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Isle of Wight

$210+ 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 8/13. Fares are subject to change and may not be available on all flights or dates of travel.
OAK — RIC
Aug 3 — Aug 101
Sun 8/3
Sun 8/10
1 adult, Economy
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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 July 29, 2025.

Round-trip from

$287
(Southwest)

One-way from

$210
(Southwest)

Popular in

May

Cheapest in

October

Average price

$430
From Oakland to Isle of Wight
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One-way flight from Oakland to Isle of Wight
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Highest demand for flights based on searches. 15% potential increase in price ($108 potential increase over avg. RT price).
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Cheapest flight prices on average. 9% potential price decrease ($54 potential savings vs. average RT price).
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Average for round-trip flights in July 2025
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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 July 29, 2025.

This Southwest deal was found by Cheapflights users on 7/28. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/65:35 amOAK - ORF
1 stop7h 00mSouthwest
Thu 11/135:30 amORF - OAK
1 stop7h 55mSouthwest
Deal found 7/28$287
This Mytrip deal was found by Cheapflights users on 7/28. 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.
Thu 11/612:15 pmOAK - ORF
3 stops22h 57mSpirit Airlines
Thu 11/138:01 amORF - OAK
3 stops30h 09mSpirit Airlines
Deal found 7/28$332
This Mytrip deal was found by Cheapflights users on 7/29. 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.
Sun 8/175:39 pmOAK - ORF
2 stops16h 05mMultiple Airlines
Wed 8/205:30 amORF - OAK
3 stops20h 57mMultiple Airlines
Deal found 7/29$410
This Delta deal was found by Cheapflights users on 7/29. 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 9/115:05 pmOAK - ORF
2 stops13h 02mDelta
Sat 9/275:30 amORF - OAK
2 stops9h 26mDelta
Deal found 7/29$528

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 July 29, 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 11/6

5:35 am-3:35 pm

1 stop7h 00m

Norfolk

Thu 11/13

5:30 am-10:25 am

1 stop7h 55m

$287

OaklandNorfolk

OAK - ORF

OAKORF

Oakland

Thu 11/6

12:15 pm-2:12 pm

3 stops22h 57m

Norfolk

Thu 11/13

8:01 am-11:10 am

3 stops30h 09m

$332

OaklandNorfolk

OAK - ORF

OAKORF

Oakland

Sun 8/17

5:39 pm-12:44 pm

2 stops16h 05m

Norfolk

Wed 8/20

5:30 am-11:27 pm

3 stops20h 57m

$410

OaklandNorfolk

OAK - ORF

OAKORF

Oakland

Thu 9/11

5:05 pm-9:07 am

2 stops13h 02m

Norfolk

Sat 9/27

5:30 am-11:56 am

2 stops9h 26m

$528

OaklandNorfolk

OAK - ORF

OAKORF

Oakland

Wed 8/13

9:55 am-9:25 pm

2 stops8h 30m

$210

OaklandNorfolk

OAK - ORF

OAKORF

Oakland

Mon 12/15

5:11 pm-7:37 pm

3 stops23h 26m

$234

OaklandNorfolk

OAK - ORF

OAKORF

Oakland

Thu 8/7

6:00 am-9:30 am

3 stops24h 30m

$314

OaklandNorfolk

OAK - ORF

OAKORF

Oakland

Mon 12/15

5:05 pm-9:02 am

2 stops12h 57m

$375

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/27

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, January is the cheapest month in which you can book a flight from Oakland, California to Isle of Wight (average of $281). Flying from Oakland, California 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 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 July 29, 2025.

When flying from Oakland, California to Isle of Wight, the time of day you decide to fly out makes little to no difference towards the overall price you’ll pay on tickets.

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 July 29, 2025.
Read reviews from past customers who have flown Southwest, Delta, and Spirit Airlines 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
4,238 reviews

Comfort

8.0

Boarding

8.1

Overall

8.0

Entertainment

7.5

Food

7.0

Crew

8.6

Reviews

1 / 20
10.0
Excellent

Merlyn,Feb 2025

LAX - SMF

New Terminal is neat, lost of stores and places to catch a bite.
Southwest
8.0
Very good
4,238 reviews
Southwest
8.0
Very good
4,238 reviews

Comfort

8.0

Boarding

8.1

Overall

8.0

Entertainment

7.5

Food

7.0

Crew

8.6

Reviews

1 / 20
10.0
Excellent

Merlyn,Feb 2025

LAX - SMF

New Terminal is neat, lost of stores and places to catch a bite.
Delta
8.0
Very good
7,979 reviews
Southwest
8.0
Very good
4,238 reviews

Comfort

8.0

Boarding

8.1

Overall

8.0

Entertainment

7.5

Food

7.0

Crew

8.6

Reviews

1 / 20
10.0
Excellent

Merlyn,Feb 2025

LAX - SMF

New Terminal is neat, lost of stores and places to catch a bite.
Spirit Airlines
6.3
Okay
8,044 reviews
Southwest
8.0
Very good
4,238 reviews

Comfort

8.0

Boarding

8.1

Overall

8.0

Entertainment

7.5

Food

7.0

Crew

8.6

Reviews

1 / 20
10.0
Excellent

Merlyn,Feb 2025

LAX - SMF

New Terminal is neat, lost of stores and places to catch a bite.

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.

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

    The cheapest airline one-way is Southwest, with whom users have recently found tickets for as low as $210. However, be on the lookout for offers from Spirit Airlines and Delta, as they are both options that can get you from Oakland, California to Isle of Wight for a low price.

  • 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, January is the cheapest month in which you can book a flight from Oakland, California to Isle of Wight (average of $281). Flying from Oakland, California 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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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 July 29, 2025.
AirlineCheapestAverageFlexibilityOn-time
SouthwestCheapest$283Average$583FlexibilityNo cancel feeOn-time63%
DeltaCheapest$296Average$362FlexibilityNo cancel feeOn-timeN/A

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