HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
Chesapeake

$195+ 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 3/25. Fares are subject to change and may not be available on all flights or dates of travel.
OAK — RIC
Feb 28 — Mar 71
Sat 2/28
Sat 3/7
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

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 January 29, 2026.

This Southwest deal was found by Cheapflights users on 1/28. 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 3/16:40 am
OAK
-
ORF
1 stop12h 50m
Southwest
Fri 3/67:20 pm
ORF
-
OAK
1 stop7h 50m
Southwest
Deal found 1/28$485
This Southwest deal was found by Cheapflights users on 1/28. 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.
Fri 3/2011:55 pm
OAK
-
ORF
1 stop12h 45m
Southwest
Sun 3/226:20 am
ORF
-
OAK
2 stops12h 15m
Southwest
Deal found 1/28$516
This Delta deal was found by Cheapflights users on 1/27. 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.
Tue 4/74:49 pm
OAK
-
ORF
2 stops13h 53m
Delta
Sat 4/117:00 am
ORF
-
OAK
2 stops12h 00m
Delta
Deal found 1/27$570
This Delta deal was found by Cheapflights users on 1/28. 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.
Mon 5/185:55 am
OAK
-
ORF
2 stops24h 08m
Delta
Mon 5/256:05 pm
ORF
-
OAK
2 stops32h 44m
Delta
Deal found 1/28$609
This Delta deal was found by Cheapflights users on 1/28. 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.
Mon 5/185:55 am
OAK
-
ORF
2 stops26h 34m
Delta
Sat 5/235:00 pm
ORF
-
OAK
2 stops31h 34m
Delta
Deal found 1/28$619
This Delta deal was found by Cheapflights users on 1/28. 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.
Mon 5/185:55 am
OAK
-
ORF
2 stops24h 08m
Delta
Sun 5/247:00 am
ORF
-
OAK
2 stops17h 34m
Delta
Deal found 1/28$645
This Delta deal was found by Cheapflights users on 1/28. 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.
Wed 5/135:55 am
OAK
-
ORF
2 stops38h 07m
Delta
Mon 5/256:05 pm
ORF
-
OAK
2 stops32h 44m
Delta
Deal found 1/28$663
This Delta deal was found by Cheapflights users on 1/28. 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.
Sat 5/165:55 am
OAK
-
ORF
2 stops26h 34m
Delta
Mon 5/256:05 pm
ORF
-
OAK
2 stops32h 44m
Delta
Deal found 1/28$664
This Delta deal was found by Cheapflights users on 1/28. 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.
Wed 5/135:55 am
OAK
-
ORF
2 stops38h 07m
Delta
Sat 5/235:00 pm
ORF
-
OAK
2 stops31h 34m
Delta
Deal found 1/28$673

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 January 29, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$485
(Southwest)

One-way from

$195
(Southwest)

Popular in

May

Cheapest in

February

Average price

$338
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. 25% potential increase in price ($183 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 14% potential price decrease ($67 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in January 2026
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 January 29, 2026.
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

Sun 3/1

6:40 am-10:30 pm

1 stop12h 50m

Norfolk

Fri 3/6

7:20 pm-12:10 am

1 stop7h 50m

$485

OaklandNorfolk

OAK - ORF

OAKORF

Oakland

Fri 3/20

11:55 pm-3:40 pm

1 stop12h 45m

Norfolk

Sun 3/22

6:20 am-3:35 pm

2 stops12h 15m

$516

OaklandNorfolk

OAK - ORF

OAKORF

Oakland

Tue 4/7

4:49 pm-9:42 am

2 stops13h 53m

Norfolk

Sat 4/11

7:00 am-4:00 pm

2 stops12h 00m

$570

OaklandNorfolk

OAK - ORF

OAKORF

Oakland

Mon 5/18

5:55 am-9:03 am

2 stops24h 08m

Norfolk

Mon 5/25

6:05 pm-11:49 pm

2 stops32h 44m

$609

OaklandNorfolk

OAK - ORF

OAKORF

Oakland

Mon 5/18

5:55 am-11:29 am

2 stops26h 34m

Norfolk

Sat 5/23

5:00 pm-9:34 pm

2 stops31h 34m

$619

OaklandNorfolk

OAK - ORF

OAKORF

Oakland

Mon 5/18

5:55 am-9:03 am

2 stops24h 08m

Norfolk

Sun 5/24

7:00 am-9:34 pm

2 stops17h 34m

$645

OaklandNorfolk

OAK - ORF

OAKORF

Oakland

Wed 5/13

5:55 am-11:02 pm

2 stops38h 07m

Norfolk

Mon 5/25

6:05 pm-11:49 pm

2 stops32h 44m

$663

OaklandNorfolk

OAK - ORF

OAKORF

Oakland

Tue 5/19

5:55 am-4:53 pm

2 stops31h 58m

Norfolk

Sat 5/23

6:05 pm-9:34 pm

2 stops30h 29m

$673

OaklandNorfolk

OAK - ORF

OAKORF

Oakland

Sat 5/16

5:55 am-11:29 am

2 stops26h 34m

Norfolk

Sat 5/23

5:00 pm-9:34 pm

2 stops31h 34m

$674

OaklandNorfolk

OAK - ORF

OAKORF

Oakland

Wed 3/25

5:50 am-9:05 pm

1 stop12h 15m

$195

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/28

Showing 1-10 of 14 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 December is currently the most expensive (average of $272). 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.

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 January 29, 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
8.0
Very good
4,267 reviews

Comfort

8.0

Entertainment

7.5

Food

7.0

Boarding

8.1

Crew

8.6

Overall

8.0

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
8.0
Very good
4,267 reviews
Southwest
8.0
Very good
4,267 reviews

Comfort

8.0

Entertainment

7.5

Food

7.0

Boarding

8.1

Crew

8.6

Overall

8.0

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 12h 50m. 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.

  • 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 $272). 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 Francisco to Raleigh flights
Los Angeles to Raleigh flights
Ontario to Dulles Intl flights
San Diego to Dulles Intl flights
Ontario to Reagan-National flights
San Diego to Reagan-National flights
Las Vegas to Dulles Intl flights
San Jose to Dulles Intl flights
Sacramento to Dulles Intl flights
San Jose to Reagan-National flights
Las Vegas to Reagan-National flights
Oakland to Reagan-National flights
Oakland to Dulles Intl flights
Santa Ana to Dulles Intl flights
Ontario to Raleigh flights
Santa Ana to Reagan-National flights
Sacramento to Reagan-National flights
Los Angeles to Norfolk flights
Ontario to Norfolk flights
Burbank to Dulles Intl flights
Las Vegas to Raleigh flights
Burbank to Reagan-National flights
Sacramento to Norfolk flights
San Francisco to Richmond flights
Los Angeles to Richmond flights
Oakland to Raleigh flights
San Francisco to Norfolk flights
San Diego to Norfolk flights
San Diego to Raleigh flights
Fresno to Dulles Intl flights
San Jose to Raleigh flights
Ontario to Richmond flights
San Diego to Richmond flights
Santa Ana to Raleigh flights
Fresno to Reagan-National flights
Palm Springs to Dulles Intl flights
Sacramento to Raleigh flights
Burbank to Raleigh flights
Las Vegas to Norfolk flights
Santa Barbara to Dulles Intl flights
Burbank to Norfolk flights
Long Beach to Dulles Intl flights
San Francisco to Greensboro flights
Sacramento to Richmond flights
Los Angeles to Greensboro flights
Las Vegas to Richmond 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 January 29, 2026.
AirlineCheapestAverageFlexibilityOn-time
SouthwestCheapest$283Average$496FlexibilityNo 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.