$234+ Cheap flights from Oakland, CA (OAK) to Chesapeake, 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 8/1. Fares are subject to change and may not be available on all flights or dates of travel.
OAK — RIC
Jul 16 — Jul 231
Round-trip
1 adult, Economy
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Find cheap flights from Oakland to Chesapeake 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 Chesapeake
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Best
Last-minute
One-way
Cheapest flights from Oakland to ChesapeakeExplore the most affordable flight options available from Oakland to Chesapeake. Find the lowest fares from popular airlines and budget airlines, with prices last updated on June 16, 2026.
Explore the most affordable flight options available from Oakland to Chesapeake. Find the lowest fares from popular airlines and budget airlines, with prices last updated on June 16, 2026.
This Southwest deal was found by Cheapflights users on 6/13. 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 7/82:40 pm
OAK
- ORF
1 stop7h 10m
Southwest
Tue 7/145:15 am
ORF
- OAK
2 stops10h 25m
Southwest
Deal found 6/13![Southwest logo]()
$396
This Southwest deal was found by Cheapflights users on 6/12. 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 8/2811:55 pm
OAK
- ORF
1 stop8h 00m
Southwest
Sat 9/56:25 am
ORF
- OAK
2 stops11h 30m
Southwest
Deal found 6/12![Southwest logo]()
$429
This Southwest deal was found by Cheapflights users on 6/11. 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.
Sat 7/46:15 am
OAK
- ORF
2 stops10h 45m
Southwest
Fri 7/107:15 pm
ORF
- OAK
1 stop8h 00m
Southwest
Deal found 6/11![Southwest logo]()
$449
This Southwest deal was found by Cheapflights users on 6/11. 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.
Sat 7/117:35 am
OAK
- ORF
2 stops10h 05m
Southwest
Fri 7/247:15 pm
ORF
- OAK
1 stop8h 00m
Southwest
Deal found 6/11![Southwest logo]()
$482
This Southwest deal was found by Cheapflights users on 6/11. 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 7/95:10 am
OAK
- ORF
1 stop7h 40m
Southwest
Thu 7/167:15 pm
ORF
- OAK
1 stop8h 00m
Southwest
Deal found 6/11![Southwest logo]()
$503
Best flights from Oakland to ChesapeakeDiscover carefully curated flight deals from Oakland to Chesapeake that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated June 16, 2026.
Discover carefully curated flight deals from Oakland to Chesapeake that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated June 16, 2026.
This Southwest deal was found by Cheapflights users on 6/13. 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 7/82:40 pm
OAK
- ORF
1 stop7h 10m
Southwest
Tue 7/145:15 am
ORF
- OAK
2 stops10h 25m
Southwest
Deal found 6/13![Southwest logo]()
$396
This Southwest deal was found by Cheapflights users on 6/10. 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 9/245:20 am
OAK
- ORF
1 stop13h 35m
Southwest
Mon 9/288:00 am
ORF
- OAK
1 stop7h 40m
Southwest
Deal found 6/10![Southwest logo]()
$420
This Southwest deal was found by Cheapflights users on 6/12. 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 8/2811:55 pm
OAK
- ORF
1 stop8h 00m
Southwest
Sat 9/56:00 am
ORF
- OAK
1 stop10h 55m
Southwest
Deal found 6/12![Southwest logo]()
$429
This Southwest deal was found by Cheapflights users on 6/11. 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.
Sat 7/46:15 am
OAK
- ORF
2 stops10h 45m
Southwest
Fri 7/104:30 pm
ORF
- OAK
2 stops10h 50m
Southwest
Deal found 6/11![Southwest logo]()
$454
This Southwest deal was found by Cheapflights users on 6/10. 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 11/17:50 pm
OAK
- ORF
2 stops10h 25m
Southwest
Sun 11/87:30 am
ORF
- OAK
1 stop8h 15m
Southwest
Deal found 6/10![Southwest logo]()
$472
This Southwest deal was found by Cheapflights users on 6/15. 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 7/177:40 pm
OAK
- ORF
2 stops10h 45m
Southwest
Thu 7/237:15 pm
ORF
- OAK
1 stop8h 00m
Southwest
Deal found 6/15![Southwest logo]()
$482
This Southwest deal was found by Cheapflights users on 6/11. 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.
Sat 7/117:35 am
OAK
- ORF
2 stops10h 05m
Southwest
Fri 7/247:15 pm
ORF
- OAK
1 stop8h 00m
Southwest
Deal found 6/11![Southwest logo]()
$482
Last-minute flights from Oakland to ChesapeakeDiscover last-minute flight deals from Oakland to Chesapeake. Data last updated June 16, 2026 and is based on user searches.
Discover last-minute flight deals from Oakland to Chesapeake. Data last updated June 16, 2026 and is based on user searches.
This Southwest deal was found by Cheapflights users on 6/11. 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.
Sat 7/46:15 am
OAK
- ORF
2 stops10h 45m
Southwest
Fri 7/107:15 pm
ORF
- OAK
1 stop8h 00m
Southwest
Deal found 6/11![Southwest logo]()
$449
This Southwest deal was found by Cheapflights users on 6/13. 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 7/82:40 pm
OAK
- ORF
1 stop7h 10m
Southwest
Tue 7/145:15 am
ORF
- OAK
2 stops10h 25m
Southwest
Deal found 6/13![Southwest logo]()
$396
This Southwest deal was found by Cheapflights users on 6/11. 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 7/95:10 am
OAK
- ORF
1 stop7h 40m
Southwest
Thu 7/167:15 pm
ORF
- OAK
1 stop8h 00m
Southwest
Deal found 6/11![Southwest logo]()
$503
This Southwest deal was found by Cheapflights users on 6/11. 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.
Sat 7/117:35 am
OAK
- ORF
2 stops10h 05m
Southwest
Fri 7/247:15 pm
ORF
- OAK
1 stop8h 00m
Southwest
Deal found 6/11![Southwest logo]()
$482
This Southwest deal was found by Cheapflights users on 6/15. 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 7/1711:55 pm
OAK
- ORF
1 stop8h 20m
Southwest
Thu 7/237:15 pm
ORF
- OAK
1 stop8h 00m
Southwest
Deal found 6/15![Southwest logo]()
$518
One-way flights from Oakland to ChesapeakeSearch for one-way flight options from Oakland to Chesapeake. Find affordable one-way fares based on user searches. Data last updated June 16, 2026.
Search for one-way flight options from Oakland to Chesapeake. Find affordable one-way fares based on user searches. Data last updated June 16, 2026.
This Southwest deal was found by Cheapflights users on 6/13. 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.
Sat 8/111:55 pm
OAK
- ORF
1 stop8h 00m
Southwest
Deal found 6/13![Southwest logo]()
$234
This Delta deal was found by Cheapflights users on 6/12. 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 9/95:05 pm
OAK
- ORF
2 stops14h 31m
Delta
Deal found 6/12![Delta logo]()
$255
This Delta deal was found by Cheapflights users on 6/11. 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 7/145:05 pm
OAK
- ORF
2 stops13h 04m
Delta
Deal found 6/11![Delta logo]()
$299
This Delta deal was found by Cheapflights users on 6/11. 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 7/136:00 am
OAK
- ORF
2 stops26h 22m
Delta
Deal found 6/11![Delta logo]()
$455
This Kiwi.com deal was found by Cheapflights users on 6/13. 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.
Sat 8/111:15 pm
OAK
- ORF
3 stops33h 00m
Multiple Airlines
Deal found 6/13![Multiple Airlines logo]()
$462
This Southwest deal was found by Cheapflights users on 6/12. 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 6/2211:55 pm
OAK
- ORF
1 stop8h 10m
Southwest
Deal found 6/12![Southwest logo]()
$489
This Southwest deal was found by Cheapflights users on 6/12. 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 6/215:10 am
OAK
- ORF
2 stops15h 45m
Southwest
Deal found 6/12![Southwest logo]()
$500
Find flight deals from Oakland to Chesapeake
Keep the following information in mind while searching for Oakland to Chesapeake flight deals. Data was last updated June 16, 2026.
Round-trip from | $396 (Southwest) |
|---|---|
One-way from | $234 (Southwest) |
Popular in | April |
Cheapest in | September |
Average price | $864 |
Cheapflights Fare Finder
Customize your flight search to find flights from Oakland to Chesapeake 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 June 16, 2026.
Use the filters below to find and compare flights from Oakland to Chesapeake that are best for you.
Fly from
Fly to
Route
Depart
Return
Cheapest round-trip
Quickest round-trip
OaklandNorfolk
OAK - ORF
OAKORF
Oakland
Wed 7/8
2:40 pm-12:50 am
1 stop7h 10m
Norfolk
Tue 7/14
5:15 am-12:40 pm
2 stops10h 25m
$396
OaklandNorfolk
OAK - ORF
OAKORF
Oakland
Thu 9/24
5:20 am-9:55 pm
1 stop13h 35m
Norfolk
Mon 9/28
8:00 am-12:40 pm
1 stop7h 40m
$420
OaklandNorfolk
OAK - ORF
OAKORF
Oakland
Fri 8/28
11:55 pm-10:55 am
1 stop8h 00m
Norfolk
Sat 9/5
6:00 am-1:55 pm
1 stop10h 55m
$429
OaklandNorfolk
OAK - ORF
OAKORF
Oakland
Sat 7/4
6:15 am-8:00 pm
2 stops10h 45m
Norfolk
Fri 7/10
4:30 pm-12:20 am
2 stops10h 50m
$454
OaklandNorfolk
OAK - ORF
OAKORF
Oakland
Sun 11/1
7:50 pm-9:15 am
2 stops10h 25m
Norfolk
Sun 11/8
7:30 am-12:45 pm
1 stop8h 15m
$472
OaklandNorfolk
OAK - ORF
OAKORF
Oakland
Fri 7/17
7:40 pm-9:25 am
2 stops10h 45m
Norfolk
Thu 7/23
7:15 pm-12:15 am
1 stop8h 00m
$482
OaklandNorfolk
OAK - ORF
OAKORF
Oakland
Sat 7/11
7:35 am-8:40 pm
2 stops10h 05m
Norfolk
Fri 7/24
7:15 pm-12:15 am
1 stop8h 00m
$482
Cheapest one-way
Quickest one-way
OaklandNorfolk
OAK - ORF
OAKORF
Oakland
Sat 8/1
11:55 pm-10:55 am
1 stop8h 00m
$234
OaklandNorfolk
OAK - ORF
OAKORF
Oakland
Wed 9/9
5:00 pm-10:35 am
2 stops14h 35m
$335
OaklandNorfolk
OAK - ORF
OAKORF
Oakland
Sat 8/1
11:15 pm-11:15 am
3 stops33h 00m
$462
Showing 1-10 of 16 resultsSorted by cheapest first
Best time to book a flight from Oakland to Chesapeake
Have a flexible travel schedule? Discover the best time to fly to Chesapeake 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 Chesapeake
OAK-C6E
OAK-ORF
How much does it cost to fly round-trip from Oakland, California to Chesapeake?
Reviews of airlines servicing Chesapeake
Get insights into the airlines that provide service to Chesapeake. 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 Chesapeake. Reviews last updated June 16, 2026.
See what other customers who have flown with Southwest from Oakland to Chesapeake have to say. You can also see how each airline compares in terms of entertainment options, comfort, food, crew/service, and boarding process.
Boarding
8.1
Food
7.0
Crew
8.6
Comfort
8.0
Overall
7.9
Entertainment
7.5
Reviews
1 / 20
8.0
ExcellentLa Tracimeldamarcos,Jun 2026
LAX - SLC
Boarding
8.1
Food
7.0
Crew
8.6
Comfort
8.0
Overall
7.9
Entertainment
7.5
Reviews
1 / 20
8.0
ExcellentLa Tracimeldamarcos,Jun 2026
LAX - SLC
Related info for your journey
Find useful and relevant information for your journey from Oakland to Chesapeake. 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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Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.
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Complete your trip
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Alternative routes for Oakland to Chesapeake
See prices for flight routes from nearby airports that may be better suited for you.
Complete your trip
Complete your trip to Chesapeake by adding a car rental and/or hotel reservation to your travel itinerary.
Search flights from Oakland to Chesapeake by cabin class
Find flights from Oakland to Chesapeake, based on your preferred cabin class, be it economy, premium economy, business, or first class.
Oakland and Chesapeake flights
Browse other Oakland and Chesapeake flight options. Last updated on June 16, 2026.
Other flights from Oakland
Browse through other flights departing from Oakland. Flights are based on user searches made on Cheapflights and were last updated on June 16, 2026.
Popular flight searches
Check out other popular destinations found by fellow travelers in 2026
Oakland to Chesapeake flights
Consider these flights traveling from Oakland to Chesapeake.
Top airline flying from Oakland to Chesapeake
Discover the top airline that operate flights from Oakland to Chesapeake. 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 June 16, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$283 | Average$524 | FlexibilityNo cancel fee | On-time63% |