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Chesapeake

$194+ 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 7/1. Fares are subject to change and may not be available on all flights or dates of travel.
OAK — RIC
Jun 17 — Jun 241
Tue 6/17
Tue 6/24
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 June 12, 2025.

Round-trip from

$269
(Southwest)

One-way from

$194
(Mytrip)

Popular in

May

Cheapest in

October

Average price

$542
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 ($101 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 June 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 June 12, 2025.

This Southwest deal was found by Cheapflights users on 6/11. 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.
Wed 9/107:00 amOAK - ORF
2 stops11h 40mSouthwest
Wed 9/173:00 pmORF - OAK
1 stop8h 40mSouthwest
Deal found 6/11$269
This Booking.com deal was found by Cheapflights users on 6/10. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/187:48 pmOAK - ORF
2 stops9h 52mSpirit Airlines
Mon 9/229:35 amORF - OAK
2 stops17h 04mSpirit Airlines
Deal found 6/10$312
This Mytrip deal was found by Cheapflights users on 6/11. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/107:30 amOAK - ORF
2 stops22h 10mMultiple Airlines
Wed 9/177:00 amORF - OAK
3 stops32h 13mMultiple Airlines
Deal found 6/11$414
This Delta deal was found by Cheapflights users on 6/11. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/115:05 pmOAK - ORF
2 stops12h 57mDelta
Sat 9/277:00 amORF - OAK
2 stops12h 31mDelta
Deal found 6/11$594

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 June 12, 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

Wed 9/10

7:00 am-9:40 pm

2 stops11h 40m

Norfolk

Wed 9/17

3:00 pm-8:40 pm

1 stop8h 40m

$269

OaklandNorfolk

OAK - ORF

OAKORF

Oakland

Thu 9/18

7:48 pm-8:40 am

2 stops9h 52m

Norfolk

Mon 9/22

9:35 am-11:39 pm

2 stops17h 04m

$312

OaklandNorfolk

OAK - ORF

OAKORF

Oakland

Wed 9/10

7:30 am-8:40 am

2 stops22h 10m

Norfolk

Wed 9/17

7:00 am-12:13 pm

3 stops32h 13m

$414

OaklandNorfolk

OAK - ORF

OAKORF

Oakland

Thu 9/11

5:05 pm-9:02 am

2 stops12h 57m

Norfolk

Sat 9/27

7:00 am-4:31 pm

2 stops12h 31m

$594

OaklandNorfolk

OAK - ORF

OAKORF

Oakland

Tue 7/1

5:30 am-6:37 pm

2 stops34h 07m

$194

OaklandNorfolk

OAK - ORF

OAKORF

Oakland

Tue 7/1

5:25 am-3:25 pm

1 stop7h 00m

$219

OaklandNorfolk

OAK - ORF

OAKORF

Oakland

Thu 7/10

8:00 am-10:40 pm

2 stops11h 40m

$309

Flights are sorted by cheapest round-trip flights first.

Deals found on 6/10

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 June 12, 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.

Rainfall in Chesapeake by month

Plan your trip to Chesapeake by taking into account the average rainfall totals by month.

In terms of precipitation, rainfall in Chesapeake ranges from 2.9 - 5.8 inches per month. July is typically the wettest month, when rainfall can reach 5.8 in. November is typically the driest time to visit Chesapeake when rainfall is around 2.9 in.

Temperature in Chesapeake by month

Plan your trip to Chesapeake by taking into account the average temperature totals by month.

If weather is an important factor for your trip to Chesapeake, use this chart to help with planning. For those seeking warmer temperatures, July is the ideal time of year to visit, when temperatures reach an average of 78.8 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 42.8 F).

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 June 12, 2025.
Alaska Airlines
8.0
Very good
10,000 reviews

Food

7.1

Entertainment

7.1

Boarding

8.1

Overall

8.0

Comfort

7.8

Crew

8.5

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.
Alaska Airlines
8.0
Very good
10,000 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Food

7.1

Entertainment

7.1

Boarding

8.1

Overall

8.0

Comfort

7.8

Crew

8.5

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.
Southwest
8.0
Very good
4,287 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Food

7.1

Entertainment

7.1

Boarding

8.1

Overall

8.0

Comfort

7.8

Crew

8.5

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.
Delta
8.0
Very good
7,946 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Food

7.1

Entertainment

7.1

Boarding

8.1

Overall

8.0

Comfort

7.8

Crew

8.5

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.
Spirit Airlines
6.3
Okay
8,052 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Food

7.1

Entertainment

7.1

Boarding

8.1

Overall

8.0

Comfort

7.8

Crew

8.5

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.

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.

  • What are the cheapest airlines to fly from Oakland, California to Chesapeake one-way?

    One-way options have recently been found by users for as low as $194 on Spirit Airlines. Other airlines that offer cheap prices include Southwest from $219 and Alaska Airlines from $309 one-way.

  • 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

See prices for flight routes from nearby airports that may be better suited for you.
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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 June 12, 2025.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$296Average$403FlexibilityNo cancel feeOn-timeN/A
SouthwestCheapest$336Average$582FlexibilityNo cancel feeOn-time63%

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