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Chesapeake

$344+ Cheap flights from Oakland, CA (OAK) to Chesapeake, VA

This is the cheapest round-trip flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 3/7. Fares are subject to change and may not be available on all flights or dates of travel.
OAK — RIC
Jan 14 — Jan 211
Wed 1/14
Wed 1/21
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 December 15, 2025.

This Southwest deal was found by Cheapflights users on 12/13. 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.
Mon 12/1511:00 amOAK - ORF
1 stop7h 05mSouthwest
Tue 1/68:50 amORF - OAK
2 stops11h 05mSouthwest
Deal found 12/13$843
This Southwest deal was found by Cheapflights users on 12/13. 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 12/1711:00 amOAK - ORF
1 stop7h 05mSouthwest
Tue 12/235:55 pmORF - OAK
1 stop9h 25mSouthwest
Deal found 12/13$877
This Delta deal was found by Cheapflights users on 12/13. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/175:55 amOAK - ORF
2 stops14h 05mDelta
Wed 12/3112:32 pmORF - OAK
2 stops37h 15mDelta
Deal found 12/13$1,018
This Delta deal was found by Cheapflights users on 12/13. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/205:53 amOAK - ORF
2 stops9h 52mDelta
Mon 12/293:45 pmORF - OAK
2 stops11h 13mDelta
Deal found 12/13$1,854
This Delta deal was found by Cheapflights users on 12/12. 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.
Fri 12/195:55 amOAK - ORF
2 stops9h 39mDelta
Sun 12/213:45 pmORF - OAK
2 stops11h 13mDelta
Deal found 12/12$2,961

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 December 15, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$344
(Southwest)

Popular in

May

Cheapest in

February

Average price

$618
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
Highest demand for flights based on searches. 25% potential increase in price ($179 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 12% potential price decrease ($60 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in December 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 December 15, 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

Sat 3/7

11:55 pm-1:45 pm

2 stops9h 50m

Norfolk

Sat 3/14

7:20 pm-12:20 am

1 stop8h 00m

$344

OaklandNorfolk

OAK - ORF

OAKORF

Oakland

Wed 1/21

4:54 pm-9:10 am

2 stops13h 16m

Norfolk

Sun 1/25

3:37 pm-11:53 pm

2 stops11h 16m

$989

OaklandNorfolk

OAK - ORF

OAKORF

Oakland

Sat 3/21

5:45 pm-9:41 am

2 stops12h 56m

Norfolk

Sun 4/5

12:28 pm-11:46 pm

2 stops14h 18m

$1,179

OaklandNorfolk

OAK - ORF

OAKORF

Oakland

Thu 2/19

4:54 pm-9:18 am

2 stops13h 24m

Norfolk

Sat 2/21

12:27 pm-9:46 pm

2 stops12h 19m

$1,269

OaklandNorfolk

OAK - ORF

OAKORF

Oakland

Wed 3/18

5:55 am-7:24 pm

2 stops10h 29m

$365

OaklandNorfolk

OAK - ORF

OAKORF

Oakland

Wed 12/31

5:53 am-12:18 am

2 stops15h 25m

$454

OaklandNorfolk

OAK - ORF

OAKORF

Oakland

Mon 12/29

5:53 am-4:10 pm

2 stops31h 17m

$498

OaklandNorfolk

OAK - ORF

OAKORF

Oakland

Sun 12/28

4:50 pm-11:51 am

2 stops16h 01m

$548

OaklandNorfolk

OAK - ORF

OAKORF

Oakland

Tue 12/30

4:50 pm-12:18 am

2 stops28h 28m

$548

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/13

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 December is currently the most expensive (average of $276). 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 December 15, 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 December 15, 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
7.9
Good
4,250 reviews

Comfort

8.0

Crew

8.6

Boarding

8.1

Food

7.0

Overall

7.9

Entertainment

7.5

Reviews

1 / 20
10.0
Excellent

William Drew,Nov 2025

SJC - HNL

Flight crew was amazing! Usually they're very good on Southwest, but this crew went above and beyond. I have never ever seen so many rounds of drink service on a flight before.
Southwest
7.9
Good
4,250 reviews
Southwest
7.9
Good
4,250 reviews

Comfort

8.0

Crew

8.6

Boarding

8.1

Food

7.0

Overall

7.9

Entertainment

7.5

Reviews

1 / 20
10.0
Excellent

William Drew,Nov 2025

SJC - HNL

Flight crew was amazing! Usually they're very good on Southwest, but this crew went above and beyond. I have never ever seen so many rounds of drink service on a flight before.

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 9h 50m. 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 December is currently the most expensive (average of $276). 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 December 15, 2025.
AirlineCheapestAverageFlexibilityOn-time
SouthwestCheapest$283Average$523FlexibilityNo cancel feeOn-time63%
DeltaCheapest$296Average$361FlexibilityNo cancel feeOn-timeN/A

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