HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
Isle of Wight

$175+ 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 5/24. Fares are subject to change and may not be available on all flights or dates of travel.
OAK — RIC
Jan 17 — Jan 241
Sat 1/17
Sat 1/24
1 adult, Economy
We work with more than 300 partners to bring you better travel deals

Find cheap flights from Oakland to Isle of Wight with Cheapflights

1. Tell us where you want to go

Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”

2. Select your favorite providers

We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.

3. Compare prices and book

Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.

Cheap 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 December 18, 2025.

This Southwest deal was found by Cheapflights users on 12/18. 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.
Thu 12/185:35 amOAK - ORF
1 stop7h 00mSouthwest
Mon 1/55:30 amORF - OAK
1 stop7h 55mSouthwest
Deal found 12/18$860
This Delta deal was found by Cheapflights users on 12/18. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/1812:30 pmOAK - ORF
2 stops20h 03mDelta
Tue 1/67:01 amORF - OAK
2 stops31h 56mDelta
Deal found 12/18$1,009
This Delta deal was found by Cheapflights users on 12/18. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/1812:30 pmOAK - ORF
2 stops20h 03mDelta
Thu 1/89:00 amORF - OAK
2 stops10h 14mDelta
Deal found 12/18$1,030
This Delta deal was found by Cheapflights users on 12/18. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/1812:30 pmOAK - ORF
2 stops26h 00mDelta
Wed 1/77:30 amORF - OAK
2 stops11h 44mDelta
Deal found 12/18$1,060

Find 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 December 18, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$344
(Southwest)

One-way from

$175
(Delta)

Popular in

May

Cheapest in

February

Average price

$618
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. 25% potential increase in price ($179 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 12% potential price decrease ($60 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in December 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 December 18, 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

Mon 2/23

6:15 am-4:00 pm

1 stop6h 45m

Norfolk

Fri 2/27

3:05 pm-12:10 am

1 stop12h 05m

$344

OaklandNorfolk

OAK - ORF

OAKORF

Oakland

Sat 3/21

5:45 pm-9:41 am

2 stops12h 56m

Norfolk

Sun 4/5

12:28 pm-11:46 pm

2 stops14h 18m

$1,179

OaklandNorfolk

OAK - ORF

OAKORF

Oakland

Thu 2/19

4:54 pm-9:18 am

2 stops13h 24m

Norfolk

Sat 2/21

12:27 pm-9:46 pm

2 stops12h 19m

$1,429

OaklandNorfolk

OAK - ORF

OAKORF

Oakland

Sun 5/24

5:05 pm-9:03 am

2 stops12h 58m

$175

OaklandNorfolk

OAK - ORF

OAKORF

Oakland

Wed 12/31

5:53 am-12:18 am

2 stops15h 25m

$454

OaklandNorfolk

OAK - ORF

OAKORF

Oakland

Mon 12/29

5:53 am-4:10 pm

2 stops31h 17m

$519

OaklandNorfolk

OAK - ORF

OAKORF

Oakland

Tue 12/30

12:34 pm-12:18 am

2 stops32h 44m

$519

OaklandNorfolk

OAK - ORF

OAKORF

Oakland

Thu 1/1

5:53 am-9:09 am

2 stops24h 16m

$550

OaklandNorfolk

OAK - ORF

OAKORF

Oakland

Wed 3/18

5:55 am-7:24 pm

2 stops10h 29m

$575

OaklandNorfolk

OAK - ORF

OAKORF

Oakland

Sun 12/28

5:53 am-4:10 pm

2 stops31h 17m

$743

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/17

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 December is currently the most expensive (average of $276). 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 December 18, 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 December 18, 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
7.9
Good
4,250 reviews

Boarding

8.1

Entertainment

7.5

Comfort

8.0

Crew

8.6

Food

7.0

Overall

7.9

Reviews

1 / 20
10.0
Excellent

William Drew,Nov 2025

SJC - HNL

Flight crew was amazing! Usually they're very good on Southwest, but this crew went above and beyond. I have never ever seen so many rounds of drink service on a flight before.
Southwest
7.9
Good
4,250 reviews
Southwest
7.9
Good
4,250 reviews

Boarding

8.1

Entertainment

7.5

Comfort

8.0

Crew

8.6

Food

7.0

Overall

7.9

Reviews

1 / 20
10.0
Excellent

William Drew,Nov 2025

SJC - HNL

Flight crew was amazing! Usually they're very good on Southwest, but this crew went above and beyond. I have never ever seen so many rounds of drink service on a flight before.

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 $344, Southwest can have you in Isle of Wight from Oakland, California in 6h 45m. 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 December is currently the most expensive (average of $276). 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

Browse thousands of different options on Cheapflights for your next trip

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

Alternative routes for Oakland to Isle of Wight

See prices for flight routes from nearby airports that may be better suited for you.
Los Angeles to Reagan-National flights
Los Angeles to Dulles Intl flights
San Francisco to Reagan-National flights
San Francisco to Dulles Intl flights
Los Angeles to Raleigh flights
San Diego to Dulles Intl flights
San Francisco to Raleigh flights
San Diego to Reagan-National flights
Ontario to Dulles Intl flights
Ontario to Reagan-National flights
Las Vegas to Dulles Intl flights
Las Vegas to Reagan-National flights
Sacramento to Dulles Intl flights
Ontario to Raleigh flights
Los Angeles to Richmond flights
Long Beach to Dulles Intl flights
Santa Ana to Dulles Intl flights
San Jose to Dulles Intl flights
Oakland to Dulles Intl flights
Santa Ana to Raleigh flights
San Francisco to Richmond flights
Burbank to Dulles Intl flights
Ontario to Richmond flights
San Diego to Norfolk flights
Burbank to Reagan-National flights
Las Vegas to Raleigh flights
Oakland to Reagan-National flights
San Jose to Reagan-National flights
Los Angeles to Norfolk flights
Sacramento to Reagan-National flights
San Diego to Richmond flights
San Diego to Raleigh flights
Santa Ana to Reagan-National flights
Oakland to Raleigh flights
San Jose to Raleigh flights
Fresno to Dulles Intl flights
Palm Springs to Dulles Intl flights
Sacramento to Raleigh flights
San Francisco to Greensboro flights
Long Beach to Reagan-National flights
Los Angeles to Greensboro flights
Ontario to Norfolk flights
Reno to Dulles Intl flights
Fresno to Reagan-National flights
Reno to Reagan-National flights
San Luis Obispo to Raleigh flights
Las Vegas to Norfolk flights
Fresno to Norfolk flights
San Luis Obispo to Reagan-National flights
Los Angeles to Charlottesville flights

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 December 18, 2025.
AirlineCheapestAverageFlexibilityOn-time
SouthwestCheapest$283Average$523FlexibilityNo cancel feeOn-time63%
DeltaCheapest$296Average$361FlexibilityNo cancel feeOn-timeN/A

100% Free

Cheapflights is completely free to use, so you can start saving the moment you arrive.

Book with Flexibility

Our users can plan ahead with confidence and find flights with no change fees

Travel Smart

Millions of people come to us for their flight needs every year. We help make travel planning easy by providing useful insights and data-driven graphs that can inform your decisions.
Site
©2025 Cheapflights