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Isle of Wight

$170+ Cheap flights from Oakland, CA (OAK) 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 12/9. Fares are subject to change and may not be available on all flights or dates of travel.
OAK — RIC
Nov 30 — Dec 71
Sun 11/30
Sun 12/7
1 adult, Economy
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Find flight deals from Oakland to Isle of Wight

Cheapest flights from Oakland to Isle of Wight
Explore the most affordable flight options available from Oakland to Isle of Wight. Find the lowest fares from popular airlines and budget airlines, with prices last updated on October 31, 2025.

This Delta deal was found by Cheapflights users on 10/29. 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.
Thu 12/115:55 amOAK - ORF
2 stops13h 35mDelta
Sun 12/1412:37 pmORF - OAK
2 stops14h 31mDelta
Deal found 10/29$389
This Southwest deal was found by Cheapflights users on 10/30. 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 12/1210:20 amOAK - ORF
2 stops10h 15mSouthwest
Sat 12/278:25 pmORF - OAK
1 stop8h 05mSouthwest
Deal found 10/30$535
This Southwest deal was found by Cheapflights users on 10/30. 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.
Sun 12/215:00 amOAK - ORF
1 stop12h 05mSouthwest
Sun 12/285:40 amORF - OAK
1 stop7h 55mSouthwest
Deal found 10/30$595
This Delta deal was found by Cheapflights users on 10/29. 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.
Thu 11/135:55 amOAK - ORF
2 stops12h 54mDelta
Mon 11/171:00 pmORF - OAK
2 stops14h 03mDelta
Deal found 10/29$693
This Delta deal was found by Cheapflights users on 10/29. 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.
Wed 11/55:55 amOAK - ORF
2 stops8h 59mDelta
Sun 11/912:42 pmORF - OAK
2 stops14h 21mDelta
Deal found 10/29$858
This Delta deal was found by Cheapflights users on 10/30. 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 12/165:55 amOAK - ORF
2 stops9h 39mDelta
Tue 1/66:00 amORF - OAK
2 stops13h 14mDelta
Deal found 10/30$1,089
This Delta deal was found by Cheapflights users on 10/29. 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.
Sat 12/205:53 amOAK - ORF
2 stops9h 11mDelta
Tue 12/304:50 pmORF - OAK
2 stops10h 08mDelta
Deal found 10/29$1,609
This Delta deal was found by Cheapflights users on 10/29. 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.
Sat 12/205:53 amOAK - ORF
2 stops12h 37mDelta
Fri 12/264:50 pmORF - OAK
2 stops10h 08mDelta
Deal found 10/29$2,299

Cheap flight deals from Oakland to Isle of Wight

Keep the following information in mind while searching for Oakland to Isle of Wight flight deals. Data was last updated October 31, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$389
(Delta)

One-way from

$170
(Southwest)

Popular in

May

Cheapest in

November

Average price

$631
Provider with most accurate pricing for San Francisco-Norfolk flight deals.
Search Deals
Provider most trusted by Cheapflights users for San Francisco-Norfolk flights.
Search Deals
From Oakland to Isle of Wight
Search Deals
One-way flight from Oakland to Isle of Wight
Search Deals
Highest demand for flights based on searches. 23% potential increase in price ($163 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 11% potential price decrease ($58 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in October 2025
Search Deals

Cheapflights Fare Finder

 
Customize your flight search to find flights from Oakland 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 October 31, 2025.
Use the filters below to find and compare flights from Oakland to Isle of Wight that are best for you.

Fly from

Oakland

Fly to

Isle of Wight

Route

Depart

Return

Price

OaklandNorfolk

OAK - ORF

OAKORF

Oakland

Thu 12/11

5:55 am-10:30 pm

2 stops13h 35m

Norfolk

Sun 12/14

12:37 pm-12:08 am

2 stops14h 31m

$389

OaklandNorfolk

OAK - ORF

OAKORF

Oakland

Fri 12/12

10:20 am-11:35 pm

2 stops10h 15m

Norfolk

Sat 12/27

8:25 pm-1:30 am

1 stop8h 05m

$535

OaklandNorfolk

OAK - ORF

OAKORF

Oakland

Sun 12/21

6:35 am-10:50 pm

2 stops13h 15m

Norfolk

Sun 12/28

5:40 am-10:35 am

1 stop7h 55m

$601

OaklandNorfolk

OAK - ORF

OAKORF

Oakland

Tue 3/10

5:55 am-10:55 pm

2 stops14h 00m

Norfolk

Wed 3/11

9:40 am-11:53 pm

2 stops17h 13m

$609

OaklandNorfolk

OAK - ORF

OAKORF

Oakland

Thu 11/13

5:55 am-9:49 pm

2 stops12h 54m

Norfolk

Mon 11/17

1:00 pm-12:03 am

2 stops14h 03m

$693

OaklandNorfolk

OAK - ORF

OAKORF

Oakland

Thu 2/19

5:05 pm-9:01 am

2 stops12h 56m

Norfolk

Sat 2/21

12:30 pm-9:38 pm

2 stops12h 08m

$899

OaklandNorfolk

OAK - ORF

OAKORF

Oakland

Tue 12/16

5:55 am-6:34 pm

2 stops9h 39m

Norfolk

Tue 1/6

6:00 am-4:14 pm

2 stops13h 14m

$1,089

OaklandNorfolk

OAK - ORF

OAKORF

Oakland

Tue 12/9

11:00 am-9:05 pm

1 stop7h 05m

$170

OaklandNorfolk

OAK - ORF

OAKORF

Oakland

Sun 11/16

5:35 am-3:35 pm

1 stop7h 00m

$284

OaklandNorfolk

OAK - ORF

OAKORF

Oakland

Mon 11/17

4:51 pm-9:19 am

2 stops13h 28m

$289

Flights are sorted by cheapest round-trip flights first.

Deals found on 10/30

Showing 1-10 of 16 results
1
2

Best time to book a flight from Oakland to Isle of Wight

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

What is the cheapest month to book a flight from Oakland, California to Isle of Wight?

Currently, August is the cheapest month in which you can book a flight from Oakland, California to Isle of Wight (average of $91). Flying from Oakland, California to Isle of Wight in July is currently the most expensive (average of $246). 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 OAK to I1W?

Find hourly flight availability from Oakland 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 October 31, 2025.

When flying from Oakland, California to Isle of Wight, the time of day you fly usually plays a role in the price. Save by searching for a flight at noon, which can drop the price by up to 32% versus a flight in the afternoon.

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 October 31, 2025.
Read reviews from past customers who have flown Southwest from Oakland to Isle of Wight. Users can see the overall rating for each airline as well as how each is rated in terms of entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.0
Very good
4,243 reviews

Comfort

8.0

Entertainment

7.5

Food

7.0

Overall

8.0

Boarding

8.1

Crew

8.6

Reviews

1 / 20
8.0
Excellent

Walter,Aug 2025

OAK - SAN

Dozens of flights and I've never seen a row's beverages forgotten. I even went back and asked the attendant to check on them and nothing. I really hope it didn't have something to do with the Black mother with her kid in the row. Otherwise it was a typical Southwest flight, rapid boarding, tolerable leg room.
Southwest
8.0
Very good
4,243 reviews
Southwest
8.0
Very good
4,243 reviews

Comfort

8.0

Entertainment

7.5

Food

7.0

Overall

8.0

Boarding

8.1

Crew

8.6

Reviews

1 / 20
8.0
Excellent

Walter,Aug 2025

OAK - SAN

Dozens of flights and I've never seen a row's beverages forgotten. I even went back and asked the attendant to check on them and nothing. I really hope it didn't have something to do with the Black mother with her kid in the row. Otherwise it was a typical Southwest flight, rapid boarding, tolerable leg room.

Related info for your journey

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

    Most people fly from Oakland (OAK) if they book a flight from Oakland to Isle of Wight. On average, Oakland has 0 outbound flights to Isle of Wight per day from 2 airlines. Oakland is conveniently located just 7.0 mi from Oakland’s city center.

  • How long is the flight from Oakland, California to Isle of Wight?

    For as low as $535, Delta can have you in Isle of Wight from Oakland, California in 10h 15m. There are 2502 mi between Oakland, California and Isle of Wight. This flight may include one or multiple stops.

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

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

  • How can I find direct flights from Oakland 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 Oakland to Isle of Wight.

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

    Yes. Cheapflights offers flight deals from Oakland 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 Oakland, California to Isle of Wight?

    Currently, August is the cheapest month in which you can book a flight from Oakland, California to Isle of Wight (average of $91). Flying from Oakland, California to Isle of Wight in July is currently the most expensive (average of $246). 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 2 airlines flying from Oakland to Isle of Wight

Discover the top 2 airlines that operate flights from Oakland 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 October 31, 2025.
AirlineCheapestAverageFlexibilityOn-time
SouthwestCheapest$283Average$550FlexibilityNo cancel feeOn-time63%
DeltaCheapest$296Average$361FlexibilityNo cancel feeOn-timeN/A

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