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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 5/19. Fares are subject to change and may not be available on all flights or dates of travel.
RIC — SAN
ene. 26 — feb. 21
dom. 1/26
dom. 2/2
1 adult, Economy
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The best prices from Chesapeake to San Diego are usually found in September or May, booked 20 days in advance, depart on a Sunday or Thursday and return on a Tuesday

Cheap flight deals from Chesapeake to San Diego

Discover tips and strategies to find the most affordable flight options for your journey from Chesapeake (C6E) to San Diego (SAN). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated enero 21, 2025.

Round-trip from

$301
(Mytrip)

One-way from

$102
(Priceline)

Popular in

March

Cheapest in

September

Average price

$400
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. 14% potential increase in price ($66 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 January 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 enero 21, 2025.

This Mytrip deal was found by Cheapflights users on 1/21. 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.
jue. 3/611:25 amORF - SAN
2 stops25h 24mSpirit Airlines
mar. 3/115:39 pmSAN - ORF
3 stops22h 36mSpirit Airlines
Deal found 1/21$301
This Mytrip deal was found by Cheapflights users on 1/21. 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.
mar. 2/257:00 amORF - SAN
3 stops29h 01mMultiple Airlines
lun. 3/32:56 pmSAN - ORF
3 stops19h 06mMultiple Airlines
Deal found 1/21$312
This Delta deal was found by Cheapflights users on 1/21. 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.
mar. 2/2512:55 pmORF - SAN
1 stop8h 07mDelta
mié. 3/1210:17 pmSAN - ORF
1 stop10h 37mDelta
Deal found 1/21$317
This United Airlines deal was found by Cheapflights users on 1/21. 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.
mar. 2/258:00 amORF - SAN
1 stop8h 11mUnited Airlines
mié. 2/2610:59 amSAN - ORF
2 stops9h 14mUnited Airlines
Deal found 1/21$322
This Kiwi.com deal was found by Cheapflights users on 1/21. 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.
mié. 6/119:22 amORF - SAN
Nonstop5h 41mBreeze Airways
lun. 6/1612:43 pmSAN - ORF
Nonstop5h 22mBreeze Airways
Deal found 1/21$346
This American Airlines deal was found by Cheapflights users on 1/21. 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. 2/83:12 pmORF - SAN
1 stop8h 53mAmerican Airlines
sáb. 2/159:55 pmSAN - ORF
1 stop7h 43mAmerican Airlines
Deal found 1/21$357
This Southwest deal was found by Cheapflights users on 1/21. 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.
mié. 2/266:35 amORF - SAN
1 stop8h 55mSouthwest
lun. 3/39:15 amSAN - ORF
2 stops9h 50mSouthwest
Deal found 1/21$403

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 enero 21, 2025.

Fly from

Any airport

Fly to

Any airport

Route

Depart

Return

Price

NorfolkSan Diego

ORF - SAN

ORFSAN

Norfolk

jue. 3/6

11:25 am-9:49 am

2 stops25h 24m

San Diego

mar. 3/11

5:39 pm-7:15 pm

3 stops22h 36m

$301

NorfolkSan Diego

ORF - SAN

ORFSAN

Norfolk

mar. 2/25

7:00 am-9:01 am

3 stops29h 01m

San Diego

lun. 3/3

2:56 pm-1:02 pm

3 stops19h 06m

$312

NorfolkSan Diego

ORF - SAN

ORFSAN

Norfolk

mar. 2/25

12:55 pm-6:02 pm

1 stop8h 07m

San Diego

mié. 3/12

10:17 pm-11:54 am

1 stop10h 37m

$317

NorfolkSan Diego

ORF - SAN

ORFSAN

Norfolk

mar. 2/25

8:00 am-1:11 pm

1 stop8h 11m

San Diego

mié. 2/26

10:59 am-11:13 pm

2 stops9h 14m

$322

NorfolkSan Diego

ORF - SAN

ORFSAN

Norfolk

mié. 6/11

9:22 am-12:03 pm

Nonstop5h 41m

San Diego

lun. 6/16

12:43 pm-9:05 pm

Nonstop5h 22m

$346

NorfolkSan Diego

ORF - SAN

ORFSAN

Norfolk

sáb. 2/8

3:12 pm-9:05 pm

1 stop8h 53m

San Diego

sáb. 2/15

9:55 pm-8:38 am

1 stop7h 43m

$357

NorfolkSan Diego

ORF - SAN

ORFSAN

Norfolk

mié. 2/26

6:35 am-12:30 pm

1 stop8h 55m

San Diego

lun. 3/3

9:15 am-10:05 pm

2 stops9h 50m

$403

NorfolkSan Diego

ORF - SAN

ORFSAN

Norfolk

mié. 3/19

3:16 pm-7:39 am

2 stops19h 23m

San Diego

sáb. 3/22

7:20 pm-8:29 pm

2 stops22h 09m

$1,260

NorfolkSan Diego

ORF - SAN

ORFSAN

Norfolk

lun. 5/19

9:17 am-11:58 am

Nonstop5h 41m

$102

NorfolkSan Diego

ORF - SAN

ORFSAN

Norfolk

mié. 2/12

3:20 pm-10:24 pm

1 stop10h 04m

$159

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/21

Showing 1-10 of 14 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.

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 January 17, 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 20 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 enero 21, 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 January 21, 2025.

Travelers seeking maximum savings on their Chesapeake to San Diego flight should consider departing on Monday evenings 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 enero 21, 2025.
Read through reviews of airlines operating flights from Chesapeake to San Diego, such as Delta and Southwest. 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
4,662 reviews

Comfort

8.1

Crew

8.7

Food

7.2

Overall

8.1

Boarding

8.2

Entertainment

7.7

Reviews

1 / 10

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

Southwest
8.1
Very good
4,662 reviews
Southwest
8.1
Very good
4,662 reviews

Comfort

8.1

Crew

8.7

Food

7.2

Overall

8.1

Boarding

8.2

Entertainment

7.7

Reviews

1 / 10

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

Breeze Airways
8.1
Very good
143 reviews
Southwest
8.1
Very good
4,662 reviews

Comfort

8.1

Crew

8.7

Food

7.2

Overall

8.1

Boarding

8.2

Entertainment

7.7

Reviews

1 / 10

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

Alaska Airlines
8.0
Very good
9,706 reviews
Southwest
8.1
Very good
4,662 reviews

Comfort

8.1

Crew

8.7

Food

7.2

Overall

8.1

Boarding

8.2

Entertainment

7.7

Reviews

1 / 10

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

Delta
8.0
Very good
8,521 reviews
Southwest
8.1
Very good
4,662 reviews

Comfort

8.1

Crew

8.7

Food

7.2

Overall

8.1

Boarding

8.2

Entertainment

7.7

Reviews

1 / 10

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

United Airlines
7.4
Good
8,984 reviews
Southwest
8.1
Very good
4,662 reviews

Comfort

8.1

Crew

8.7

Food

7.2

Overall

8.1

Boarding

8.2

Entertainment

7.7

Reviews

1 / 10

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 Breeze Airways, which is currently one of the cheapest options available, starting at $102. American Airlines flights start at $159 while deals on United Airlines start at $202 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 enero 21, 2025.
AirlineCheapestAverageFlexibilityOn-time
Breeze AirwaysCheapest$135Average$315FlexibilityNo cancel feeOn-timeN/A
Spirit AirlinesCheapest$144Average$274FlexibilityNo cancel feeOn-time65%
FrontierCheapest$152Average$288FlexibilityNo cancel feeOn-time62%
DeltaCheapest$228Average$480FlexibilityNo cancel feeOn-timeN/A
JetBlueCheapest$245Average$349FlexibilityNo cancel feeOn-time62%
United AirlinesCheapest$248Average$514FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$274Average$532FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$332Average$478FlexibilityNo cancel feeOn-time63%
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