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Chesapeake

$230+ 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 6/30. Fares are subject to change and may not be available on all flights or dates of travel.
OAK — RIC
Jul 9 — Jul 161
Thu 7/9
Thu 7/16
1 adult, Economy
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Cheap flight deals from Oakland to Chesapeake

Cheapest flights from Oakland to Chesapeake
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 9, 2026.

This Southwest deal was found by Cheapflights users on 6/6. 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 7/45:15 am
OAK
-
ORF
2 stops10h 20m
Southwest
Fri 7/107:15 pm
ORF
-
OAK
1 stop8h 00m
Southwest
Deal found 6/6$413
This Southwest deal was found by Cheapflights users on 6/8. 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 9/178:30 pm
OAK
-
ORF
2 stops10h 00m
Southwest
Sun 9/204:40 pm
ORF
-
OAK
1 stop8h 50m
Southwest
Deal found 6/8$430
This Southwest deal was found by Cheapflights users on 6/9. 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 7/95:45 am
OAK
-
ORF
1 stop8h 40m
Southwest
Thu 7/167:15 pm
ORF
-
OAK
1 stop8h 00m
Southwest
Deal found 6/9$467
This Southwest deal was found by Cheapflights users on 6/7. 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 7/1911:55 pm
OAK
-
ORF
2 stops8h 45m
Southwest
Sun 8/305:05 pm
ORF
-
OAK
2 stops9h 30m
Southwest
Deal found 6/7$477
This Southwest deal was found by Cheapflights users on 6/5. 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.
Tue 6/232:40 pm
OAK
-
ORF
1 stop7h 05m
Southwest
Tue 6/305:15 am
ORF
-
OAK
1 stop9h 55m
Southwest
Deal found 6/5$523

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 9, 2026.

Round-trip from

$413
(Southwest)

One-way from

$230
(Southwest)

Popular in

April

Cheapest in

September

Average price

$588
From Oakland to Chesapeake
Search Deals
One-way flight from Oakland to Chesapeake
Search Deals
Highest demand for flights based on searches. 37% potential increase in price ($346 potential increase over avg. RT price).
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Cheapest flight prices on average. 25% potential price decrease ($121 potential savings vs. average RT price).
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Average for round-trip flights in June 2026
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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 9, 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

Price

Cheapest round-trip

OaklandNorfolk

OAK - ORF

OAKORF

Oakland

Sat 7/4

5:15 am-6:35 pm

2 stops10h 20m

Norfolk

Fri 7/10

7:15 pm-12:15 am

1 stop8h 00m

$413
Quickest round-trip

OaklandNorfolk

OAK - ORF

OAKORF

Oakland

Thu 7/9

11:55 pm-11:40 am

2 stops8h 45m

Norfolk

Thu 7/16

7:15 pm-12:15 am

1 stop8h 00m

$472

OaklandNorfolk

OAK - ORF

OAKORF

Oakland

Sun 7/19

11:55 pm-10:45 am

1 stop7h 50m

Norfolk

Sun 8/30

5:05 pm-11:35 pm

2 stops9h 30m

$472

OaklandNorfolk

OAK - ORF

OAKORF

Oakland

Tue 6/23

2:40 pm-12:45 am

1 stop7h 05m

Norfolk

Tue 6/30

5:15 am-12:10 pm

1 stop9h 55m

$523

OaklandNorfolk

OAK - ORF

OAKORF

Oakland

Sat 7/4

6:00 am-7:44 pm

2 stops10h 44m

Norfolk

Sat 7/11

6:00 am-4:21 pm

2 stops13h 21m

$894
Cheapest one-way

OaklandNorfolk

OAK - ORF

OAKORF

Oakland

Tue 6/30

12:35 pm-12:45 am

1 stop9h 10m

$230

OaklandNorfolk

OAK - ORF

OAKORF

Oakland

Wed 9/9

5:05 pm-10:36 am

2 stops14h 31m

$265

OaklandNorfolk

OAK - ORF

OAKORF

Oakland

Wed 7/22

5:05 pm-9:09 am

2 stops13h 04m

$380

OaklandNorfolk

OAK - ORF

OAKORF

Oakland

Tue 7/21

6:00 am-11:22 am

2 stops26h 22m

$384
Quickest one-way

OaklandNorfolk

OAK - ORF

OAKORF

Oakland

Sun 6/14

11:55 pm-10:45 am

1 stop7h 50m

$489

Flights are sorted by cheapest round-trip flights first.

Deals found on 6/5

Showing 1-10 of 14 resultsSorted by cheapest first
1
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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.
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

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 9, 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.
Southwest
7.9
Good
4,240 reviews

Entertainment

7.5

Boarding

8.1

Crew

8.6

Comfort

8.0

Food

7.0

Overall

7.9

Reviews

1 / 20
8.0
Excellent

La Tracimeldamarcos,Jun 2026

LAX - SLC

The second flight was not as comfortable as the first as we had to change planes to what seemed to be a slightly older aircraft. The seats weren’t as comfortable as the other plane. But it wasn’t bad.
Southwest
7.9
Good
4,240 reviews
Southwest
7.9
Good
4,240 reviews

Entertainment

7.5

Boarding

8.1

Crew

8.6

Comfort

8.0

Food

7.0

Overall

7.9

Reviews

1 / 20
8.0
Excellent

La Tracimeldamarcos,Jun 2026

LAX - SLC

The second flight was not as comfortable as the first as we had to change planes to what seemed to be a slightly older aircraft. The seats weren’t as comfortable as the other plane. But it wasn’t bad.

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.

  • What airport do you fly from for flights from Oakland to Chesapeake?

    Oakland (OAK), located 7.0 mi from the city center, is the airport you fly out of when you book flights from Oakland to Chesapeake. 1 airline have flights from Oakland to Chesapeake on a regular basis. Booking flights from Oakland to Chesapeake should not be difficult; the airport handles an average of 0 outbound flights to Chesapeake per day.

  • How long is the flight from Oakland, California to Chesapeake?

    Departing from Oakland, California to Chesapeake will take you 10h 20m. Airlines will cover a distance of 2502 mi.

  • Can I find deals for flights from Oakland to Chesapeake that include hotel bookings?

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

  • How can I find direct flights from Oakland to Chesapeake?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Oakland to Chesapeake.

  • Can I find deals for business class flights from Oakland to Chesapeake?

    Yes. Cheapflights offers flight deals from Oakland to Chesapeake by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

See more FAQs

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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 9, 2026.
AirlineCheapestAverageFlexibilityOn-time
SouthwestCheapest$283Average$514FlexibilityNo cancel feeOn-time63%

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