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Chesapeake

$109+ 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 8/21. Fares are subject to change and may not be available on all flights or dates of travel.
OAK — RIC
jul. 14 — jul. 211
lun. 7/14
lun. 7/21
1 adult, Economy
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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 julio 9, 2025.

Round-trip from

$161
(Southwest)

One-way from

$109
(Southwest)

Popular in

May

Cheapest in

September

Average price

$417
From Oakland to Chesapeake
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One-way flight from Oakland to Chesapeake
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Highest demand for flights based on searches. 14% potential increase in price ($106 potential increase over avg. RT price).
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Cheapest flight prices on average. 9% potential price decrease ($53 potential savings vs. average RT price).
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Average for round-trip flights in July 2025
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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 julio 9, 2025.

This Southwest deal was found by Cheapflights users on 7/8. 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.
sáb. 9/139:45 amOAK - ORF
2 stops10h 10mSouthwest
mié. 9/1710:40 amORF - OAK
2 stops12h 00mSouthwest
Deal found 7/8$161
This Delta deal was found by Cheapflights users on 7/7. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
lun. 8/184:58 pmOAK - ORF
2 stops13h 08mDelta
mar. 8/266:51 amORF - OAK
2 stops12h 25mDelta
Deal found 7/7$307
This Mytrip deal was found by Cheapflights users on 7/8. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
jue. 7/246:00 amOAK - ORF
3 stops13h 35mSpirit Airlines
lun. 7/285:20 pmORF - OAK
2 stops18h 08mSpirit Airlines
Deal found 7/8$358
This Mytrip deal was found by Cheapflights users on 7/8. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
sáb. 9/136:00 amOAK - ORF
3 stops13h 48mMultiple Airlines
mié. 9/177:00 amORF - OAK
2 stops27h 03mMultiple Airlines
Deal found 7/8$433

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 julio 9, 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

sáb. 9/13

9:45 am-10:55 pm

2 stops10h 10m

Norfolk

mié. 9/17

10:40 am-7:40 pm

2 stops12h 00m

$161

OaklandNorfolk

OAK - ORF

OAKORF

Oakland

lun. 8/18

4:58 pm-9:06 am

2 stops13h 08m

Norfolk

mar. 8/26

6:51 am-4:16 pm

2 stops12h 25m

$307

OaklandNorfolk

OAK - ORF

OAKORF

Oakland

jue. 7/24

6:00 am-10:35 pm

3 stops13h 35m

Norfolk

lun. 7/28

5:20 pm-8:28 am

2 stops18h 08m

$358

OaklandNorfolk

OAK - ORF

OAKORF

Oakland

sáb. 9/13

6:00 am-10:48 pm

3 stops13h 48m

Norfolk

mié. 9/17

7:00 am-7:03 am

2 stops27h 03m

$433

OaklandNorfolk

OAK - ORF

OAKORF

Oakland

jue. 8/21

8:40 am-10:50 pm

2 stops11h 10m

$109

OaklandNorfolk

OAK - ORF

OAKORF

Oakland

jue. 8/21

6:00 am-12:44 pm

3 stops27h 44m

$145

OaklandNorfolk

OAK - ORF

OAKORF

Oakland

sáb. 7/26

6:00 am-8:15 am

3 stops23h 15m

$239

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/8

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 julio 9, 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 julio 9, 2025.
See what other customers who have flown with Southwest, Delta, and Spirit Airlines 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
4,253 reviews

Boarding

8.1

Crew

8.6

Overall

8.0

Entertainment

7.6

Comfort

8.0

Food

7.0

Reviews

1 / 20
10.0
Excellent

Merlyn,Feb 2025

LAX - SMF

New Terminal is neat, lost of stores and places to catch a bite.
Southwest
8.0
Very good
4,253 reviews
Southwest
8.0
Very good
4,253 reviews

Boarding

8.1

Crew

8.6

Overall

8.0

Entertainment

7.6

Comfort

8.0

Food

7.0

Reviews

1 / 20
10.0
Excellent

Merlyn,Feb 2025

LAX - SMF

New Terminal is neat, lost of stores and places to catch a bite.
Delta
8.0
Very good
7,958 reviews
Southwest
8.0
Very good
4,253 reviews

Boarding

8.1

Crew

8.6

Overall

8.0

Entertainment

7.6

Comfort

8.0

Food

7.0

Reviews

1 / 20
10.0
Excellent

Merlyn,Feb 2025

LAX - SMF

New Terminal is neat, lost of stores and places to catch a bite.
Spirit Airlines
6.3
Okay
8,060 reviews
Southwest
8.0
Very good
4,253 reviews

Boarding

8.1

Crew

8.6

Overall

8.0

Entertainment

7.6

Comfort

8.0

Food

7.0

Reviews

1 / 20
10.0
Excellent

Merlyn,Feb 2025

LAX - SMF

New Terminal is neat, lost of stores and places to catch a bite.

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.

  • 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.

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Alternative routes for Oakland to Chesapeake

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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 julio 9, 2025.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$296Average$382FlexibilityNo cancel feeOn-timeN/A
SouthwestCheapest$336Average$583FlexibilityNo cancel feeOn-time63%

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