$245+ 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 7/1. Fares are subject to change and may not be available on all flights or dates of travel.
OAK — RIC
Mar 5 — Mar 121
1 adult, Economy
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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
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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
Best
Last-minute
One-way
Cheapest flights from Oakland to Isle of WightExplore 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 February 3, 2026.
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 February 3, 2026.
This Southwest deal was found by Cheapflights users on 2/2. 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 4/27:35 pm
OAK
- ORF
2 stops10h 30m
Southwest
Tue 4/76:25 pm
ORF
- OAK
1 stop8h 00m
Southwest
Deal found 2/2![Southwest logo]()
$354
This Southwest deal was found by Cheapflights users on 2/1. 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 7/811:55 pm
OAK
- ORF
1 stop7h 50m
Southwest
Wed 7/157:50 am
ORF
- OAK
1 stop7h 40m
Southwest
Deal found 2/1![Southwest logo]()
$379
This Southwest deal was found by Cheapflights users on 2/1. 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 2/156:30 am
OAK
- ORF
1 stop11h 40m
Southwest
Sat 2/212:40 pm
ORF
- OAK
1 stop11h 05m
Southwest
Deal found 2/1![Southwest logo]()
$445
This Southwest deal was found by Cheapflights users on 2/1. 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.
Mon 2/168:10 pm
OAK
- ORF
2 stops10h 10m
Southwest
Fri 2/205:30 am
ORF
- OAK
1 stop8h 20m
Southwest
Deal found 2/1![Southwest logo]()
$504
This Southwest deal was found by Cheapflights users on 2/1. 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 7/1011:55 pm
OAK
- ORF
1 stop8h 20m
Southwest
Fri 7/177:05 am
ORF
- OAK
1 stop8h 35m
Southwest
Deal found 2/1![Southwest logo]()
$521
Best flights from Oakland to Isle of WightDiscover carefully curated flight deals from Oakland to Isle of Wight that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated February 3, 2026.
Discover carefully curated flight deals from Oakland to Isle of Wight that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated February 3, 2026.
This Southwest deal was found by Cheapflights users on 2/2. 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 4/27:35 pm
OAK
- ORF
2 stops10h 30m
Southwest
Tue 4/74:25 pm
ORF
- OAK
2 stops10h 00m
Southwest
Deal found 2/2![Southwest logo]()
$359
This Southwest deal was found by Cheapflights users on 2/1. 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 7/811:55 pm
OAK
- ORF
1 stop7h 50m
Southwest
Wed 7/157:50 am
ORF
- OAK
1 stop7h 40m
Southwest
Deal found 2/1![Southwest logo]()
$379
This Southwest deal was found by Cheapflights users on 2/1. 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 2/156:30 am
OAK
- ORF
1 stop11h 40m
Southwest
Sat 2/212:40 pm
ORF
- OAK
1 stop11h 05m
Southwest
Deal found 2/1![Southwest logo]()
$445
This Southwest deal was found by Cheapflights users on 1/31. 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 7/1011:55 pm
OAK
- ORF
1 stop8h 20m
Southwest
Fri 7/177:05 am
ORF
- OAK
1 stop8h 35m
Southwest
Deal found 1/31![Southwest logo]()
$521
Last-minute flights from Oakland to Isle of WightDiscover last-minute flight deals from Oakland to Isle of Wight. Data last updated February 3, 2026 and is based on user searches.
Discover last-minute flight deals from Oakland to Isle of Wight. Data last updated February 3, 2026 and is based on user searches.
This Southwest deal was found by Cheapflights users on 2/2. 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 2/125:15 am
OAK
- ORF
2 stops11h 00m
Southwest
Tue 2/175:45 am
ORF
- OAK
1 stop8h 20m
Southwest
Deal found 2/2![Southwest logo]()
$573
This Delta deal was found by Cheapflights users on 2/2. 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 2/1212:40 pm
OAK
- ORF
2 stops31h 20m
Delta
Mon 2/233:45 pm
ORF
- OAK
2 stops11h 06m
Delta
Deal found 2/2![Delta logo]()
$657
This Delta deal was found by Cheapflights users on 2/2. 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 2/1212:40 pm
OAK
- ORF
2 stops31h 20m
Delta
Sun 2/227:03 am
ORF
- OAK
2 stops19h 48m
Delta
Deal found 2/2![Delta logo]()
$811
This Delta deal was found by Cheapflights users on 2/2. 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.
Fri 2/1312:40 pm
OAK
- ORF
2 stops25h 15m
Delta
Mon 2/233:45 pm
ORF
- OAK
2 stops11h 06m
Delta
Deal found 2/2![Delta logo]()
$763
This Delta deal was found by Cheapflights users on 2/2. 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 2/1412:40 pm
OAK
- ORF
2 stops19h 50m
Delta
Mon 2/233:45 pm
ORF
- OAK
2 stops11h 06m
Delta
Deal found 2/2![Delta logo]()
$803
This Southwest deal was found by Cheapflights users on 2/1. 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 2/156:30 am
OAK
- ORF
1 stop11h 40m
Southwest
Sat 2/212:40 pm
ORF
- OAK
1 stop11h 05m
Southwest
Deal found 2/1![Southwest logo]()
$445
This Southwest deal was found by Cheapflights users on 2/1. 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.
Mon 2/168:10 pm
OAK
- ORF
2 stops10h 10m
Southwest
Fri 2/205:30 am
ORF
- OAK
1 stop8h 20m
Southwest
Deal found 2/1![Southwest logo]()
$504
One-way flights from Oakland to Isle of WightSearch for one-way flight options from Oakland to Isle of Wight. Find affordable one-way fares based on user searches. Data last updated February 3, 2026.
Search for one-way flight options from Oakland to Isle of Wight. Find affordable one-way fares based on user searches. Data last updated February 3, 2026.
This Southwest deal was found by Cheapflights users on 2/1. 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 7/11:10 pm
OAK
- ORF
2 stops8h 35m
Southwest
Deal found 2/1![Southwest logo]()
$245
This Southwest deal was found by Cheapflights users on 2/1. 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 7/25:30 am
OAK
- ORF
2 stops14h 55m
Southwest
Deal found 2/1![Southwest logo]()
$293
This Delta deal was found by Cheapflights users on 2/2. 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 3/185:55 am
OAK
- ORF
2 stops11h 27m
Delta
Deal found 2/2![Delta logo]()
$365
This Delta deal was found by Cheapflights users on 2/2. 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.
Sun 6/215:05 pm
OAK
- ORF
2 stops12h 58m
Delta
Deal found 2/2![Delta logo]()
$463
This Kiwi.com deal was found by Cheapflights users on 2/1. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/17:50 pm
OAK
- ORF
3 stops44h 36m
Multiple Airlines
Deal found 2/1![Multiple Airlines logo]()
$546
This Delta deal was found by Cheapflights users on 2/1. 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.
Mon 3/305:55 am
OAK
- ORF
2 stops9h 27m
Delta
Deal found 2/1![Delta logo]()
$605
This Kiwi.com deal was found by Cheapflights users on 2/1. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 7/28:05 pm
OAK
- ORF
3 stops46h 10m
Multiple Airlines
Deal found 2/1![Multiple Airlines logo]()
$1,115
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 February 3, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $354 (Southwest) |
One-way from | $245 (Southwest) |
Popular in | May |
Cheapest in | February |
Average price | $296 |
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 February 3, 2026.
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 4/2
7:35 pm-9:05 am
2 stops10h 30m
Norfolk
Tue 4/7
4:25 pm-11:25 pm
2 stops10h 00m
$359
OaklandNorfolk
OAK - ORF
OAKORF
Oakland
Wed 7/8
11:55 pm-10:45 am
1 stop7h 50m
Norfolk
Wed 7/15
7:50 am-12:30 pm
1 stop7h 40m
$379
OaklandNorfolk
OAK - ORF
OAKORF
Oakland
Sun 2/15
6:30 am-9:10 pm
1 stop11h 40m
Norfolk
Sat 2/21
2:40 pm-10:45 pm
1 stop11h 05m
$445
OaklandNorfolk
OAK - ORF
OAKORF
Oakland
Fri 7/10
11:55 pm-11:15 am
1 stop8h 20m
Norfolk
Fri 7/17
7:05 am-12:40 pm
1 stop8h 35m
$521
OaklandNorfolk
OAK - ORF
OAKORF
Oakland
Wed 7/1
1:10 pm-12:45 am
2 stops8h 35m
$245
OaklandNorfolk
OAK - ORF
OAKORF
Oakland
Thu 7/2
5:30 am-11:25 pm
2 stops14h 55m
$293
OaklandNorfolk
OAK - ORF
OAKORF
Oakland
Wed 3/18
5:55 am-8:22 pm
2 stops11h 27m
$365
OaklandNorfolk
OAK - ORF
OAKORF
Oakland
Sun 6/21
5:05 pm-9:03 am
2 stops12h 58m
$463
OaklandNorfolk
OAK - ORF
OAKORF
Oakland
Thu 7/2
8:05 pm-9:15 pm
3 stops46h 10m
$1,115
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.
OAK-ORF
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
OAK-I1W
OAK-ORF
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 $272). 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 February 3, 2026.
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.
Comfort
8.0
Entertainment
7.5
Food
7.0
Boarding
8.1
Overall
8.0
Crew
8.6
Reviews
1 / 20
10.0
ExcellentWilliam Drew,Nov 2025
SJC - HNL
Comfort
8.0
Entertainment
7.5
Food
7.0
Boarding
8.1
Overall
8.0
Crew
8.6
Reviews
1 / 20
10.0
ExcellentWilliam Drew,Nov 2025
SJC - HNL
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.
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Alternative routes for Oakland to Isle of Wight
See prices for flight routes from nearby airports that may be better suited for you.
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 February 3, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$283 | Average$496 | FlexibilityNo cancel fee | On-time63% | |
| Cheapest$296 | Average$361 | FlexibilityNo cancel fee | On-timeN/A |