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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 9/17. Fares are subject to change and may not be available on all flights or dates of travel.
SAN — RIC
jul. 19 — jul. 261
sáb. 7/19
sáb. 7/26
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 julio 14, 2025.

Round-trip from

$198
(Breeze Airways)

One-way from

$99
(Breeze Airways)

Popular in

March

Cheapest in

September

Average price

$395
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. 16% potential increase in price ($74 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 July 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 julio 14, 2025.

This Breeze Airways deal was found by Cheapflights users on 7/13. 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.
sáb. 8/3011:53 amSAN - ORF
Nonstop5h 22mBreeze Airways
sáb. 9/69:21 amORF - SAN
Nonstop6h 06mBreeze Airways
Deal found 7/13$218
This FlightHub deal was found by Cheapflights users on 7/13. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
jue. 9/117:47 pmSAN - ORF
2 stops14h 23mSpirit Airlines
jue. 10/169:35 amORF - SAN
1 stop7h 40mSpirit Airlines
Deal found 7/13$255
This JetBlue deal was found by Cheapflights users on 7/13. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
jue. 9/118:15 pmSAN - ORF
1 stop10h 25mJetBlue
jue. 10/1610:25 amORF - SAN
1 stop11h 32mJetBlue
Deal found 7/13$293
This Delta deal was found by Cheapflights users on 7/13. 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.
sáb. 8/306:15 amSAN - ORF
1 stop9h 25mDelta
sáb. 9/66:00 amORF - SAN
1 stop7h 13mDelta
Deal found 7/13$301
This Southwest deal was found by Cheapflights users on 7/11. 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.
mar. 8/266:25 amSAN - ORF
1 stop7h 50mSouthwest
mar. 9/210:40 amORF - SAN
2 stops11h 05mSouthwest
Deal found 7/11$306
This FlightHub deal was found by Cheapflights users on 7/13. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
jue. 9/185:37 pmSAN - ORF
1 stop21h 14mMultiple Airlines
dom. 9/215:24 amORF - SAN
2 stops16h 18mMultiple Airlines
Deal found 7/13$318
This American Airlines deal was found by Cheapflights users on 7/13. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
sáb. 8/309:45 amSAN - ORF
2 stops9h 42mAmerican Airlines
sáb. 9/611:30 amORF - SAN
1 stop10h 12mAmerican Airlines
Deal found 7/13$334

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 julio 14, 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

sáb. 8/30

11:53 am-8:15 pm

Nonstop5h 22m

Norfolk

sáb. 9/6

9:21 am-12:27 pm

Nonstop6h 06m

$218

San DiegoNorfolk

SAN - ORF

SANORF

San Diego

jue. 9/11

7:47 pm-1:10 pm

2 stops14h 23m

Norfolk

jue. 10/16

9:35 am-2:15 pm

1 stop7h 40m

$255

San DiegoNorfolk

SAN - ORF

SANORF

San Diego

jue. 9/11

8:15 pm-9:40 am

1 stop10h 25m

Norfolk

jue. 10/16

10:25 am-6:57 pm

1 stop11h 32m

$293

San DiegoNorfolk

SAN - ORF

SANORF

San Diego

sáb. 8/30

6:15 am-6:40 pm

1 stop9h 25m

Norfolk

sáb. 9/6

6:00 am-10:13 am

1 stop7h 13m

$301

San DiegoNorfolk

SAN - ORF

SANORF

San Diego

mar. 8/26

6:25 am-5:15 pm

1 stop7h 50m

Norfolk

mar. 9/2

10:40 am-6:45 pm

2 stops11h 05m

$306

San DiegoNorfolk

SAN - ORF

SANORF

San Diego

jue. 9/18

5:37 pm-5:51 pm

1 stop21h 14m

Norfolk

dom. 9/21

5:24 am-6:42 pm

2 stops16h 18m

$318

San DiegoNorfolk

SAN - ORF

SANORF

San Diego

sáb. 8/30

9:45 am-10:27 pm

2 stops9h 42m

Norfolk

sáb. 9/6

11:30 am-6:42 pm

1 stop10h 12m

$334

San DiegoNorfolk

SAN - ORF

SANORF

San Diego

mié. 9/17

1:12 pm-9:25 pm

Nonstop5h 13m

$99

San DiegoNorfolk

SAN - ORF

SANORF

San Diego

jue. 9/18

7:47 pm-1:10 pm

2 stops14h 23m

$111

San DiegoNorfolk

SAN - ORF

SANORF

San Diego

mar. 9/23

8:15 pm-9:40 am

1 stop10h 25m

$147

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/13

Showing 1-10 of 15 results
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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 July 11, 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 julio 14, 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 July 13, 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 julio 14, 2025.
Read reviews from past customers who have flown Southwest, Delta, and Breeze Airways 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
4,242 reviews

Entertainment

7.6

Overall

8.0

Crew

8.6

Boarding

8.1

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
4,242 reviews
Southwest
8.0
Very good
4,242 reviews

Entertainment

7.6

Overall

8.0

Crew

8.6

Boarding

8.1

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
7,956 reviews
Southwest
8.0
Very good
4,242 reviews

Entertainment

7.6

Overall

8.0

Crew

8.6

Boarding

8.1

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.
Breeze Airways
8.0
Very good
187 reviews
Southwest
8.0
Very good
4,242 reviews

Entertainment

7.6

Overall

8.0

Crew

8.6

Boarding

8.1

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.
United Airlines
7.4
Good
8,858 reviews
Southwest
8.0
Very good
4,242 reviews

Entertainment

7.6

Overall

8.0

Crew

8.6

Boarding

8.1

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.
JetBlue
7.3
Good
2,908 reviews
Southwest
8.0
Very good
4,242 reviews

Entertainment

7.6

Overall

8.0

Crew

8.6

Boarding

8.1

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 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.

  • 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 Spirit Airlines and JetBlue, 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, 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.

See more FAQs

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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 julio 14, 2025.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$98Average$300FlexibilityNo cancel feeOn-time65%
Breeze AirwaysCheapest$134Average$274FlexibilityNo cancel feeOn-timeN/A
DeltaCheapest$188Average$459FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$206Average$466FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$306Average$474FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$350Average$471FlexibilityNo cancel feeOn-time63%

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