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$108+ 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 1/29. Fares are subject to change and may not be available on all flights or dates of travel.
RIC — SAN
Jan 14 — Jan 211
Wed 1/14
Wed 1/21
1 adult, Economy
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Cheapflights Tip: The best prices from Chesapeake to San Diego are usually found in August or May, booked 68 days in advance, depart on a Tuesday or Friday and return on a Tuesday

Cheap 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 December 15, 2025.

This United Airlines deal was found by Cheapflights users on 12/14. 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 12/256:00 amORF - SAN
1 stop8h 05mUnited Airlines
Wed 12/3110:30 pmSAN - ORF
1 stop9h 08mUnited Airlines
Deal found 12/14$387
This Delta deal was found by Cheapflights users on 12/14. 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 12/313:45 pmORF - SAN
1 stop8h 11mDelta
Sat 1/108:05 amSAN - ORF
1 stop8h 24mDelta
Deal found 12/14$452
This Delta deal was found by Cheapflights users on 12/13. 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.
Wed 12/243:45 pmORF - SAN
1 stop8h 11mDelta
Thu 1/16:15 amSAN - ORF
1 stop9h 15mDelta
Deal found 12/13$513
This Breeze Airways deal was found by Cheapflights users on 12/13. 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.
Wed 12/249:21 amORF - SAN
Nonstop6h 06mBreeze Airways
Mon 12/291:12 pmSAN - ORF
Nonstop5h 13mBreeze Airways
Deal found 12/13$518
This American Airlines deal was found by Cheapflights users on 12/14. 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 12/249:04 amORF - SAN
2 stops9h 51mAmerican Airlines
Thu 1/110:48 pmSAN - ORF
1 stop7h 54mAmerican Airlines
Deal found 12/14$560
This United Airlines deal was found by Cheapflights users on 12/14. 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 12/315:15 pmORF - SAN
1 stop19h 29mUnited Airlines
Sat 1/1011:10 amSAN - ORF
2 stops9h 20mUnited Airlines
Deal found 12/14$594
This Kiwi.com deal was found by Cheapflights users on 12/13. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/209:21 amORF - SAN
Nonstop6h 06mMultiple Airlines
Sun 1/41:06 pmSAN - ORF
3 stops46h 00mMultiple Airlines
Deal found 12/13$610
This Kiwi.com deal was found by Cheapflights users on 12/14. 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 12/213:09 pmORF - SAN
3 stops25h 06mMultiple Airlines
Wed 12/241:12 pmSAN - ORF
Nonstop5h 13mMultiple Airlines
Deal found 12/14$615

Find 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 December 15, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$248
(Kiwi.com)

One-way from

$108
(Kiwi.com)

Popular in

March

Cheapest in

August

Average price

$468
Provider with most accurate pricing for Norfolk-San Diego flight deals.
Search Deals
Provider most trusted by Cheapflights users for Norfolk-San Diego flights.
Search Deals
From Chesapeake to San Diego
Search Deals
One-way flight from Chesapeake to San Diego
Search Deals
Highest demand for flights based on searches. 20% potential increase in price ($107 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 2% potential price decrease ($13 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in December 2025
Search Deals

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 December 15, 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

Wed 12/31

3:45 pm-8:56 pm

1 stop8h 11m

San Diego

Sat 1/10

6:15 am-7:30 pm

1 stop10h 15m

$322

NorfolkSan Diego

ORF - SAN

ORFSAN

Norfolk

Sat 1/10

1:45 pm-8:20 pm

1 stop9h 35m

San Diego

Sat 1/17

9:45 pm-9:40 am

1 stop8h 55m

$322

NorfolkSan Diego

ORF - SAN

ORFSAN

Norfolk

Sat 1/10

3:04 pm-7:39 pm

1 stop7h 35m

San Diego

Fri 1/16

11:43 am-11:15 pm

1 stop8h 32m

$337

NorfolkSan Diego

ORF - SAN

ORFSAN

Norfolk

Mon 2/23

1:05 pm-9:10 pm

2 stops11h 05m

San Diego

Sat 2/28

7:05 am-5:15 pm

1 stop7h 10m

$342

NorfolkSan Diego

ORF - SAN

ORFSAN

Norfolk

Fri 1/9

6:30 am-2:20 pm

1 stop10h 50m

San Diego

Mon 1/12

6:25 am-5:50 pm

2 stops8h 25m

$342

NorfolkSan Diego

ORF - SAN

ORFSAN

Norfolk

Mon 3/2

3:30 pm-8:37 pm

1 stop8h 07m

San Diego

Tue 3/3

6:15 am-5:17 pm

1 stop8h 02m

$357

NorfolkSan Diego

ORF - SAN

ORFSAN

Norfolk

Sat 2/28

12:27 pm-6:51 pm

1 stop9h 24m

San Diego

Tue 3/3

12:00 pm-11:13 pm

1 stop8h 13m

$357

NorfolkSan Diego

ORF - SAN

ORFSAN

Norfolk

Thu 1/8

8:50 am-2:20 pm

1 stop8h 30m

San Diego

Mon 1/12

10:05 am-8:30 pm

1 stop7h 25m

$365

NorfolkSan Diego

ORF - SAN

ORFSAN

Norfolk

Tue 3/3

5:40 am-10:48 am

1 stop8h 08m

San Diego

Tue 3/3

10:30 pm-9:18 am

1 stop7h 48m

$377

NorfolkSan Diego

ORF - SAN

ORFSAN

Norfolk

Thu 1/8

8:50 am-4:55 pm

2 stops11h 05m

San Diego

Thu 1/15

6:20 am-4:00 pm

1 stop6h 40m

$385

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/12

Showing 1-10 of 21 results
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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 December 12, 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 68 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, September is the cheapest month in which you can book a flight from Chesapeake to San Diego (average of $127). Flying from Chesapeake to San Diego in March is currently the most expensive (average of $332). 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 December 15, 2025.

It’s optimal to fly from Chesapeake to San Diego in the morning. By choosing this option you can save up to 25% on the cost of your flight, compared to a flight at noon.

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 December 13, 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. Sunday 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 December 15, 2025.
Get a feel of what it's like to fly with Breeze Airways, Southwest, and Delta 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.
Breeze Airways
8.2
Very good
248 reviews

Crew

8.8

Overall

8.2

Comfort

8.2

Boarding

8.4

Food

6.7

Entertainment

6.7

Reviews

1 / 16
10.0
Excellent

Anonymous,Dec 2025

RSW - ISP

There was no food offered so I had to just put okay. Other than that all was great.
Breeze Airways
8.2
Very good
248 reviews
Breeze Airways
8.2
Very good
248 reviews

Crew

8.8

Overall

8.2

Comfort

8.2

Boarding

8.4

Food

6.7

Entertainment

6.7

Reviews

1 / 16
10.0
Excellent

Anonymous,Dec 2025

RSW - ISP

There was no food offered so I had to just put okay. Other than that all was great.
Southwest
7.9
Good
4,249 reviews
Breeze Airways
8.2
Very good
248 reviews

Crew

8.8

Overall

8.2

Comfort

8.2

Boarding

8.4

Food

6.7

Entertainment

6.7

Reviews

1 / 16
10.0
Excellent

Anonymous,Dec 2025

RSW - ISP

There was no food offered so I had to just put okay. Other than that all was great.
Delta
7.9
Good
8,008 reviews
Breeze Airways
8.2
Very good
248 reviews

Crew

8.8

Overall

8.2

Comfort

8.2

Boarding

8.4

Food

6.7

Entertainment

6.7

Reviews

1 / 16
10.0
Excellent

Anonymous,Dec 2025

RSW - ISP

There was no food offered so I had to just put okay. Other than that all was great.
United Airlines
7.4
Good
9,092 reviews
Breeze Airways
8.2
Very good
248 reviews

Crew

8.8

Overall

8.2

Comfort

8.2

Boarding

8.4

Food

6.7

Entertainment

6.7

Reviews

1 / 16
10.0
Excellent

Anonymous,Dec 2025

RSW - ISP

There was no food offered so I had to just put okay. Other than that all was great.
American Airlines
7.2
Good
11,051 reviews
Breeze Airways
8.2
Very good
248 reviews

Crew

8.8

Overall

8.2

Comfort

8.2

Boarding

8.4

Food

6.7

Entertainment

6.7

Reviews

1 / 16
10.0
Excellent

Anonymous,Dec 2025

RSW - ISP

There was no food offered so I had to just put okay. Other than that all was great.

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 is 1 flight from Chesapeake to San Diego per day from 7 different airlines.

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

    There are many flights that can get you from Chesapeake to San Diego in 8h 11m. Fly via Delta or Southwest to get the fastest option. There are 2324 mi between Chesapeake and San Diego. Both multi-stop and nonstop flights can be found to your destination and back.

  • 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 $96. Southwest flights start at $148 while deals on American Airlines start at $150 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, September is the cheapest month in which you can book a flight from Chesapeake to San Diego (average of $127). Flying from Chesapeake to San Diego in March is currently the most expensive (average of $332). 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
La Mesa
Poway
Lemon Grove
Julian
National City

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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 December 15, 2025.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$127Average$252FlexibilityNo cancel feeOn-time65%
JetBlueCheapest$143Average$292FlexibilityNo cancel feeOn-time62%
Breeze AirwaysCheapest$198Average$342FlexibilityNo cancel feeOn-timeN/A
DeltaCheapest$211Average$458FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$248Average$478FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$283Average$533FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$313Average$478FlexibilityNo cancel feeOn-time63%

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