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$56+ 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 7/9. Fares are subject to change and may not be available on all flights or dates of travel.
RIC — SAN
jun 17 — jun 241
ter 6/17
ter 6/24
1 adult, Economy
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Cheapflights Tip: The best prices from Chesapeake to San Diego are usually found in September or October, booked 80 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 junho 12, 2025.

Round-trip from

$252
(CheapOair)

One-way from

$56
(FlightHub)

Popular in

March

Cheapest in

September

Average price

$456
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 ($104 potential increase over avg. RT price).
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Cheapest flight prices on average. 2% potential price decrease ($12 potential savings vs. average RT price).
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Average for round-trip flights in June 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 junho 12, 2025.

This CheapOair deal was found by Cheapflights users on 6/9. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
sex 8/159:32 amORF - SAN
Nonstop5h 41mBreeze Airways
sex 8/2212:58 pmSAN - ORF
Nonstop5h 22mBreeze Airways
Deal found 6/9$252
This FlightHub deal was found by Cheapflights users on 6/9. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
qua 7/95:20 pmORF - SAN
2 stops19h 35mSpirit Airlines
sex 7/115:13 pmSAN - ORF
2 stops15h 03mSpirit Airlines
Deal found 6/9$254
This JetBlue deal was found by Cheapflights users on 6/10. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
qui 9/410:25 amORF - SAN
1 stop11h 32mJetBlue
seg 9/88:15 pmSAN - ORF
1 stop10h 25mJetBlue
Deal found 6/10$273
This Delta deal was found by Cheapflights users on 6/11. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
qua 9/311:43 amORF - SAN
1 stop9h 10mDelta
seg 9/159:40 pmSAN - ORF
1 stop8h 22mDelta
Deal found 6/11$297
This American Airlines deal was found by Cheapflights users on 6/11. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
seg 9/156:00 amORF - SAN
1 stop7h 20mAmerican Airlines
seg 9/159:19 pmSAN - ORF
1 stop9h 57mAmerican Airlines
Deal found 6/11$315
This CheapOair deal was found by Cheapflights users on 6/11. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
qua 7/95:20 pmORF - SAN
2 stops19h 35mMultiple Airlines
seg 7/1412:58 pmSAN - ORF
Nonstop5h 22mMultiple Airlines
Deal found 6/11$333
This FlightHub deal was found by Cheapflights users on 6/12. 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.
dom 8/312:53 pmORF - SAN
1 stop14h 04mFrontier
sáb 8/98:00 amSAN - ORF
1 stop24h 51mFrontier
Deal found 6/12$346
This Southwest deal was found by Cheapflights users on 6/11. 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.
seg 9/1512:10 pmORF - SAN
2 stops10h 40mSouthwest
seg 9/159:10 pmSAN - ORF
1 stop9h 40mSouthwest
Deal found 6/11$353
This United Airlines deal was found by Cheapflights users on 6/10. 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.
qua 10/84:53 pmORF - SAN
1 stop8h 21mUnited Airlines
seg 10/138:39 pmSAN - ORF
2 stops9h 58mUnited Airlines
Deal found 6/10$402
This Alaska Airlines deal was found by Cheapflights users on 6/10. 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 Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
sex 7/45:57 amORF - SAN
1 stop8h 23mAlaska Airlines
sáb 8/167:39 amSAN - ORF
2 stops12h 43mAlaska Airlines
Deal found 6/10$462

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 junho 12, 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

sex 8/15

9:32 am-12:13 pm

Nonstop5h 41m

San Diego

sex 8/22

12:58 pm-9:20 pm

Nonstop5h 22m

$252

NorfolkSan Diego

ORF - SAN

ORFSAN

Norfolk

qua 7/9

5:20 pm-9:55 am

2 stops19h 35m

San Diego

sex 7/11

5:13 pm-11:16 am

2 stops15h 03m

$254

NorfolkSan Diego

ORF - SAN

ORFSAN

Norfolk

qui 9/4

10:25 am-6:57 pm

1 stop11h 32m

San Diego

dom 9/7

8:15 pm-9:40 am

1 stop10h 25m

$273

NorfolkSan Diego

ORF - SAN

ORFSAN

Norfolk

qua 9/3

12:22 pm-8:41 pm

1 stop11h 19m

San Diego

qua 9/17

10:40 pm-9:02 am

1 stop7h 22m

$297

NorfolkSan Diego

ORF - SAN

ORFSAN

Norfolk

seg 9/15

6:00 am-10:20 am

1 stop7h 20m

San Diego

seg 9/15

9:19 pm-10:16 am

1 stop9h 57m

$315

NorfolkSan Diego

ORF - SAN

ORFSAN

Norfolk

qua 7/9

5:20 pm-9:55 am

2 stops19h 35m

San Diego

seg 7/14

12:58 pm-9:20 pm

Nonstop5h 22m

$333

NorfolkSan Diego

ORF - SAN

ORFSAN

Norfolk

seg 9/15

12:10 pm-7:50 pm

2 stops10h 40m

San Diego

seg 9/15

9:10 pm-9:50 am

1 stop9h 40m

$353

NorfolkSan Diego

ORF - SAN

ORFSAN

Norfolk

qua 10/8

4:53 pm-10:14 pm

1 stop8h 21m

San Diego

seg 10/13

8:39 pm-9:37 am

2 stops9h 58m

$402

NorfolkSan Diego

ORF - SAN

ORFSAN

Norfolk

sex 7/4

5:57 am-11:20 am

1 stop8h 23m

San Diego

sáb 8/16

7:39 am-11:22 pm

2 stops12h 43m

$462

NorfolkSan Diego

ORF - SAN

ORFSAN

Norfolk

qua 7/9

5:20 pm-9:55 am

2 stops19h 35m

$56

Flights are sorted by cheapest round-trip flights first.

Deals found on 6/10

Showing 1-10 of 19 results
1
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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 June 9, 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 80 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 junho 12, 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 June 8, 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.

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 junho 12, 2025.
Read through reviews of airlines operating flights from Chesapeake to San Diego, such as Breeze Airways, Alaska Airlines and Southwest. You can also see how each airline stacks up in terms of entertainment options, comfort, food, crew/service, and boarding process.
Breeze Airways
8.1
Very good
178 reviews

Food

6.7

Boarding

8.3

Entertainment

6.6

Overall

8.1

Comfort

8.2

Crew

8.8

Reviews

1 / 11
10.0
Excellent

Dena,Dec 2024

LAS - BDL

It was comfortable and the crew was great! A few free snacks offered would be nice!
Breeze Airways
8.1
Very good
178 reviews
Breeze Airways
8.1
Very good
178 reviews

Food

6.7

Boarding

8.3

Entertainment

6.6

Overall

8.1

Comfort

8.2

Crew

8.8

Reviews

1 / 11
10.0
Excellent

Dena,Dec 2024

LAS - BDL

It was comfortable and the crew was great! A few free snacks offered would be nice!
Alaska Airlines
8.0
Very good
10,000 reviews
Breeze Airways
8.1
Very good
178 reviews

Food

6.7

Boarding

8.3

Entertainment

6.6

Overall

8.1

Comfort

8.2

Crew

8.8

Reviews

1 / 11
10.0
Excellent

Dena,Dec 2024

LAS - BDL

It was comfortable and the crew was great! A few free snacks offered would be nice!
Southwest
8.0
Very good
4,287 reviews
Breeze Airways
8.1
Very good
178 reviews

Food

6.7

Boarding

8.3

Entertainment

6.6

Overall

8.1

Comfort

8.2

Crew

8.8

Reviews

1 / 11
10.0
Excellent

Dena,Dec 2024

LAS - BDL

It was comfortable and the crew was great! A few free snacks offered would be nice!
Delta
8.0
Very good
7,950 reviews
Breeze Airways
8.1
Very good
178 reviews

Food

6.7

Boarding

8.3

Entertainment

6.6

Overall

8.1

Comfort

8.2

Crew

8.8

Reviews

1 / 11
10.0
Excellent

Dena,Dec 2024

LAS - BDL

It was comfortable and the crew was great! A few free snacks offered would be nice!
United Airlines
7.4
Good
8,790 reviews
Breeze Airways
8.1
Very good
178 reviews

Food

6.7

Boarding

8.3

Entertainment

6.6

Overall

8.1

Comfort

8.2

Crew

8.8

Reviews

1 / 11
10.0
Excellent

Dena,Dec 2024

LAS - BDL

It was comfortable and the crew was great! A few free snacks offered would be nice!

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 Spirit Airlines, which is currently one of the cheapest options available, starting at $56. Breeze Airways flights start at $99 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 Chesapeake?

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

Browse thousands of different options on Cheapflights for your next trip

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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 junho 12, 2025.
AirlineCheapestAverageFlexibilityOn-time
JetBlueCheapest$143Average$266FlexibilityNo cancel feeOn-time62%
Spirit AirlinesCheapest$144Average$282FlexibilityNo cancel feeOn-time65%
Breeze AirwaysCheapest$165Average$316FlexibilityNo cancel feeOn-timeN/A
DeltaCheapest$213Average$462FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$248Average$485FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$274Average$492FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$313Average$473FlexibilityNo cancel feeOn-time63%

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