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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 9/26. Fares are subject to change and may not be available on all flights or dates of travel.
RIC — SAN
oct. 11 — oct. 181
sáb. 10/11
sáb. 10/18
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 68 days in advance, depart on a Tuesday or Friday 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 septiembre 11, 2025.

Round-trip from

$214
(Southwest)

One-way from

$99
(Breeze Airways)

Popular in

March

Cheapest in

September

Average price

$285
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 ($12 potential savings vs. average RT price).
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Average for round-trip flights in September 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 septiembre 11, 2025.

This Southwest deal was found by Cheapflights users on 9/9. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mar. 10/286:25 pmORF - SAN
1 stop7h 20mSouthwest
mar. 11/119:45 pmSAN - ORF
1 stop8h 40mSouthwest
Deal found 9/9$214
This Breeze Airways deal was found by Cheapflights users on 9/9. 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 Breeze Airways is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mié. 10/19:21 amORF - SAN
Nonstop6h 06mBreeze Airways
sáb. 10/41:12 pmSAN - ORF
Nonstop5h 13mBreeze Airways
Deal found 9/9$238
This Booking.com deal was found by Cheapflights users on 9/8. 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.
lun. 9/226:53 pmORF - SAN
2 stops30h 31mFrontier
jue. 9/256:27 pmSAN - ORF
1 stop20h 23mFrontier
Deal found 9/8$242
This Southwest deal was found by Cheapflights users on 9/10. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
lun. 10/63:55 pmORF - SAN
1 stop10h 10mSouthwest
mié. 10/299:10 pmSAN - ORF
1 stop9h 05mSouthwest
Deal found 9/10$243
This American Airlines deal was found by Cheapflights users on 9/10. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
sáb. 10/43:43 pmORF - SAN
1 stop9h 53mAmerican Airlines
mié. 10/86:20 amSAN - ORF
1 stop10h 28mAmerican Airlines
Deal found 9/10$249
This United Airlines deal was found by Cheapflights users on 9/10. 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.
mié. 11/126:20 amORF - SAN
2 stops9h 44mUnited Airlines
sáb. 11/1510:51 amSAN - ORF
1 stop7h 47mUnited Airlines
Deal found 9/10$254
This Southwest deal was found by Cheapflights users on 9/9. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mar. 9/306:05 amORF - SAN
1 stop7h 25mSouthwest
jue. 10/29:10 pmSAN - ORF
1 stop9h 05mSouthwest
Deal found 9/9$255
This Breeze Airways deal was found by Cheapflights users on 9/10. 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 Breeze Airways is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
sáb. 11/159:21 amORF - SAN
Nonstop6h 06mBreeze Airways
lun. 11/171:12 pmSAN - ORF
Nonstop5h 13mBreeze Airways
Deal found 9/10$258
This American Airlines deal was found by Cheapflights users on 9/10. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
jue. 11/131:18 pmORF - SAN
1 stop10h 46mAmerican Airlines
mar. 11/1810:47 amSAN - ORF
1 stop8h 55mAmerican Airlines
Deal found 9/10$263

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 septiembre 11, 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

mié. 10/29

6:20 pm-11:10 pm

1 stop7h 50m

San Diego

lun. 11/3

6:50 am-5:35 pm

1 stop7h 45m

$255

NorfolkSan Diego

ORF - SAN

ORFSAN

Norfolk

mié. 10/29

9:21 am-12:27 pm

Nonstop6h 06m

San Diego

lun. 11/3

1:12 pm-9:25 pm

Nonstop5h 13m

$258

NorfolkSan Diego

ORF - SAN

ORFSAN

Norfolk

lun. 10/6

9:21 am-12:27 pm

Nonstop6h 06m

San Diego

mié. 10/29

1:12 pm-9:25 pm

Nonstop5h 13m

$258

NorfolkSan Diego

ORF - SAN

ORFSAN

Norfolk

sáb. 10/4

9:21 am-12:27 pm

Nonstop6h 06m

San Diego

sáb. 10/11

1:12 pm-9:25 pm

Nonstop5h 13m

$258

NorfolkSan Diego

ORF - SAN

ORFSAN

Norfolk

vie. 10/24

9:21 am-12:27 pm

Nonstop6h 06m

San Diego

lun. 11/3

1:12 pm-9:25 pm

Nonstop5h 13m

$258

NorfolkSan Diego

ORF - SAN

ORFSAN

Norfolk

lun. 10/6

3:55 pm-11:05 pm

1 stop10h 10m

San Diego

mié. 10/29

9:00 am-9:50 pm

2 stops9h 50m

$259

NorfolkSan Diego

ORF - SAN

ORFSAN

Norfolk

vie. 11/7

4:15 pm-10:50 pm

1 stop9h 35m

San Diego

mié. 11/12

6:40 am-4:45 pm

1 stop7h 05m

$268

NorfolkSan Diego

ORF - SAN

ORFSAN

Norfolk

sáb. 10/4

9:21 am-12:27 pm

Nonstop6h 06m

San Diego

mié. 10/8

1:12 pm-9:25 pm

Nonstop5h 13m

$268

NorfolkSan Diego

ORF - SAN

ORFSAN

Norfolk

lun. 9/29

9:21 am-12:27 pm

Nonstop6h 06m

San Diego

mié. 10/29

1:12 pm-9:25 pm

Nonstop5h 13m

$268

NorfolkSan Diego

ORF - SAN

ORFSAN

Norfolk

mar. 9/30

6:34 am-12:03 pm

1 stop8h 29m

San Diego

vie. 10/3

6:22 am-5:42 pm

1 stop8h 20m

$270

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/10

Showing 1-10 of 22 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 August 29, 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, 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 septiembre 11, 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 September 7, 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 septiembre 11, 2025.
Get a feel of what it's like to fly with Southwest, Breeze Airways, 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.
Southwest
8.0
Very good
4,248 reviews

Comfort

8.0

Overall

8.0

Boarding

8.1

Food

7.0

Crew

8.6

Entertainment

7.5

Reviews

1 / 20
8.0
Excellent

Walter,Aug 2025

OAK - SAN

Dozens of flights and I've never seen a row's beverages forgotten. I even went back and asked the attendant to check on them and nothing. I really hope it didn't have something to do with the Black mother with her kid in the row. Otherwise it was a typical Southwest flight, rapid boarding, tolerable leg room.
Southwest
8.0
Very good
4,248 reviews
Southwest
8.0
Very good
4,248 reviews

Comfort

8.0

Overall

8.0

Boarding

8.1

Food

7.0

Crew

8.6

Entertainment

7.5

Reviews

1 / 20
8.0
Excellent

Walter,Aug 2025

OAK - SAN

Dozens of flights and I've never seen a row's beverages forgotten. I even went back and asked the attendant to check on them and nothing. I really hope it didn't have something to do with the Black mother with her kid in the row. Otherwise it was a typical Southwest flight, rapid boarding, tolerable leg room.
Breeze Airways
8.0
Very good
205 reviews
Southwest
8.0
Very good
4,248 reviews

Comfort

8.0

Overall

8.0

Boarding

8.1

Food

7.0

Crew

8.6

Entertainment

7.5

Reviews

1 / 20
8.0
Excellent

Walter,Aug 2025

OAK - SAN

Dozens of flights and I've never seen a row's beverages forgotten. I even went back and asked the attendant to check on them and nothing. I really hope it didn't have something to do with the Black mother with her kid in the row. Otherwise it was a typical Southwest flight, rapid boarding, tolerable leg room.
Delta
8.0
Very good
7,960 reviews
Southwest
8.0
Very good
4,248 reviews

Comfort

8.0

Overall

8.0

Boarding

8.1

Food

7.0

Crew

8.6

Entertainment

7.5

Reviews

1 / 20
8.0
Excellent

Walter,Aug 2025

OAK - SAN

Dozens of flights and I've never seen a row's beverages forgotten. I even went back and asked the attendant to check on them and nothing. I really hope it didn't have something to do with the Black mother with her kid in the row. Otherwise it was a typical Southwest flight, rapid boarding, tolerable leg room.
United Airlines
7.4
Good
8,937 reviews
Southwest
8.0
Very good
4,248 reviews

Comfort

8.0

Overall

8.0

Boarding

8.1

Food

7.0

Crew

8.6

Entertainment

7.5

Reviews

1 / 20
8.0
Excellent

Walter,Aug 2025

OAK - SAN

Dozens of flights and I've never seen a row's beverages forgotten. I even went back and asked the attendant to check on them and nothing. I really hope it didn't have something to do with the Black mother with her kid in the row. Otherwise it was a typical Southwest flight, rapid boarding, tolerable leg room.
American Airlines
7.2
Good
10,000 reviews
Southwest
8.0
Very good
4,248 reviews

Comfort

8.0

Overall

8.0

Boarding

8.1

Food

7.0

Crew

8.6

Entertainment

7.5

Reviews

1 / 20
8.0
Excellent

Walter,Aug 2025

OAK - SAN

Dozens of flights and I've never seen a row's beverages forgotten. I even went back and asked the attendant to check on them and nothing. I really hope it didn't have something to do with the Black mother with her kid in the row. Otherwise it was a typical Southwest flight, rapid boarding, tolerable leg room.

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.

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

    There are many flights that can get you from Chesapeake to San Diego in 6h 06m. Fly via Southwest or Breeze Airways 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.

  • 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
La Mesa
Poway
Lemon Grove
Coronado
Imperial Beach
National City
Alpine

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See prices for flight routes from nearby airports that may be better suited for you.
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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 septiembre 11, 2025.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$127Average$277FlexibilityNo cancel feeOn-time65%
JetBlueCheapest$143Average$266FlexibilityNo cancel feeOn-time62%
Breeze AirwaysCheapest$168Average$332FlexibilityNo cancel feeOn-timeN/A
DeltaCheapest$213Average$465FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$248Average$509FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$287Average$495FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$316Average$471FlexibilityNo cancel feeOn-time63%

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