort

7.9

Crew

8.5

Overall

8.0

Boarding

8.2

Food

7.1

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.
JetBlue
7.3
Good
2,922 reviews
Alaska Airlines
8.0
Very good
9,961 reviews

Entertainment

7.1

Comfort

7.9

Crew

8.5

Overall

8.0

Boarding

8.2

Food

7.1

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.

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 $190 on American Airlines. Other airlines that offer cheap prices include Spirit Airlines from $206 and Delta from $227 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, Montego Bay Sangster Intl - Portland or Santo Domingo Las Americas - 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 $368). 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

Traveling to a place near Caribbean?

Book flights to Caribbean if you plan to visit one of these locations
Beaverton
Lincoln City
Seaside
Clackamas
Vancouver
McMinnville
Lake Oswego
Hillsboro
Gresham
Astoria
Long Beach
Cannon Beach
Tigard
Hood River
Woodburn
Depoe Bay
Pacific City
Stevenson
Troutdale
Longview

Browse thousands of different options on Cheapflights for your next trip

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Alternative routes for Caribbean to Portland

See prices for flight routes from nearby airports that may be better suited for you.
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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 abril 29, 2025.
AirlineCheapestAverageFlexibilityOn-time
JetBlueCheapest$288Average$487FlexibilityNo cancel feeOn-time62%
United AirlinesCheapest$312Average$585FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$342Average$610FlexibilityNo cancel feeOn-time71%
DeltaCheapest$354Average$587FlexibilityNo cancel feeOn-timeN/A
SouthwestCheapest$424Average$570FlexibilityNo cancel feeOn-time63%

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