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Isle of Wight

$141+ Cheap flights from Portland (PDX) to Isle of Wight, VA

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 10/15. Fares are subject to change and may not be available on all flights or dates of travel.
PDX — RIC
Oct 16 — Oct 231
Thu 10/16
Thu 10/23
1 adult, Economy
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Cheapflights Tip: The best prices from Portland to Isle of Wight are usually found in January or September, booked 88 days in advance, depart on a Thursday or Tuesday and return on a Thursday

Cheap flight deals from Portland to Isle of Wight

Keep the following information in mind while searching for Portland to Isle of Wight flight deals. Data was last updated September 16, 2025.

Round-trip from

$337
(American Airlines)

One-way from

$141
(Kiwi.com)

Popular in

December

Cheapest in

January

Average price

$422
From Portland to Isle of Wight
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One-way flight from Portland to Isle of Wight
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Highest demand for flights based on searches. 6% potential increase in price ($34 potential increase over avg. RT price).
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Cheapest flight prices on average. 2% potential price decrease ($14 potential savings vs. average RT price).
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Average for round-trip flights in September 2025
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Find flight deals from Portland to Isle of Wight

Cheapest flights from Portland to Isle of Wight
Explore the most affordable flight options available from Portland to Isle of Wight. Find the lowest fares from popular airlines and budget airlines, with prices last updated on September 16, 2025.

This American Airlines deal was found by Cheapflights users on 9/15. 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 10/1411:58 pmPDX - ORF
1 stop9h 25mAmerican Airlines
Tue 10/216:13 pmORF - PDX
1 stop7h 53mAmerican Airlines
Deal found 9/15$337
This American Airlines deal was found by Cheapflights users on 9/15. 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 10/139:52 pmPDX - ORF
1 stop9h 50mAmerican Airlines
Tue 10/213:44 pmORF - PDX
1 stop9h 05mAmerican Airlines
Deal found 9/15$348
This United Airlines deal was found by Cheapflights users on 9/15. 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.
Fri 12/51:14 pmPDX - ORF
1 stop6h 45mUnited Airlines
Mon 12/84:45 pmORF - PDX
1 stop8h 30mUnited Airlines
Deal found 9/15$374
This American Airlines deal was found by Cheapflights users on 9/15. 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 12/511:59 pmPDX - ORF
2 stops11h 43mAmerican Airlines
Mon 12/82:35 pmORF - PDX
1 stop8h 42mAmerican Airlines
Deal found 9/15$379
This Southwest deal was found by Cheapflights users on 9/15. 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.
Fri 12/56:05 amPDX - ORF
2 stops8h 30mSouthwest
Mon 12/812:15 pmORF - PDX
2 stops12h 45mSouthwest
Deal found 9/15$384
This American Airlines deal was found by Cheapflights users on 9/14. 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 10/299:52 pmPDX - ORF
1 stop9h 50mAmerican Airlines
Sun 11/23:52 pmORF - PDX
1 stop8h 23mAmerican Airlines
Deal found 9/14$392

Cheapflights Fare Finder

 
Customize your flight search to find flights from Portland to Isle of Wight 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 September 16, 2025.
Use the filters below to find and compare flights from Portland to Isle of Wight that are best for you.

Fly from

Portland

Fly to

Isle of Wight

Route

Depart

Return

Price

PortlandNorfolk

PDX - ORF

PDXORF

Portland

Mon 11/17

11:59 pm-1:58 pm

2 stops10h 59m

Norfolk

Wed 11/19

4:52 pm-10:35 pm

1 stop8h 43m

$353

PortlandNorfolk

PDX - ORF

PDXORF

Portland

Fri 12/5

6:05 am-5:35 pm

2 stops8h 30m

Norfolk

Mon 12/8

12:15 pm-10:00 pm

2 stops12h 45m

$384

PortlandNorfolk

PDX - ORF

PDXORF

Portland

Wed 10/29

9:52 pm-10:42 am

1 stop9h 50m

Norfolk

Sun 11/2

3:52 pm-9:15 pm

1 stop8h 23m

$392

PortlandNorfolk

PDX - ORF

PDXORF

Portland

Thu 10/30

11:58 pm-12:05 pm

2 stops9h 07m

Norfolk

Sun 11/2

1:18 pm-9:15 pm

1 stop10h 57m

$408

PortlandNorfolk

PDX - ORF

PDXORF

Portland

Mon 2/16

9:45 pm-9:01 am

1 stop8h 16m

Norfolk

Fri 2/20

12:30 pm-7:18 pm

1 stop9h 48m

$412

PortlandNorfolk

PDX - ORF

PDXORF

Portland

Sat 10/11

1:15 pm-11:00 pm

1 stop6h 45m

Norfolk

Fri 10/17

7:10 pm-11:55 pm

1 stop7h 45m

$414

PortlandNorfolk

PDX - ORF

PDXORF

Portland

Fri 12/5

11:19 pm-11:56 am

1 stop9h 37m

Norfolk

Sun 12/7

6:05 am-11:48 am

1 stop8h 43m

$418

PortlandNorfolk

PDX - ORF

PDXORF

Portland

Thu 10/23

7:35 pm-9:15 am

2 stops10h 40m

Norfolk

Mon 10/27

7:10 pm-11:55 pm

1 stop7h 45m

$418

PortlandNorfolk

PDX - ORF

PDXORF

Portland

Sun 11/9

5:45 am-3:35 pm

1 stop6h 50m

Norfolk

Fri 11/14

11:35 am-8:45 pm

2 stops12h 10m

$423

PortlandNorfolk

PDX - ORF

PDXORF

Portland

Mon 10/6

10:58 pm-2:01 pm

2 stops12h 03m

Norfolk

Wed 10/8

4:23 pm-10:08 pm

1 stop8h 45m

$427

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/15

Showing 1-10 of 22 results
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Best time to book a flight from Portland to Isle of Wight

Have a flexible travel schedule? Discover the best time to fly to Isle of Wight 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 Isle of Wight

How far ahead should I book a flight from Portland to Isle of Wight?

Use this chart to determine the optimal time to book a round-trip flight from Portland to Isle of Wight. Price data was last updated on September 12, 2025.

To ensure you get the cheapest price possible for a flight from Portland to Isle of Wight, you should look to book at least 88 days in advance of your intended travel date. The price of your flight may increase if you delay and leave booking until a week or so before departure.

What is the cheapest month to book a flight from Portland to Isle of Wight?

Currently, January is the cheapest month in which you can book a flight from Portland to Isle of Wight (average of $281). Flying from Portland to Isle of Wight in March is currently the most expensive (average of $351). 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 I1W?

Find hourly flight availability from Portland to Isle of Wight. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated September 16, 2025.

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

What is the cheapest day to fly from Portland to Isle of Wight?

Use this chart to determine the cheapest time to fly round-trip from Portland to Isle of Wight. Price data was last updated on December 16, 2024.

Travelers seeking maximum savings on their Portland to Isle of Wight flight should consider departing on Monday evenings when fares are most often at their lowest. Sunday mornings flights should be avoided if possible as fares are typically the most expensive at this time.

Reviews of airlines servicing Isle of Wight

Get insights into the airlines that provide service to Isle of Wight. 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 Isle of Wight. Reviews last updated September 16, 2025.
Get a feel of what it's like to fly with Southwest, Delta, and United Airlines from Portland to Isle of Wight by reading reviews from past customers. Users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.0
Very good
4,242 reviews

Food

7.0

Comfort

8.0

Entertainment

7.5

Overall

8.0

Boarding

8.1

Crew

8.6

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
Southwest
8.0
Very good
4,242 reviews
Southwest
8.0
Very good
4,242 reviews

Food

7.0

Comfort

8.0

Entertainment

7.5

Overall

8.0

Boarding

8.1

Crew

8.6

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
Delta
8.0
Very good
7,957 reviews
Southwest
8.0
Very good
4,242 reviews

Food

7.0

Comfort

8.0

Entertainment

7.5

Overall

8.0

Boarding

8.1

Crew

8.6

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
United Airlines
7.4
Good
8,924 reviews
Southwest
8.0
Very good
4,242 reviews

Food

7.0

Comfort

8.0

Entertainment

7.5

Overall

8.0

Boarding

8.1

Crew

8.6

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
American Airlines
7.2
Good
10,000 reviews
Southwest
8.0
Very good
4,242 reviews

Food

7.0

Comfort

8.0

Entertainment

7.5

Overall

8.0

Boarding

8.1

Crew

8.6

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines

Related info for your journey

Find useful and relevant information for your journey from Portland to Isle of Wight. 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 Isle of Wight?

    Portland (PDX), located 6.0 mi from the city center, is the airport you fly out of when you book flights from Portland to Isle of Wight. 4 airlines have flights from Portland to Isle of Wight on a regular basis. Booking flights from Portland to Isle of Wight should not be difficult; the airport handles an average of 0 outbound flights to Isle of Wight per day.

  • How long is the flight from Portland to Isle of Wight?

    A quick flight from Portland to Isle of Wight can take about 8h 30m. United Airlines provides one of the quickest options available for as low as $384. The distance from Portland to Isle of Wight is about 2446 mi. When browsing for deals, the options you’ll see will be for both nonstop flights and flights with stops.

  • What are the cheapest airlines to fly from Portland to Isle of Wight one-way?

    One-way options have recently been found by users for as low as $163 on Frontier. Other airlines that offer cheap prices include United Airlines from $169 and Southwest from $185 one-way.

  • Can I find deals for flights from Portland to Isle of Wight that include hotel bookings?

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

  • How can I find direct flights from Portland to Isle of Wight?

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

  • Can I find deals for business class flights from Portland to Isle of Wight?

    Yes. Cheapflights offers flight deals from Portland to Isle of Wight 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 Isle of Wight?

    Currently, January is the cheapest month in which you can book a flight from Portland to Isle of Wight (average of $281). Flying from Portland to Isle of Wight in March is currently the most expensive (average of $351). 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 Isle of Wight

See prices for flight routes from nearby airports that may be better suited for you.
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Top 4 airlines flying from Portland to Isle of Wight

Discover the top 4 airlines that operate flights from Portland to Isle of Wight. 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 September 16, 2025.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$323Average$490FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$332Average$650FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$334Average$513FlexibilityNo cancel feeOn-time69%
SouthwestCheapest$387Average$522FlexibilityNo cancel feeOn-time63%

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