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Isle of Wight

$192+ 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 5/5. Fares are subject to change and may not be available on all flights or dates of travel.
PDX — RIC
Apr 22 — Apr 291
Wed 4/22
Wed 4/29
1 adult, Economy
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Cheap 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 March 23, 2026.

This Southwest deal was found by Cheapflights users on 3/22. 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.
Tue 5/55:40 am
PDX
-
ORF
1 stop12h 30m
Southwest
Tue 5/126:25 pm
ORF
-
PDX
1 stop7h 45m
Southwest
Deal found 3/22$354
This American Airlines deal was found by Cheapflights users on 3/18. 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.
Wed 4/2211:47 pm
PDX
-
ORF
1 stop7h 17m
American Airlines
Wed 5/63:12 pm
ORF
-
PDX
1 stop9h 26m
American Airlines
Deal found 3/18$383
This Southwest deal was found by Cheapflights users on 3/18. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/227:25 pm
PDX
-
ORF
2 stops11h 00m
Southwest
Wed 5/66:25 pm
ORF
-
PDX
1 stop7h 45m
Southwest
Deal found 3/18$388
This American Airlines deal was found by Cheapflights users on 3/18. 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 4/1411:23 pm
PDX
-
ORF
1 stop7h 49m
American Airlines
Sat 4/253:20 pm
ORF
-
PDX
1 stop8h 43m
American Airlines
Deal found 3/18$390
This Delta deal was found by Cheapflights users on 3/22. 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 4/1411:51 am
PDX
-
ORF
1 stop9h 46m
Delta
Wed 4/222:03 pm
ORF
-
PDX
1 stop10h 59m
Delta
Deal found 3/22$397
This Delta deal was found by Cheapflights users on 3/22. 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 4/147:32 pm
PDX
-
ORF
2 stops10h 27m
Delta
Sat 4/182:03 pm
ORF
-
PDX
1 stop10h 59m
Delta
Deal found 3/22$402
This American Airlines deal was found by Cheapflights users on 3/20. 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 4/1311:47 pm
PDX
-
ORF
1 stop7h 17m
American Airlines
Sat 4/251:32 pm
ORF
-
PDX
1 stop10h 31m
American Airlines
Deal found 3/20$403

Find 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 March 23, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$354
(Southwest)

One-way from

$192
(United Airlines)

Popular in

November

Cheapest in

October

Average price

$635
Provider with most accurate pricing for Portland-Norfolk flight deals.
Search Deals
Provider most trusted by Cheapflights users for Portland-Norfolk flights.
Search Deals
From Portland to Isle of Wight
Search Deals
One-way flight from Portland to Isle of Wight
Search Deals
Highest demand for flights based on searches. 11% potential increase in price ($68 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 3% potential price decrease ($20 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in March 2026
Search Deals

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 March 23, 2026.
Use the filters below to find and compare flights from Portland to Isle of Wight that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

PortlandNorfolk

PDX - ORF

PDXORF

Portland

Tue 5/5

5:40 am-5:50 pm

2 stops9h 10m

Norfolk

Tue 5/12

11:10 am-9:00 pm

2 stops12h 50m

$359

PortlandNorfolk

PDX - ORF

PDXORF

Portland

Tue 5/5

11:55 pm-10:55 am

1 stop8h 00m

Norfolk

Tue 5/12

6:00 am-11:37 am

1 stop8h 37m

$397

PortlandNorfolk

PDX - ORF

PDXORF

Portland

Tue 5/12

7:45 pm-9:31 am

2 stops10h 46m

Norfolk

Wed 5/20

5:14 pm-10:35 pm

1 stop8h 21m

$402

PortlandNorfolk

PDX - ORF

PDXORF

Portland

Fri 4/17

11:15 pm-11:52 am

2 stops9h 37m

Norfolk

Sat 4/25

7:07 am-4:07 pm

2 stops12h 00m

$442

PortlandNorfolk

PDX - ORF

PDXORF

Portland

Sat 5/9

7:40 pm-9:20 am

2 stops10h 40m

Norfolk

Sat 5/16

1:15 pm-10:05 pm

2 stops11h 50m

$448

PortlandNorfolk

PDX - ORF

PDXORF

Portland

Wed 8/5

8:44 pm-12:45 pm

2 stops13h 01m

Norfolk

Wed 8/19

5:50 am-10:44 am

1 stop7h 54m

$472

PortlandNorfolk

PDX - ORF

PDXORF

Portland

Mon 7/6

9:20 pm-9:25 am

1 stop9h 05m

Norfolk

Sat 7/11

3:10 pm-10:45 pm

2 stops10h 35m

$472
Quickest round-trip

PortlandNorfolk

PDX - ORF

PDXORF

Portland

Thu 5/21

2:12 pm-12:41 am

1 stop7h 29m

Norfolk

Mon 5/25

6:00 am-11:38 am

1 stop8h 38m

$492

PortlandNorfolk

PDX - ORF

PDXORF

Portland

Fri 5/8

11:03 pm-11:20 am

1 stop9h 17m

Norfolk

Mon 5/11

4:39 pm-11:44 pm

2 stops10h 05m

$498

PortlandNorfolk

PDX - ORF

PDXORF

Portland

Sat 5/2

7:45 pm-10:55 am

2 stops12h 10m

Norfolk

Wed 5/6

12:50 pm-9:06 pm

1 stop11h 16m

$505

Flights are sorted by cheapest round-trip flights first.

Deals found on 3/22

Showing 1-10 of 17 resultsSorted by cheapest first
1
2

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 March 13, 2026.

To ensure you get the cheapest price possible for a flight from Portland to Isle of Wight, you should look to book at least 27 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, May is the cheapest month in which you can book a flight from Portland to Isle of Wight (average of $225). Flying from Portland to Isle of Wight in November is currently the most expensive (average of $415). 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.

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 March 23, 2026.
Get a feel of what it's like to fly with Southwest,Delta, andUnited 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
4,324 reviews

Crew

8.6

Entertainment

7.5

Comfort

8.0

Food

7.0

Overall

8.0

Boarding

8.1

Reviews

1 / 20
2.0
Mediocre

Dominic,Mar 2026

MCO - SMF

I had to try and sleep on the floor of the Austin airport. I spent 12 hours there. The airline policies were so poor, that a near violent argument broke out between the people in front of me and the flight attendants - making for a super stressful situation at 30,000 feet. Garbage airline choice by Kayak Garbage idea to book a flight with a layover. Next time I will pay for a quality booking myself, and somehow force the company to reimburse it.
Southwest
8.0
Very good
4,324 reviews
Southwest
8.0
Very good
4,324 reviews

Crew

8.6

Entertainment

7.5

Comfort

8.0

Food

7.0

Overall

8.0

Boarding

8.1

Reviews

1 / 20
2.0
Mediocre

Dominic,Mar 2026

MCO - SMF

I had to try and sleep on the floor of the Austin airport. I spent 12 hours there. The airline policies were so poor, that a near violent argument broke out between the people in front of me and the flight attendants - making for a super stressful situation at 30,000 feet. Garbage airline choice by Kayak Garbage idea to book a flight with a layover. Next time I will pay for a quality booking myself, and somehow force the company to reimburse it.
Delta
7.9
Good
8,319 reviews
Southwest
8.0
Very good
4,324 reviews

Crew

8.6

Entertainment

7.5

Comfort

8.0

Food

7.0

Overall

8.0

Boarding

8.1

Reviews

1 / 20
2.0
Mediocre

Dominic,Mar 2026

MCO - SMF

I had to try and sleep on the floor of the Austin airport. I spent 12 hours there. The airline policies were so poor, that a near violent argument broke out between the people in front of me and the flight attendants - making for a super stressful situation at 30,000 feet. Garbage airline choice by Kayak Garbage idea to book a flight with a layover. Next time I will pay for a quality booking myself, and somehow force the company to reimburse it.
United Airlines
7.4
Good
9,460 reviews
Southwest
8.0
Very good
4,324 reviews

Crew

8.6

Entertainment

7.5

Comfort

8.0

Food

7.0

Overall

8.0

Boarding

8.1

Reviews

1 / 20
2.0
Mediocre

Dominic,Mar 2026

MCO - SMF

I had to try and sleep on the floor of the Austin airport. I spent 12 hours there. The airline policies were so poor, that a near violent argument broke out between the people in front of me and the flight attendants - making for a super stressful situation at 30,000 feet. Garbage airline choice by Kayak Garbage idea to book a flight with a layover. Next time I will pay for a quality booking myself, and somehow force the company to reimburse it.
American Airlines
7.1
Good
11,489 reviews
Southwest
8.0
Very good
4,324 reviews

Crew

8.6

Entertainment

7.5

Comfort

8.0

Food

7.0

Overall

8.0

Boarding

8.1

Reviews

1 / 20
2.0
Mediocre

Dominic,Mar 2026

MCO - SMF

I had to try and sleep on the floor of the Austin airport. I spent 12 hours there. The airline policies were so poor, that a near violent argument broke out between the people in front of me and the flight attendants - making for a super stressful situation at 30,000 feet. Garbage airline choice by Kayak Garbage idea to book a flight with a layover. Next time I will pay for a quality booking myself, and somehow force the company to reimburse it.

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. Southwest provides one of the quickest options available for as low as $397. 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 $131 on Allegiant Air. Other airlines that offer cheap prices include American Airlines from $156 and United Airlines from $169 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, May is the cheapest month in which you can book a flight from Portland to Isle of Wight (average of $225). Flying from Portland to Isle of Wight in November is currently the most expensive (average of $415). 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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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 March 23, 2026.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$203Average$464FlexibilityNo cancel feeOn-timeN/A
SouthwestCheapest$218Average$496FlexibilityNo cancel feeOn-time63%
United AirlinesCheapest$278Average$471FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$331Average$481FlexibilityNo cancel feeOn-time71%

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