Chesapeake

$112+ 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 1/7. Fares are subject to change and may not be available on all flights or dates of travel.
SAN — RIC
Jan 11 — Jan 181
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Cheapflights Tip: The best prices from San Diego to Chesapeake are usually found in May or August, booked 90 days in advance, depart on a Tuesday or Thursday and return on a Tuesday

Cheap 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 December 12, 2025.

This United Airlines deal was found by Cheapflights users on 12/10. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/2412:56 pmSAN - ORF
1 stop7h 45mUnited Airlines
Thu 1/16:20 amORF - SAN
1 stop8h 25mUnited Airlines
Deal found 12/10$346
This Breeze Airways deal was found by Cheapflights users on 12/11. 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 Breeze Airways is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/121:12 pmSAN - ORF
Nonstop5h 13mBreeze Airways
Mon 12/159:21 amORF - SAN
Nonstop6h 06mBreeze Airways
Deal found 12/11$398
This United Airlines deal was found by Cheapflights users on 12/11. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/2511:12 amSAN - ORF
2 stops8h 47mUnited Airlines
Sat 1/36:30 amORF - SAN
1 stop8h 00mUnited Airlines
Deal found 12/11$417
This Kiwi.com deal was found by Cheapflights users on 12/10. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/131:12 pmSAN - ORF
Nonstop5h 13mBreeze Airways
Wed 12/179:21 amORF - SAN
Nonstop6h 06mBreeze Airways
Deal found 12/10$428
This Kiwi.com deal was found by Cheapflights users on 12/9. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 12/211:06 pmSAN - ORF
1 stop28h 39mMultiple Airlines
Mon 1/52:04 pmORF - SAN
2 stops36h 12mMultiple Airlines
Deal found 12/9$444
This Expedia deal was found by Cheapflights users on 12/10. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/241:12 pmSAN - ORF
Nonstop5h 13mMultiple Airlines
Thu 1/16:00 amORF - SAN
1 stop8h 51mMultiple Airlines
Deal found 12/10$473
This Kiwi.com deal was found by Cheapflights users on 12/9. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/121:12 pmSAN - ORF
Nonstop5h 13mMultiple Airlines
Mon 12/158:38 amORF - SAN
3 stops41h 08mMultiple Airlines
Deal found 12/9$501

Find 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 December 12, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$236
(Super.com)

One-way from

$112
(Kiwi.com)

Popular in

March

Cheapest in

May

Average price

$478
Provider with most accurate pricing for San Diego-Norfolk flight deals.
Provider most trusted by Cheapflights users for San Diego-Norfolk flights.
From San Diego to Chesapeake
One-way flight from San Diego to Chesapeake
Highest demand for flights based on searches. 11% potential increase in price ($49 potential increase over avg. RT price).
Cheapest flight prices on average. 2% potential price decrease ($9 potential savings vs. average RT price).
Average for round-trip flights in December 2025

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 December 12, 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 5/8

12:55 pm-9:18 pm

Nonstop5h 23m

Norfolk

Sat 5/16

9:51 am-12:33 pm

Nonstop5h 42m

$236

San DiegoNorfolk

SAN - ORF

SANORF

San Diego

Sat 1/10

12:40 pm-11:45 pm

1 stop8h 05m

Norfolk

Sat 1/17

10:24 am-4:54 pm

1 stop9h 30m

$322

San DiegoNorfolk

SAN - ORF

SANORF

San Diego

Tue 1/20

12:40 pm-11:10 pm

1 stop7h 30m

Norfolk

Sat 1/24

10:24 am-6:31 pm

2 stops11h 07m

$327

San DiegoNorfolk

SAN - ORF

SANORF

San Diego

Mon 1/12

6:15 am-5:13 pm

1 stop7h 58m

Norfolk

Mon 1/19

5:20 am-9:58 am

1 stop7h 38m

$337

San DiegoNorfolk

SAN - ORF

SANORF

San Diego

Thu 1/15

6:20 am-4:00 pm

1 stop6h 40m

Norfolk

Sun 1/18

5:35 pm-10:20 pm

1 stop7h 45m

$337

San DiegoNorfolk

SAN - ORF

SANORF

San Diego

Thu 1/15

10:52 am-11:30 pm

2 stops9h 38m

Norfolk

Sun 1/18

10:05 am-3:33 pm

1 stop8h 28m

$342

San DiegoNorfolk

SAN - ORF

SANORF

San Diego

Fri 1/9

12:32 pm-11:19 pm

1 stop7h 47m

Norfolk

Wed 1/14

10:24 am-6:31 pm

2 stops11h 07m

$342

San DiegoNorfolk

SAN - ORF

SANORF

San Diego

Fri 1/9

6:15 am-5:13 pm

1 stop7h 58m

Norfolk

Thu 1/15

5:35 am-10:33 am

1 stop7h 58m

$352

San DiegoNorfolk

SAN - ORF

SANORF

San Diego

Tue 1/20

11:08 am-10:55 pm

2 stops8h 47m

Norfolk

Sat 1/24

10:38 am-6:44 pm

2 stops11h 06m

$352

San DiegoNorfolk

SAN - ORF

SANORF

San Diego

Fri 1/9

10:50 am-11:05 pm

2 stops9h 15m

Norfolk

Sat 1/17

10:24 am-6:31 pm

2 stops11h 07m

$367

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/10

Showing 1-10 of 20 results
1
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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 December 5, 2025.

Booking 90 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, May is the cheapest month in which you can book a flight from San Diego to Chesapeake (average of $122). Flying from San Diego to Chesapeake in January is currently the most expensive (average of $307). 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 December 12, 2025.

A simple way to save on the total cost of your ticket is to fly from San Diego to Chesapeake in the afternoon. If you’re flexible enough to do this you can expect to save up to 59% on your trip compared to booking a flight in the evening.

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 December 12, 2025.
Read reviews from past customers who have flown Breeze Airways, Southwest, 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.

Food

6.7

Comfort

8.2

Crew

8.8

Entertainment

6.6

Boarding

8.4

Overall

8.2

Reviews

1 / 15
8.0
Excellent

Lyle,Dec 2025

BDL - RSW

Seating was comfortable, crew excellent, no food or entertainment offered.

Food

6.7

Comfort

8.2

Crew

8.8

Entertainment

6.6

Boarding

8.4

Overall

8.2

Reviews

1 / 15
8.0
Excellent

Lyle,Dec 2025

BDL - RSW

Seating was comfortable, crew excellent, no food or entertainment offered.

Food

6.7

Comfort

8.2

Crew

8.8

Entertainment

6.6

Boarding

8.4

Overall

8.2

Reviews

1 / 15
8.0
Excellent

Lyle,Dec 2025

BDL - RSW

Seating was comfortable, crew excellent, no food or entertainment offered.

Food

6.7

Comfort

8.2

Crew

8.8

Entertainment

6.6

Boarding

8.4

Overall

8.2

Reviews

1 / 15
8.0
Excellent

Lyle,Dec 2025

BDL - RSW

Seating was comfortable, crew excellent, no food or entertainment offered.

Food

6.7

Comfort

8.2

Crew

8.8

Entertainment

6.6

Boarding

8.4

Overall

8.2

Reviews

1 / 15
8.0
Excellent

Lyle,Dec 2025

BDL - RSW

Seating was comfortable, crew excellent, no food or entertainment offered.

Food

6.7

Comfort

8.2

Crew

8.8

Entertainment

6.6

Boarding

8.4

Overall

8.2

Reviews

1 / 15
8.0
Excellent

Lyle,Dec 2025

BDL - RSW

Seating was comfortable, crew excellent, no food or entertainment offered.

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, American Airlines, and Delta can get you from San Diego to Chesapeake in just under 5h 23m. Your travel time can differ by up to 2h 42m. 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.

  • What are the cheapest airlines to fly from San Diego to Chesapeake one-way?

    The cheapest airline one-way is Breeze Airways, with whom users have recently found tickets for as low as $99. However, be on the lookout for offers from American Airlines and Delta, as they are both options that can get you from San Diego to Chesapeake for a low price.

  • 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, May is the cheapest month in which you can book a flight from San Diego to Chesapeake (average of $122). Flying from San Diego to Chesapeake in January is currently the most expensive (average of $307). 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

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Alternative routes for San Diego to Chesapeake

See prices for flight routes from nearby airports that may be better suited for you.

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 December 12, 2025.
AirlineCheapestAverageFlexibilityOn-time
Breeze AirwaysCheapest$139Average$318FlexibilityNo cancel feeOn-timeN/A
DeltaCheapest$191Average$465FlexibilityNo cancel feeOn-timeN/A
FrontierCheapest$196Average$272FlexibilityNo cancel feeOn-time62%
United AirlinesCheapest$241Average$485FlexibilityNo cancel feeOn-time69%
SouthwestCheapest$308Average$475FlexibilityNo cancel feeOn-time63%
American AirlinesCheapest$315Average$480FlexibilityNo cancel feeOn-time71%

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