HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
Chesapeake

$323+ 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 11/15. Fares are subject to change and may not be available on all flights or dates of travel.
OAK — RIC
Oct 14 — Oct 211
Tue 10/14
Tue 10/21
1 adult, Economy
We work with more than 300 partners to bring you better travel deals

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

We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.

3. Compare prices and book

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

Keep the following information in mind while searching for Oakland to Chesapeake flight deals. Data was last updated September 14, 2025.

Round-trip from

$323
(Southwest)

Popular in

November

Cheapest in

September

Average price

$342
From Oakland to Chesapeake
Search Deals
Highest demand for flights based on searches. 28% potential increase in price ($250 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 10% potential price decrease ($59 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in September 2025
Search Deals

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 September 14, 2025.

This Southwest deal was found by Cheapflights users on 9/14. 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 11/157:40 amOAK - ORF
1 stop11h 40mSouthwest
Sun 11/165:30 amORF - OAK
1 stop7h 55mSouthwest
Deal found 9/14$323
This Southwest deal was found by Cheapflights users on 9/11. 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.
Tue 10/75:50 amOAK - ORF
1 stop7h 35mSouthwest
Sat 10/114:50 pmORF - OAK
1 stop7h 25mSouthwest
Deal found 9/11$402
This Delta deal was found by Cheapflights users on 9/12. 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.
Tue 11/114:51 pmOAK - ORF
2 stops13h 28mDelta
Fri 11/148:30 amORF - OAK
2 stops10h 41mDelta
Deal found 9/12$410
This Delta deal was found by Cheapflights users on 9/12. 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.
Mon 10/65:55 amOAK - ORF
2 stops31h 27mDelta
Tue 10/146:17 pmORF - OAK
2 stops32h 36mDelta
Deal found 9/12$422
This Kiwi.com deal was found by Cheapflights users on 9/14. 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.
Mon 9/296:30 amOAK - ORF
2 stops27h 57mMultiple Airlines
Fri 10/39:21 amORF - OAK
1 stop27h 40mMultiple Airlines
Deal found 9/14$438
This Southwest deal was found by Cheapflights users on 9/11. 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 10/25:35 amOAK - ORF
1 stop9h 35mSouthwest
Sat 10/44:50 pmORF - OAK
1 stop7h 25mSouthwest
Deal found 9/11$439
This Southwest deal was found by Cheapflights users on 9/13. 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 11/266:40 amOAK - ORF
2 stops13h 10mSouthwest
Mon 12/13:25 pmORF - OAK
2 stops11h 55mSouthwest
Deal found 9/13$445
This Delta deal was found by Cheapflights users on 9/13. 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 9/206:00 amOAK - ORF
2 stops12h 08mDelta
Sat 9/275:30 amORF - OAK
2 stops13h 54mDelta
Deal found 9/13$458

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 September 14, 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 11/15

7:40 am-10:20 pm

1 stop11h 40m

Norfolk

Sun 11/16

5:30 am-10:25 am

1 stop7h 55m

$323

OaklandNorfolk

OAK - ORF

OAKORF

Oakland

Tue 10/7

5:50 am-4:25 pm

1 stop7h 35m

Norfolk

Sat 10/11

4:50 pm-9:15 pm

1 stop7h 25m

$402

OaklandNorfolk

OAK - ORF

OAKORF

Oakland

Tue 11/11

4:51 pm-9:19 am

2 stops13h 28m

Norfolk

Fri 11/14

8:30 am-4:11 pm

2 stops10h 41m

$410

OaklandNorfolk

OAK - ORF

OAKORF

Oakland

Tue 10/7

4:51 pm-11:29 am

2 stops15h 38m

Norfolk

Tue 10/14

6:17 pm-11:53 pm

2 stops32h 36m

$422

OaklandNorfolk

OAK - ORF

OAKORF

Oakland

Mon 9/29

6:30 am-1:27 pm

2 stops27h 57m

Norfolk

Fri 10/3

9:21 am-10:01 am

1 stop27h 40m

$438

OaklandNorfolk

OAK - ORF

OAKORF

Oakland

Thu 10/2

5:35 am-6:10 pm

1 stop9h 35m

Norfolk

Sat 10/4

4:50 pm-9:15 pm

1 stop7h 25m

$439

OaklandNorfolk

OAK - ORF

OAKORF

Oakland

Wed 11/26

6:40 am-10:50 pm

2 stops13h 10m

Norfolk

Mon 12/1

3:25 pm-12:20 am

2 stops11h 55m

$445

OaklandNorfolk

OAK - ORF

OAKORF

Oakland

Tue 9/23

5:05 pm-9:07 am

2 stops13h 02m

$405

OaklandNorfolk

OAK - ORF

OAKORF

Oakland

Sun 9/21

5:05 pm-11:32 am

2 stops15h 27m

$505

OaklandNorfolk

OAK - ORF

OAKORF

Oakland

Fri 9/19

5:05 pm-11:32 am

2 stops15h 27m

$505

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/12

Showing 1-10 of 13 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, January is the cheapest month in which you can book a flight from Oakland, California to Chesapeake (average of $281). Flying from Oakland, California to Chesapeake in March is currently the most expensive (average of $351). 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 September 14, 2025.

Regardless of the time of day you decide to fly, the ticket price will remain around the same. Book flights from Oakland, California to Chesapeake as you normally would.

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 September 14, 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
4,245 reviews

Crew

8.6

Boarding

8.1

Food

7.0

Comfort

8.0

Overall

8.0

Entertainment

7.5

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
4,245 reviews
Southwest
8.0
Very good
4,245 reviews

Crew

8.6

Boarding

8.1

Food

7.0

Comfort

8.0

Overall

8.0

Entertainment

7.5

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 11h 40m. 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, January is the cheapest month in which you can book a flight from Oakland, California to Chesapeake (average of $281). Flying from Oakland, California to Chesapeake in March is currently the most expensive (average of $351). 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.

See more FAQs

Browse thousands of different options on Cheapflights for your next trip

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

Alternative routes for Oakland to Chesapeake

See prices for flight routes from nearby airports that may be better suited for you.
Los Angeles to Reagan-National flights
Los Angeles to Dulles Intl flights
San Francisco to Reagan-National flights
San Francisco to Dulles Intl flights
San Diego to Dulles Intl flights
Ontario to Dulles Intl flights
San Diego to Reagan-National flights
Los Angeles to Raleigh flights
Ontario to Reagan-National flights
San Francisco to Raleigh flights
Santa Ana to Reagan-National flights
Santa Ana to Dulles Intl flights
Sacramento to Dulles Intl flights
San Jose to Dulles Intl flights
Las Vegas to Reagan-National flights
Las Vegas to Dulles Intl flights
San Jose to Reagan-National flights
Ontario to Raleigh flights
Oakland to Dulles Intl flights
Sacramento to Reagan-National flights
San Francisco to Richmond flights
Burbank to Reagan-National flights
Los Angeles to Norfolk flights
Fresno to Dulles Intl flights
Burbank to Dulles Intl flights
San Francisco to Norfolk flights
Las Vegas to Raleigh flights
San Diego to Richmond flights
San Diego to Raleigh flights
Los Angeles to Richmond flights
San Diego to Norfolk flights
Santa Ana to Raleigh flights
Los Angeles to Greensboro flights
Oakland to Reagan-National flights
Palm Springs to Dulles Intl flights
Los Angeles to Charlottesville flights
Reno to Dulles Intl flights
Palm Springs to Reagan-National flights
San Jose to Raleigh flights
Burbank to Raleigh flights
Ontario to Norfolk flights
Sacramento to Raleigh flights
Reno to Reagan-National flights
Fresno to Reagan-National flights
Long Beach to Dulles Intl flights
Los Angeles to Roanoke flights
Oakland to Raleigh flights
Las Vegas to Norfolk flights
Ontario to Richmond flights
San Luis Obispo to Dulles Intl flights

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 September 14, 2025.
AirlineCheapestAverageFlexibilityOn-time
SouthwestCheapest$283Average$573FlexibilityNo cancel feeOn-time63%
DeltaCheapest$296Average$361FlexibilityNo cancel feeOn-timeN/A

100% Free

Cheapflights is completely free to use, so you can start saving the moment you arrive.

Book with Flexibility

Our users can plan ahead with confidence and find flights with no change fees

Travel Smart

Millions of people come to us for their flight needs every year. We help make travel planning easy by providing useful insights and data-driven graphs that can inform your decisions.