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.

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).

What is the cheapest time of day to fly from OAK to C6E?

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.

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. 1 airline 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.

Find Cheap Flights from Oakland, CA to Chesapeake

Home Search by date Vacation packages Hotels Flight deals Car rental Travel tips & news

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.

Find flight deals from Oakland to Chesapeake

Popular in	April
Cheapest in	February
Average price	$565

Highest demand for flights based on searches. 23% potential increase in price ($220 potential increase over avg. RT price).

Search Deals

Cheapest flight prices on average. 17% potential price decrease ($108 potential savings vs. average RT price).

Search Deals

Average for round-trip flights in November 2026

Search Deals

Reviews of airlines servicing Chesapeake

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

4,214 reviews

Reviews

1 / 20

8.0

Excellent

La Tracimeldamarcos,Jun 2026

LAX - SLC

The second flight was not as comfortable as the first as we had to change planes to what seemed to be a slightly older aircraft. The seats weren’t as comfortable as the other plane. But it wasn’t bad.

Southwest

8.0

Very good

4,214 reviews

Southwest

8.0

Very good

4,214 reviews

Reviews

1 / 20

8.0

Excellent

La Tracimeldamarcos,Jun 2026

LAX - SLC

Related info for your journey

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. 1 airline 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.

See more FAQs

Browse thousands of different options on Cheapflights for your next trip

Alternative routes

Complete your trip

Flights by cabin class

Other flight options

Other flights from Oakland

Popular flights

Top destinations

Alternative routes for Oakland to Chesapeake

Los Angeles to Reagan-National flights

Los Angeles to Dulles Intl flights

San Francisco to Dulles Intl flights

San Francisco to Reagan-National flights

San Diego to Dulles Intl flights

Los Angeles to Raleigh flights

Ontario to Dulles Intl flights

San Francisco to Raleigh flights

Ontario to Reagan-National flights

San Diego to Reagan-National flights

Santa Ana to Dulles Intl flights

Sacramento to Dulles Intl flights

Las Vegas to Dulles Intl flights

Fresno to Dulles Intl flights

Fresno to Reagan-National flights

Bakersfield to Reagan-National flights

Burbank to Dulles Intl flights

Las Vegas to Reagan-National flights

Long Beach to Dulles Intl flights

Santa Ana to Reagan-National flights

Bakersfield to Dulles Intl flights

San Jose to Dulles Intl flights

Ontario to Raleigh flights

Las Vegas to Raleigh flights

Los Angeles to Norfolk flights

Sacramento to Reagan-National flights

San Jose to Reagan-National flights

Long Beach to Reagan-National flights

San Diego to Norfolk flights

Oakland to Dulles Intl flights

Oakland to Reagan-National flights

Burbank to Reagan-National flights

Burbank to Raleigh flights

San Diego to Raleigh flights

Ontario to Richmond flights

Los Angeles to Greensboro flights

Ontario to Norfolk flights

Oakland to Raleigh flights

Long Beach to Raleigh flights

Los Angeles to Richmond flights

Reno to Dulles Intl flights

Sacramento to Raleigh flights

Santa Barbara to Dulles Intl flights

Reno to Reagan-National flights

Palm Springs to Dulles Intl flights

San Francisco to Charlottesville flights

Las Vegas to Norfolk flights

San Diego to Richmond flights

Top airline flying from Oakland to Chesapeake

Airline	Cheapest	Average	Flexibility	On-time
Southwest	Cheapest$368	Average$533	FlexibilityNo cancel fee	On-time63%

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.

Find cheap flights from Oakland to Chesapeake with Cheapflights

1. Tell us where you want to go

2. Select your favorite providers

3. Compare prices and book

Find flight deals from Oakland to Chesapeake

Popular in

Cheapest in

Average price

Reviews of airlines servicing Chesapeake

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.

Related info for your journey

What airport do you fly from for flights from Oakland to Chesapeake?

Can I find deals for flights from Oakland to Chesapeake that include hotel bookings?

How can I find direct flights from Oakland to Chesapeake?

Can I find deals for business class flights from Oakland to Chesapeake?

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.

Complete your trip

Complete your trip to Chesapeake by adding a car rental and/or hotel reservation to your travel itinerary.

Search flights from Oakland to Chesapeake by cabin class

Find flights from Oakland to Chesapeake, based on your preferred cabin class, be it economy, premium economy, business, or first class.

Oakland and Chesapeake flights

Browse other Oakland and Chesapeake flight options. Last updated on November 4, 2026.

Other flights from Oakland

Browse through other flights departing from Oakland. Flights are based on user searches made on Cheapflights and were last updated on November 4, 2026.

Popular flight searches

Check out other popular destinations found by fellow travelers in 2026

Oakland to Chesapeake flights

Consider these flights traveling from Oakland to Chesapeake.

Top airline flying from Oakland to Chesapeake

100% Free

Book with Flexibility

Travel Smart

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

Find cheap flights from Oakland to Chesapeake with Cheapflights

1. Tell us where you want to go

2. Select your favorite providers

3. Compare prices and book

Find flight deals from Oakland to Chesapeake

Popular in

Cheapest in

Average price

Reviews of airlines servicing Chesapeake

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.

Related info for your journey

What airport do you fly from for flights from Oakland to Chesapeake?

Can I find deals for flights from Oakland to Chesapeake that include hotel bookings?

How can I find direct flights from Oakland to Chesapeake?

Can I find deals for business class flights from Oakland to Chesapeake?

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.

Complete your trip

Complete your trip to Chesapeake by adding a car rental and/or hotel reservation to your travel itinerary.

Search flights from Oakland to Chesapeake by cabin class

Find flights from Oakland to Chesapeake, based on your preferred cabin class, be it economy, premium economy, business, or first class.

Oakland and Chesapeake flights

Browse other Oakland and Chesapeake flight options. Last updated on November 4, 2026.

Other flights from Oakland

Browse through other flights departing from Oakland. Flights are based on user searches made on Cheapflights and were last updated on November 4, 2026.

Popular flight searches

Check out other popular destinations found by fellow travelers in 2026

Oakland to Chesapeake flights

Consider these flights traveling from Oakland to Chesapeake.

Top airline flying from Oakland to Chesapeake

100% Free

Book with Flexibility

Travel Smart