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Chesapeake

$99+ Cheap flights from San Diego (SAN) 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 9/13. Fares are subject to change and may not be available on all flights or dates of travel.
SAN — RIC
Sep 8 — Sep 151
Mon 9/8
Mon 9/15
1 adult, Economy
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Cheapflights Tip: The best prices from San Diego to Chesapeake are usually found in September or October, booked 56 days in advance, depart on a Tuesday or Thursday and return on a Tuesday

Cheap flight deals from San Diego to Chesapeake

Keep the following information in mind while searching for San Diego to Chesapeake flight deals. Data was last updated September 3, 2025.

Round-trip from

$208
(Breeze Airways)

One-way from

$99
(Breeze Airways)

Popular in

March

Cheapest in

September

Average price

$284
From San Diego to Chesapeake
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One-way flight from San Diego to Chesapeake
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Highest demand for flights based on searches. 15% potential increase in price ($71 potential increase over avg. RT price).
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Cheapest flight prices on average. 2% potential price decrease ($10 potential savings vs. average RT price).
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Average for round-trip flights in September 2025
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Find flight deals from San Diego to Chesapeake

Cheapest flights from San Diego to Chesapeake
Explore the most affordable flight options available from San Diego to Chesapeake. Find the lowest fares from popular airlines and budget airlines, with prices last updated on September 3, 2025.

This Breeze Airways deal was found by Cheapflights users on 9/1. 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 Breeze Airways is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/261:12 pmSAN - ORF
Nonstop5h 13mBreeze Airways
Sat 9/279:21 amORF - SAN
Nonstop6h 06mBreeze Airways
Deal found 9/1$208
This Expedia deal was found by Cheapflights users on 9/1. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/51:12 pmSAN - ORF
Nonstop5h 13mBreeze Airways
Fri 9/129:21 amORF - SAN
Nonstop6h 06mBreeze Airways
Deal found 9/1$209
This Breeze Airways deal was found by Cheapflights users on 9/3. 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 Breeze Airways is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/51:12 pmSAN - ORF
Nonstop5h 13mBreeze Airways
Sat 9/139:21 amORF - SAN
Nonstop6h 06mBreeze Airways
Deal found 9/3$218
This Booking.com deal was found by Cheapflights users on 9/2. 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 9/256:27 pmSAN - ORF
1 stop20h 23mFrontier
Sun 9/285:47 pmORF - SAN
2 stops27h 07mFrontier
Deal found 9/2$219
This Breeze Airways deal was found by Cheapflights users on 9/1. 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 Breeze Airways is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/121:12 pmSAN - ORF
Nonstop5h 13mBreeze Airways
Mon 9/159:21 amORF - SAN
Nonstop6h 06mBreeze Airways
Deal found 9/1$228
This Breeze Airways deal was found by Cheapflights users on 9/2. 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 Breeze Airways is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/11:12 pmSAN - ORF
Nonstop5h 13mBreeze Airways
Mon 10/69:21 amORF - SAN
Nonstop6h 06mBreeze Airways
Deal found 9/2$238
This Booking.com deal was found by Cheapflights users on 9/2. 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 9/256:27 pmSAN - ORF
1 stop20h 23mFrontier
Mon 9/296:53 pmORF - SAN
2 stops54h 31mFrontier
Deal found 9/2$242
This Breeze Airways deal was found by Cheapflights users on 9/2. 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 Breeze Airways is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/41:12 pmSAN - ORF
Nonstop5h 13mBreeze Airways
Wed 10/89:21 amORF - SAN
Nonstop6h 06mBreeze Airways
Deal found 9/2$258
This Priceline deal was found by Cheapflights users on 9/2. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/41:12 pmSAN - ORF
Nonstop5h 13mBreeze Airways
Mon 10/69:21 amORF - SAN
Nonstop6h 06mBreeze Airways
Deal found 9/2$265
This Delta deal was found by Cheapflights users on 9/3. 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 9/246:15 amSAN - ORF
1 stop7h 35mDelta
Mon 9/295:55 pmORF - SAN
1 stop8h 29mDelta
Deal found 9/3$277

Cheapflights Fare Finder

 
Customize your flight search to find flights from San Diego 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 3, 2025.
Use the filters below to find and compare flights from San Diego to Chesapeake that are best for you.

Fly from

San Diego

Fly to

Chesapeake

Route

Depart

Return

Price

San DiegoNorfolk

SAN - ORF

SANORF

San Diego

Fri 9/26

1:12 pm-9:25 pm

Nonstop5h 13m

Norfolk

Sat 9/27

9:21 am-12:27 pm

Nonstop6h 06m

$208

San DiegoNorfolk

SAN - ORF

SANORF

San Diego

Sat 9/13

1:12 pm-9:25 pm

Nonstop5h 13m

Norfolk

Wed 9/17

9:21 am-12:27 pm

Nonstop6h 06m

$218

San DiegoNorfolk

SAN - ORF

SANORF

San Diego

Thu 9/25

6:27 pm-5:50 pm

1 stop20h 23m

Norfolk

Sun 9/28

5:47 pm-5:54 pm

2 stops27h 07m

$219

San DiegoNorfolk

SAN - ORF

SANORF

San Diego

Wed 9/24

1:12 pm-9:25 pm

Nonstop5h 13m

Norfolk

Mon 9/29

9:21 am-12:27 pm

Nonstop6h 06m

$228

San DiegoNorfolk

SAN - ORF

SANORF

San Diego

Mon 9/15

1:12 pm-9:25 pm

Nonstop5h 13m

Norfolk

Sat 9/20

9:21 am-12:27 pm

Nonstop6h 06m

$238

San DiegoNorfolk

SAN - ORF

SANORF

San Diego

Wed 10/1

1:12 pm-9:25 pm

Nonstop5h 13m

Norfolk

Mon 10/6

9:21 am-12:27 pm

Nonstop6h 06m

$238

San DiegoNorfolk

SAN - ORF

SANORF

San Diego

Thu 9/25

6:27 pm-5:50 pm

1 stop20h 23m

Norfolk

Mon 9/29

6:53 pm-10:24 pm

2 stops54h 31m

$242

San DiegoNorfolk

SAN - ORF

SANORF

San Diego

Thu 10/2

6:27 pm-5:50 pm

1 stop20h 23m

Norfolk

Mon 10/6

6:53 pm-11:50 pm

2 stops31h 57m

$242

San DiegoNorfolk

SAN - ORF

SANORF

San Diego

Fri 10/24

1:12 pm-9:25 pm

Nonstop5h 13m

Norfolk

Mon 10/27

9:21 am-12:27 pm

Nonstop6h 06m

$258

San DiegoNorfolk

SAN - ORF

SANORF

San Diego

Sat 9/13

1:12 pm-9:25 pm

Nonstop5h 13m

$99

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/3

Showing 1-10 of 18 results
1
2

Best time to book a flight from San Diego to Chesapeake

Have a flexible travel schedule? Discover the best time to fly to Chesapeake from San Diego 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 San Diego to Chesapeake

How far ahead should I book a flight from San Diego to Chesapeake?

Use this chart to determine the optimal time to book a round-trip flight from San Diego to Chesapeake. Price data was last updated on August 29, 2025.

Booking 56 days in advance of your planned departure date is, on average, the best time to get cheap flights from San Diego to Chesapeake. The general trend is that the closer you book to the departure date, the more expensive your flight will be.

What is the cheapest month to book a flight from San Diego to Chesapeake?

Currently, January is the cheapest month in which you can book a flight from San Diego to Chesapeake (average of $281). Flying from San Diego 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 SAN to C6E?

Find hourly flight availability from San Diego 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 3, 2025.

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

What is the cheapest day to fly from San Diego to Chesapeake?

Use this chart to determine the cheapest time to fly round-trip from San Diego to Chesapeake. Price data was last updated on August 31, 2025.

Travelers seeking maximum savings on their San Diego to Chesapeake flight should consider departing on Saturday afternoons when fares are most often at their lowest. Sunday evenings flights should be avoided if possible as fares are typically the most expensive at this time.

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 3, 2025.
Read reviews from past customers who have flown Southwest, Breeze Airways, and Delta from San Diego to Chesapeake. Users can see the overall rating for each airline as well as how each is rated in terms of entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.0
Very good
4,238 reviews

Crew

8.6

Boarding

8.1

Comfort

8.0

Food

7.0

Entertainment

7.5

Overall

8.0

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
4,238 reviews
Southwest
8.0
Very good
4,238 reviews

Crew

8.6

Boarding

8.1

Comfort

8.0

Food

7.0

Entertainment

7.5

Overall

8.0

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.
Breeze Airways
8.0
Very good
201 reviews
Southwest
8.0
Very good
4,238 reviews

Crew

8.6

Boarding

8.1

Comfort

8.0

Food

7.0

Entertainment

7.5

Overall

8.0

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.
Delta
8.0
Very good
7,972 reviews
Southwest
8.0
Very good
4,238 reviews

Crew

8.6

Boarding

8.1

Comfort

8.0

Food

7.0

Entertainment

7.5

Overall

8.0

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.
United Airlines
7.4
Good
8,937 reviews
Southwest
8.0
Very good
4,238 reviews

Crew

8.6

Boarding

8.1

Comfort

8.0

Food

7.0

Entertainment

7.5

Overall

8.0

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.
American Airlines
7.2
Good
10,000 reviews
Southwest
8.0
Very good
4,238 reviews

Crew

8.6

Boarding

8.1

Comfort

8.0

Food

7.0

Entertainment

7.5

Overall

8.0

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 San Diego 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 San Diego to Chesapeake?

    For a flight from San Diego to Chesapeake, you will be flying from San Diego. San Diego (SAN) is just 2.6 mi from the center of the city. San Diego is the only San Diego airport and it handles 0 outbound flights to Chesapeake per day. 6 airlines have flights to Chesapeake from San Diego on a regular basis.

  • How long is the flight from San Diego to Chesapeake?

    Breeze Airways and Frontier can get you from San Diego to Chesapeake in just under 5h 13m. Your travel time can differ by up to 15h 10m. The distance from San Diego to Chesapeake is about 2324 mi. When browsing for deals, the options you’ll see will be for both nonstop flights and flights with stops.

  • Can I find deals for flights from San Diego to Chesapeake that include hotel bookings?

    Yes. In addition to deals on San Diego to Chesapeake flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from San Diego to Chesapeake?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from San Diego to Chesapeake.

  • Can I find deals for business class flights from San Diego to Chesapeake?

    Yes. Cheapflights offers flight deals from San Diego 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 San Diego to Chesapeake?

    Currently, January is the cheapest month in which you can book a flight from San Diego to Chesapeake (average of $281). Flying from San Diego 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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Top 6 airlines flying from San Diego to Chesapeake

Discover the top 6 airlines that operate flights from San Diego 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 3, 2025.
AirlineCheapestAverageFlexibilityOn-time
Breeze AirwaysCheapest$137Average$285FlexibilityNo cancel feeOn-timeN/A
Spirit AirlinesCheapest$156Average$341FlexibilityNo cancel feeOn-time65%
DeltaCheapest$189Average$464FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$206Average$466FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$313Average$484FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$316Average$467FlexibilityNo cancel feeOn-time63%

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