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Chesapeake

$154+ 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 11/19. Fares are subject to change and may not be available on all flights or dates of travel.
OAK — RIC
Nov 28 — Dec 51
Fri 11/28
Fri 12/5
1 adult, Economy
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Find 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 October 29, 2025.

This Delta deal was found by Cheapflights users on 10/27. 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 12/45:55 amOAK - ORF
2 stops13h 35mDelta
Sat 12/66:35 amORF - OAK
2 stops12h 35mDelta
Deal found 10/27$328
This Southwest deal was found by Cheapflights users on 10/28. 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.
Sun 12/75:35 amOAK - ORF
1 stop7h 00mSouthwest
Sat 12/132:05 pmORF - OAK
1 stop9h 25mSouthwest
Deal found 10/28$349
This Southwest deal was found by Cheapflights users on 10/27. 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 12/49:00 amOAK - ORF
2 stops10h 00mSouthwest
Sat 12/62:05 pmORF - OAK
1 stop9h 25mSouthwest
Deal found 10/27$364
This Delta deal was found by Cheapflights users on 10/28. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 12/74:50 pmOAK - ORF
2 stops13h 19mDelta
Sat 12/131:00 pmORF - OAK
2 stops12h 00mDelta
Deal found 10/28$368
This Delta deal was found by Cheapflights users on 10/29. 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 12/115:55 amOAK - ORF
2 stops13h 35mDelta
Sun 12/1412:37 pmORF - OAK
2 stops14h 31mDelta
Deal found 10/29$389
This Southwest deal was found by Cheapflights users on 10/28. 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 11/276:40 amOAK - ORF
1 stop7h 00mSouthwest
Thu 12/410:05 amORF - OAK
2 stops11h 30mSouthwest
Deal found 10/28$424
This Southwest deal was found by Cheapflights users on 10/28. 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.
Wed 12/179:20 amOAK - ORF
2 stops8h 45mSouthwest
Sat 12/278:25 pmORF - OAK
1 stop8h 05mSouthwest
Deal found 10/28$553

Cheap flight deals from Oakland to Chesapeake

Keep the following information in mind while searching for Oakland to Chesapeake flight deals. Data was last updated October 29, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$328
(Delta)

One-way from

$154
(Delta)

Popular in

May

Cheapest in

November

Average price

$631
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 Chesapeake
Search Deals
One-way flight from Oakland to Chesapeake
Search Deals
Highest demand for flights based on searches. 23% potential increase in price ($163 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 11% potential price decrease ($58 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in October 2025
Search Deals

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 October 29, 2025.
Use the filters below to find and compare flights from Oakland to Chesapeake that are best for you.

Fly from

Oakland

Fly to

Chesapeake

Route

Depart

Return

Price

OaklandNorfolk

OAK - ORF

OAKORF

Oakland

Thu 12/4

5:55 am-10:30 pm

2 stops13h 35m

Norfolk

Sat 12/6

6:35 am-4:10 pm

2 stops12h 35m

$328

OaklandNorfolk

OAK - ORF

OAKORF

Oakland

Sun 12/7

5:35 am-3:35 pm

1 stop7h 00m

Norfolk

Sat 12/13

6:10 am-3:20 pm

2 stops12h 10m

$354

OaklandNorfolk

OAK - ORF

OAKORF

Oakland

Thu 12/4

9:00 am-10:00 pm

2 stops10h 00m

Norfolk

Sat 12/6

2:05 pm-8:30 pm

1 stop9h 25m

$364

OaklandNorfolk

OAK - ORF

OAKORF

Oakland

Sun 12/7

4:50 pm-9:09 am

2 stops13h 19m

Norfolk

Sat 12/13

1:00 pm-10:00 pm

2 stops12h 00m

$368

OaklandNorfolk

OAK - ORF

OAKORF

Oakland

Thu 12/11

5:55 am-10:30 pm

2 stops13h 35m

Norfolk

Sun 12/14

12:37 pm-12:08 am

2 stops14h 31m

$389

OaklandNorfolk

OAK - ORF

OAKORF

Oakland

Thu 11/27

6:40 am-4:40 pm

1 stop7h 00m

Norfolk

Thu 12/4

10:05 am-6:35 pm

2 stops11h 30m

$424

OaklandNorfolk

OAK - ORF

OAKORF

Oakland

Wed 12/17

9:20 am-9:05 pm

2 stops8h 45m

Norfolk

Sat 12/27

8:25 pm-1:30 am

1 stop8h 05m

$553

OaklandNorfolk

OAK - ORF

OAKORF

Oakland

Thu 11/13

5:35 am-3:35 pm

1 stop7h 00m

Norfolk

Sun 11/16

5:30 am-10:25 am

1 stop7h 55m

$574

OaklandNorfolk

OAK - ORF

OAKORF

Oakland

Wed 11/19

4:51 pm-9:19 am

2 stops13h 28m

$154

OaklandNorfolk

OAK - ORF

OAKORF

Oakland

Sun 11/16

5:35 am-3:35 pm

1 stop7h 00m

$284

Flights are sorted by cheapest round-trip flights first.

Deals found on 10/28

Showing 1-10 of 18 results
1
2

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

What is the cheapest month to book a flight from Oakland, California to Chesapeake?

Currently, August is the cheapest month in which you can book a flight from Oakland, California to Chesapeake (average of $91). Flying from Oakland, California to Chesapeake in July is currently the most expensive (average of $246). 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 C6E?

Find hourly flight availability from Oakland to Chesapeake. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated October 29, 2025.

It’s optimal to fly from Oakland, California to Chesapeake at noon. By choosing this option you can save up to 32% on the cost of your flight, compared to a flight in the afternoon.

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 October 29, 2025.
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
8.0
Very good
4,241 reviews

Overall

8.0

Boarding

8.1

Entertainment

7.5

Crew

8.6

Food

7.0

Comfort

8.0

Reviews

1 / 20
8.0
Excellent

Walter,Aug 2025

OAK - SAN

Dozens of flights and I've never seen a row's beverages forgotten. I even went back and asked the attendant to check on them and nothing. I really hope it didn't have something to do with the Black mother with her kid in the row. Otherwise it was a typical Southwest flight, rapid boarding, tolerable leg room.
Southwest
8.0
Very good
4,241 reviews
Southwest
8.0
Very good
4,241 reviews

Overall

8.0

Boarding

8.1

Entertainment

7.5

Crew

8.6

Food

7.0

Comfort

8.0

Reviews

1 / 20
8.0
Excellent

Walter,Aug 2025

OAK - SAN

Dozens of flights and I've never seen a row's beverages forgotten. I even went back and asked the attendant to check on them and nothing. I really hope it didn't have something to do with the Black mother with her kid in the row. Otherwise it was a typical Southwest flight, rapid boarding, tolerable leg room.

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. 2 airlines 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 7h. Airlines will cover a distance of 2502 mi. Both multi-stop and nonstop flights can be found to your destination and back.

  • 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.

  • What is the cheapest month to book a flight from Oakland, California to Chesapeake?

    Currently, August is the cheapest month in which you can book a flight from Oakland, California to Chesapeake (average of $91). Flying from Oakland, California to Chesapeake in July is currently the most expensive (average of $246). 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.

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Top 2 airlines flying from Oakland to Chesapeake

Discover the top 2 airlines 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 October 29, 2025.
AirlineCheapestAverageFlexibilityOn-time
SouthwestCheapest$283Average$550FlexibilityNo cancel feeOn-time63%
DeltaCheapest$296Average$361FlexibilityNo cancel feeOn-timeN/A

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