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$102+ Cheap flights from Chesapeake, VA to San Diego (SAN)

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 8/22. Fares are subject to change and may not be available on all flights or dates of travel.
RIC — SAN
Aug 3 — Aug 101
Sun 8/3
Sun 8/10
1 adult, Economy
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Cheapflights Tip: The best prices from Chesapeake to San Diego are usually found in September or August, booked 56 days in advance, depart on a Tuesday or Sunday and return on a Tuesday

Cheap flight deals from Chesapeake to San Diego

Keep the following information in mind while searching for Chesapeake to San Diego flight deals. Data was last updated July 29, 2025.

Round-trip from

$198
(Breeze Airways)

One-way from

$102
(Priceline)

Popular in

March

Cheapest in

September

Average price

$372
From Chesapeake to San Diego
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One-way flight from Chesapeake to San Diego
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Highest demand for flights based on searches. 20% potential increase in price ($108 potential increase over avg. RT price).
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Cheapest flight prices on average. 2% potential price decrease ($11 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 Chesapeake to San Diego

Cheapest flights from Chesapeake to San Diego
Explore the most affordable flight options available from Chesapeake to San Diego. Find the lowest fares from popular airlines and budget airlines, with prices last updated on July 29, 2025.

This Breeze Airways deal was found by Cheapflights users on 7/27. 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 9/59:21 amORF - SAN
Nonstop6h 06mBreeze Airways
Wed 9/101:12 pmSAN - ORF
Nonstop5h 13mBreeze Airways
Deal found 7/27$198
This Booking.com deal was found by Cheapflights users on 7/28. 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.
Mon 8/115:20 pmORF - SAN
2 stops19h 35mSpirit Airlines
Thu 8/141:17 pmSAN - ORF
2 stops20h 27mSpirit Airlines
Deal found 7/28$224
This JetBlue deal was found by Cheapflights users on 7/28. 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.
Fri 9/510:25 amORF - SAN
1 stop11h 30mJetBlue
Fri 9/129:35 pmSAN - ORF
1 stop9h 21mJetBlue
Deal found 7/28$273
This Delta deal was found by Cheapflights users on 7/28. 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 8/2711:43 amORF - SAN
1 stop9h 10mDelta
Sat 9/68:00 amSAN - ORF
1 stop7h 40mDelta
Deal found 7/28$301
This Southwest deal was found by Cheapflights users on 7/28. 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 8/2710:40 amORF - SAN
2 stops11h 05mSouthwest
Sat 9/611:30 amSAN - ORF
1 stop7h 00mSouthwest
Deal found 7/28$306
This Mytrip deal was found by Cheapflights users on 7/27. 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.
Sun 8/109:05 amORF - SAN
3 stops27h 50mMultiple Airlines
Wed 8/131:17 pmSAN - ORF
3 stops24h 22mMultiple Airlines
Deal found 7/27$308
This American Airlines deal was found by Cheapflights users on 7/27. 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.
Wed 9/104:40 pmORF - SAN
1 stop8h 03mAmerican Airlines
Wed 9/1710:45 pmSAN - ORF
1 stop8h 22mAmerican Airlines
Deal found 7/27$311

Cheapflights Fare Finder

 
Customize your flight search to find flights from Chesapeake to San Diego 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 July 29, 2025.
Use the filters below to find and compare flights from Chesapeake to San Diego that are best for you.

Fly from

Chesapeake

Fly to

San Diego

Route

Depart

Return

Price

NorfolkSan Diego

ORF - SAN

ORFSAN

Norfolk

Fri 9/5

9:21 am-12:27 pm

Nonstop6h 06m

San Diego

Wed 9/10

1:12 pm-9:25 pm

Nonstop5h 13m

$198

NorfolkSan Diego

ORF - SAN

ORFSAN

Norfolk

Mon 8/11

5:20 pm-9:55 am

2 stops19h 35m

San Diego

Thu 8/14

1:17 pm-12:44 pm

2 stops20h 27m

$224

NorfolkSan Diego

ORF - SAN

ORFSAN

Norfolk

Fri 9/5

10:25 am-6:55 pm

1 stop11h 30m

San Diego

Fri 9/12

9:35 pm-9:56 am

1 stop9h 21m

$273

NorfolkSan Diego

ORF - SAN

ORFSAN

Norfolk

Wed 8/27

11:43 am-5:53 pm

1 stop9h 10m

San Diego

Sat 9/6

8:00 am-6:40 pm

1 stop7h 40m

$301

NorfolkSan Diego

ORF - SAN

ORFSAN

Norfolk

Wed 8/27

10:40 am-6:45 pm

2 stops11h 05m

San Diego

Sat 9/6

11:30 am-9:30 pm

1 stop7h 00m

$306

NorfolkSan Diego

ORF - SAN

ORFSAN

Norfolk

Sun 8/10

9:05 am-9:55 am

3 stops27h 50m

San Diego

Wed 8/13

1:17 pm-4:39 pm

3 stops24h 22m

$308

NorfolkSan Diego

ORF - SAN

ORFSAN

Norfolk

Wed 9/10

4:40 pm-9:43 pm

1 stop8h 03m

San Diego

Wed 9/17

10:45 pm-10:07 am

1 stop8h 22m

$311

NorfolkSan Diego

ORF - SAN

ORFSAN

Norfolk

Fri 8/22

9:32 am-12:13 pm

Nonstop5h 41m

$102

NorfolkSan Diego

ORF - SAN

ORFSAN

Norfolk

Mon 8/11

6:28 pm-9:55 am

2 stops18h 27m

$110

NorfolkSan Diego

ORF - SAN

ORFSAN

Norfolk

Tue 9/23

10:41 am-6:58 pm

1 stop11h 17m

$147

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/28

Showing 1-10 of 15 results
1
2

Best time to book a flight from Chesapeake to San Diego

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

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

Use this chart to determine the optimal time to book a round-trip flight from Chesapeake to San Diego. Price data was last updated on July 25, 2025.

The price you pay for your flight from Chesapeake to San Diego may vary depending on when you book. For the best chance of a lower fare, look to book 56 days in advance of your trip. Fares are likely to increase a fortnight or so before your departure date.

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

Currently, August is the cheapest month in which you can book a flight from Chesapeake to San Diego (average of $286). Flying from Chesapeake to San Diego in March is currently the most expensive (average of $366). 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 C6E to SAN?

Find hourly flight availability from Chesapeake to San Diego. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated July 29, 2025.

When flying from Chesapeake to San Diego, the time of day you decide to fly out makes little to no difference towards the overall price you’ll pay on tickets.

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

Use this chart to determine the cheapest time to fly round-trip from Chesapeake to San Diego. Price data was last updated on July 27, 2025.

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

Reviews of airlines servicing San Diego

Get insights into the airlines that provide service to San Diego. 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 San Diego. Reviews last updated July 29, 2025.
Get a feel of what it's like to fly with Southwest, Delta, and Breeze Airways from Chesapeake to San Diego by reading reviews from past customers. Users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.0
Very good
4,238 reviews

Comfort

8.0

Entertainment

7.5

Boarding

8.1

Food

7.0

Crew

8.6

Overall

8.0

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

Comfort

8.0

Entertainment

7.5

Boarding

8.1

Food

7.0

Crew

8.6

Overall

8.0

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
7,977 reviews
Southwest
8.0
Very good
4,238 reviews

Comfort

8.0

Entertainment

7.5

Boarding

8.1

Food

7.0

Crew

8.6

Overall

8.0

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
190 reviews
Southwest
8.0
Very good
4,238 reviews

Comfort

8.0

Entertainment

7.5

Boarding

8.1

Food

7.0

Crew

8.6

Overall

8.0

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
8,899 reviews
Southwest
8.0
Very good
4,238 reviews

Comfort

8.0

Entertainment

7.5

Boarding

8.1

Food

7.0

Crew

8.6

Overall

8.0

Reviews

1 / 20
10.0
Excellent

Merlyn,Feb 2025

LAX - SMF

New Terminal is neat, lost of stores and places to catch a bite.
American Airlines
7.2
Good
10,000 reviews
Southwest
8.0
Very good
4,238 reviews

Comfort

8.0

Entertainment

7.5

Boarding

8.1

Food

7.0

Crew

8.6

Overall

8.0

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 Chesapeake to San Diego. 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 into for flights to San Diego from Chesapeake?

    If you book a flight to San Diego from Chesapeake, you will be flying to San Diego, which is the city’s only airport. San Diego (SAN) is located 2.6 mi from the center of San Diego. There are 0 flights from Chesapeake to San Diego per day from 7 different airlines.

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

    To fly one-way, consider booking your trip with Breeze Airways, which is currently one of the cheapest options available, starting at $102. Spirit Airlines flights start at $110 while deals on JetBlue start at $147 one-way.

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

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

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

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

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

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

    Currently, August is the cheapest month in which you can book a flight from Chesapeake to San Diego (average of $286). Flying from Chesapeake to San Diego in March is currently the most expensive (average of $366). 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

Traveling to a place near San Diego?

Book flights to San Diego if you plan to visit one of these locations
El Cajon
Chula Vista
Coronado
Poway
National City
Lemon Grove
Imperial Beach
La Mesa
Alpine
Santee

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Top 7 airlines flying from Chesapeake to San Diego

Discover the top 7 airlines that operate flights from Chesapeake to San Diego. 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 July 29, 2025.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$136Average$248FlexibilityNo cancel feeOn-time65%
JetBlueCheapest$143Average$266FlexibilityNo cancel feeOn-time62%
Breeze AirwaysCheapest$174Average$319FlexibilityNo cancel feeOn-timeN/A
DeltaCheapest$213Average$471FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$248Average$482FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$293Average$495FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$316Average$471FlexibilityNo cancel feeOn-time63%

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