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$99+ 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 5/7. Fares are subject to change and may not be available on all flights or dates of travel.
RIC — SAN
Feb 25 — Mar 41
Tue 2/25
Tue 3/4
1 adult, Economy
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The best prices from Chesapeake to San Diego are usually found in September or May, booked 81 days in advance, depart on a Sunday or Thursday 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 February 20, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$345
(Delta)

One-way from

$161
(FlightHub)

Popular in

March

Cheapest in

September

Average price

$523
Provider with most accurate pricing for Norfolk-San Diego flight deals.
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Provider most trusted by Cheapflights users for Norfolk-San Diego flights.
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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. 18% potential increase in price ($89 potential increase over avg. RT price).
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Cheapest flight prices on average. 3% potential price decrease ($13 potential savings vs. average RT price).
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Average for round-trip flights in February 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 February 20, 2025.

This CheapOair deal was found by Cheapflights users on 2/19. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 3/148:22 pmORF - SAN
2 stops38h 08mSpirit Airlines
Wed 3/198:07 pmSAN - ORF
2 stops12h 40mSpirit Airlines
Deal found 2/19$343
This Mytrip deal was found by Cheapflights users on 2/18. 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.
Mon 3/37:00 amORF - SAN
3 stops29h 01mMultiple Airlines
Thu 3/68:14 pmSAN - ORF
1 stop21h 20mMultiple Airlines
Deal found 2/18$346
This Delta deal was found by Cheapflights users on 2/18. 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.
Tue 3/2512:34 pmORF - SAN
1 stop14h 10mDelta
Tue 4/17:15 amSAN - ORF
1 stop12h 41mDelta
Deal found 2/18$349
This Southwest deal was found by Cheapflights users on 2/19. 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 3/263:20 pmORF - SAN
2 stops10h 30mSouthwest
Wed 4/26:35 amSAN - ORF
1 stop6h 25mSouthwest
Deal found 2/19$352
This American Airlines deal was found by Cheapflights users on 2/19. 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.
Sat 4/55:00 amORF - SAN
1 stop7h 15mAmerican Airlines
Sat 4/126:30 amSAN - ORF
1 stop7h 34mAmerican Airlines
Deal found 2/19$356
This Kiwi.com deal was found by Cheapflights users on 2/19. 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.
Wed 6/49:22 amORF - SAN
Nonstop5h 41mBreeze Airways
Mon 6/1612:43 pmSAN - ORF
Nonstop5h 22mBreeze Airways
Deal found 2/19$365
This United Airlines deal was found by Cheapflights users on 2/20. 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 4/176:10 amORF - SAN
1 stop8h 13mUnited Airlines
Tue 4/2210:16 amSAN - ORF
2 stops10h 21mUnited Airlines
Deal found 2/20$402

Find flights from Chesapeake to San Diego within your budget

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 February 20, 2025.

Fly from

Chesapeake

Fly to

San Diego

Route

Depart

Return

Price

NorfolkSan Diego

ORF - SAN

ORFSAN

Norfolk

Mon 3/24

4:22 pm-11:20 pm

1 stop9h 58m

San Diego

Tue 4/1

2:40 pm-12:03 am

1 stop6h 23m

$345

NorfolkSan Diego

ORF - SAN

ORFSAN

Norfolk

Mon 3/3

9:19 am-9:01 am

1 stop26h 42m

San Diego

Thu 3/6

8:14 pm-8:34 pm

1 stop21h 20m

$346

NorfolkSan Diego

ORF - SAN

ORFSAN

Norfolk

Wed 3/26

3:20 pm-10:50 pm

2 stops10h 30m

San Diego

Wed 4/2

6:35 am-4:00 pm

1 stop6h 25m

$352

NorfolkSan Diego

ORF - SAN

ORFSAN

Norfolk

Thu 3/20

12:42 pm-7:41 am

3 stops45h 59m

San Diego

Thu 3/27

6:15 am-6:46 pm

3 stops33h 31m

$355

NorfolkSan Diego

ORF - SAN

ORFSAN

Norfolk

Tue 3/25

6:00 am-2:03 pm

2 stops11h 03m

San Diego

Mon 3/31

9:30 pm-9:21 am

1 stop8h 51m

$357

NorfolkSan Diego

ORF - SAN

ORFSAN

Norfolk

Wed 6/4

9:22 am-12:03 pm

Nonstop5h 41m

San Diego

Mon 6/16

12:43 pm-9:05 pm

Nonstop5h 22m

$365

NorfolkSan Diego

ORF - SAN

ORFSAN

Norfolk

Sun 3/16

7:00 am-12:39 pm

1 stop8h 39m

San Diego

Wed 3/26

6:30 am-6:14 pm

1 stop8h 44m

$413

NorfolkSan Diego

ORF - SAN

ORFSAN

Norfolk

Wed 5/7

9:22 am-12:03 pm

Nonstop5h 41m

$99

NorfolkSan Diego

ORF - SAN

ORFSAN

Norfolk

Wed 5/7

3:34 pm-7:28 am

2 stops18h 54m

$100

NorfolkSan Diego

ORF - SAN

ORFSAN

Norfolk

Sat 3/22

5:03 am-9:27 am

1 stop7h 24m

$170

Flights are sorted by cheapest round-trip flights first.

Deals found on 2/20

Showing 1-10 of 14 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.

Travel insights for flights from Chesapeake to San Diego

Get recent, data-driven insights about flights from Chesapeake to San Diego including ideal travel times, pricing trends, and more.

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 February 14, 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 81 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 February 20, 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 February 16, 2025.

Travelers seeking maximum savings on their Chesapeake to San Diego flight should consider departing on Sunday 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.

Rainfall in San Diego by month

Plan your trip to San Diego by taking into account the average rainfall totals by month.

In terms of precipitation, rainfall in San Diego ranges from 0.0 - 2.3 inches per month. February is typically the wettest month, when rainfall can reach 2.3 in. July is typically the driest time to visit San Diego when rainfall is around 0.0 in.

Temperature in San Diego by month

Plan your trip to San Diego by taking into account the average temperature totals by month.

If weather is an important factor for your trip to San Diego, use this chart to help with planning. For those seeking warmer temperatures, August is the ideal time of year to visit, when temperatures reach an average of 71.6 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 57.2 F).

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 February 20, 2025.
Read through reviews of airlines operating flights from Chesapeake to San Diego, such as Southwest, Breeze Airways and Alaska Airlines. You can also see how each airline stacks up in terms of entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.1
Very good
4,411 reviews

Food

7.1

Boarding

8.2

Overall

8.1

Entertainment

7.6

Comfort

8.1

Crew

8.7

Reviews

1 / 20

8.0
Excellent

Christine,Aug 2024

DEN - LGB

No issues. I needed pre boarding and I was able to get it without issue

Southwest
8.1
Very good
4,411 reviews
Southwest
8.1
Very good
4,411 reviews

Food

7.1

Boarding

8.2

Overall

8.1

Entertainment

7.6

Comfort

8.1

Crew

8.7

Reviews

1 / 20

8.0
Excellent

Christine,Aug 2024

DEN - LGB

No issues. I needed pre boarding and I was able to get it without issue

Breeze Airways
8.1
Very good
150 reviews
Southwest
8.1
Very good
4,411 reviews

Food

7.1

Boarding

8.2

Overall

8.1

Entertainment

7.6

Comfort

8.1

Crew

8.7

Reviews

1 / 20

8.0
Excellent

Christine,Aug 2024

DEN - LGB

No issues. I needed pre boarding and I was able to get it without issue

Alaska Airlines
8.0
Very good
9,697 reviews
Southwest
8.1
Very good
4,411 reviews

Food

7.1

Boarding

8.2

Overall

8.1

Entertainment

7.6

Comfort

8.1

Crew

8.7

Reviews

1 / 20

8.0
Excellent

Christine,Aug 2024

DEN - LGB

No issues. I needed pre boarding and I was able to get it without issue

Delta
8.0
Very good
8,219 reviews
Southwest
8.1
Very good
4,411 reviews

Food

7.1

Boarding

8.2

Overall

8.1

Entertainment

7.6

Comfort

8.1

Crew

8.7

Reviews

1 / 20

8.0
Excellent

Christine,Aug 2024

DEN - LGB

No issues. I needed pre boarding and I was able to get it without issue

United Airlines
7.4
Good
8,765 reviews
Southwest
8.1
Very good
4,411 reviews

Food

7.1

Boarding

8.2

Overall

8.1

Entertainment

7.6

Comfort

8.1

Crew

8.7

Reviews

1 / 20

8.0
Excellent

Christine,Aug 2024

DEN - LGB

No issues. I needed pre boarding and I was able to get it without issue

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 8 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 Spirit Airlines, which is currently one of the cheapest options available, starting at $161. American Airlines flights start at $170 while deals on United Airlines start at $226 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 Chesapeake?

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

Browse thousands of different options on Cheapflights for your next trip

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Top 8 airlines flying from Chesapeake to San Diego

Discover the top 8 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 February 20, 2025.
AirlineCheapestAverageFlexibilityOn-time
Breeze AirwaysCheapest$135Average$316FlexibilityNo cancel feeOn-timeN/A
Spirit AirlinesCheapest$144Average$282FlexibilityNo cancel feeOn-time65%
FrontierCheapest$152Average$288FlexibilityNo cancel feeOn-time62%
DeltaCheapest$226Average$478FlexibilityNo cancel feeOn-timeN/A
JetBlueCheapest$245Average$335FlexibilityNo cancel feeOn-time62%
United AirlinesCheapest$246Average$504FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$274Average$524FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$348Average$472FlexibilityNo cancel feeOn-time63%
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